Ah, the "what to wear on date night" struggle. Whether you've been married for 10 years or just started seeing someone new, odds are you know it well: Saturday evening rolls around and suddenly everything in your closet looks too sexy or not sexy enough. It's annoying to be sure, and can also cut into your confidence—who wants to feel self-conscious when you're trying to flirt? So we asked five incredibly chic woman about what they wear for a big night and rounded up the merch to match. Consider it your pre-game cheat sheet.
Ashley Graham, Model
"I love a fitted crop top and pencil skirt set that accentuates my curves. It's shows just enough skin so that I feel sexy, but also very sophisticated. This striped set by Nadia Tarr is one of my favorites. Her clothes are made for every body shape."
Aurora James, Brother Vellies Creative Director
"I think confidence is the sexiest thing you can have on a date, so I typically stick to my favorites—a lace dress if it’s a more intimate occasion, or I’ll drape a fuzzy cardigan over an open back to balance the look.”
Marissa Webb, Banana Republic Creative Director
"The last time I went out with my fiancé, I wore a menswear-inspired three-piece short suit—a vest, blazer, black shorts, gladiator heels, and a top hat! I like this look because it felt unique and different than a typical 'date night' outfit. It represents my personality well."
Monica Paolini, Sea Designer
“I’m six months pregnant and wearing jumpsuits every day, even on date night. It looks casual because it’s a little unexpected, but super cool."
Get the look: Sea jumpsuit, $445; farfetch.com.
Shiona Turini, Creative Consultant
"My go-to date night outfit is typically a high-waisted jean, pant, or skirt paired with my black crop top. It’s something that I wear all the time, so not only am I comfortable in it, I’m confident in it, which is so important when dating. I know it’s a flattering silhouette, and the balance of the high waist with a shorter top shows skin but leaves much to the imagination. It’s sexy, but not overly so."