These five style bloggers are no strangers to picking out the perfect outfit; they’ve all documented their inspiring ensembles on their respective blogs and won a loyal following of fans in the process. Now they’re helping us tackle one of life’s great dilemmas: what to wear on a first date.

Emily Schuman

Location: Los Angeles, CA 


What she’s wearing:

Blazer: Vintage (flea market)
Tank: J.Crew
Pearl necklace: Forever 21
Handmade shark tooth necklace: From her Etsy shop
Jeans: 7 For All Mankind
Shoes: Seychelles
Clutch: Vintage (flea market).

Why it’s her perfect first date outfit:
"I think my look is put together and casual but the layered necklaces and metallic heels add a flirty touch."

…love Maegan
Location: Los Angeles, CA 


What she’s wearing:

Ali Ro ( – see invite on her blog)
Shoes: Calvin Klein (Bloomingdales)
Earrings: Vintage (stolen from her mom)
Bag: Deux Lux (Urban Outfitters)

Why it’s her perfect first date outfit:
"There’s one thing I know about first dates and that is that they are awkward and uncomfortable so I think it’s best to wear something that is the exact opposite of that. You don’t want to be yanking a strapless top up or adjusting a belt or making sure a skirt is in place. You want to be able to focus your attention on your date and not yourself. Speaking of your date, most boys/men aren’t necessarily into fashion. They like it clean and simple and pretty and sexy. I think this is the perfect first date outfit because while the dress is sexy it doesn’t scream "I’m open for business!" …if ya know what I mean. If you’re going to show some leg, keep the cleavage at bay – and vice versa. You don’t want to give away the farm, so to speak, all on the first date. You want him to want more …if you like him, that is."

Jessica Schroeder
Location: Brooklyn, NY 


What she’s wearing:

Jacket: Vintage and from a thrift store
Tank: Target
Skirt: Target
Sunglasses: Urban Outfitters
Shoes: Simply Vera by Vera Wang (Kohl’s)

Why it’s her perfect first date outfit:
"On a first date I want to feel confident, cute, girly and tall. But most importantly I want to feel like myself, which is why this outfit is a perfect first date look. To avoid being too sexy, I like to pick between showing more arms/collarbone and some legs. I like the playfulness of this skirt and how it lets the jacket really shine. The colors, beading and cut of the jacket all send a message to my date that I’m easygoing and ready to have fun. This outfit also works for the office (with flats) and moves easily into cocktail hour."


Rebecca Roe, The Clothes Horse
Location: Fort Lewis, WA 


What she’s wearing:

: H&M
Dress: H&M
Shoes: From a shop she can’t remember in Japan
Necklace: Handmade by Rebecca

Why it’s her perfect first date outfit:
"This outfit is perfect for a first date because no matter the activity or location these are clothes I feel wonderfully comfortable in; nothing is brand new and I’m wearing my two favorite colors. The movement of this dress never fails to make me feel like dancing and first dates should always involve some sort of dancing…even if it is the secretive "happy dance" at the end of the night."

Keiko Lynn
Location: Brooklyn, NY 

Websites: and

What she’s wearing:

Dirndl: Vintage
Blouse: Thrifted (and reconstructed by Keiko)
Belt: Thrifted
Shoes: Jeffrey Campbell

Why it’s her perfect first date outfit:
"My ideal first date involves a hanging out in a park, complete with swing sets, and possibly even a kite. The gingham in the dress makes me think of a classic picnic blanket, and the overall look is typical of my everyday outfits. I’d like the guy to get to know the real me, not an idealized version of myself. If I’m comfortable in what I’m wearing (and my surrounding environment), I’m more relaxed, and less prone to awkward small talk."


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