What to Wear to a Singles Event
By Eryn | Meet Cute Club
This is a question I get more than you'd think. And it's a good one because what you wear to a singles event genuinely matters, not because anyone is judging your outfit, but because of how it affects you.
Here's a practical guide.
The Goal: Feel Like Yourself on a Good Day
The worst thing you can wear to a singles event is something that makes you feel uncomfortable, self-conscious or unlike yourself. If you spend the evening tugging at your hemline or wondering if your shoes were a mistake, that energy shows up in your conversations.
The best thing you can wear is something that makes you feel confident, put-together and recognizably you. Not a costume. Not your most impressive outfit. Just you, on a good day.
Read the Room (and the Venue)
The right outfit depends heavily on where you're going.
Casual activity-based events (pickleball, trivia, bowling):
Dress for the activity, but still put in a little effort
For pickleball: athletic wear is expected, but choose something you feel good in, not your oldest gym clothes
For trivia: smart casual — jeans that fit well, a top you'd wear to a nice dinner with friends
Sneakers are completely fine; just make sure they're clean
Cocktail-style events (wine mixers, holiday parties, hotel venues):
Dressy-casual is usually the right zone, a step up from everyday but not black tie
A dress or nice blouse with trousers for women; a blazer or button-down for men
This is the occasion to wear the thing you've been saving for a reason
Outdoor or garden events:
Layers are your friend; Richmond evenings can be unpredictable
Avoid very high heels on grass
Bright colors and prints work beautifully in natural light
A Note on Effort
Here's the real answer to "what should I wear": wear something that shows you tried. Not in a desperate way but in a way that communicates you took this seriously enough to put in a little thought.
The effort reads as respect, for yourself and for the people you're about to meet. It also just makes for a better night. People who feel good in what they're wearing tend to be more relaxed, more open and more fun to talk to.
What Not to Wear
Anything that requires constant adjustment
Shoes you can't walk in — events involve a lot of standing and moving around
Something that feels like a costume unless it's a themed event
Your most professional work outfit unless it genuinely reflects your personal style
The Real Secret
The most attractive thing you can bring to a singles event isn't your outfit; it's your presence. Being genuinely curious about the people you meet, asking good questions and showing up with some energy and warmth will do more for your evening than any outfit choice.
But the outfit helps. Get dressed like you mean it.
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Eryn is a certified matchmaker and the founder of Meet Cute Club, a Richmond, VA-based matchmaking, dating strategy, and singles events company.
