Casual date outfits for all of you who are dating a guy_girlie_them who always makes sure you are overdressed for a date – here. POV, planning the perfect date outfit can be tricky – you want to look stylish yet relaxed, trendy yet classy. But today we will give you some style ideas for a casual date in 2025. And yes, that includes a bunch of casual date outfits for a date at home. Whether you’re heading out for a first date or cozying up at home, this outfit edit will walk you through the best looks for every casual date scenario, ensuring you feel confident and chic no matter the occasion or location. But that is not all. Here are some casual date outfits for all of you who were googling and asking tiktok how to dress up jeans for a date, too. Furthermore, how to style a dress for a casual date. And a lot more! Now scroll down to see the best casual date outfits for 2025.

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SO YOU TEND TO DRESS UP – THIS IS WHAT MAKES AN OUTFIT CASUAL FOR A DATE

If you’re someone who loves to dress up, or if your everyday style leans towards the more polished side, transitioning to a casual date look might feel a bit difficult. However, ‘casual’ doesn’t mean sloppy or uninspired. It’s about taking those dressier elements and softening them, finding a harmonious blend of sophistication and ease.

Think of it as elevating your ‘off-duty’ style (and yes, I mean leggings and sweatpants), ensuring you’re both comfortable and confident. This article will break down the key components of a successful casual date outfit, helping you adapt your personal style to the relaxed atmosphere of a casual date.

THE BEST CASUAL DATE OUTFITS FOR 2025

All the casual date outfits presented in this article are shoppable – find all the links under the collages. The links will take you to the store(s) where you can purchase that outfit.

And if you need more help or have more questions, you can always book a styling session with me. Just fill out this form and I will help you.

Now, scroll down to see what to wear on a casual date to make your guy’s_girlie’s_their heart skip a beat.

LAID-BACK CASUAL FIRST DATE OUTFITS

Starting with the all-important first date outfits that are perfect for making a great first impression without trying too hard. Pov, it’s just one actually – as you will only need this first date outfit and never again have to think about what to wear on a first date. The date will go so well, you will only need to think about the date outfits for the dates that will follow.

1 MINI PINK DRESS WITH DENIM JACKET AND MATCHING HEELS

First dates are all about making a good impression while staying true to yourself. For a laid-back first date, you want an outfit that exudes confidence without feeling overly formal. We’re talking pieces that allow you to relax and focus on getting to know your date, rather than worrying about your attire.

A cute dress is never a miss for the first date. Layer it with a denim jacket to bring the casual into the mix.

Now imagine this scenario. You push open the diner door, and enter. The air smells like vanilla shake syrup and pistachio. White vinyl booths glow under neon lights, and your heart does a little skip as you spot him. He’s standing by the jukebox. As you approach, he turns, a surprised but delighted expression on his face. “Hey,” he says, his voice a little louder than usual to be heard over the jukebox’s soft music. “You look… amazing.”

“Hey,” you reply, a smile spreading across your face. “You too.”

He laughs, a warm, genuine sound. “I was just trying to pick a song that wouldn’t scare you off.” He gestures towards the rows of song titles. “Any requests?”

“Surprise me,” you say, your eyes sparkling. “But make it something fun.”

He scans the titles, a thoughtful expression on his face. “Alright, how about this?” He presses a few buttons, and a classic rock and roll tune fills the air. “Perfect for a first date, right?”

“Definitely,” you reply, laughing. “Now, are we going to stand here, or are we getting milkshakes?”

“Milkshakes it is,” he says, gesturing towards a red vinyl booth. “Lead the way.”

You slide into the booth and your denim jacket slips off one shoulder, but you don’t fix it. The pink of your dress catches the retro gleam of the soda fountain, soft as cotton candy, and for a heartbeat, you feel like the main character in a film where the lighting always gets it right.

FASHIONABLE CASUAL COFFEE DATE OUTFITS

Surely, after wearing the casual first date outfit from above, they_she_he will do something spectacular for the second date.

But perhaps you are seeing this outfit edit too late and already wore something else for your first date. Surely, you have rizz and he just texted you “coffee?”.

Now, an invitation like this deserves nothing but a minimalistic approach. Something laid off but fashionable – we must not overlook the modern café setting just because someone isn’t making an effort to write a proper invitation.

*Though we need to give them_her_him credit for using words instead of emojis.

2 RUFFLED TRANSCENDENT PINK SILK BLOUSE TUCKED IN MODERN BLUE SKINNY JEANSAND CHERRY LACQUER KITTEN HEEL SLINGBACK POINTY PUMPS WITH LEOPARD TOP KNOT HEADBAND

A sense of effortless ease comes with a pair of blue skinny jeans. And you need to try a modern skinny jeans that take the effortlessness to a whole new level.

Obv you don’t need to elevate your new modern blue skinny jeans for a causal day. But bring some romance to the mix. Reach for a transcendent pink blouse (preferably silk) adorned with ruffles or vertical embroidery that is extra flirty.

