The Single Man’s Guide To Dressing For A Night Out

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Gentlemen, take heed: What you wear out for a night on the town can make a big difference to two things:
  1. Your interactions with the fairer sex (your ability to pick up women / possibly end up in a girl’s bed).
  2. Your own self-confidence and how others perceive you (your ability to chat with people and be socially successful).
Trendy man all dressed upWhy? It’s simple, really, and it all boils down to perceptions.
Your outfit says a lot about you and your personality whether you like it or not.
It’s like a personal statement that you wear (quite literally) around town.
Before you even say hello, people will evaluate you (and come to conclusions about you and your personality) based on the information they have available.

Clothes — a Kind of Name Tag

Since you’re not wearing a name tag, a uniform, or carrying a sign that describes your personality, your appearance (and specifically your outfit) is all that others can use to evaluate you.  As a result, what you wear can have a major impact on your social interactions (and, ultimately, how much fun you have).
Beyond the “message” you’re sending to others with your clothing, you also have to take other things into consideration:  will there be a dress code at an establishment you’re going to visit?  Will you need to dress for cold or hot weather?  Are you going to need storage for your wallet, phone, umbrella, etc., or will accessories simply be an annoyance?
Let’s talk about the perfect outfit for a night out on the town.(Note: this article will assume that you’re going somewhere like a restaurant, a pub, a movie theatre, a bar, a nightclub, etc., and that you live in North America or Europe, where cultural and religious considerations are not an issue).
  • If you are going to be (or think you might be) going somewhere with a dress code — or, at the very least, somewhere ‘classy’ — then you need to dress with that in mind.  A cocktail party at a Hollywood social club, for instance, demands a tuxedo. Anything less will be totally unacceptable.  On the other hand, if you’re only going to a local watering hole with friends, then you can get away with your favorite football jersey and a pair of jeans (although I’d recommend against the jersey).
  • Generally speaking, it’s better to “overdress,” especially if you’re not sure where you’re going to end up.  A suit and tie is not at all out of place at a restaurant, a nightclub, or a theatre.  A muscle shirt and flip flops, however, is likely to be frowned upon at a lot of places.
  • If a main goal of your evening is to meet women, then it helps to have some sort of “peacocking” element to your outfit.  If you’re not familiar with the term, “peacocking” means wearing or carrying a particularly outrageous clothing item that serve as a conversation starter with the ladies.  There are so many options for a “peacocking” item, but I tend to error on the side of elegance and try to pick something a bit more subtle.  A fedora or unusual (yet formal / classy) hat is a good choice, as is a tie with something funny on it (sayings, photos, etc.).  If the situation allows, then a large flag or floppy necklace draped around your neck is sure to get you some attention from the ladies on the dance floor.
  • Handsome man with arm around hot girlUse your clothes to portray self-confidence.  As I mention in my article on how to look confident, you can wear something a bit edgy or unique to give off the impression that you’re a trend-setter who isn’t afraid to stand out in a crowd. Usually, you don’t need to go with something crazy to achieve this — a bright shirt, interesting hat, or unique jacket can all give off an air of “alpha male” without drawing negative attention to yourself.  There’s a fine line with this, so don’t go overboard. Just go with an outfit that looks like it might be worn by your favourite trendy celeb to promote a trendy clothing brand (think David Beckham, Brad Pitt, Will Smith, etc.).  
  • Don’t wear sunglasses after dark (just don’t f***ing do it, man!).  Sunglasses are arguably the single best accessory item for men who want to get noticed in a positive way (see my note about portraying self-confidence above), but should never be worn unless you’re outside in the sun.  They’re called SUNglasses, after all!
  • Pay attention to your shoes.  Women will notice your shoes, and so will other fashion-conscious men.  Shoes are often the thing that separates a trendy, fashion-saavy alpha male from a guy who tries hard to look the part.  Make sure your shoes are appropriate for the venue you’re going to, and make sure they suit the rest of your outfit.
And finally…
More tips on what to wear to the club will be posted in a future blog entry, so stay tuned for that.  In the meantime, good luck out there!