Dress Code: More Ideas On Date Night

After our last date-centric installment of Dress Code, we received some good questions on dressing for post-work, at-home, and “club” dates — all very good situations that deserve to be sartorially explored.

Scenario #1: Post-Work. This is, after all, a common scenario.

If you work in a business-wear office, well, on the one hand, your creativity is a bit stifled. On the other hand, there’s nothing you can do about it, so relax. Chances are you’re not heading from the firm to a dive (that’s just bad planning!) and, failing one of those fashion editor desk-drawers full of different shoes and accessories, your best best is probably a top that’ll dress up or down when you take off your jacket. Think a fancy-schmancy tee, a pretty shell, or even a blouse with the sleeves rolled up in jaunty fashion. It’s not like your date won’t know you’re coming from work.

If your office is more casual, you’re probably okay, anyway: just do the old structured-jacket-over-something-you-like thing over something that makes you feel good, be that a dress, “slacks” (a word which, along with “jamboree,” “hep-cat” and “supper” my mother never let us use for obscure reasons) or maybe a print top.

My biggest issue, in these situations, is having to schlep around a huge work bag which, especially in many a cramped restaurant, is both a hazard and a serious space-hog. Whenever possible, it’s nice to be able to leave such a bag at the office. If it’s a Friday or you have to work later, usually a restaurant can find a cranny or closet for your stuff.

If you’re coming from a job that requires specific gear – say, the theatre teacher who wrote in to inquire about duds for trade jobs – well, now’s the time to say, “I’m coming from work and I’ll be in jeans, so how’s about a burger/beer/diner/picnic?” Again, theoretically whoever you’re seeing has some idea of what it is you do, so none of this should come as a shock!

Here are some suggested pieces — they may or may not work for you, but at the very least they might inspire you when you’re hitting the racks, from Forever21 to Neiman to Strawberry.

Scenario #2: The Club: I am uniquely ill-equipped to advise on this issue. I like to “dance,” but I can say with some certainty that I have never been to “the club.” But! We live to serve, so I polled my most social friends. The consensus was: comfort. Said one friend, “this is the one case where I turn to American Apparel: their jersey dresses fit me well, are comfortable, and – if you size up! – are actually fairly sexy without being crass.”

Said another, “You don’t want to compete in the “sexy” sweepstakes – or, I don’t.” Instead, she favors vintage men’s coveralls from thrift stores and eBay, cuffed, with a heel. Which illustrates a good philosophical approach: When you feel like this is a dressing game you don’t want to play, hit another playing field and dress in another direction.

I find velvet ropes about the most horrible thing in the world and will do a lot to avoid them. But when and if it’s called for in the line of duty and friendship, I prefer to look weird. I have a miniature hat I like for such occasions. This stands out, sometimes makes people think you must know something awesome, and at the very least will cheer you up while you endure the trauma.

With that in mind, some diverse ideas/visuals:

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Scenario #3: The At-Home Date: A few people asked about this, wanting to know how to balance comfort with kempt while watching a movie on the couch or noshing on takeout. This, more than most, is a personal issue. I like caftans and vintage lounging pajamas —random, but that’s what feels good for me personally. However, when I asked around, I found that I was alone in this proclivity, which isn’t totally unexpected. A few ideas I did hear:

Comfortable jeans, a camisole and a big, soft cardigan
A loose cotton dress (think 90s-style sun-dress) and a sweater
Leggings and some kind of long top – think a tunic, an oversized sweater, or a men’s button-down.

Scenario #3: The Married Couple’s Date Night: This initially seemed counterintuitive, because if ever there was a situation where you can wear what you want, it seems like a night out with the person who knows you best would be it. Then again, sometimes you want to look special for your partner. (Also, Date Night, with its oddly formal costumes, may have sent the wrong message.)

Depending on what you’re doing, it seems like you can either be totally casual and comfortable — or else, a good opportunity to try something new, or go a bit eccentric. I love going out with my fiance because he enjoys my wackiest ensembles, and how often do I get to wear a miniature vintage hat? After all, you can be yourself — so why not do it? And despite my feelings about under-dressing being preferable (controversial, I know, but that’s just me!), I often like to get wildly overdressed for such dates — say, a prom dress to the pizzeria. If you like to have fun with your clothes, your husband is a low-risk opportunity to do so.

Some concepts I like, whether it’s a little dressed up or a little dressed down: