What to Wear on a First Date, According to a Professional Matchmaker
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Every first date has potential. The potential to change your life forever. Or provide comedic fodder for the group chat. Or, at the very least, add another notch to your belt of LinkedIn connections. What most first dates don’t come with, however, is a dress code.
On the surface, this kind of open-ended outfitting assignment might seem thrilling. But day of, getting dressed for a first date can land even the most measured minimalist in the back of her closet, rifling through expired going-out tops and unworn pieces that missed their return window.
Before you end up in the kind of closet tailspin that ends with you, a vintage tee, and a seven-course tasting menu, take a beat—and some grounding advice from professional matchmaker Julie Nguyen: “On a first date, clothes are one of the things you can control in your first impression. When you feel like yourself in what you’re wearing, your nervous system softens, and you become more receptive to connection—that’s what actually makes a first date feel good,” she says. “Pick a first date outfit that's comfortable, elevates your best features, and feels like a true expression of who you are.”
And don’t sleep on your more-personal pieces: “The best first date outfits come with built-in memories or stories,” Nguyen says. “Jewelry that reflects your traveling adventures, or a sweater tied to a meaningful moment with your best friend. Pieces that feel good and give you something natural to share and weave into conversation.”
Ahead, we tapped Nguyen for her tips on how to dress for three first-date scenarios.
The Lunch Date
“There’s something more vulnerable about a first meeting in the daytime,” Nguyen says. “You’re more fully seen, with less mood lighting to lean on. You want to feel like yourself, but slightly elevated, so the date can move into whatever comes next without needing a reset.” Opt for cream-hued separates, simple accessories, and a low heel (in case what comes next is a stroll).
The Cocktail Hour
“When your outfit looks and feels great, you can just show up for the date to assess chemistry. You’re able to stay in your body and actually engage with the moment,” Nguyen says. Think trusted denim you look and feel amazing in, a structured satin tank, and a blazer you can slip on, off, or over your shoulders. “If you’re wearing something that doesn’t quite feel right or something uncomfortable that you keep adjusting, it creates a subtle anxiety,” says Nguyen. “You can't drop into the experience, and it keeps you from fully relaxing into your body.”
The Dinner à Deux
“With a dinner date, there’s a shift. The lighting softens, the energy becomes more flirtatious,” Nguyen says. “Think sharper lines, a sexy silk dress, a lower neckline, or a kitten heel. You can play around and create curiosity with your look—and make your outfit part of the pacing of how much you reveal.” Take this LBD: You might start out the evening with the French lace neckline peeking out from under your cardigan, but as the evening unfolds, maybe you shrug off the sweater and let one of those spaghetti straps drift off of your shoulder.
