Date-night ensembles can be tricky in the wintertime. Last week, one of my friends jokingly asked me, "How do you look hot but stay warm all at the same time?" And to that I say, don't worry. I've got you covered—literally and figuratively.
In the warmer months, you can toss on an easy dress or top and skirt and be on your way, but when temperatures drop, it takes a lot more to layer up for practicality and still feel cute. Cutout knits and bodysuits, faux-leather pieces, and body-hugging dresses are on my list of subtle ways to nail date night while staying pragmatic. Finish the ensemble off with a classic longline coat and heeled boots for function and fashion. Although these night-out pieces make a statement, they are also a variation of multifunctional items that can be styled for many occasions, so they are definitely worth the investment.
Below, I've picked the pieces that will have you planning a date or a night around town in no time.
The viral Skims dress but in a shimmery material.
A thermal top with a hint of skin.
Completely covered pieces in sheer fabrics are a top 2023 trend.
Faux-leather pants are one of my most reliable ways to keep warm and chic.
Boots are a foolproof way to wear heels yet stay warm.
A midi skirt with tall boots underneath is on my list for my next date night.
Show shoulder in a long-sleeve satin top.
This is the perfect winter-date dress in a ribbed fabric with a small cutout.
These faux-leather pants will update any top for nighttime.
For a fancier evening, opt for a long-sleeve sequin top.
These closed-toe pumps make a date-night statement.
Soft ruching and luxe black satin give this winter top an evening feel.
A fun bag is my favorite way to dress up a simpler look.
Style this satin top with faux-leather trousers.
Elevate your traditional hoops with sparkle.
Put this leather shacket over one of your go-to sleeveless date-night tops for added warmth.
Metallic handbags are my winter night-out staple.
Pretty ruching makes this long-sleeve top dressy.
Two-tone earrings are as versatile as they are on-trend.
Layer this corset top over a sheer long-sleeve top or under a leather jacket.
Wear this with the matching top or with a dressy bodysuit.
Winter white boots make the best statement.
Add sheer tights and tall boots to make a minidress work for winter.
A high slit on an otherwise covered-up dress is date-night perfection.
The cutout detail on this bodysuit elevates it for the evening.
Choose a slate tone for a change in your faux leather.
The sheen on this comfortable bodysuit is elevated and cool.
The fancy way to wear leggings on a date? A split hem.
Details upgrade this comfortable knit midi dress.
Next: What to Wear to a Dinner Party: 9 Easy Yet Stylish Looks That Always Impress
-
Don't Pack Up Your Sweaters Just Yet—Cool Fashion People Are Repurposing Them in the Chicest Way for SummerAll the outfit inspiration is inside.
-
Goodbye, Boring Basics—This Is the Elegant Trend New Yorkers Are Wearing With Tank Tops This SummerObsessed.
-
3 Aesthetic Pairings to Try If Your Wardrobe's Starting to Feel StaleFoolproof solutions.
-
I Can't Stand It When People Follow These Fashion Rules to a TIt's time to break the rules.
-
10 Style Tips That Will Make You Look Rich This SummerNumber four is already trending.
-
Brand Layering: The Art of Knowing Which Labels to Pair With Each OtherThe ultimate styling hack.
-
The Simple Styling Trick That Turns Pencil Skirts From Corporate to Chic in 5 Seconds or LessIt's completely free and ready to copy.
-
I Miss Going-Out Tops—These 30 Feel Very 2025Justice for the elevated piece.
