One of the things I noticed when I moved to Boston is that, in general, it’s a fairly casual city. On the one hand, it’s nice that, unlike in New York, I don’t feel poor every time I leave my house wearing clothes that aren’t designer. Since I don’t actually own any clothes from designer labels, trying to keep up or fit in would be a serious challenge.
On the other hand, it’s a weird feeling to know I could walk out my front door in a T-shirt and a pair of pajama pants and not stand out at all. Part of that is a factor of living close to a college campus, but it’s also because calling Boston a “casual city” undersells just how casually a lot of people dress here. Bro-tanks and basketball shorts are most guys’ clothes of choice in the non-winter months regardless of where they’re going, and even a year after first visiting, it still feels weird.
Then again, Boston isn’t the only place in the country where guys regularly dress like slobs. It’s a nationwide epidemic. While nobody can force you to change how you dress, you really should make a concerted effort to dress well everywhere you go.
A lot of it has to do with taking pride in yourself. In the same way that brushing your teeth and showering regularly shows you have enough pride to make sure you’re clean and pleasant-smelling when you go somewhere, putting in the effort to wear nice, appropriate clothes also shows that you take pride in yourself.
Dressing well is also a great confidence booster, which improves all aspects of our life. Yes, it will likely help you succeed professionally and make you more attractive to the ladies, but more importantly, you feel better about yourself when you know you’re well-dressed and look good. That feel-good vibe will be picked up on by others, but even if it isn’t, improving your mood alone is worth putting in the extra effort.
One of the biggest objections to the suggestion that you should dress well is that those clothes are uncomfortable, and comfort is more important than style. If you buy quality clothes that fit you, though, you don’t have to make that trade-off. Do it right, and you’ll look stylish and feel comfortable.
Other guys push back, saying their clothes shouldn’t matter and that they want people to judge them based on who they are, not how they look. That sounds great, but unfortunately, the world isn’t a perfect place, and you’re always going to have to deal with being judged based on how you dress and groom yourself. Trust me when I tell you it’s much simpler to buy a few dress shirts than it is to change human nature.
What I’m not saying, however, is that you need to wear a suit and tie at all times. There are quite a few situations where a well-tailored suit and tie would be perfect for the occasion, but there are just as many situations where you would be severely over-dressed.
Depending on the situation, even a tie can be too much. For example, while bow ties are in right now, wearing one with a dress shirt to a dive bar will probably make you stand out in a bad way, not a good way.
Instead, it’s much better to try to dress well for the specific occasion. As long as they fit you well, a pair of flat-front khakis and a V-neck T-shirt are probably nice enough for a walk around the neighborhood or a run to the store. That look would also probably be fine for eating at Chipotle, but if you’re headed to a restaurant where you’re going to have a waiter, you probably want to bump it up to at least a button-down.
It might take a little time to figure out what’s considered dressing well for each situation, but in time you’ll figure it out, and the increased self-confidence and better impressions that you make will be worth the time it takes.