"Never Have I Ever": How To Dress For A Blind Date

Even though we like to think we’ve been there and done that, there are certain life events that even our most experienced editors have yet to encounter. In this, our ultimate style guide was born. We’ve enlisted the help of a few R29ers to bring you useful shopping tips that’ll prep your closet for every major milestone, so you’re never left saying, “What do I wear?”
"I've found that I'm simply too much of a romantic (read: paranoid) to make online dating work. I also can't imagine introducing my family to my 'boyfriend I met online, and no, he's not like the Craigslist Killer, Grandma, he's just a person who was also on the Internet, looking for love.' I simply want to meet someone organically. And, if a trusted friend is willing to set me up on a blind date, I'd even be willing to forego all pre-date research. But, since a blind date is 100% about first impressions, what am I supposed to wear?"
—Vanessa Golembewski, editorial assistant
Whether you're meeting at a dive bar, fancy restaurant, or coffee shop, click through for quick tips on how to shop for a blind date.
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For a Fancy Restaurant

If you’re heading to a swanky spot, you need to get a little gussied up. You want to come across sophisticated, yet cute; put-together, yet impossibly sleek. And, lucky for you, LBDs were invented to accomplish just that. Go for a style that’s classic with just a touch of eye-catching detail (like a lace-trimmed hem, pictured here) to keep it interesting.
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Statement Heels

Show up in statement heels like these to make a really good first impression. Warning: These puppies are tall, so they may only work at the actual dinner table. No this-went-well-time-for-late-night-dancing for you.
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Glam Bag

A glitzy bag brings your entire sophisticated look together.
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For a Dive Bar

Meetin’ up in a dive bar? Go casual, but not in a laundry-day kind of way. Start your look with casual-but-refined skinnies.
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Graphic Pullover

A graphic pullover keeps your vibe relaxed and fashion-forward.
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Low-Heeled Boots

No need to rock heels at a bar, but maybe you don't want to wear flats either. Go for a low-heeled boot that'll give you just a bit of height (and maybe an extra dose of confidence).
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For a Coffee Shop

There couldn’t be an easier location for a blind date than a coffee shop. Because, if it’s going terribly, a cup of coffee can be really quick (score!), and you can wear just about anything you want. For a sweet and approachable look, go for a flirty, printed dress.
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Moto Jacket

A downtown-esque moto jacket gives your look just the right amount of edge.
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Cool Booties

A stacked heel won't kill your feet just in case that coffee leads to a long, romantic stroll.

Loeffler Randall Fenton Buckle Bootie, $450, available at Loeffler Randall.

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