Getting ready for a first date can be nerve-wracking. Sure, in a perfect world, first impressions would be based more on our brains and beliefs than our looks, but what we choose to wear on a date actually matters more than we’d like to admit. Finding a winter date night outfit on top of all that stress tends to be the ultimate struggle. How do you look cute when it’s extremely cold and miserable outside?
Being uncomfortable in your clothes always puts a damper on the night, and being cold because you didn’t prepare for winter weather, well, that’s additional stress you can avoid by appropriately dressing for the season. Your jacket can absolutely be a key part of your sexy date-night look, or you can dress to impress underneath and wow your partner the moment you take your coat off. Read on for 20 date-night outfits that are cool, comfortable, and are bound to remain in your date’s mind long after you say goodbye.
Originally posted October 2015. Updated November 2023.
1. Sheer Blouse + Leather Pants
This cool combination is a little bit little sexy, a bit little sweet, and perfect for times when you’re trying to keep things comfortable but are still hoping to add some oomph.
2. Floaty Dress + Boots
A girly, twirly dress is always date night material, but pairing one with a casual pair of boots makes it great for daytime adventures, too (plus, the longer the length, the more warmth).
3. Blazer + Baggy Jeans
There’s no need to buy a whole new wardrobe for a first date. Stick with your tried and true staples, like your favorite baggy jeans, and dress them up with a blazer and closed-toe heels.
4. Sherpa Coat + Coordinating Bottoms
Something about cozy, fuzzy sherpa just says, “Let’s cuddle before this date is over.”
5. Blazer Dress + OTK Boots
If your winter date involves a bougie dinner or any other fancy (indoor!) plans, skip the tights and show a little leg with a short hemline and over-the-knee boots.
6. Sweater Dress + Chain Belt
If you ask us, chain belts make everything cooler. Pair one with a comfy-cozy sweater dress to instantly elevate this easy outfit and give it a fancy twist.
7. All White + Pop of Color
Winter white is definitely a thing, but if you’re hoping to keep your outfit from feeling too much like a uniform, add a fun, statement-making shoe.
8. Short Dress + Matching Tights
Black tights get the job done when it comes to warmth, but if you’re hoping to add interest to your date night outfit, choose a color from your dress and highlight it with an opaque pair.
9. Midi Dress + Leather Jacket
If it’s kinda-warm-but-still-winter weather, pair a more spring-like midi dress with a leather jacket, then slip on boots, flats, or sneakers for the perfect in-between pairing. Then, if it does end up warming up, you can remove your jacket and still look fab!
10. Statement Coat + Neutral ‘Fit
If you’re doing some sort of outdoor date activity (ice skating, farmer’s market shopping, etc.), making your jacket part of your look is key. Try a bold, patterned coat paired with an otherwise neutral ensemble.
11. Sequin Dress + White Booties
If you ask us, sequins are always a great date option. A scrunchy pair of white or cream boots will help to keep the look from feeling too over-the-top while also adding a seasonal spin.
12. Slit Skirt + Belt
You know those wearing vs. styling videos making the rounds on the Internet? Here’s a perfect example. Even if the goal is to layer for warmth, keep your chunky sweater and skirt combo from feeling too laid-back by cinching you waist with a belt and trying a maxi with a slit.
13. A Simple Look + Scarf
If your outfit mostly consists of wardrobe basics, add a fun scarf that can double as both a patterned accessory and a cool conversation-starter.
14. Two-Piece Sweater Set
What goes great with a first-date sweater? The matching skirt, obviously!
15. Faux Fur + Statement Earrings
Here’s an easy recipe for dressing up jeans: a faux fur jacket, fun statement earrings, and a red bag for a pop of color. Chef’s kiss.
16. Crop Top + Trench
Play around with proportion by styling a cropped tee with a long, luxe trench coat. It’s the best of both words — showing a little skin but staying warm while doing so.
A metallic midi is a major statement, but when dressed down with a cozy sweater and cute kicks, it makes for the perfect “trying-but-not-TOO-hard” date look.
18. Structured Power Suit
Going with a structured power suit is a sorta-sneaky trick for looking pulled-together. While always sleek and eye-catching, this pre-made outfit is easy to slip on in a pinch. Add a T-shirt or turtleneck and a pair of sneakers to keep the set from feeling too formal.
19. Slip Dress + Mock Neck
Make a slip dress work for a winter date night by layering it over a long-sleeved turtleneck. Not only will this move allow you to rock those summer staples all year long, it’s also a great way to play around with color, patterns, and express your personal style.
20. Denim + More Denim
The best thing about denim-on-denim outfits is that they don’t have to match perfectly (although if they do, that’s great, too). Break out your favorite pair of jeans and style them with a oversized jacket in a contrasting colorway, creating an outfit that’s playful and fashion-forward. If you’re really feeling daring, add a denim hat, too.
21. Leather Shorts + Boots
Shorts in the winter? We’re all for it — especially if they’re faux leather material. Swap out your mini skirt for this unexpected alternative, then add a sweater, long boots, and maybe even tights to keep yourself from shivering all night long.
22. Pleated Skirt + Loafers
Sure, this pairing might seem a little Gossip Girl, but preppy pieces are definitely seasonal and will look super cute when paired with a cup of coffee at a cafe.
23. Trousers + Pointed-Toe Heels
If you’re not into denim and it’s too chilly to wear a dress or skirt, trousers are the answer. A baggy pair will feel as cozy as sweats, and while you can definitely keep them casual with flats, a pair of heels will really take this outfit to the next level.
24. Vest + Cargo Pants
Aim for a slightly athleisure vibe with a pair of cargo pants. While you can keep your top simple, opting for a long-sleeved tee or turtleneck, a puffer vest will add some interest and bring the look together.
25. Matching Set + Fluffy Fleece
Winter is winter, and no one expects you to risk hypothermia for a shot at love. Lean into the cozy nature of the season and show up for your brunch date in a coordinating set with a fleece overtop. Dressing cute yet comfortably might even help you loosen up (and will also keep you from fidgeting with annoying straps and ties).
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