Now for the shoes, go with cherry lacquer patent leather kitten heel pointy slingbacks. The washed blue jeans bring enough of casual to this outfit. And a little heel won’t make this outfit too precious for a casual date.

3 CHIC BLACK TOP WITH GREY TAILORED PANTS WITH LILAC SUEDE SNEAKERS AND LONG TRENCH COAT WITH PEARL HAIR PINS

On the second thought, a casual coffee date is rarely a romantic date. Knowing you, I know you need a casual coffee date outfit for a date with your girlies. Pov, you will want to share all about the romantic casual date you just had with your girlfriends over a coffee tomorrow.

STYLISH CASUAL BRUNCH DATE OUTFITS

If your coffee date goes well, brunch might be the next step. These outfits are stylish and comfortable, but chic enough for brunch in any setting.

4 BLUE JEANS AND WHITE T-SHIRT WITH KITTEN HEEL SLINGBACKS

Imagine this. Tuesday (OK, I ‘m not sure about the day of the week, but if we take you had your first date on Friday, and then you met again over the weekend or on Munday, Tuesday seems a good day for a casual romantic brunch date – pov any casual brunch date) sunlight spills through the café’s open windows, gauzy and golden, turning your coffee cup into liquid amber.

He chose the corner table (yes, we dropped other pronouns – but note we are still inclusive in our minds) — the one draped in ivy and with the scent of browned butter and airplane. OK, maybe I should have dropped this little detail too – we all know it smells disgusting.

But your white T-shirt drinks the light, glowing like a blank page as you lean forward to get the menu.

“You look incredible,” he says. A blush creeps up your neck, and you smile, “Thank you. Are we having pancakes today?”

The waiter approaches, his smile warm and welcoming. You order a stack of pancakes to share and champagne. Pov champagne is not casual, is it? But we can’t drink coke – not even diet.

“For the Tuesday thrill,” he jokes, and your laugh tangles with the clink of cutlery, the espresso machine’s rhythmic sigh.

When the pancakes arrive, they’re a tower of golden indulgence. You split them with the edge of your fork, and the syrup pools like liquid sunlight. He steals a strawberry from your plate, mischief in his eyes, and the champagne bubbles dissolve on your tongue—sharp, sweet, effervescent as the way his knee brushes yours beneath the table.

“These are amazing,” you murmur, your eyes meeting his. He smiles, a warm, genuine smile that makes your heart flutter.
“I knew you’d like them,” he says, reaching for the champagne. “Another sip?”

You nod, and he refills your glass, the bubbles tickling your nose. The café is still buzzing, but the brunch crowd has thinned, leaving a more intimate atmosphere. You lean back in your chair, feeling content and relaxed.

“This was perfect,” you say, your voice soft.

“It was,” he agrees, his eyes holding yours. “We should do this again soon.”

You smile, a slow, knowing smile. “I’d like that.”

“But I want to take you to lunch next,” he smiles.

EASY CASUAL LUNCH DATE OUTFITS

Moving from brunch to a more casual lunch? These outfits are effortless and versatile, suitable for any dining spot. And yes, we put together easy looks that work whether you’re grabbing a sandwich or heading to a bistro for a proper meal.

5 DENIM JACKET ON A FLORAL BLOUSE AND MIDI PLEATED SKIRT WITH STILETTO PUMPS

The midday sun is glowing above the bustling sidewalk as you make your way to the restaurant where you’ll be meeting your date for lunch. You’re feeling a little nervous but mostly excited. You’ve been looking forward to this lunch date since, ha most likely since yesterday when he texted you, and you’re determined to make a good impression. But keep it casual. Last minute invitation for lunch at this spot?!

You’re wearing your floral blouse and vintage midi pleated skirt that flutters in the breeze paired with stilettos – because it’s lunch date. And a denim jacket, obviously, to make the outfit casual for the location and the nature of the date.

As you approach the restaurant, you spot your date sitting at the terrace. He’s looking out at the street, a smile playing on his lips. You quicken your pace, your heart pounding in your chest.

“Hey,” you say, sliding into the seat across from him.

“Hey, yourself,” he replies, his smile widening. “You look amazing.”

Your cheeks flush with warmth. “Thanks,” you say, “You don’t look too bad yourself.”

You slip off your denim jacket, letting it drape over the back of the wrought-iron chair, and the breeze toys with the hem of your floral blouse. Somewhere, wind chimes sing. His eyes catch the movement, pausing on the way the midday light turns the blossoms on your blouse into something alive.

“You’ve outdone the garden,” he says, nodding to the hydrangeas spilling from terracotta pots. You laugh, but the sound dissolves into the hum of bees, the clink of ice cubes swirling in mint-infused lemonade. The pleats of your skirt fan out as you sit, brushing against his calf beneath the table. You don’t pull away.

The waiter arrives with crusty bread still warm from the oven, its steam mingling with the scent of rosemary and your perfume—something citrusy, reckless.

