Brunette from Wall Street what to wear to a first date in winter the best first date winter outfits


First date winter outfits 2024 here! Because I know you have been wondering what to wear on a first date in winter. POV You have been thinking about your first date outfit ever since the Thanksgiving dinner party. So what to wear to a first date in winter 2024? One of these first date outfits for winter 2024, obviously! Whether you favour baddie styles with sensual cutouts or a wisp of romance with tulle and ruffles, I recommend you save those date outfit ideas for the second date. You want to look chic and cool on the first date.

Obviously, you should dress up for the first date – no matter the weather or cold, but do yourself a favour and don’t fool the guy with the 2-hour version of you. Scroll down to see the best first date winter outfits and pick the best first date winter outfit idea that fits your personal style and won’t look out of place no matter where he is taking you to. Ps. I made sure to put together the most fashionable first date winter outfits for the most popular first dates in 2024.

I get a commission for purchases or clicks made through links in this post.

Put yourself together for the first date in winter 2024, make the seamless transition from the dating app to the real life dating with the best winter date wardrobe.

From cool denim pieces that offer comfort and spontaneity to a fabulous dress that brings that little special but not turning you into the 2 hour version of you, discover every option for the most popular first dates.

Indeed, dressing up for the first date comes with its own rules. It’s a canon event. While you don’t need to impress him all over again – you already impressed him to ask you out on a date. You want him to fall for you even more.

POV Barbie bimbo style is still in fashion for winter 2024, moreover a key fashion trend and the biggest styling trend. But you don’t want to dress like a bimbo for the first date. That is not you.

Given you were pointed to Brunette from Wall Street, your style is more refined, feminine, or chic. Or, in the best case, all three.

Remember, it is important to stay true to your style. But at the same time, you wish to look cool and collected, not too sexy but not boring either. 

As challenging as dressing up for the first date is, here are the best first date winter outfits that are easy to copy.


By the way, all the collages and product galleries in this first winter date outfit edit are hyperlinked and available for immediate purchase via links within the content itself. You can shop for the perfect first date winter outfit instantly. To shop for the look you want to wear, simply click on the items you need to build your favourite first date outfit. Your clicks will take you to the online stores where you can purchase the selected items.


A dinner date in fancy restaurant or nothing, no cap. According to tiktok dating experts you shouldn’t say yes to anything less.

Surely, you will want to go big on impact. But let me tell you one secret – you just need to put on a dress. It will always be a dress that captures his heart and convinces him to slip a ring on your finger. Find the perfect dress, and he’ll be yours forever.


Imagine stepping into the restaurant, the soft glow of ambient lighting casts a warm, golden hue across the room. The air is infused with the tantalizing scent of culinary delights, and you feel a delightful blend of excitement and nervous anticipation. Glancing around, you notice the intimate ambiance, the clinking of fine glassware, and the soft hum of laughter. He’s already there, patiently waiting, his eyes scanning the entrance with anticipation.

The LouLou Borneo long black wool coat (btw the sleeves of this coat are supposed to be long, so take your normal size) gracefully drapes over your shoulders, an elegant prelude to the enchanting little black dress beneath. Your new little black dress, caresses your silhouette, its simplicity concealing allure. The Gianvito Rossi satin bloom pumps, with each step, leave a trail of subtle sophistication on the polished floor.

As you approach, his gaze is fixed, and time seems to pause for just a moment. A fleeting pause, a widening of his eyes. Your new long black coat cascades like a waterfall, creating an aura of mystery and allure. The dress reveals just enough to leave him captivated.

He rises from his seat, and you can see emotions playing across his face – surprise, admiration, and a touch of awe. A small, appreciative smile graces his lips, and it’s as if the world outside the restaurant ceases to exist.

The host gestures towards a secluded corner table. And as you walk together, the rhythmic tap of your heels on the floor echoes the beating of your hearts in synchrony.


