Pertinent failures in bold. I am a teacher and manager and I don’t dress like either, whatever the Hell you mean by that. Dressing well isn’t “defining” myself, it’s showing people that I care about myself, which many people (women and men alike) find appealing.

And you don’t get tailored clothes, you get clothes tailored.

I guess i was a bit sleep addled, i was trying to encourage people to dress who they are, not dress down. Don’t wear that “This is not a Fugazi” T-Shirt from 20 years ago because you’re still trying to be cool or identify with indie bands when your pushing paper all day long, or go to some random expensive store and buy fashionable clothes to try and conjure up some identity like we did when we were teenagers, wear good clothes that reflect who you really are.

You are not your job. Wearing a T-shirt of your favorite band identifies you to other fans of that band. That may or not be what you want, but it is in effect a method of identifying what tribe you are a member of or aspire to be a member of.

Everything you wear makes a statement about who you are, not just what you do.

I program for a living. If that were the basis of my interactions with others I guess I’d wear some funny programming shirt. But I don’t want that.

If you wear sweat and mustard stained Final Fantasy T-shirts, then that will be offering a basis for conversation with others. Whether that’s your goal or not depends on you.

I wore a Trogdor shirt once. I learned my lesson after that.

I wear a lot of submission grappling/BJJ shirts now, because I enjoy having random people come up and ask me “Whoa, is that like UFC stuff? You can actually do that?” and so it’s a way of advertising the sport and getting people to my gym.

I wish to hear more about this. Awesome story incoming?

Nothing that great. The problem was at that time Strongbad was really popular on the Internet, and for whatever reason geeks would see that shirt and immediately strike ridiculously awkward conversations. I had three separate conversations that day that made me realize that, hey, maybe I don’t want to wear something that puts me into awkward encounters like that.

This was like 5 years ago, but if I recall the first one was random dude suddenly yelling “Oh man, I LOVE THAT SHOW! TROGGGGGDOR!!! TROGGGGDORRR! BURNINATING THE COUNTRY SIDE!!! HAHAHAHAH, MAN THAT SHOW IS AWESOME!” This was like at a UPS Store of all places, and I was cornered as the guy proceeded to interrogate me about which character I liked the best, etc.

Then later that day I got into a similar conversation by someone who proceeded to tell me the entire life story of the Chapman brothers, I guess the people who do Strongbad.

Then finally before getting home, and this one is fuzzy, but it was something at a grocery store and I can’t recall the specifics, but it was along the same lines – someone saw the shirt, then immediately monopolized my time in a shopping aisle and treated me like his long lost BFF.

Here’s a tip… If you find a store you like and let them add you to their email list, you’ll get a flood of special offers and discounts from them. I get offers from Banana Republic for 30% off a single item (with free shipping for online purchases) just about every other day. This comes in real handy for gift shopping.