He tears off a piece, golden crumbs dusting his fingertips, and offers it to you. Your stilettos dig into the gravel as you lean in, the sharp click of heels grounding you, even as your pulse races.

He mentions the book tucked in his bag, dog-eared and coffee-stained, and you picture him reading in bed, morning light on his shoulders.

He reaches to refill your glass. “I should probably get going,” you say reluctantly.

“Let me walk with you,” he says, his eyes lingering on your face.

SPORTY CASUAL WALK DATE OUTFITS

Following the plot, he is walking you back home. But we know you won’t get far in those heels. Btw Have you seen the walkable city outfit edit?

You don’t need to check it right now. I have some sporty outfits that are ideal for a casual walk, blending style with functionality. As stretchy as leggings but not sloppy, you will look chic and comfy for a leisurely stroll.

6 SAFARI JACKET WITH BLACK SLIM-FIT PANTS AND VEJA SNEAKERS

The sun is warm on your hair as you walk hand-in-hand along the riverbank. The water glistens, reflecting the sunlight like a thousand diamonds.

He matches your pace, close enough that his sleeve brushes yours whenever the path narrows. You pretend not to notice. Ahead, willows dip their fingers into the river, and a swan glides past, trailing a V of ripples. 

“Race you to the bench?” he teases, but you’re already ahead, laughing as your hair flares behind you.

The air smells of wet stone and ice cream from the ice cream store above you. He leans over the railing, pointing to fish darting like silver commas beneath the surface. “Bet they’re gossiping about us,” he says, and you roll your eyes, but your chest tightens when his shoulder presses against yours.

You walk. Past two kids kissing on the stairs, past ice cream carts painting the breeze with vanilla, past the shadow of a hilltop castle that looms like a storybook illustration. Your sneakers leave ghost prints in the pollen-dusted path. He stops to skip a flat stone—one, two, three hops—and you study the way his brow furrows.

When you reach the bench, you sit down, taking all the space.

“One more lap?” he asks.

7 SILK SLIP TOP WITH BLUE MODERN SKINNY JEANS AND SNEAKERS

So let’s do one more lap. But let’s seize the occasion and put on a new outfit.

SIMPLE CASUAL PARK DATE OUTFITS

With the weather warming up, a park date is a delightful option. It’s all about enjoying the outdoors and each other’s company. Let’s look at simple casual park date outfits that combine comfort with a touch of style, perfect for a sunny afternoon.

8 MINI DRESS WITH SNEAKERS

Imagine the sweet air and blooming flowers, and the sun on your nose as you walk hand-in-hand.

The river winks through the trees, and your dress, soft as the new leaves overhead, flutters above your knees.

He walks beside you, close enough that his shadow merges with yours.

“Look,” he murmurs, pointing to a duckling paddling frantically to keep up with its mother. You crouch to watch, the hem of your dress grazing dewy grass. The bow slips loose, and he reaches to retie it. His fingers graze the nape of your neck, warm and deliberate. “There,” he says, though it’s lopsided, and you both laugh.

You walk. And your sneakers kick up dandelion fluff, and he plucks one from your hair, holding it aloft. “Make a wish,” he dares. You blow, and the seeds scatter, carried toward the river.

You find a secluded bench nestled beneath a willow tree. You sit down, and your date pulls you close and wraps his arm around your shoulders. 

You lean into him, feeling the warmth of his body against yours.

“This is perfect,” you whisper, your voice barely audible above the gentle rustling of leaves.

9 OVERSIZED DENIM JACKET ON A CROP TOP AND SHORT PLEATED SKIRT WITH SUEDE SNEAKERS AND BUCKET HAT

The park breathes in shades of green and yellow – those golden fllowors (ha, I don’t know what they are called, but I’m sure you have seen them on the meadow before – our meadows are covered with these wildflowers come May) punch through rain-damp earth.

You hike your oversized denim jacket higher, its sleeves swallowing your wrists, as you lean to pluck one flower. Your skirt flirts with the breeze, while suede sneakers sink into flowers.

He smirks at your bucket hat, tilted rakishly over one eye.

“What?” you ask, though you know.

“Nothing. It’s just… very you.”

You swat his arm, but your laughter blends with the creak of swings in the distance. The path curves past trees, and he plucks a cattail, tickling your neck until you snatch it away.

The crop top beneath your jacket peeks out as you stretch, and his eye pauses on the strip of sun-warmed skin before he looks up, faking interest in a circling hawk.

You wander off the trail and you deliberately let your jacket slips off one shoulder as you crouch to inspect a cluster of violets. He kneels beside you, close enough that his breath stirs the bucket hat’s brim.

“Found a secret,” he says, pointing to a hollow log swarming with ladybugs. You count them aloud, voices hushed, until a squirrel scolds you from above.

He spreads his jacket on the ground, claiming it’s to “save the suede,” but you know it doesn’t get dirty that fast – it’s lilac.