A masterclass in contemporary femininity, this dress is a true investment piece for every girlie who wants to look sexy. From a diamanté neckline to contemporary cutouts and a sleek slit, discover the enduring charm of the dress that will steal his heart the moment you take off the coat.


Dressing up for a museum comes with its own set of rules. Moreover, for a museum date.

You don’t want to wear anything too opulent or casual, as you normally would to a modern gallery. But it is still important to look cute.

Here are four cute first date winter outfits for a museum date or gallery date that are cute but not too much. POV I could come up with four more – I love going to art galleries.


The one and done option to keep you looking put together and feel warm in the cold museum, go for a short tweed dress. Easily styled with black knee high boots and a short coat (this one is 100% doubleface wool and pink), it transitions seamlessly into evening dressing with a spritz of date night perfume.


If you are not into dresses, play around with different fabrics and silhouettes for a cute fashion forward approach to winter datewear.

Intricate options of a ruffled blouse and tweed shorts with knee high boots with a cool girl attitude bring a contemporary update to a short pink coat.

For a gallery date you might prefer to stand out with boujee elegance.


Boujee elegant and demanding attention edged with a cropped top under the blazer and tweed shorts layered with an elegant winter coat, you will be front and centre in his mind.

Picture this: You’re on the bustling winter street, walking to the art gallery for your first date. The air is crisp, and a light dusting of snow paints the cityscape in a soft, ethereal glow.

pink wool coat envelops you in its warmth, a bold yet whimsical statement against the winter backdrop. 

Beneath the pink coatblack socks peek out, a subtle detail that adds a touch of boujee to your fit. The contrast between the delicate pink and the sheer black creates a harmony that mirrors the art awaiting you at the gallery. It’s a visual prelude to the masterpieces you’re about to see.

Completing the look, patent leather Mary Jane pumps adorn your look. The glossy finish adds a hint of sophistication, and the Mary Jane style imparts a playful charm. I bought mine at Rouje. And I love them, even though I don’t find them as comfortable as Gucci heeled loafers. If you know you know, cringe, you also know Mary Jane pumps with multiple buckles are the most fashionable pumps of the season. Perhaps, Reformation Mary Jane pumps are more comfortable – see them in product gallery below.

Emotions swirl as you approach the art gallery. Anticipation and excitement intertwine, creating a symphony of feelings.

As you approach the entrance of the art gallery, the winter evening air crackling with anticipation, you catch his eye for the first time. He stands there, framed against the subtle glow of the gallery lights, awaiting your arrival. In that fleeting moment, as he beholds you in your curated fit, his expression transforms into a symphony of emotions. This pink coat draws his attention immediately.


For the romantic in you, choose an elegant silk blouse in a dreamy colour paired with vegan leather pants and ballet flats.

Ignore what the weather looks like outside, ballet flats are the shoes you want to wear at the gallery. As a bonus, ballet flats will put him to the test. POV He will pass the test if he offers you a ride back home, making sure you don’t have to walk home in the snow.


Make the easy transition to date night with a spritz of perfume, hair accessories or makeup.


If you are rushed for time and know you won’t actually have time to get dressed for the date after a busy day at work, you can elevate your chic pantsuit with smokey eyes and a gloss you carry around in your purse.

By the way, did you know there is something about shiny lips that make men’s heart skip a beat? Science.


If you don’t like wearing lip gloss, give a Y2K spin on elegance with a short suit and knee high boots.

A short suit always offers a fine balance between looking sexy and showing too much on a first date.

Going mini makes everything more special. But tone down with a cream coat. You don’t want to bring an extra dose of sass to the first date.


When the air is crisp and the streets are adorned with a delicate layer of snow, a library serves as an unconventional yet enchanting setting for a first date. The hushed whispers of bookshelves, the soft glow of reading lamps, and the faint scent of aging paper create an ambiance that is both intimate and intellectual.

But what to wear?


