Super cozy and stylish first date winter date night outfits. What more does a girl want?
First dates are anxiety-inducing roller coasters. Throw in miserable, cold weather and it’s no wonder we can’t pick a cute outfit for our first date outfit in winter!
In a perfect world, our outfits wouldn’t matter to us or our dates, but it’s not a perfect world. First impressions matter more than we should care. Plus, how we dress says a lot about who we are too.
Most importantly though, a good outfit is an instant confidence boost. If you look good to you, you’re already off to a good start on a date.
Does the perfect look for a first date or winter date night outfit exist? It sure does and I have outfit inspiration to move you in the right direction.
It’s time to dress stylishly for the right season with these winter first date outfits. Plus, you’ll impress your date and, most importantly, yourself!
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In This Post
What Should I Wear On A First Date In The Winter?
When it comes to dressing in the winter, you better be prepared. Here’s a couple of effortless tips to get you started.
- Invest in some quality layering and thermal pieces. These will keep you toasty and warm throughout the date.
- Pull out some statement pieces and accessories to spice up your look. Some simple jewelry will instantly elevate an outfit.
- Don’t forget about coats! Winter is the coat season galore. A good coat will keep you stylish and warm. Plus, it’s most likely the first piece your date sees you in before you take it off.
Don’t let the bitter cold stop you from going on your first date in the winter! Who knows, it might turn into something special. 😉
It’s time to stop worrying about what to wear on a first date in the winter. Keep reading to find 14 easy first date winter date night outfits that are ready for immediate copying!
14 Date Night Outfits For Winter
- Cutout Turtleneck + Wide Leg Jeans + Sherpa Coat
There’s nothing more cozy and wintery than sweaters for me. However, instead of the typical plain sweater, try one with cutouts. This adds some visual interest and a unique eye-catching detail. Perfect way to add subtle personality to a first date outfit in winter!
Pair this with wide leg jeans and some booties to complete the look. Don’t forget to throw on a cute sherpa coat. There’s something about fuzzy sherpa coats that makes me in the mood for cuddles. 😉
- Sweater Dress + Thigh High Boots
There isn’t a better time to wear sweater dresses than winter, especially for a first date too! These body-hugging and slimming dresses highlight your figure and are completely date appropriate. This is a staple for winter date outfits!
Opt for a midi length sweater dress with a side slit. The longer length will keep your legs warm and the side slit detail will highlight the legs.
Pair the midi sweater dress with some over-the-knee boots and a long wrap coat. Voila, your first date for winter date night outfit is complete!
- Midi Slip Dress + Moto Jacket + Waterfall Earrings
Here’s an outfit that’s perfect for a date night dinner or party look. For this look, pair a midi satin slip dress with a moto jacket.
Midi slip dresses are feminine and incredibly easy to dress up or down. Opt for slip dresses made of satin or silk for that subtle sheen.
Next, throw on a faux leather moto jacket. Not only will the moto jacket keep you warm, but it’s incredibly stylish and creates a lovely contrast with the feminine slip dress dress.
Slip into a pair of stiletto booties and accessorize with a pair of sparkly waterfall earrings. This look will surely grab your date’s attention!
- Red Sweater + Midi Leather Skirt + Leather Booties
There’s nothing more holiday or cold weather chic than this outfit combination. To get this look, pull on a vibrant red sweater and pair it with a black midi leather skirt.
I’m in love with how well red hues pair with a black leather skirt. The red is such a vibrant and fierce color that complements a leather skirt so well.
To top it all off, pull on a pair of black leather booties with a block heel. The block heel will give you some extra height and better comfort than a stiletto heel.
- Graphic Tee + Straight Leg Jeans + Teddy Coat
Heading to a casual date and desperately in need of date night outfits for winter? Here’s an outfit that’s comfy, but cozy for a casual first date outfit.
There’s nothing wrong with wearing a graphic tee to a date. A good graphic tee speaks to your personality and it might even be a great conversation starter too.