You lie back, watching clouds fray at the edges, and he traces a maple seed’s spin through the air. “This spot,” he says, “would be perfect for…”

“For what?”

He plucks a blade of grass, tucks it behind your ear. “Tomorrow. Blanket. Strawberries. You’ll see.” And you will, because I have a video for that outfit. But first, this cute casual walk date from the story.

COMFORTABLE CASUAL PICNIC DATE OUTFITS

Speaking of picnics, these outfits are comfortable and practical, ensuring you look good while lounging on a blanket. Think a breezy dress with sneakers perfect for sharing snacks and soaking up the sun.

10 MINI DRESS AND SNEAKERS

The wind steals the ribbon from your hair as you crest the hill, the meadow rolling out below like a fever dream of summer. Daisies bow in unison, and your new dress – crisp as a bedsheet hung to dry – snaps at your knees.

You settle onto the blanket, the wind whipping strands of your hair across your face.

“It’s a bit blustery, isn’t it?” you say, laughing as you chase a rogue napkin.

“Just adds to the adventure,” he replies, grinning. “Besides, it’ll keep us cool.”

He hands you a slice of asparagus tart, the flaky pastry warm from the sun, and you take a bite, the savory filling bursting with flavor.

The first bite is all crunch and salt, the tart’s filling silken with goat cheese and lemon zest.

“Mmm, this is delicious,” you say.

“Wait till you try the scones,” he says, his eyes twinkling. He opens a small container, revealing scones filled with strawberries and cream, the bright red berries a stark contrast to the creamy white.

The scones are chaos—cream smears your wrist, strawberries tumble onto the blanket, and when he leans to get the bottle of champagne out of the picnic basket, the bottle slips from his hand, tumbling towards the edge of the blanket. He lunges forward, his body close to yours, his hand instinctively reaching out to catch it. Your fingers intertwine.

He looks up, his eyes locked with yours, a slow smile spreading across his face. Slowly, he leans in, his breath warm against your skin. You close your eyes, anticipating the touch of his lips. But then, for the plot, you pick up a strawberry, and pop it into his mouth.

He stares at you, surprised, his eyes wide. You wink, and he bursts out laughing.

11 GINGHAM DRESS WITH A SWEATER AND BOOTIES

Now you know I don’t approve of a dress and western ankle boots if the dress is short. And a no sweater for a date is a rule I swear by, but for a casual picnic date with your girlies, this combination can be a success.

PRETTY CASUAL BEACH DATE OUTFITS

If your picnic sparks a bigger adventure, maybe you’re off to the beach. These outfits are pretty and beach-ready, perfect for a day by the sea.

12 SHORT DENIM JACKET ON A LONG SHEER LACE DRESS AND SNEAKERS

Picture this: the midday sun beats down on the beach as you squint against the glimmer, the salty air whipping through your hair as you walk hand-in-hand with him.

He stops, pulling you close, and you both stare out at the endless expanse of the ocean. The waves crash against the shore. And you can hear his heart beat.

He turns to you, his eyes sparkling in the sunlight. “You look incredible,” he says, staring at your dress.

You blush, feeling a warmth spread across your cheeks. “Thank you,” you say, but your voice is barely audible above the roar of the waves.

He smiles and reaches for your hand. 

“Let’s find a spot on the pier,” he suggests.

You follow him, your heart pounding in your chest. The weathered wood of the pier creaks beneath your feet as you walk. But you find a secluded spot.

He pulls you close, his arm around your waist. You lean against him, feeling the warmth of his body radiating through the denim jacket.

MODERN CASUAL ART GALLERY DATE OUTFITS

While wearing anything too casual is just not it for a gallery date, a modern exhibition might take a more casual form.

13 NAVY BUTTON DOWN SHIRT WITH MATCHING SHORTS AND BLACK ESPADRILLE WEDGES WITH PEARL HAIR PIN

Now it is challenging for me to help you visualise the scenery for this plot as I don’t know what you will see (pov that’s the thing about modern art – everyone sees a different thing). But let’s give it a try.

He lingers at your shoulder, smelling of ink and bergamot. “Looks like a robot’s nervous system,” he says, nodding to the sculpture.

“Or a chandelier that forgot how to shine,” you counter, and his laugh bounces off the vaulted ceiling, too loud for the whispering crowd.

You drift. Past a canvas splattered with neon Rorschach blots, past a glass cube droning with trapped bees. The pearl hairpin winks in your periphery whenever you tilt your head. And its shine clashes with the LED strips overhead.

He stops at an installation of floating mirrors, angled to fracture reflections. “Here,” he says, steering you into the light.

The glass splinters you both into a hundred shards—your navy silhouette sharp against his charcoal linen, the pearl hairpin in your hair pictures a constellation of tiny moons.

His thumb grazes your elbow as he points to a warped fragment. “That one’s my favorite. You look… abstract.”

“You look pretentious,” you shoot back, but your voice cracks.