Now, while I would not wear anything too revealing or anything that would make his imagination flutter (I prefer to stand out with quiet elegance, besides that’s what books are for), I know you wish to wear a knitted dress for the first date this winter. Cringe, I find it too alluring, but this first date outfit with a knit dress will be a W for you, no cap.

Style it with shoes in matching color – preferably flats.

Imagine this: You are meeting at a library. The air is infused with the comforting scent of aged paper and the soft murmur of whispered conversations. A library, an unconventional yet charming choice that promises a unique blend of intellect and romance.

Emotions swirl in the air—the excitement of a first encounter, the shared love for literature, and the unspoken connection that unfolds amidst the towering shelves of books.

Draped in a long rib-knit dress, you exude quiet confidence. The dress, while modest, hints at allure, its rib-knit texture providing a tactile charm. The pastel hue brings a softness to the wintry scene, making you stand out like a delicate bloom against a backdrop of literary treasures.

Over your shoulders, the LouLou Studio Borneo coat in black wool (it’s made of 90% of wool and 10% of cashmere and it’s so soft and warm) adds a layer of sophistication. The coat, with its simple yet refined design, complements the hushed atmosphere of the library. The black wool provides a stark yet complementary contrast to the gentle pastels, creating a look that is both refined and cozy.

Your steps are hushed, thanks to the Aquazzura pointy ballet flats in a matching color. The flats, both practical and stylish, are the best for a leisurely stroll through the aisles of books. Btw I bought mine in EU36.5 – I usually size up for ballet flats – but I think I should have bought them in my normal size EU36.


Let me tell you a secret; cool girl dressing for the first date has never been this easy. With an expanded array of options for a bookshop date, denim comes dressed up with playful jackets and bags that pop.


Bring a fashion forward approach to a bookshop date with a bag big enough only for a poetry book.

Take a fresh approach to dating with a more simple choice of silhouettes. At the same time, a long coat and white silk button down land with plenty of attitudes. Romantic but cool, this effortless first date winter outfit still makes an impact with details that are interpreted through a lively and joyful colour palette.


Edged in shearling or covered with leather, a fabulous first winter date outfit comes extra fashionable with grey cuffed jeans and high boots.

From barrel or wide-leg cuffed jeans to cool girl’s favourite leather trimmed shearling jacket, black and grey hues with a pop of trendy pastel blue will have you looking a treat for the second date ahead.

Ps. You can wear this outfit for a walk date as well – but change the boots. Or even better, opt for the next winter walk date outfit.


Don’t opt out of leggings and a chunky sweater if a sweater and leggings are what you usually wear if he asked you out for a walk. But I hope you do. Especially if you wear leggings made of artificial fibres.


Not to shame any brand, but lelosi fibre leggings (leggings made of polyamide and elastane) are a no for a first date. Or any date but a date in the gym. But on the other hand, you might just want to show him what he will get. If he can do with it, he is marriage material.

Even so, I know you will feel more confident in an outfit that delivers classiness.

If you live in leggings, opt for equally stretchy and comfortable skinny wool pants instead of microfibres, polyamide or elastane. With the softness and stretch, you will not feel any difference in comfort. But your spirits will be uplifted and you will look refined.

Embrace modern practicality with elegance when you pair your new “black leggings” with a double breasted coat and combat boots for the promenade.


You might want to stay warm and comfortable, but there is no excuse to sacrifice style points just because it is very cold and snowy.

A chic puffer jacket and skinny pants with inuikii boots will keep you looking stunning for a walk date in the snow.


If you are feeling overwhelmed by the outfit choices for the first date and still deciding between two first date outfits for winter 2024, go through FAQ – it will help, for sure.

What outfit to wear on a first date in winter?

It depends on where he is taking you, but you can’t go wrong with a dress. Even so, check the first date winter outfits presented in this article to see all date outfits for the first date.

What winter trends 2024 you don’t want to miss for the first date?

