Tee shirts are played out. There was a time when you had to look a certain way to fit into a certain group. That was middle & high school. Remember? You had to wear Polo & Tommy Hilfiger to fit in with the preps, DC to fit in with the skate/snowboarders, etc. Then you graduated high school & realized that people don’t always fit into the confines of their clothes. Back then tees had a very important role. You needed them to show others where you fit in. They were a quick orientation to who you were, so your classmates could know whether to avoid you or not.
As a grown man though they are not that useful. Let me tell you why:
1. First off they are one of the most unflattering articles of clothing a man can wear. They hide nothing at the right size, notice above, this average guy shows a gut with a properly fitting tee. The other problem is that if you get a size up, they add much more mass, and look boxy. You basically have to be in great shape to look good in a tee.
2. They can be stupid. My theory is to not wear any tee with words on it. As soon as I see a guy with a “funny” shirt on, I know he is a douche. I think with style people don’t get that you want people to be impressed by the way you dress. If your sense of humor is ‘shock value’ then say something shocking, don’t wear a stupid shirt to try to show what you find funny. If you want to be a nerd, wear nerdy glasses and nice clothes, don’t wear a shirt with a nerd joke on it. If you rock baggy cargo sorts and a tee like the one above, everyone who sees you will know you are stuck in your frat-boy/womanizing party days and may be fun to have a couple of drinks with, & while girls with daddy-issues may appreciate their attention, once the sack-taps start you can count your friends minus this bro. When I see writing on a shirt, I only try to read it to find out how much of a tool the dude wearing it is.
3. Cartoon shirts. Don’t do it. Everyone likes cartoons. Everyone likes superheros. Wow, you like Batman? Let me guess, you liked the most recent trilogy best? Point made. Just don’t wear screen-printed tees, words or cartoons or pictures.
4. Band tees. Okay, please, don’t buy band shirts for tours you haven’t been to. It’s pretty obvious wearing a shirt like the above when you were born in the 80’s. Since the internet has ruined the music industry clothes no longer define what music people listen to (sorry 90’s). Since you had soccer mom’s singing along to “Go Shawty! It’s yo’ birfday!”, sagging your pants has never quite been the same (thanks Fiddy). With all the genre bending in music today, to try yo stay confined to one style is pretty close minded. The only band shirts you can get away with are obscure groups you have seen live, even then, these are only useful to lounge around and go grocery shopping with, not a staple in your wardrobe please.
5. Sports/athletic shirts. There is nothing a shirt like the above can tell me about a person I can’t already deduce. If you wear it and are overweight, I know you like to watch sports and hate to play them. If you are in good shape & wear it, I know you like to be in good shape and workout. I could have come to those conclusions with a plain white tee. Keep it to actual sports games (live or home, not at the bar) and playing sports/being active/working out. When wearing them, choose something simple, like the pic on the right, not the left.
Here’s the thing: People are complex. If you dress yourself in a tee that puts you in a stereotype, you are only doing yourself a disservice. You don’t want to be fully stereotyped on sight by everyone you see. You want some mystery(think James Bond, Bruce Wayne), it attracts people to you & your personality. You don’t want people assuming who you are at first sight, that is a fashion fail.
What to do:
Take a hint from Ryan Gosling. He is wearing what is called a Henley. This has buttons on the neck of the shirt and is way classier than a tee. It also is better at hiding a little bit of belly chub.
Also, take a hint from JGL. Stripes & V-necks are great for tees, not screen-printed images that make it look like you are still in high school. If you were smart enough to graduate, you should know your style should’ve graduated too.
Henley, V-necks & stripes are the way to go casual.