Struggling to find chic yet comfy outfits for early summer? Here’s your guide to effortless style! Casual cold summer outfits here! It’s finally warming up, and it’s time to shed heavy layers. While the weather isn’t quite ready for sundresses and shorts just yet, you can still embrace the spirit of summer with these cold summer casual outfits perfect for the late spring/early summer transition. In fact, this guide focuses on creating stylish casual outfits for the late spring/early summer transition (think late May to June 24th). Scroll down to discover some outfit inspiration for this in-between period (May – June 24th) and learn how to transition your summer wardrobe into these casual cold summer outfits! Whether you’re brunching with friends or enjoying a cozy bonfire night, these casual cold summer outfit ideas will keep you comfortable and on-trend.

OGLAS Links in this post are affiliate links, which means I may earn a commission if you click on them and make a purchase. But trust me, these outfit ideas are worth checking out!

Ready to Ditch the Chill (But Not All Your Layers)? Let’s be honest, summer is what we’ve all been waiting for! But even though you’re itching to wear that gorgeous new dress you bought after reading the SS26 trends report, you don’t have to wait until June.

Here’s the good news: you CAN wear some of your summer clothes even before the official summer season arrives! This article will show you how to style your favorite summer pieces with some clever layering for a casual and effortlessly chic late spring/early summer look.

You will see how to master the cold summer layering! We’ll show you how to incorporate boujee summer dresses and cute tops you’ve been eyeing into stylish outfits perfect for the in-between season.

Explore how to style flowy summer dresses and lightweight sweaters for cooler temperatures.

So, how do you wear summer clothes before summer?

THE BEST CASUAL COLD SUMMER OUTFITS 2026

P.S. Missing a key piece to complete these transitional looks? No worries!** Shop the collages** – all the product links are included so you can grab the exact clothes, shoes, and accessories you see in the pictures. The collages and product galleries are hyperlinked.

And if you want to know more about the size and fit of the clothes/shoes before purchasing it –  subscribe to Brunette from Wall Street Substack. It’s all there. Plus, the 101 style guide for every outfit. Yes, I’m telling you why we paired that dress with those shoes and that bag.

*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.

CASUAL AND COOL COLD SUMMER OUTFITS

Find the perfect match for a day in the city. From staple white T-shirt and blue jeans to playful silk slip top that will take you to the casual rooftop party.

1 Timeless Style: WHITE T-SHIRT WITH BLUE JEANS AND STRAPY SANDALS

Or relax in the sunshine with a classic spring/summer casual staple. Life is a breeze in white T-shirt and blue jeans. Whether layered with a trench coat when it rains or finished with a thin sweater layered casually on your shoulders when the sun comes out, simply pair with strappy sandals for the city.

Picture this: You wake to a moody early summer morning, the city skyline softened by a blanket of clouds. The air is mild, not cold, but the dark sky hints at a day that could go either way. You put on this outfit I put together for you and step out of your apartment into the crisp early summer morning. The city humming with the clatter of coffee shops and the faint scent of rain is still in the air. Your to-do list is long. You need to go to the post office, do the grocery run, maybe quick stop at your favorite bookstore.

2 Trendy Coffee Date: BLACK SILK SLIP TOP WITH BLUE JEANS AND SNEAKERS

By the time you finish your list, the clouds part, and the sun bathes the cobblestone streets in golden light. You close the umbrella and let the outfit shine as you head to a cozy cafeteria to meet your friends.

You step into the cozy cafeteria, the sun streaming through the windows after a cloudy morning, throwing a warm glow over the wooden tables. 

All the girlies are already sitting at the table, drinking bubbles and iced matcha. Obv, they have ordered the same for you, too.

Your friends greet you with smiles, one saying, “That top is stunning! You always look so put-together!” and you laugh, giving her a welcome hug before you sit down.

The afternoon stretches out, the sun lighting up the patio, and you feel completely in your element – relaxed, cool, and ready for more. We need to take you to one more place, this top is truly giving.

Whether matched with blue jeans and sneakers for the day or bedazzled with a pair of earrings for the evening, a black silk slip top can be dressed up or down with ease.

Easy to wear and effortless to style with other bottoms from your summer capsule wardrobe, a silk slip top will be your new wardrobe favourite. From a slip top with lace trim (like mine) to modern skinny jeans, shop pieces that can be dressed down with ease for a casual date night.

FASHIONABLE CASUAL EARLY SUMMER OUTFITS

It is time to discover the styles that are topping everybody’s wish list. Stay in the know with these casual summer coveted options.

3 Trendy Date Night: BLACK SILK SLIP TOP WITH WIDE-LEG PANTS AND POINTY FLATS

Take on early summer with ease in a dark and chic palette of navy and green. From sun up to sun down, the key to staying modern is in this season’s most beloved styles.

Pared back silhouettes give extra allure for a date night – simply step into pointy kitten heels for a picture-perfect ensemble.

4 Effortless Chic for Brunch and Beyond: CHERRY CODED RED TANK TOP WITH GREY BAGGY JEANS AND SAMBAE SNEAKERS

Uniting the best of both seasons, spring and summer, and eyeing fall at the same time, a cherry coded red tank top paired with baggy jeans and sambas meet the dynamic movement. I know you still want to wear sambas. And this is a fashionable outfit with sambas – thanks to the baggy jeans and top.

While wide-legged jeans are cut for effortless ease, a tank top is perfect for fun in the sun. Just make sure you don’tforget sunscreen.

