What To Wear On A First Date: Tips & Outfit Ideas For Looking Your Absolute Best

January 15, 2015 by Claudia Saide
shefinds | Style
view slideshow

First dates are totally nerve-racking, but getting dressed for one is the real kicker—what exactly do you wear for your first encounter with the man that might possibly be the one? (Sorry, didn’t mean to make it worse.) The truth is, getting dressed for your first date with a new dude doesn’t have to be as stressful as you think—as long as you follow a few really simple rules. Obviously, we knew you’d want to know what those rules are, so we jotted em down below. We also thought that you might want specific outfit ideas, which is why we pulled together 10 perfect first date outfits—each one is followed by similar pieces that you can buy. Once you’re through reading and looking through the slideshow, getting dressed for that first date will be as easy as pie. Enjoy!

The outfit should fit the outing. Don’t show up for a bowling date in a cocktail dress and pumps—you’re going to have to change your shoes, and the image of a cocktail dress and bowling shoes is rather unsightly, don’t you agree? Inquire about what type of date it’s going to be, and dress accordingly.

Be you. A first date is not the time for experimentation. If you can’t stand girly dresses, don’t wear one on a first date. Not only is it giving the guy the wrong message, but you’ll likely exude insecurity if you’re not happy with what you’re wearing.

Don’t be overly trendy. I die for culottes, so it kills me to say this, but you should probably hold off on wearing anything super trendy on a first date—that includes culottes, pantsuits, floppy hats, and sweatpants. Guys don’t follow fashion the way we do, and they might find it odd if you show up to dinner in a pair of sweatpants (even if they’re cashmere, and paired with high-heels), so it’s best to hold off on anything trendy until date three or four—by then, he’ll already be smitten.

Be comfortable. If you can’t walk in high-heels, skip them—your date won’t judge you for wearing a chunky low heel or flats, but he likely will if you’re walking like your constipated.

Don’t reveal too much. Obviously you want to show off your bread and butter, but too much of anything is never a good thing. It’s totally acceptable to rock a minidress, but if it’s bordering your crotch area, it’s way too short. Same goes for cleavage—just a little exposure is all you need.

Wear clothing that fits. Sometimes, we like to squeeze into something that’s a size too small just to feel better about ourselves, but a first date is so not the time to be doing that. Your date is not going to see the tag inside your clothes, but he might see the muffin-top emerging from above your waistband.

When in doubt, grab your best fitting jeans. Since denim is essentially like a blank canvas, it’s a great base to build a first date outfit around. If it’s a movie date, throw on a cozy sweater and your favorite boots. If you’re meeting for an early evening drink, you can do jeans with a pretty blouse and pumps. Since you already know how great your ass looks in them (or else why would you wear them every other day), you’ll have a head-start in the confidence category.

[Photo: Haute Inhabit]

From Our Partners

Learn more about RevenueStripe...

From Our Partners

Learn more about RevenueStripe...


This Cozy Sweater *Literally* Has Thousands Of Rave Reviews At Everlane

January 14, 2019 by Jessica Harrington
We want every color!


This Coat Is SO Flattering, No One Will Believe It Was Under $50!

January 13, 2019 by Jessica Harrington
We want one in every color!


You Need To Buy This $35 Jacket From Zara Before The Price Goes Back Up!

January 12, 2019 by Jessica Harrington
It's so chic!


Once And For All, These Are The Best Bras To Buy If You Have Big Boobs

January 9, 2019 by Emily Belfiore
You're welcome in advanced!


Every Woman Should Own This Flattering Midi Cardigan--It Looks Good On Everyone

Chances are you already have a bunch of pullover and ...


This Cozy Knit Poncho Sweater Is Selling Like Crazy At Nordstrom Right Now

There are some people who feel more empowered than ever ...