Because it slips seamlessly into both skirts and pants, a bodysuit is pretty much the most versatile piece you can have in your date night wardrobe—and this simple one, with its strategically placed cutouts, is great for mixing and matching.
If you are headed out, you can't go wrong with a slinky slip dress. This rust-hued one is a little less on-the-nose than something bright red, but feels just as elegant.
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For late brunch at your favorite spot, keep it casual with a smocked top and jeans. (Psst: The poplin top can also be worn off-the-shoulder.)
Whatever your plans, it's still winter, which means bundling up against the elements is a must. This rosy teddy coat makes layering feel fancy.
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If your idea of the perfect date night involves Netflix and ordering in, Brooklinen's cotton pajama set is the ultimate cozy attire option—and it happens to make a great gift, too.
Swap these leather-lookalike trousers for your go-to jeans to instantly elevate any outfit. Whether you're pairing them with a white tee or a silky blouse, this sleek option makes everything look better.
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You don't have to give up your knitwear—just make it a little more date night-appropriate. This cropped cardigan is oh so cute and comes in nine different colors.
What's the year-round equivalent of an LBD? A long, slinky black slip dress, which you can make winter-appropriate by slipping a cozy cardigan over it and swapping the strappy heels for heeled boots.
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Dress up your favorite jeans with this asymmetric bodysuit, which tucks in easily to avoid a bulky silhouette. A pair of statement earrings adds just the right amount of glitz.
With its satin-y material and side slit, this pretty slip skirt makes anything—even a chunky sweater—feel fancy.
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This color-blocked tank is all about the details, from the different-colored panels to the delicate bows holding the whole thing together.
Dinner out in freezing temps means a sweater dress is definitely a good idea. Pair this cream-colored one with your chunkiest boots to edge it up.
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Dresses not your thing? Pick up a flowy jumpsuit for your cocktail date instead. We love the cutout detailing on this simple LNA Banx one.
You can't miss with the colors of the season. Staud's color-blocked dress is long enough to keep you warm if you're venturing out of the house, but still looks casual.
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A black mini skirt? Classic. A black mini skirt with crystal fringe detailing? Classic with a twist, and definitely perfect for a night out dancing.
We love the subtle collarbone cut-out that makes this otherwise basic style pop.
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Looking for a soft knit that still lets you show some skin? This two-piece set is the way to go. Wear them together or style the woven bandeau under a jacket for some contrast.
Give this ultra-girly dress some edge by pairing it with combat boots or a leather jacket for dinner out.
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If pinks and reds aren't really your style, try a monochromatic look with this ivory skirt as the first ingredient. Add an equally cozy cream-colored sweater and some neutral knee-high boots to complete the outfit.
This inexpensive (faux!) leather jacket is perfect for when you need to spice up a frilly dress or blouse. Not to mention, it's just a great layering piece to have on-hand for more casual events.

Elly Leavitt is a fashion and luxury commerce editor with over seven years of experience covering fashion and design. Her writing can be found in Harper’s BAZAAR, ELLE, Town & Country, Esquire, ELLE Decor, and more. Previously, she was an editor at Domino magazine. You can probably find her in line at Trader Joe's. You will never find her at SoulCycle.
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