5 Casual Dinner Party: CROCHET TOP WITH BAGGY JEANS AND SANDALS

Now you can elevate those jeans just a little bit for a casual dinner party.

Channel relaxed elegance in this season’s brilliant crochet top and raffia sandals. Accented with sardines and shells, these Aquazzura sandals are perfect one-and-done options for a night out/in.

6 Morning school drop-off to afternoon playground: STRIPED CARDIGAN WITH SUPER SHORT BUTTER YELLOW SHORTS AND SNEAKERS

Casual styles for cold summer mornings come courtesy of boujee knits and a vibrant palette. Discover a one-and-done outfit with super short tweed shorts (preferably in butter yellow – I’m obsessed with these) and a striped cardigan sweater with skater sneakers that will take the guesswork out of dressing down when you need to drop off the kids.

Picture this, you wake to the soft glow of an early summer morning, the air crisp with a hint of dew. The kids are buzzing, backpacks half-zipped, and you’ve got ten minutes to get everyone out the door. Obv, you’re not frazzled. You reach for an outfit I curated just for you – a chic striped knit cardigan, yellow shorts, and comfy sneakers. No endless wardrobe decisions, no stress. Just a trendy outfit that says this mom is fashion forward, cool, and ready to conquer the day.

7 Cozy Comfort Late Spring Outfit: BLUE CARDIGAN SWEATER WITH CAPRIS AND SLIPPERS

No kids, no stress and capri pants? Well, this outfit is for you!

Capri pants – the most fashionable piece in your transitional capsule wardrobe for 2026, pair effortlessly with comfy blue cardigan sweater for cosy chic. Discover this casual cold summer outfit proposal for your day off.

8 WHITE T-SHIRT WITH TRANSCENDENT PINK PANTS AND SNEAKERS

Now maybe you go to work. But you still want to dress casually.

You step into the office, the soft hum of keyboards and the faint scent of coffee filling the air as morning clouds linger outside the windows. The day is mild, not cold, and you feel a quiet confidence as you settle at your desk.

The outfit I put together for you – a crisp white T-shirt, tailored transcendent pink pants that strike the perfect balance of professional and chic, and sleek white sneakers – carries you through with effortless style.

The morning flies by with meetings and emails, the tailored pants keeping you polished as you stride confidently to the conference room, the T-shirt offering a relaxed vibe that still feels office-appropriate.

A colleague compliments your sneakers, saying, “You make casual look so sharp!” and you smile, feeling in control without the stress of overthinking your wardrobe.

COLD SUMMER CASUAL LAYERING FOR UNPREDICTABLE WEATHER

I know, the casual cold summer outfits I have just shown you just calls for a relaxing day at home. But don’t let it make you stay inside for too long. Close your journal, and put on that pretty long sleeve dress.

9 City Strolls in Style: LONG SLEEVE SHORT WHITE SHIRT DRESS AND SNEAKERS

Easy-going options that flatter the form, a long sleeved short white shirt dress is an effortless option that takes you from work to play. Pair with sneakers and amp it up with cute socks for a date with girlies.

SPRING TO SUMMER CASUAL OUTFITS WITH TRANSITIONING SUMMER DRESSES

When the occasion calls for a dress, look no further. Playful summer dresses can be layered with a denim jacket or a striped shirt for a breezy summer feeling by the beach.

But first, let’s see what to wear to a casual date. I hear a really good food truck is coming.

10 Casual Date on the Street: BOMBER JACKET ON A MINI BUTTER YELLOW DRESS AND SNEAKERS

You meet your date by the food truck, the air filled with the sizzle of food and the hum of laughter, and you feel a spark ofexcitement.

You’re dressed in a butter yellow mini dress that glows in the sunlight, a sleek bomber jacket adding a cool edge, and comfy Veja sneakers that let you stroll with ease.

11 Casual Date at the Diner: DENIM JACKET ON A MINI PINK CROCHET DRESS AND KITTEN HEELS

You step into the retro diner, the jukebox humming softly. And sunlight streams through the windows, bouncing off the checkered floors after a cloudy morning. It’s Thursday afternoon, and the city outside hums with early summer energy.

A flutter of excitement hits you as you spot your date waving from a white vinyl booth. The outfit I curated for you feels perfect for the moment. A pink crochet dress that radiates sunny charm, a sleek denim jacket adding a cool edge, and comfy kitten heels.

You slide into the booth, the denim jacket keeping you cozy in the diner’s air-conditioned chill. Meanwhile the pink dress catches your date’s eye, its playful hue sparking a smile.

The waitress brings over a single milkshake with two straws and you both laugh as you lean in to share it. The neon sign above buzzes softly, enlightening the scene, and you feel like you’re in a classic movie moment straight out of my video.

Your date compliments your look, saying, “You make casual look so good!” and you beam, feeling effortlessly charming.

12 Effortless Boujee for a Picnic: STRIPED SHIRT ON SHORT FLORAL DRESS AND CANVAS SNEAKERS

Put a smile on his/her/their face when you show up in a floral dress. Discover the new way of layering your new summer dress with a striped shirt. Match with canvas sneakers for effortless fun in the harbour.

13 Denim for Date: DENIM JACKET ON LONG BLUE LACE DRESS AND SNEAKERS

Denim jacket and sneakers add casual flair to every look. Dress casually but impress in a long blue lace dress.

FAQ CASUAL FOR COLD SUMMER DAYS 2026

Still unsure which outfit to pick? Just fill out this form and I will help you.

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