First dates are nerve-wracking enough without throwing style into the equation. A thousand thoughts go through your head during those pre-date hours, like “What if we run out of things to talk about?,” “What if this person is boring?,” and, of course, “What the heck am I going to wear?” Pulling together a classy, seasonally appropriate winter outfit like a midi dress that will leave a lasting impression in all the right ways is a serious test of patience and sartorial savvy, but that’s where these six outfits come in. They take all the guesswork out of getting dressed so you can step out of the house feeling confident and stress-free. Here’s what to wear on your first date this winter.

For a Flirty, Festive First Date Outfit


An LBD steps in to save the day when you’re in a style bind — it’s effortlessly chic and crazy versatile. Layer it over a jazzed-up turtleneck in a dreamy plum hue and pair it with elegant drop earrings and festive shimmery tights. Slip on a pair of block heeled ankle boots and add a metallic clutch for good measure.

& Other Stories Strap Velvet Dress ($95), ASOS Knit Tunic With High Neck in Metallic ($69), Bauble Bar Tempest Drops ($32), H&M Glittery Over-the-Knee-Look Tights ($13)

For a Fancy Cocktail First Date Outfit


A long-sleeved jumpsuit with a playful cutout strikes just the right balance of classy and sassy, making it the ultimate date-night piece. Rock it with ladylike Mary Janes with a modern edge and a luxe faux fur coat that introduces a note of glam.

Reformation Ferris Jumpsuit ($258), ASOS Pentagon High Heels ($76), Warehouse Faux Fur Mix Afghan Coat ($174) + Forumla X Nail Polish in Temptation ($11)

For a Next-Level Netflix and Chill First Date


For chillin’ on the indoors or heading out to catch a flick with a crowd, a cozy knit is probably looking pretty prime. Make your favorite sweater feel after-hours appropriate by styling it with a pair of leather look leggings and lace-up stiletto booties.

ASOS Chunky Cardi in Cutabout Rib ($81), Charles & Keith Speed Lace Booties ($83), Whistles Studded Envelope Clutch ($140) + Nightwalker Tie Me Up Faux Leather Pants ($218)

For a Coffee Meetup First Date Outfit


Casual cafe dates call for something effortless, elegant and understated, and this outfit definitely delivers. Jeans ground the getup in laid-back territory, while a layered cape and drape front shirt have the whole sophisticated thing on lock. Toss on a thin necklace and a few stackable rings for a bit of minimalist polish; then head out the door in a pair of shearling-lined block heel booties.

COS Layered Wool Cape ($225), Madewell Indigo Dyed Wrap Overlay Shirt ($80), Charlotte Russe Shearling-Cuffed Block Heel Hiking Booties ($43) + Mother Denim The Looker ($205)

For an NYE First Date Outfit


Capture the essence of the cold weather season with a silvery skirt and embellished sweater that channel shimmering icicles and falling snowflakes. To match the contemporary feel of the combo, pair the outfit with of-the-moment accessories, like a high-shine clutch in a rich wine-colored hue and cheetah print ghillies.

Topshop Livonia Skirt by Unique ($250), & Other Stories Embellished Merino Wool Sweater ($125), SMK Paper Bag Clutch ($47) + Topshop Gold Round Toe Ghillie Shoes ($120)

For a Right-After-Work First Date Outfit


This classic getup is anything but boring, serving up a healthy dose of texture and drama. Fringe adds a fun, funky vibe to an understated top, while jacquard trousers feel a little bit regal without going over the top. A knotted necklace makes the navy top really pop, while velvety pumps are the perfect on-trend way to pull together the look.

J.Crew Sweatshirt With Fringe Hem ($80), Mango Jacquard Suit Trousers ($80), Zara Block Heel Velvet Shoes ($50) + COS Knot Detail Necklace ($50)

For more date-night style inspo, follow us on Pinterest!