*Admittedly, this is not my finest casual gallery date outfit. And it is the one I happened to wear IRL when I went to the gallery on my way to the spa. And no, I was not planning to go to the gallery that day at all. But the traffic was low, and the spa was not opened yet, so we wanted to seize our time at the location – there are four things at the location: the spa, the gallery, the museum and the natural park with salt pans and wild birds. So the gallery it was.

TRENDY CASUAL GAME DAY DATE OUTFITS

If art isn’t your thing and sports are more your speed, these trendy game day outfits are great for cheering on your team together.

2 outfits – because I know some of you want to wear a cute dress for a game day date.

*Cool girlies wear team’s logo (or the number of their favourite player) on the back of their oversized denim jacket. Think patches, embroidery, or just write it down with a sharpy.

14 OVERSIZED DENIM JACKET ON A TANK TOP AND BLUE JEANS WITH NIKE LOW DUNK SNEAKERS

The Staples Center roars, popcorn grease hangs in the air – oh I just hate that, bass-thump music rattling your ribs as you climb the stairs.

The crowd surges as Luka sinks a warmup three, and you grip his arm, nails digging into his sleeve. “That’s why he’s MVP.”

He peels your hand off, laughing. “You want a hotdog?”

You don’t look away from the court. “With everything.”

He hesitates. “Relish?”

“Everything.”

“Relish is a crime,” he says with a naughty voice, but he’s already sidestepping spilled beer and popcorn carcasses, vanishing into the concession line.

Your date returns with a cardboard tray of hotdogs, the foil wrappers glint under the jumbotron’s glare. “Extra mustard,” he says, sliding in, knee bumping yours as he passes one over.

The crowd roars. You’re halfway through a bite when the lights dim, spotlight slicing the court. The hotdog grease stains your thumb, and he offers a napkin—too late. 

Luka wins the tip-off, and you’re on your feet, mustard bottle crushed in your fist. “That’s him,” you hiss as Luka Euro-steps around two defenders.

“That’s a travel,” he mutters, but you don’t care. The scoreboard bleeds purple and gold.

He steals a fry from your tray.

The din of the crowd fades to a hum. “You’ve got—” he starts, voice low, thumb brushing the corner of your jaw. You freeze, the fry halfway to his lips, as his look drops to the streak of yellow on his thumb.

“A crime scene,” he whispers, holding your stare. The neon jumbotron lights halo his profile—the faint stubble, the too-casual smirk—and your pulse thrums louder than the buzzer.

He licks the mustard off his thumb, slow. “Sweet.”

You don’t breathe.

The crowd erupts as Luka scores, but neither of you turn. His knee presses into yours beneath the tray, and the fry falls, forgotten. “Still think relish is a crime?” you whisper.

He leans closer, you can smell his cologne cutting through the grease – cedar and something reckless – it smells awfull (ha you need to get him a new cologne). “Only if you’re the judge.”

The arena roars.

You don’t hear it.

The third quarter’s already a blur of fast breaks and fouls. When Luka sinks a half-court shot, you leap up, nacho cheese splattering your Dunk. He tugs you back down, grip firm on your wrist. “They’ll revoke your fan card if you waste cheese,” he scolds, but he’s laughing, eyes crinkled at the corners.

15 OVERSIZED DENIM JACKET ON A MINI DRESS WITH NEW BALANCE SNEAKERS

Now a casual game day date outfit for all the Bama girlies.

The Quad hums with bourbon and barbecue smoke, the air sticky and you can feel a W. Your denim jacket hangs loose, sleeves shoved to your elbows, as you pick through tailgates dotted with crimson jerseys and checkered tablecloths.

He finds you at the Coke bottle toss, two Sweet Waters sweating in his grip. “Hey you,” he says, “are you ready?”.

You snatch the beer. “Let’s go.”

The roar of the crowd is deafening as you and your date enter the stadium. “Roll Tide!” your date shouts, raising his voice above the din. You join in, your voice hoarse with excitement.

He steals a fried Oreo from your napkin, powdered sugar dusting his stubble. “You’ve got—” you start, swiping your thumb across his jaw. His breath hitches. The chimes ring, and you both pretend not to notice.

Your sneakers stick to beer-slick concrete as you climb. He steers you to the seats, palm searing your lower back.

Alabama scores on the first drive. You leap up, and he catches your waist before you tumble into the frat bros below.

You turn, just enough to catch his look—stubbornly steady, though the stadium’s shaking. His thumbs press into the dip of your waist. The marching band blares, trumpets sharp as your pulse, and you think: This is the real touchdown.

By halftime, you’re sharing a foam finger. He traces the team logo, knuckles brushing your knee. “Bet you couldn’t name three players,” he teases.

You tilt closer, your lips grazing the shell of his ear. “Bet you still sleep with that Bryant Bank plushie.” His laugh vibrates against your cheek, warm and bourbon-tinged, as his thumb hooks under the dress’s lace trim.

