Getting ready for a first date is nerve-wracking—no doubt about it. But it’s 2020, and first impressions are more about our brains and beliefs than what we look like, right? Well, in a perfect world, yes. But what we choose to wear on a first date actually matters a whole lot more than we’d like to admit to ourselves, and picking the right look when it’s cold and miserable outside can leave you feeling, well, the latter. Does the perfect winter date night outfit exist? Allow me to do some research.
Dates are anxiety-filled enough, and being uncomfortable in your clothes only makes things worse. Being cold because you didn’t prepare for winter weather? That’s just another stressful situation you might as well avoid by dressing appropriately. Your jacket can absolutely be a key part of your cute date-night look, or you can dress to impress underneath and wow your partner with a great look the moment you take your coat off! Read on for 20 date-night outfits that are cool, comfortable, and won’t make your date think you don’t know what season it is.
Originally posted October 2015. Updated February 2020.
1. Sheer Blouse + Leather Pants
A little sexy, a little sweet, this look will keep your date guessing.
2. Floaty Dress + Sneakers
A girly, twirly dress is always date-night material, but pairing one with casual sneakers makes it great for daytime dates, too.
3. Blazer + Boyfriend Jeans
Want to wear heels even in the winter? Make sure they’re a closed-toe style! Best to pair them with something casual, like a tee and jeans, and throw a chic blazer overtop to pull the look together.
4. Sherpa Coat + Wide-Leg Jeans
Something about cozy, fuzzy sherpa just screams, “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
IMHO, chain belts make everything cooler. Pair one with your go-to, comfy-cozy sweater dress and it instantly becomes date-appropro.
7. All White + Pop of Color
If your partner doesn’t think winter white is a thing, you should NOT be on this date. It’s just not meant to be, I’m sorry!
8. Short Dress + Matching Tights
Black tights get the job done when it comes to warmth, but choosing a color from your dress and using your tights to highlight it is a great way to make your look a little more standout.
9. Midi Dress + Leather Jacket
If it’s kinda-warm-but-still-winter weather, pair a more springy midi dress with a leather jacket and booties to ensure you don’t look seasonally confused. Plus, if it does end up being warm out, 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 me, sequins are always a great date option. Stick with boots instead of heels so your date doesn’t think you’re stopping by a prom after dinner.
12. Slit Skirt + Cinched Waist
A long skirt and chunky sweater will keep you warm, but a surprise slit and a belt to cinch the waist keep the look cute.
13. Jeans + Cardi + Scarf
If your outfit feels a little simple, a fun scarf 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
And now, the perfect how-to-dress-up-jeans recipe: a cropped faux fur jacked, fun statement earrings, and a red bag. Chef’s kiss.
16. Crop Top + Trench
Something about the contrast of a long trench coat and a cropped tee just feels so right for date night.
17. Casual Sweater + Metallic Skirt
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
Boss babes go on dates, too! A pale pink power suit is a definite Do.
19. Slip Dress + Mock Neck
Layer your summery slip dress over a long-sleeved turtleneck or mock neck top for a winter-friendly date look.
20. Denim + More Denim
Do NOT show up to your date in a cheesy Canadian tuxedo. DO show up in this cute take on the look, featuring a denim jacket, a classic white tee and jeans in a contrasting shade of denim.