A midi winter dress, full midi skirt, grey jeans, leather trimmed shearling jacketdouble breasted coat, kitten heel booties, knee high bootsballet flats, shortsuit, sheer blouse, shorts.

What to wear on a first dinner date in winter?

Something cool and chic – yet not the “2-hour version of you” outfit. Check fashionable winter outfits for the first date presented in this article for some first date outfit inspiration.

What is the best first date outfit for a dinner date in winter?

You can’t go wrong with a little black dress with long sleeves and a long coat, or either of winter dinner date outfits presented in this article.

What to wear on a casual first date female winter?

A fashionable casual winter outfit. Check fashionable casual winter outfits that are perfect for the first date presented in this article to see the best casual first date winter outfits for winter 2024.

What to wear on a first date walk winter?

For a walk in the city you can wear a fashionable winter jacket like a leather trimmed shearling jacket with jeans and trendy winter boots, accessorised with a skinny scarf, wool gloves and a cashmere twist knot headband instead of a beanie, balaclava or any other winter hat that drops shadow to your face. Or a double breasted coat with skinny wool pants and combat boots and a headband if you are going to promenade. For a walk in the snow, opt for a trendy puffer jacketskinny snow pants or high shine leather pants, and inuikii boots. Ps. Check the best first date walk winter outfits presented in this article to see what bag to wear with these trendy first date winter walk date outfits in winter 2024.

Can you wear leggings on a first date winter?

Only black leggings that can be labelled as black skinny wool pants.

What is the best first date outfit for a bookshop date in winter?

A short coat with a silk button down and grey jeans with booties. But you can also wear a leather trimmed shearling jacket with grey skinny jeans and high boots. Check trendy first date winter outfits presented in this article to see how to accessorise these fashionable bookshop date outfits for a first date in winter.

Are jeans ok for a first date in winter?

Yes, jeans are ok for a first date in winter – for women. Check the best first date winter outfit with jeans in this article.

What is the best first date outfit for a library date in winter?

As you prepare for the date, consider the practicality of warmth without sacrificing style. The library’s temperature may vary, so layering becomes key. A sophisticated coat will complement the intellectual atmosphere of the setting. Underneath, a carefully chosen outfit reveals a hint of your personality, a subtle glimpse into the person beyond the pages. Check the best first winter date outfits in this article for some ideas.

What is the best first date outfit for a museum date in winter?

A short coat with a tweed dress and knee high boots. Or a sheer blouse with tweed shorts and knee boots. Finally, that fancy date outfit with pants and booties presented in this article.

What is the best first date outfit for a gallery date in winter?

navy coat with a silk blouse and black vegan leather pants with pointy ballet flats, or a short coat with shorts and Mary Jane pumps.

Can you wear sweater for the first date in winter?

Preferably not – a sweater is never a good option to wear to a date. But a cropped sweater styled with fashionable pants and double breasted coat can actually be a good choice for the first date in winter. Even so, you will prefer first date winter outfits presented in this article more.

What is the best simple outfit for a first date winter?

For winter 2024, a double breasted coat with a silk blouse and grey jeans with booties. See the outfit – it’s presented in this article.

What your first date outfit says about you winter 2024?

The first date winter outfits presented in this article say you are chic and cool, low maintenance but high value. Romantic, but not a drama queen. Elegant and classy, but never boring or granny.

What is the best first date outfit coffee winter 2024?

It depends on the cafeteria, but you can’t go wrong with any of the bookshop winter date outfits presented in this article.

What is the best first date outfit brunch winter 2024?

Either of the museum winter date outfits presented in this article.

What is the best first date outfit drinks winter 2024?

A pretty blouse and leather pants, or shorts and knee high boots. Or a black pantsuit with some hair accessories – if you are rushed for time and don’t have time to get changed before the date and can only add a little touch-up in the car. See the first date winter outfits for a night out presented in this article for more inspiration.


Now that you have picked your first date outfit, you better check the second date winter outfits immediately. More dates will follow!