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Last week, we talked about first date venues, but arguably, a more pressing issue is dating attire. It can be tough to strike that balance of looking like you tried… but not too hard. In light of this, we devised a real-life sartorial choose-your-own-adventure. Here are three different date looks — which do you prefer?
LOOK #1: Sleek & Sexy
Have you ever been intimidated by an item of clothing, only to try it on and discover it’s your new best friend? This skirt is like that. It’s surprisingly flattering, and feels sophisticated and edgy at the same time.
In my twenty-something, Carrie-Bradshaw-emulating days, I spent far too many nights tottering around the city in heels. But dates are supposed to be fun. And you know what’s not fun? Pinchy toes.
So these days, I choose flats. You never know where the night will take you: rooftop drinks, meandering walks, impromptu bowling… It’s nice to have shoes that let you frolic, should the mood strike.
A denim jacket keeps it casual, with just a hint of tomboy.
(Sources: Skirt, camisole, jacket, vintage bag, heart ring, oval ring, shoes)
LOOK #2: Laidback & Playful
This look feels the most flirty and feminine of the bunch. The crystals say, “I care! I dressed up for you,” while the T-shirt says, “but in a casual, non-committal sort of way.” Plus it’s comfortable as can be.
I love how these look like ballet shoes, but the pointy toe keeps them feeling fresh (and not too precious). Plus, pointy shoes elongate your legs (a must for my five-foot-tall frame).
Last but not least, “The gemstones draw attention to your boobs,” my friend helpfully pointed out. So, there’s that.
LOOK #3: Casual Bohemian
When it comes to dates, my philosophy is to wear what puts you at ease. Dating is awkward enough without clothes that leave you tugging, itching or watching how you sit.
This outfit is the closest to my everyday jeans-and-tee uniform. Because what could be comfier? A silk tank elevates boyfriend jeans, while a vintage necklace and statement shoes make it feel like a proper “outfit.” Quoth the wise Jenna Lyons, “As far as I’m concerned, leopard is a neutral.” (You can see all the colors here.)
And of course, a swipe of red lipstick provides the finishing touch.
Yay! Dating.
(Sources: Camisole, vintage jeans, vintage necklace, ring, shoes)
So, please tell me: What do you wear on a date? Which look is your favorite?
(Photos by Nicki Sebastian for Cup of Jo. This post is sponsored by J. Crew, a brand that has hung in our closets for years. Thank you for supporting the brands that support Cup of Jo.)
