Once temps drop, assembling the ideal date night outfit becomes infinitely more tricky — and you may already be stumped. Here, though, you’ll find chic winter date night outfits already planned: Anxiety-reducers and statement-makers combined, these pieces can help you dress to bring out your best self and stay warm. Look for statement outerwear (to make a good first impression) and lean on sheer panels, pops of skin, studs, and other bold, sexy touches that’ll balance out more covered-up outfits. And then there’s color: Classic black and bold red — or burgundy, a sophisticated take on the standard that’s in every fashion girl’s closet this year. Scroll on to shop the cuffing season edit.
1. A Red Wool Coat That Makes A Stunning First Impression
In a bold, look-at-me red, this wool-blend coat makes an immediate, stunning first impression. Minimally designed with a notch collar, buttoned front, and two side pockets, a slight barrel shape lends avant garde structure to the oversize silhouette — which you can layer over sweaters without creating bulk.
Available sizes: X-Small-Small — Medium-Large | Available colors: 2
2. A Merino Sweater Dress That Takes No Prisoners
From its fluttery mini skirt to the long bell-shaped sleeves and its trending chianti shade (a major player this season), this dress takes no prisoners. Crafted from pure Merino wool sourced from a regenerative farm, the soft knit will help keep you cozy on chilly nights. Try layering a pair of sheer tights underneath for a little extra (and extra-sexy) coverage.
Available sizes: X-Small — X-Large | Available colors: 2
3. A Heritage Shoulder Bag From An Iconic Brand
You can’t miss with this shoulder bag, from iconic brand COACH — based on an archival design, this version is updated in chocolate-hued pebble leather for a look that’s achingly on-trend. Designed with an outer slip pocket and an inner zipper pocket to separate the two inner multifunction pockets, it’s got room for all your essentials while remaining compact enough for evening — with optional top handle and crossbody straps so you can change up its look.
Available colors: 15
4. A Surprisingly Spicy Midi Sweater Dress
With long sleeves, a midi length, and a rolled mock neckline, this is the dress to reach for on cold weather date nights — the clingy knit is surprisingly sexy. The pullover design fits close through the bodice but eases up a bit past the hips, so you can add tights or a pair of calf-hugging boots while maintaining the smooth silhouette.
Available sizes: 0 — 12 | Available colors: 2
5. A Sheer-Paneled Bodysuit For Showing A Little Skin
Thanks to sheer panels at the neck and sleeves, this bodysuit shows a little skin without actually leaving your skin bare to the elements — an ideal compromise between comfort and fashion. Opaque from the chest down, the contrasting textures create instant visual interest, and the snap closure keeps the design securely in place underneath your bottom of choice.
Available sizes: Small — XX-Large | Available colors: 9
6. A Floor-Grazing Dress That Bares Your Back
Topped with a coat, the long sleeves, high neckline, and maxi length of this dress will keep you perfectly covered while you’re on your way to your date — and you can reveal the ultra-hot open back design once you’re out of the cold. The body-skimming, ruched knit only adds to its suggestive appeal.
Available sizes: Small — Large | Available colors: 1
7. Ankle Booties With A Statement-Making Block Heel
The hero feature of these ankle boots is that chunky triangular 3-inch block heel; it contrasts with the slim, ankle-hugging shaft and square toe, transforming any ensemble into an immediate look. The sleek design (which includes a convenient side-zip closure) can be used to balance baggy jeans and chunky knits or to zhuzh a simple sweater dress — you’ll wear these constantly.
Available sizes: 35 — 41 | Available colors: 1
8. A Turtleneck Bodysuit In The Shade Of The Season
Red has always been a go-to for date night looks; in a rich raspberry shade, this bodysuit samples the deeper shades fashion insiders have favored for the winter 2024/2025 season. Designed with a snap gusset, the highly stretchy knit molds to your shape, providing a spicy counterpoint to the long sleeves and high turtleneck.
Available sizes: One size | Available colors: 6
9. Wide-Leg Jeans With Sexy Studded Trim
Silver-toned studs run up the sides of these jeans, tracing the front and back pockets — and adding seriously sexy detail to the on-trend slouchy silhouette. Designed with a zip fly, the high waist keeps the look polished — add a pair of heels and a fitted top to keep proportions balanced.
Available sizes: 23 — 34 | Available colors: 15
10. An Occasion-Worthy Mesh & Rhinestone Maxi Dress
If you and your date are headed to an event, this deep wine-hued dress is up to the task. Designed with sheer mesh overlay and studded all over with rhinestones, it’s elegant enough for cocktail parties and semi-formal events — and the long sleeves and maxi length offer enough coverage for wintry evenings.
Available sizes: XX-Small — X-Large (including petite and tall sizes) | Available colors: 1
11. A Paperclip Necklace To Add A Trendy Finishing Touch
Don’t underestimate the power of accessories in creating a cold-weather date night look; crafted from genuine gold plated over sturdy brass, this paperclip necklace goes with virtually any style of top, adding a delicate on-trend gleam and drawing the eye towards the neck. Try styling it with the toggle closure in front for a little added edge.
Available colors: 1
12. A Button-Down Shirt In Luxe Satin
Luxe liquid satin transforms this button-down shirt into a date night-ready piece — and the long-sleeved design is ideal on evenings when you prefer a little extra coverage. The classically collared button-cuff silhouette is darted at the waist and bust for a tailored fit; dial up the spice by leaving a few buttons undone.
Available sizes: 0 — 16 | Available colors: 2
13. Faux Leather Pants In A Rich Wine Hue
A sophisticated twist on the standard sexy red, these faux leather pants are rendered in a rich wine hue. The rich color and texture combine with a straight leg and high waist to create a silhouette that’s easily dressed up or down; a sleek heeled bootie would make a stylish (and warm) pairing.
Available sizes: 00 — 18 | Available colors: 3
14. A Sequin & Feather Jumpsuit To Make Jaws Drop
Jaws will drop when you arrive in this jumpsuit; the combination of a fluffy feathered bodice and sequined pants is nothing short of breathtaking. Mesh paneling at the midriff further draws the eye, while a belt at the waist adds playful structure — your date doesn’t stand a chance.
Available sizes: XX-Small — 2X-Large | Available colors: 1
15. An Off-The Shoulder Midi Dress In The Coziest Knit
In the coziest curve-skimming knit, this dress is ideal for a cold weather date night — especially given the on-trend burgundy hue. An off-the-shoulder neckline shows a little skin, contrasting the long sleeves and knee-length hem; with tall boots, you’ve got a look that’s sophisticated and low-key sultry.
Available sizes: XX-Small — X-Large | Available colors: 3
16. Glossy Stiletto Boots That’ll Replace Your Going-Out Heels
The Retrofête Lyra boots are winter’s answer to the going-out shoe. Their knee-high shaft keeps you plenty warm while a sharp stiletto heel and glossy croc-embossed patent leather lend an almost BDSM-inspired flavor; better still, they’ll pair well with everything from wide-leg trousers to virtually any length of skirt.
Available sizes: 35 — 41 | Available colors: 3
17. Fleece-Lined Tights That Only Look Sheer
If you want the look of sheer stockings without paying the price in cold weather, these budget-friendly tights are going to be your secret weapon. They’re lined in deep-pile fleece that’ll keep you warm as you dash from the cab, with a faux sheer finish that implies a flash of leg but doesn’t put you at risk of frostbite.
Available sizes: X-Small-Small — Medium-Large | Available colors: 14