Tuck your graphic tee into high-waisted straight leg jeans to streamline your look. Don’t forget to layer on a fuzzy teddy coat for that necessary warm layer!
- Jean Jacket + White Tee + Leather Leggings
Here’s one of the best chic and casual date night outfits for winter to keep in your back pocket. Pair a white tee with leather leggings and throw on a jean jacket.
For extra warmth, go for jean jackets with thick lining and leggings that are lined with fleece. The extra lining makes a huge difference if your winters are freezing cold!
As for shoes, I recommend combat boots for their comfort and style. This look is simple, but you really can’t go wrong with it.
- Cable Knit Sweater + Mini Skater Skirt + Thigh High Boots
It’s time to bust out those chunky cable knit sweaters! Winter is the perfect season for all chunky cable knit pieces. They’re the perfect staple for a first date outfit in winter.
In this outfit, pair a neutral-colored, chunky cable knit sweater with a mini skirt. I know, mini skirts are not exactly winter appropriate, but here’s a few tips to layer up and still be warm in a mini skirt!
Pull on a pair of thigh high boots to keep your legs warm. These long boots will cover up most of your legs and keep them toasty. Still not enough? Layer a pair of thermal tights underneath for extra warmth.
You’ll be surprised how cute skater skirts can look with a chunky knit sweater and thigh high boots. I bet your date will like it too. 😉
- Mock Neck Mini Dress + Duster Cardigan
Speaking of layering, here’s another fun look that repurposes a mini dress for the cold weather. This look features a mock neck mini dress with a duster cardigan layered on top. This a such a cute outfit if you’re struggling to figure out what to wear on a first date in winter.
I am really fond of how the long duster cardigan grazes the mid-calf area. Plus, the mini dress’ shorter length helps show off your legs.
If this is not warm enough, I recommend layering up with some sheer tights. Then, pair this look with knee high boots.
Finally, shrug on a long trench coat for the final layer and you’re ready to head out the door!
- Sleeveless Plaid Mini Dress + White Button Down + Chunky Combat Boots
Plaid is one of my favorite prints to wear in the winter and it’s completely fitting for a date. Wear a plaid mini dress over a white button down and pair it with black combat boots.
There’s something really cute about a plaid mini dress paired with chunky combat boots. I’m getting preppy and edgy vibes from this look.
Since this is another mini dress, don’t forget to pull on some thermal or sheer tights for extra warmth too!
- Maxi Dress + Knee High Boots
Maxi dresses work great for dates too, especially for dinner dates or places that require you to dress up. It’s a one and done outfit that’s super easy to put together.
Plus, the extra long length covers the legs and pairs especially well with heels too. It’s one of my favorite date night outfits for winter.
For this look, wear a maxi dress and knee high boots with heels. Heels are especially important because they will help prevent the maxi dress from dragging on the floor and prevent the dress from overwhelming your figure. This is very crucial for those who are petite!
- Bodysuit + Leather Pants + Camel Coat
Here’s a classic and timeless outfit with a hint of leather. For this look, pair a bodysuit with neutral-colored leather pants.
A bodysuit is amazing because it hugs the body nicely and stays tucked in no matter what. Pair this with leather pants and you’ve got a chic match made in heaven.
Match the leather pants with a similar colored pointed boots.
Of course, you can’t forget the equally classic wrap wool coat as the finishing touch.
- Sleeveless Turtleneck Vest + Sequin Skirt + Mid Calf Boots
Looking for something a bit more sparkly and special? Here’s an outfit that effortlessly sparkles away to catch your date’s attention.
Pair a sleeveless turtleneck vest with a sparkly sequin skirt. Then, throw on a pair of mid-calf boots.
Now go off and party the night away with your date!
- Cropped Blazer + Velvet Slip Dress + Stiletto Boots
This look is put-together yet sensual at the same time. For this outfit, slip into a velvet slip dress and throw on a cropped black blazer.
I am particularly fond of crushed velvet textures. Velvet on a slip dress is literal perfection! The cropped blazer makes this outfit perfect for more formal dinner dates too.
