Dear Midtown Girl,

I’ve been exchanging emails with a guy from an online dating site for the past 2 weeks. He finally called me, asked me out and is taking me to a rooftop bar in the city for our first date. I usually wear skinny cropped jeans & a pretty tank, but since it’s a rooftop & I’ll be heading there after work, I want to look sexy without overdone. Any tips on what to wear?

Definitely! First, since it’s crazy hot outside you definitely want to dress weather appropriate (since sweat is not an option) but rooftop worthy. I prefer skirts/dresses to pants/jeans for a first date bc why dress the same way as the guy, right??

Second, mini dresses are super sexy, but not appropriate for the office, so something slightly above the knee is ideal. Add a blazer to this hi lo dress (the sheer top is TDF) during the day. After work, add some fabulush baubles (just a few statement pieces are enough), amaze stilettos & extra gloss for pouty perfection.

1. Three Floor Delight Dress

2. Kate Spade New York Big Time Necklace

3. Tory Burch Woven Clutch

4. Report Crispin Sandal

P.S. – If you don’t love your feet, then make sure to wear something with a peep toe as opposed to an open sandal, bc trust me, on a rooftop, your date will totes be eyeing your toes (#thishappened).

Have a fabulush date! Dahlings, feel free to email me your dating questions or leave them in the comments below 😉