Mimosas and Manhattan | The Single Girl's Guide to the Ultimate First Date Outfit

Dress | She Inside
Shoes | Ego Official
Glasses | Tom Ford

As some of you may know, I am very new to the whole “New York dating scene”. So all of these “let me hook you up with my friend,” or “you’ll meet someone at a bar,” or even “why aren’t you on bumble” reactions from my friends tends to get a bit overwhelming. But alas, I caved and have recently brushed off my flirting techniques (they are mostly all from high school when a good make out sess. got you a boyfriend – but apparently people have matured a bit so I have had to improvise. I have put my once polished skills to the test and have gone out on a few dates – they weren’t all bad but they weren’t all good either. From freaking out at the thought of lettuce in my teeth, to having to convince a guy I met at a bar the night before that no, I was not in fact British but that sometimes I just use an accent to charm my way to the front of the bar’s bathroom line (true story), to listening to a guy talk about his dominatrix ex-girlfriend (which was actually very interesting) – let’s just say the outfit that I chose to wear is generally the absolute last thing I want to worry about. Which is why I have created the single girl’s formula for the perfect first date outfit.

Show Off Your Best Assets but not your Ass: Trust me, this one was hard for me to wrap my head around (mostly because I have always been a proud owner of a larger rump). But leading with your lady lumps is the ultimate NO NO for a first date. Pick another body part you are particularly proud to show off. Right now for me, that is my arms and back so I opted for this sleeveless midi dress with a delicate back interest.

Heels should not go over 2+ inches: Chances are your prince charming is not even going to glance at your feet (unless he has a foot fettish and that she be a hard pass) but shoes can make all of the difference for your level of comfort. I am all about adding a little height without towering over my prey (yes, this is how I refer to the newbies…so watch out) so a sandal with a two inch heel is the perfect compromise. Plus if you wear a lower heel and he makes you walk a few blocks instead of getting a taxi, he wont think you are high-maintenance (just wait till he gets to know you).

Go for your “natural hair”: My hair is 100% my comfort blanket and combing my fingers through it is also one of those high-school flirting techniques that I have yet to part ways with. According to a poll I took of my single guy friends, they generally liked when a girl wore her hair down and natural (little did they know if took one blowdryer, a flatiron, an intensive Amika Nourishing Mask and an entire can of hairspray to get my hair looking “natural”). I think having your hair down provides a sort of shield while also allowing a flirting “prop” if you will.

Kelly