How To Dress for a Date

I had a date the other night. It went well, whatever, but we all know the most important point of interest regarding that sentence is what did I wear? 

What I wore is the exact outfit a friend told me not to wear: a blue and white striped men’s button down shirt with the front tucked into a pair leather pants, and emerald satin open-toed Stella McCartney shoes with gems that look like Candy Buttons stamped on their heels. Oh, and they have ankle straps.

“Why can’t I wear this?” I asked. I thought I looked pretty good. I was even planning on brushing my hair.

“Because you’re wearing a men’s shirt,” she retorted. “It’s huge. Wear a dress instead.”

Hahahahah. A dress. On a date. That’s so funny. But it actually is, because I had never before even considered wearing a skirt on a date, let alone a one-piece frock. Similarly to what Leandra mused earlier this week, I tend to underdress for occasions that might typically call for a more “dressed-up” wardrobe — especially when it comes to dating.

It’s probably some sort of defense mechanism. If I dress like I didn’t really try, then surely that sends a cavalier attitude to the world like, “Hey, look at me, I’m so cool, I’m wearing pants.” And didn’t Leandra mention in that anterior post that this attitude can often be traced back to some sort of primitive, poignant moment? Maybe in kindergarten I went on a playdate that I can’t seem to remember, and perhaps I showed up in some giant pink confection while my friend Donald Ducked-it in a diaper and tee.

More likely, however, at least in the case of me and my date, is that it boils down to comfort. Dates are awkward. You don’t know where to put your elbows or if your resting face looks too bitchy, and you want to touch your brow to see if it’s furrowing, but then what if he thinks you’re doing some secret signal to a friend in the back of the restaurant that means, “Get me out of here?” One time a guy made us share one burrito (one) and then took my half after I’d eaten two bites. If that doesn’t send a cautionary tale of wearing comfortable-enough clothes to hightail it the fuck out of there, then I don’t know what does.

But dressing “lax” can also help you in the event of a good date. What if you walk through a park? Or if you decide to be all rom-com chic and go for a spin around the old skating rink? If your knees are locked together from a too-tight skirt or wobbly heels, or you can’t lift your arms for fear of a wardrobe malfunction, it’s possible that you’ll regret dressing up.

So while all of that answers what I wore and why I wore it, it doesn’t really help get you dressed, so, let’s get dressed:

Start with pants. You can’t go wrong with leather or its faux counterpart, as no matter what’s happening up top they make your outfit look all the more cool.  I’m also partial to baggier denim, cuffed at the ankle with room for a serious pair of shoes.

Shoes are next. You should really be able to walk. Try the coolest heels you own because you did buy them for a reason after all (though at the moment I can’t stop thinking about simple pumps), but do not pass Go unless you’re sure you can walk at least two blocks without crying and/or vomiting from pain. If you’re all about flats — great. You’ll be that much happier after two glasses of wine.

When it comes to tops I always look for a great oversized button down, regardless of what my friend said. They’re classic and sexy in a Lauren Hutton-esque way. Roll up your sleeves, add some necklaces, bracelets or a cuff and feel like a strong-ass woman.

If you still prefer to take the skirt route in these colder months, opt for an A-Line style, tights and a (maybe?) cropped sweater. The look is pretty but not saccharine and still emanates a vibe that you’ll want to channel when you get the OMG-I’m-nervous jitters.

And that’s that. If this guide seems mind-numbingly simple that’s simply because it should be. Don’t over-think. It’s supposed to be fun. Just be weary of your elbows and we’ll get through this.

Now — if you don’t mind — I need to hear some fashion-fostered dating stories, so, please, indulge me.

Image via Marie Claire Russia