Dressing your age?

About a month ago I was sitting at my friend Sean's house, talking to my friends Craig and Mairead. Craig mentioned something about being on a "dressing my age" kick and how he just bought a bunch of new polo shirts. He also said that B and Sean don't dress their age because they wear t-shirts, hoodies, jeans, hats, etc. (I believe he made a comparison to rappers somewhere in there, too). There are a few reasons why that was funny based on his own fashion tendencies (one word: heely's), but that's not what got me thinking. I have a bunch of customers at work who are in their 30's and 40's and dress the same as Brian. My dad even dresses like younger guys, wearing Abercrombie shorts and plain t-shirts from Banana Republic. Is any guy over the age of 24 who dresses casually considered to be an immature dresser?

Admittedly, Brian does NOT dress up. He has a bunch of polo shirts but they're "cool" polo shirts (Polo, Crooks and Castles, etc.). He has a pair of khaki's somewhere. He has one pair of non-sneakers (if you're not counting Timbs and Nike ACG's) which he affectionately refers to as his "funeral shoes". He has a suit, which makes an appearance about once every year or two when someone gets married and stays stuffed in a bag in the back of the closet in between. Even at weddings he puts his own casual spin on things, like at our friends' when he wore a suit with Nike Supreme Blazers and a Brooklyn Dodgers hat.

Until maybe last year I've had a complete identity crisis when it comes to how to dress. I'm 25 but I definitely lean towards a younger style of dressing. My job doesn't help, unless I want to ruin nice clothes/shoes I'm forced to dress in jeans and t-shirts and hoodies. I sometimes push it a little (like today, I'm wearing gold sandals and a nicer tank top):


...but I try and keep my nice clothes nice.

It's not easy being a 20-something. Are we kids still? Are we stuffy grown-ups? It's a very in-between age group. The brand I fight with the most is Victoria's Secret PINK. It's obviously aimed toward high school/college-aged girls. I have a bunch of their sweatpants (which I don't really wear outside) and a few hoodies, but sometimes I question it, like "Am I too old to be wearing this stuff?" I don't FEEL too old, but then when I see 12-year-old girls wearing the same clothes as me it's weird. I feel like one of those 50-year-old moms I see wearing Juicy tracksuits who just refuse to admit they're not teenagers. All that aside, I recently decided that I don't really care anymore. That I'm just going to wear what I like and if I get judged (or carded for a lotto ticket) then so be it. I will proudly wear one of my three Hello Kitty shirts out in public with no remorse.