“Wanna check my bed and see?” he murmurs, all faux innocence, while the foam finger topples to the floor.

You pluck a pretzel from his lap, slow.

TRENDING ARCADE DATE NIGHT OUTFITS

Instead of a loud stadium, how about a playful night out? These trending arcade date outfits are comfy and cute, ideal for a night of games.

16 PINK TANK TOP WITH SHORTS AND AIR JORDAN HIGH TOP SNEAKERS

Just imagine all the neon lights and the smell of cotton candy and popcorn in the air.

He feeds quarters into Skee-ball, sleeves rolled to show off his new Phillip Pattek. “Bet you can’t beat my high score,” he says, nodding to the leaderboard scrawled with ACE 420.

“Ready to get our game on?” you ask, a playful glint in your eye.

“You bet,” he replies, his eyes sparkling with anticipation.

The ball rolls. Clunk. 50 points.

He whistles. “Lucky shot.”

You lean into the next throw, shorts riding up just enough to make him adjust his stance. Clatter. 100. “Still luck?”

His hand lands on your waist, steering you aside. “Move over, rookie.”

The game blurs. His Skee-balls ricochet like grenades, tokens pile up, and when he snatches the last ticket from the machine, you grab it with your teeth. He freezes. Your lips graze his knuckles. Static.

“Cheat,” he rasps.

“Cry,” you shoot back, ticket still clamped between your teeth.

At the air hockey table, he slams the puck so hard it flies off, nearly decapitating your cousin with a light-up sword. You’re bent over laughing when he crowds you against the prize counter, palms braced on either side.

“Rematch. Now.”

He’s all strategy, muttering about torque and grip. You’re pure chaos, jamming the joystick until a neon-green alien plush tumbles loose. “For you,” you say, tossing it at his chest.

He pins it under his arm, feigning disgust. “It’s ugly.”

“Like your Skee-ball form.”

By midnight, you’re splitting milkshake. He steals the cherry from your straw, and you press the cold cup to his neck, laughing as he flinches. “Truce?” he asks, catching your wrist.

His thumb traces your pulse point. The arcade fades to white noise.

When you cash in tickets, he swaps your candy stash for a plastic ring. “For luck,” he says, sliding it onto your pinky.

RIZZ CASUAL ICE CREAM DATE OUTFITS

With sugar on high – we know you had that extra large cotton candy and you didn’t want to share, ice cream parlour is the right place for your next date.

17 OVERSIZED HOUNDSTOOTH BLAZER ON A WHITE BUTTON DOWN SHIRT AND BLUE JEANS WITH WHITE WESTERN ANKLE BOOTS

Summer, spring, fall or winter, there is no wrong season for a scoop of ice cream. Or three – I always order three.

“Pistachio, pistachio-cookie, and coconut?” He raises a brow, nudging your boot with his sneaker.

“Yes,” you reply with sparkling eyes.

The ice cream arrives in a scalloped glass bowl, with a cookie on top. You take the cookie out and hold it out to him. “Here,” you say, voice softer than the parlor’s vanilla-scented air. “Before I change my mind.”

He hesitates. The afternoon light slants through the window, gilding the cookie in your hand. “You hate sharing,” he says, but leans in anyway, lips parting.

You pull back, just an inch. “Not sharing. Gifting.”

His laugh is a warm rumble as he takes the cookie.

He bites. The cookie crumbles, a fleck sticking to his lower lip. “Sweet,” he murmurs, eyes on yours.

“The cookie?”

“Sure.”

“Double dare you to keep up.”

He doesn’t. His mint chip sits untouched as he steals bites of your pistachio, his spoon clinking against yours. The chair groans when he leans forward, and his knee locks against yours beneath the table. “You’ve got—” he starts, thumb swiping coconut flakes from the corner of your mouth.

You drag your spoon through the melting wreckage, watching him mimic the motion. “Why pistachio twice?” he asks, kicking your boot again.

“Why mint chip ever?”

18 PINK LACE DRESS WITH BLACK ESPADRILLE WEDGES AND BLACK HEADBAND

The sun beats down, but you escape the sun on the cobblestone street. You take a sit outside the ice cream parlour. The air is thick with the sounds of children’s laughter, the clinking of spoons against glass bowls, and the distant hum of the city.

Minutes tick by. No waiter.

You smooth the pink lace of your dress against the wrought-iron chair, your hair catching the breeze. He promised you the best pistachio gelato in Italy. He promised.

“Seems we’ll wait a bit longer,” you say, chuckling.

“It’ll be worth it,” he replies, smiling.

Twenty minutes pass. A couple beside you receives their order—a towering sundae with a sparkler—and he flinches at the fizz-pop.

You touch his wrist. “It’s okay,” you say, toeing your espadrille against his shoe.“ I’m happy just—”

He stands abruptly, chair screeching. “Stay here.”

He disappears inside the brightly lit shop. You watch through the window as he jostles through the crowd.

