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What to Wear on a First Date: Guide for Men

Dress appropriately for your outdoor date.

If impressing your potential life partner is one of your goals for the big event, consider this "what to wear on a first date" guide for men your starting point. Sure, perhaps it's not the best idea to consider your date an "event" - you want it to be relaxed and fun, after all - but a few pointers in the wardrobe department will ensure that you look your best.

Dress to Impress

Most first dates are casual, but that doesn't mean your outfit should be sloppy. The first date is your opportunity to make an unforgettable first impression. Though it's your personality that should ultimately be the deciding factor, it's no secret that one's appearance is important. If you look messy, unkempt and as if you didn't spend a moment thinking about your outfit, you can usually count on disappointing your date. If, however, you dress well - at the minimum, this means simply paying attention to your wardrobe and looking clean and polished - you stand a great chance of impressing your date.

What to Wear On A First Date: Guide for Men

There are several factors that tie into what one should wear on a first date. Similar to any other occasion, the two most important are the weather and the environment. If, for example, you're headed to a park on a hot summer day, you would clearly need to dress with comfort in mind. On the other hand, if you're ice skating at an outdoor arena in the winter, you will have to bundle up.

Another factor to consider is fit. Nothing is more important for men or for women. Clothing that fits properly is far more likely to flatter your overall look and put you in the most presentable light possible than clothing that is ill-fitting or even just slightly constricting. Forgo the too-snug sweaters and slightly too-short pants. If ever there was a great time to look your very best, it's a first date.

The Environment

You'll want to dress for the occasion, or lack of occasion. These tips will help you choose wisely, based on where you're headed.

  • Casual lunch dates don't require you to dress to the nines. If you're headed to a chain restaurant, a coffee shop or a laid-back deli, stick with a pair of pressed khakis and a smart button-down shirt, unbuttoned at the top to keep it ultra casual.
  • Fancy dinner dates, such as those that require reservations at more upscale establishments, do require more attention. Most of these restaurants have dress codes to begin with, so you'll need to dress with that in mind, too. A chic suit with a great cut in a dark color is suitable (and yes, you should wear a tie).
  • Movie theater dates are especially common for the very first get together. It's easy, it's relaxed and it's in a relatively social setting. You may plan on heading out to eat before or after the film, so dress with that point in mind. There's no need to go all out - jeans with a great fit (forgo the baggy, extra-slouchy cuts at all costs), a tucked-in polo or button-down shirt and a jacket is a suitable outfit choice. If you're headed to a restaurant dinner later (as opposed to a casual diner-style setting), consider a sport coat - it will add a level of polish to the look, even with denim.

The Weather

It's easy enough to dress appropriately for each season, but throwing in the first date factor may make it tricky.

  • Winter may or may not be that harsh depending on where you live. If you're forced to deal with frigid conditions, try a pair of jeans (or pants, depending on where you're headed), a sweater and a wool coat to finish it off with polish. Be sure to wear a nice top beneath your sweater. Remember you can always peel a few layers off if it gets uncomfortably warm.
  • Summer, of course, calls for the ultimate in comfortable apparel. Chances are great that you'll choose an outdoor event for your first date - maybe a picnic, lunch at an outdoor table or a walk in the park. Don't hesitate to wear shorts (lengthy, of course, in a universal shade like khaki). Try a knit polo shirt as a complement to the shorts, with a pair of neat (read: not over-worn or dirty) sandals. If this means buying a new pair just for the first date, do it. It's worth it.
  • Spring may be the easiest season to dress for you; you're dealing with not much more than a bit of wind and perhaps the occasional sprinkle and plenty of sunshine. Take advantage and dress in your favorite dressy-casual outfit.
  • Fall is similar, except it will be cooler. Throw a sweater into the mix and you'll be more comfortable.

Things to Remember

No "what to wear on a first date" guide for men would be complete without a few warnings thrown in for good measure. Avoid these faux pas and your first date will hopefully be a complete success!

  • Avoid the obvious faux pas: Dirty, wrinkled clothes are out, as are too-tight or too-loose clothes. Think neatness and a good fit.
  • In general, sports attire (like that New York Giants jersey you wear all through football season) is out - unless you're going to a related event (like a game, for example, or watching a game at a bar - and even then, you will be better off with something more put together).
  • Just as you shouldn't under-dress, you shouldn't overdo it either. Your date might be overwhelmed to see you in a luxurious tuxedo for a dinner date. If you're headed somewhere fancy and an extra-dressy ensemble is absolutely required, be sure your date is aware beforehand!
  • Your footwear and socks are important. If you're wearing sandals, lose the socks. If you're wearing a great pair of shiny dress shoes, by all means leave the white socks behind. Your shoes should be clean and neat, not scruffy and dirty.
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What to Wear on a First Date: Guide for Men