Here at DateSpaces, we’re looking for ways to help you daters out there get your chance for romance. So we’re starting a new feature on The Daily Dater: “First Date Fashionista.” One of our staffers will provide you, the readers, with critiques and help on what to wear (and what not to wear!) on your first dates. Here’s our request: send a picture of what you’re planning to wear on a first date (we’ll keep it anonymous - take the pic from the neck down) to: charles@datespaces.com. We’ll alternate men and women. Meanwhile, the First Date Fashionista has given her take on the question that inspired us to start up this feature. Enjoy!
When the wind chill dips below 20?F, all you can think about is where you stashed the ski mask that matches your “I-can-take-out-people-like-a-linebacker” parka. But fear not, we’ll help you channel your inner rosy-cheeked ski-bunny. Kia from Hoboken asks: “I’ve got a first date tomorrow, and nothing in my closet looks good! How can I look hot when the temperatures are anything but sizzling?”
People, leave your Uggs at home. We do not endorse outdoor slippers for first dates. If you’ve got absolutely nothing in the closet, think about picking up a little somethin’ from the store the day before—a sharp button down or a silk blouse for the ladies. First impressions count. That, and touchable material will render sweaty hands irrelevant. We encourage laying out your clothes to assure punctuality and relative calm. (Who wants to come home to a room looking like a post-Macy’s 75% off holiday sale?)
Generally speaking, most first dates tend to be a meet-for-coffee/drink or dinner deal, so you should aim for a funked up version of your usual business casual attire.
Guys: A nice shirt (read: button up or sweater) and/or a nice blazer get high marks. Just try not to clash too much and you’ll be fine. Consider combing your hair, maybe even running a dollop of gel through. Decent going out shoes do not include sneakers, unless they are really cool throwbacks that don’t scream “New Kids on the Block.” And for the love of God—limit the cologne. It really isn’t necessary to dump the whole bottle on yourself. As for pants, jeans are always a safe bet, with the exception of anything frayed, distressed, tie-dyed or hole-y. If you are coming from work…well then hot damn, you’re rollin’.
Gals: In the winter months, we think it’s a good call to focus on your backside. Save the movie star cleavage for the second or third date. It is in your best interest to leave something to the imagination. But, you can wear that skirt, dress or pair of pants that make your ass look like a slice of heaven. Think sleek lines, and keep it simple since your comfort is critical (you should be more concerned about what your date is saying than your feet screaming to be cut off). A sophisticated pair of boots that you can actually walk in, either under or over, will add demure sex appeal. No jewelry that provides a soundtrack (although we love romantic date music). For makeup, go light on the eyeliner and heavy on the lip-gloss; a dab of eye shadow and rosy blush will perk up your face too. Spice up your outfit up with a colorful top, whether by layering shirts and sweaters, or even cropped jackets. Stay away from anything bulky. Work clothes will suffice, but bring along an accessory or change of top so you’ll have a little sass to your step.
What are some of your favorite first date fashions? Post them below.


Charles is your last name Dickens? I’m only half referring to your verbosity.
See you in my dreams you prosetitute.
At first I was going to report this posting, but then I realized how clever it was. Ricky was saying PROSE-titute.
I agree…very clever, Ricky. I’m impressed.
Sir: I followed your advice to the letter, and I’ll have you know it did not have the desired affect. My lady left me mid-meal after receiving a call on her Blackberry. She said it was urgent but she later said it was her mother. Or sister? Or girlfriend? I can’t remember. In short, I am left underwhelmed and questioning your credentials. Did you go to an accredited college? Are YOU single? PROVE me wrong, good sir. Is there anything else you can offer me in the way of advice. I look forward to your response.
Single in Woodside,
Which piece of advice didn’t work? We’re happy to help you out and answer your question in a future “Ask Our Staff.” Just send an email to charles@datespaces.com .