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8 Non-Basic First Date Outfits (Liquid Courage Not Included)

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I have a confession to make. Through many months of Bumble-ing, I have approximately 2 first date outfits. Sometimes, my lackluster outfit matched the quality of the date, but other times I wished I was wearing something with a little more thought than my favorite black skinny jeans and a black silk tank, or the same jeans with an olive-colored tank. This outfit especially stopped serving me once we hit June here in the south, and the jeans felt less like a comfort blanket and more like...just a blanket. I definitely think comfort is paramount for being your best self when meeting a new person, but, like dating itself, sometimes trying something outside of the box is worth it. Below: eight unexpected outfits for a first date (or a night out with friends, a treat yo’self dinner, sitting on your porch with a book- you do you).



1) Overalls
Hear me out: while overalls have been seen on the festival circuit for a while now, they can be made night-time appropriate with a feminine top that counteracts the youthfulness, and chunky espadrilles or heeled booties. No eye-rolling Coachella vibes here. Perfect date night casual outfit.




2) Paperbag waist trousers + slim top
This silhouette is super flattering and is prime for tacos or tapas (you don’t want to be constricted). Add a structured jacket if you, unlike us here at JGD in NC, foresee temperatures dropping below “Do I look sweaty?” Fahrenheit.



3) Back Focus
They’ll hate to see you leave, but will love to watch you go. Date night outfit summer - in love!


4) Sexy/Sporty
A bold skate skirt + throw-back athleisure hits it out of the park (one of the few sports metaphors I know the meaning of!).


5) Sleeve volume
Whip out something with an avant-garde touch, like the exaggerated sleeves below, for dinner at a chic new restaurant.




6) Caftan
Looking like an eccentric old hippie IS in my life plan, but for now, keep the look sleek (and like you do NOT have any ceramic cat figurines, and only an average amount of nude abstract art) with a deep-v neckline and cinched waist.

7) Joggers + heels
Back to athleisure: take a cue from Zendaya here (or always, she has killer style) and dress up slouchy joggers with heels and a classic top.


8) Jorts + statement top
For a casual night at a brewery or outdoor concert, you can’t go wrong with distressed denim shorts. Elevate the look with a statement top- neckline interest or a bold print will do the trick.