Elevate this look with a pair of stiletto boots and you’re ready to stun your date!
- Oversized Statement Cardigan + Flared Pants
Here’s a fun and cozy look for casual winter date nights. Pair an oversized statement cardigan over a square neck sweater. Then finish it off with flared pants in a neutral color.
This look requires you to step out of your comfort zone and experiment with bold prints. You can keep the bold prints on your cardigan or mix it with printed pants.
Don’t forget pointed ankle boots too! These boots pair especially well with flared pants and help elongate your legs even further.
Whatever you choose, this look is fun to play with and will help you express your personality.
What Should A Woman Wear On A Casual First Date?
A casual first date is one of the easier outfits that you can put together. A simple blouse or sweater, jeans, and booties will do the trick for winter first date outfits. Even a casual dress will work too.
Avoid wearing the formal clothes you would typically wear to a fancy dinner date or event. Don’t overdo it with extremely high stiletto heels or over accessorizing.
Don’t overdo it with extremely high stiletto heels or over accessorizing.
If it’s just a casual date, keep it simple. Ask yourself what you would typically wear out casually. Then, make it slightly special with minimal gold jewelry.
Most importantly, have fun with your date!
Related: What To Wear On A First Date For Drinks? Let Me Inspire You!
What To Wear On A Date When It’s Freezing?
The problem with date nights in the winter is that it’s so bitter cold! The key to staying warm is to layer up and wear thermal pieces underneath too.
Be prepared for any frigid weather and temperature fluctuations with a few layering pieces in your closet. Some great layering options include lightweight jackets, sweater vests, and cardigans. These are great to have on hand to layer on top of your outfit.
I also highly recommend wearing thermal layers too. Thermal clothing is the base layer you wear under your outfit. They help trap body heat way better than regular clothes.
Wear thermals to protect your legs, arms and especially the core. Your core is extremely important because it keeps the body warm throughout.
Thermals also help regulate your body temperature since it’s in direct contact with your skin, so you don’t have to worry about overheating. I really can’t stress thermals enough for the winter!
Your core is extremely important because it keeps the body warm throughout.
Finally, we can’t forget to include a thick and comfortable winter coat. As long as you remember to layer up, wear thermals, and invest in a quality winter coat, you’re all set!
Don’t forget to check out the date night outfits for winter above for inspiration too.
Is It OK To Wear Jeans On A First Date?
Of course! Jeans are great for casual dates and will go well with just about any casual top. They’re also incredibly versatile too.
You can dress up a pair of jeans with heels or stiletto boots. Moreover, swap the casual top for a white button down or satin blouse to elevate the look.
Unless you’re going to a fancy restaurant or venue that has a specific dress code, it’s absolutely ok to wear jeans on a first date. I particularly recommend high-waisted straight leg jeans for it’s flattering and looser fit.
What To Wear On A Walking Date
If you’re going on a walking date, it’s important to wear something comfortable and warm. Here’s a few tips for you to keep in mind.
Make sure you layer up, wear thermals, and a thick winter coat for warmth. This is so crucial because you don’t want to be shivering throughout your date. Plus, you won’t be able to pay attention to anything else besides the miserable cold.
Throw on some winter accessories, such as a knitted scarf, beanie, and gloves. Trust me, these small things make a huge difference in frigid temperatures. Always protect exposed skin from the cold!
Throw on some winter accessories, such as a knitted scarf, beanie, and gloves.
Finally, make sure you wear comfortable shoes. Flat boots are a stylish choice and would be great for light walking on a date.
However, if you know you would be walking for a long time, sneakers are recommended. Opt for white sneakers, which pair with almost anything!
That’s a wrap! I hope these first date night outfits for winter give you the style inspiration and confidence boost to meet your date and brave the winter weather. Happy dating!
Disclosure: Vain Affair is reader-supported. When you buy through affiliate links on our website, we’ll make a small commission, without impacting your price. Thank you. Learn more.
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