What To Wear On the First & Second Dates

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Editor’s note: Have a date coming up & need help figuring out what to wear? Email us at thedatereport at and we’ll have our experts put together a look for you.

Today we have The One-Two Punch — first and second date outfits from Caroline Jarvis, our newest fashion contributor.

One Two Punch

Date #1: On the first date, it’s important to keep it casual. No one has to know that your bedroom is littered with piles of the rejected first date outfits you tried on all afternoon. But there’s a fine line between First Date Casual and Running To The Bodega For Chips and Salsa Casual, and it’s a pretty important one. The key to looking casually put together is to keep it utterly simple. A pair of slim fit pants in a dark wash, paired with a light, loose top will make you look relaxed and breezy, even if you’re feeling a little bit anxious. Heels are totally unnecessary, and if you’re already nervous, you certainly don’t need to worry about twisting an ankle in six inch platforms. You’re here to get to know each other, so wear something that makes you feel confident and comfortable, and then forget about it completely.

[top – $28, jeans – $100, sandals – $90, clutch – $100, bracelet – $50]

Related: 17 Things Guys Say they Hate To See You Wear On A First Date

Date #2: Ok, so you’ve established that you like each other and you’d like to see each other again. It’s time to take it up a notch, sartorially. Assuming your second date isn’t a picnic in the park, now is the time to knock him dead with something a little less girl next door, a little more bombshell. If you choose something slightly daring, like a short skirt with lace detail, keep your color palette neutral. You don’t want your clothes to overwhelm your personality. Stick to a couple of bright colored accessories, and for the love of god, only wear heels if you’re sure you won’t be doing a lot of walking.

[top – $64, skirt – $96, shoes – $90, clutch – $31, necklace – $63]

Related: Why I Believe In Buying A New Outfit For Every First Date


Caroline is a twenty-something former film student, frequent subway-crier and headboard enthusiast. She lives in Brooklyn and blogs here. Follow her on twitter: @carojarvis.