He returns with two glass bowls filled with more ice cream you have ever seen in one cup. He smiles when he sees you, his eyes twinkling with amusement.

“You look like a summer dream,” he says, his voice a low rumble that sends a shiver down your spine.

“Thanks,” you reply, “now give me my ice cream.”

19 A PINK TANK TOP AND PINK MINI SKIRT WITH OVERSIZED DENIM JACKET AND PINK KITTEN HEEL MULES

When dress is not your vibe, reach for a cute pink skirt and a tank top. Pair with an oversized denim jacket and step into kitten heel mules if you are running late. Obv we don’t want that ice cream to melt.

FEMININE CASUAL BAR DATE OUTFITS

If your special someone calls for casual drinks – but at the bar, these feminine outfits are casual yet flirty, perfect for a relaxed evening at a bar.

20 WHITE SILK SHIRT WITH MODERN INDIGO SKINNY JEANS AND SANDALS

Roll up the sleeves and make it look casual even if you are wearing heels. You are still in jeans, so by the evening dress code – this is casual by definition. But less is more. So just make sure you don’t over accessorise. A bag is the only accessory you need. But preferly leave that at home.

21 BLACK TANK TOP WITH BLUE JEANS AND BLACK SLINGBACK MID HEEL PUMPS

Imagine sticky vinyl booths, whiskey-stained mahogany, and Bruce Springsteen riff crackling from the jukebox. His knee finds yours under the table, most likely a reflex, but his smile is dashing.

“Why here?” you ask, though you already know.

He orders two glasses of red, fingers drumming the table (oh you hate that). “Remember the night we…”

“You’re nervous,” you say, toeing off a slingback to brush his calf.

He stiffens. “Why would I be nervous?”

“Because you’re terrible at surprises.”

He exhales, defeated, and pulls a Polaroid from his wallet—a snapshot of you here, 18 years old, laughing into a whiskey glass. “I wanted to recreate our first date. But the new guy doesn’t know how to muddle cherries, the jukebox broke, and…” He gestures to the neon sign now advertising KARAOKE WEDNESDAYS.

You sip the too-sweet drink, wincing. “We could fix it.”

“How?”

You stand, slingbacks dangling from your fingertips. “First date rules. No mentioning the mortgage, the kids, or the dog’sIBS.”

He grins, wolfish. “And?”

“And…We pretend we’re strangers.”

You stride to the bar, swaying, and order a tequila shot. He follows, playing along, his hand grazing the bare skin of your waist. “Can I buy you a drink?” he asks, voice rough with the game.

“Depends.” You spin to face him. “You look like trouble.”

“I’ have MBA.”

“Trouble,” you repeat, licking salt from your wrist.

He steals the tequila, lips brushing your thumb as he takes the lime from your fingers. The burn is bright, messy, perfect. You drag him to the broken jukebox. The wires spill out like guts, and you sing off-key into a phantom microphone. He laughs into your neck, hands spanning your hips, and for a heartbeat, you’re 18 again—all hunger and no maps.

“Ask me.”

“Ask you what?”

“What you asked me then.”

“You believe in forever?”

He kisses you, slow and deep, tasting of tequila and the years. “Only with you.”

22 BLACK TANK TOP WITH MIDI DENIM SKIRT AND SANDALS WITH A BLACK HEADBAND

Wait, you need to wear this tank top twice. Let’s put you in another plot.

So, the bar thrums with the lazy energy of a Saturday night—a few regulars hunched over beers, there are couples occupying almost every table, a ceiling fan chopping the smell of fried pickles and Cosmopolitan.

You spot your hubby leaning against the bar, a mischievous glint in his eyes, his gaze sweeping the room. When he spots you, a slow smile spreads across his face.

“You made it,” he says, his voice a low rumble that sends a shiver down your spine.

“Of course, I did,” you reply, your voice playful. “Wouldn’t want to miss out on a night with you.”

He pulls out the stool for you, his eyes lingering on you for a moment longer than necessary. You feel a blush creeping up your neck, but you meet his gaze, a playful challenge in your eyes.

You slide onto a stool, the denim skirt brushing your knees, and remove your bag off the shoulder. The black headband digs into your temples, but you leave it— it’s comfortable, plus he likes it when your hair’s out of your face.

The bartender approaches, and you order your drinks.

The drinks arrive, and you raise your glass.

“To us,” he says, his voice barely audible above the voices of the crowd.

“To us! How was your day?”

“We closed the deal. And yours? What did you do?”

“Golf. Spa. And I painted for a little bit. You know a painting for the tea room.” “The painting of you and your sister or Medo? I still can’t believe how well you can paint a dog.”

The bartender refills the chips. You challenge him to a game of “worst hypotheticals” — Do you bet that guy over there would rather… fight a raccoon or host a toddler’s birthday party? His answers get increasingly unhinged, his laugh louder, his hand touching your hair.

“Cheat,” you say, swatting him away.

