

DSQUARED2 Compact Jersey Ruffle Dress
Vera Wang Collection Off-Shoulder Dress With Tulip Skirt
Zimmermann Floral Slip Dress
DKNY Maxi Dress With Bodysuit
J Brand Ready-to-Wear Gale Sweatshirt Dress
M Missoni Color Block Tie Waist Dress
Text message from my date: I’m worried that my fashion is horrible
My response: I just figured out what I’m wearing and I’m not going to iron the shirt I’m wearing so come however!
This was the exchange I had while getting ready for a first date last week. I had been thinking about what I was going to wear and when I got home, I passed Bec’s men’s red and black checkered button down shirt hanging in the hallway- washed the night before- and grabbed it en route to my bedroom. There, I tied the bottom of the shirt at my waist and because of my low-waisted J Brand Vera Skinny Jeans, allowed a breath of skin to show. With a wavy ponytail and plenty of face framing pieces in motion, I sprinted out of my place in my comfortable Report Signature black heels, as my date had already texted asking for my drink order.
I tend to go pretty casual on a first date. It’s my I’m-not-going-to-try-too-hard-here-because-I’d-like-to-think-I-don’t-need-to shtick. A sunrise-ending date and a few nights later, I was discussing with a girlfriend what she was planning to wear on a first date of her own. While we didn’t get into specifics, we did establish that she likes to wear a dress on a first date.
So it got me thinking about the types of dresses I’d wear on a first date. I discovered I’d wear an array of varying styles- but with one constant that grounds the entire look. For each dress above, the hair would be the defining factor- the balance, or contradiction. If the dress is fancy like the Vera Wang Collection one, I’d wear a more relaxed hairstyle, like a loose side braid. For a casual dress like the J Brand one, I’d wear a more froufrou hairstyle, like perfectly-crafted waves.
And the dresses I chose may not be your ideals and that is fine. Take inspiration in them, or embrace the fact that we won’t be sitting next to each other in the same dress on our respective dates. Because to be perfectly honest, the best dress you can wear is an honest one- that which you feel your most self in.