EFFORTLESSLY CASUAL DINNER OUTFITS

From the bar to a bite, these effortlessly chic dinner outfits ensure you look great without overdressing.

23 SILK SLIP TOP WITH WIDE-LEG TROUSERS AND KITTEN HEEL SLINGBACKS

Visualise this: the bistro hums with warm, unpretentious energy—soft jazz tangled with clinking cutlery, the air is sweet and you can smell browned butter and rosemary, and Coca-Cola. You sit at your usual table.

“They gave us extra focaccia,” he says, tearing a piece. “Your charm worked again.”

You lean in, the silk catching the candlelight. Of course.”

The waiter, who’s memorized your orders since January (pov you are truly memorable)—brings the Chianti without asking. You toast to night without kids crawling under the table. His eyes follow the slip’s neckline as you laugh, and you can see a special glow in his eyes.

The food arrives: pizza for you, Porchetta for him. You swap plates halfway, forks clashing. “You always steal the crispy skin,” he accuses, spearing burrata from your pizza.

“You always let me,” you counter, nudging his ankle with your heel.

FLIRTY CASUAL MOVIE NIGHT OUTFITS

Or maybe you’re winding down with a film tonight. Movie nights call for comfort, but these flirty outfits will keep you cute and cozy, whether you’re at the cinema or on the couch.

24 TRANSCENDENT PINK BLOUSE WITH BLUE JEANS AND FLATS

The screen flickers with the opening credits—a romcom so cheesy even the soundtrack winks. You tuck your feet under his thighs and sink into the cushions. He tosses a box of popcorn into your lap, kernels spilling onto your jeans. “You’re supposed to share,” you say, but he’s already stolen a handful, butter glinting on his fingertips.

“Relax, it’s a metaphor,” he deadpans, nodding to the movie. The heroine trips into the hero’s arms, and you both groan.“Groundbreaking.”

But the story gets deep. Just when a kernel lands on your blouse. You retaliate by stuffing a handful down the back of his shirt. He yelps, crushing the popcorn box between you as he pins your wrists. “Truce?” he asks, breath warm and salty.

“Never.”

You lob a kernel at his forehead; he retaliates by balancing a piece on your nose. The romcom’s dialogue fades to white noise—“Love is messy!” the heroine cries—as popcorn rains down like confetti. A piece gets caught in your hair, and he plucks it free, fingers grazing your earlobe.

“You’re a menace,” he says, but his thumb traces the lace trim of your blouse.

The movie’s couple kisses in the rain. You’re too busy wrestling for the last kernel, his laughter vibrating through your ribs. The flats go flying, popcorn crunches under your knees, and suddenly you’re nose-to-nose, the screen casting his face in sapphire light.

“You’re missing the plot,” he whispers.

“You are the plot,” you shoot back, flicking butter at his chin.”

25 BOMBER JACKET ON A GREEN SATIN DRESS AND SLINGBACKS

If you are looking for a combination of romantic, pretty and casual, forget about jeans and wear a bomber jacket instead!

Layer it on a green dress that adds a touch of allure but it’s not too much for a casual date.

RELAXED CASUAL HOME DATE OUTFITS

And finally, if movie night turns into staying in, these relaxed outfits are comfortable and stylish for a home date – perfect for an intimate night of Netflix and chill.

26 BLUE JEANS WITH WHITE T-SHIRT

You are already sitting in the bed as he joins you with a large popcorn box in his hands.

“Just like in the movies,” he says, a mischievous glint in his eyes.

You smile, “You shouldn’t have.”

You settle in, the buttery scent of popcorn fills the air – you hate that, but the popcorn is so good. The movie starts, and you’re instantly drawn into the story – a classic rom-com, of course. You laugh at the witty banter, your eyes occasionally glancing at him, watching his reactions.

But then the romcom takes a left turn and there is a haunted Airbnb—and you yelp, popcorn scattering across the sheets.

“Told you it’d get weird,” he says, pausing the movie. His arm brushes yours as he reaches for the empty bowl. “More wine?”

“Yes. And turn the light on.”

CUTE CASUAL HIKING DATE OUTFITS

If your special someone is hardcore about sports, and a pleasant walk in the park just isn’t their idea of romantic and casual and they take you to the mountains instead – this is for you.

27 CASUAL CUTE HIKING DATE OUTFIT WITH LEGGINGS

This cute hiking outfits is both practical and stylish, with moisture-wicking layers and trendy boots for the trails. And sorry, I don’t have any plot for this one to share with you here. Leaving it exclusively for the Substack paid subscribers.

FAQ CASUAL OUTFITS FOR A DATE

Let me know what outfit you like the most. And, if you want a 1 on 1 styling session or just have questions about these outfits – fill out this consultation form and I will help you.

MORE DATE OUTFITS

So this is how to dress up for a casual date night. *We created a special group to discuss about casual date ideas and these outfits. Join us. Or *You can leave your comment and express your feelings 🤍 🛒 😶‍🌫️🤭 here. Up next: cute date outfits.