Grow up and dress like a man.
Why?
Because you are a Grown-Ass Man!As summer approaches here in the Midwest I want to do my part to help men all over the city dress appropriately.
Men, think to yourself, would a 2nd grade boy look cute in this outfit? If the answer is “yes” then you should not be wearing it.
Why, you ask.
Because you are a grown-ass man!
Many men of the thirty-ish age are having an Arrested Development Crisis. Not knowing how to dress like a Man is a prevalent manifestation of this crisis. Men (30 and up!) are walking around looking like frat boys, poor college kids, ironic high schoolers and in some cases, even grade-schoolers.

For instance, the man on the left can easily be identified as a Man, where the same cannot be said for his cohort on the right.

Recently, a 29 year old male friend walked into Urban Outfitters. Zombie-like, he headed toward their wall of ironic t-shirts. Images include, Oscar the Grouch, The Pillsbury Dough Boy, different scenes from Where the Wild Things Are, and amazingly, the Teenage Mutant Ninja Turtles, among others.
I had to step in.
STOP! I yelled.
These shirts are cute on a grade schooler, perhaps a little funny on a High School student and getting annoying when worn by college “kids”. IT IS NOT ACCEPTABLE FOR A GROWN-ASS MAN! I know it is confusing, they make it in your size (up to XXXL!), they sell it in “MENSWEAR”, but it is not for you!
Imagine a sign that says 18 and under.

Lucky for you, JCO is here to offer some wonderful unsolicited advice, so let's begin at the beginning.
As a Grown Man you need to make decisions about what type of clothes you want to wear and go from there. Like it or not, your appearance goes a long way in people's first impressions of you.
So, what type of clothes do you want to wear?
Let's assume that you want to wear the type of clothes that will attract a Grown Woman.
If this is not the case, Stop Reading (and go find yourself an 18 year old girlfriend).
The idea is to dress to impress.

Wouldn't it be weird if a 30 year old woman was wearing one of the above T-shirts?
Do you wanna see some nice and grown C-cup boobies in a sparkly Hello Kitty shirt? NO WAY! That would be a red flag!
Let me hit you with a quick list of things we (Grown Women) don't want to see you wearing:
1. Cargo Shorts and Cargo Pants (Camo is even more offensive)
Exceptions include: being on Active Duty, working on a boat, yard work, home repair.

At right, an example of proper camo/cargo execution. Please note that the model is 6 years old.
2. Baseball Hats
Exceptions include: At a baseball game – from little league to the majors, caps at sporting events are OK, be they indoors or outdoors. Otherwise, it is basically NEVER OK to wear a Baseball Hat indoors. NO type of hat is acceptable in a restaurant, in a church, or in someones home. Removing your hat is a sign of respect. When in doubt, REMOVE IT. Worried about your hair...? What are you, a chick. Get over yourself and show some respect.
3. Flip-flops
Exceptions include: At the pool, at or with-in 3 blocks of the beach and in your own home. Or, if you live in Hawaii. This is confusing for guys because Women wear flip-flops to show off their cute manicured toes. When you start manicuring YOUR toes, you can wear them out and about. Until then, keep your nasty Shrek Feet to yourself and put on some Man Shoes.

4. Ironic/Graphic Shirts
Exceptions include: NONE. OK...1 or 2 in your wardrobe may be passable, for instance, if your name is Raphael maybe the Ninja Turtle shirt is OK...IF you were a fan and IF you have a girlfriend already because FYI - no grown woman is down with that shit. Better to go vintage than cutesy, however, and to be safe, just stick to sports shirts.

Does this guy look cool to you?!?!
5. Overtly trendy items, i.e. anything with appliqué.
Exceptions include: none

6. Sneakers with nice clothes (i.e. sneakers with a suit or slacks) – get some grown-ass shoes already!
Exceptions include: Very few men can pull this look off. If you are wondering if you are one of those men -YOU AREN'T.
Besides not attracting Grown Women, some clubs and bars won't even let you in sporting this kid-gear. Case in point below.

This guy (name with-held) was trying to meet up with some hot girls at a birthday party for a prominent Chicago drug dealer at a Chicago bar with a not-very-strict dress code. When he arrived the bouncer denied him entrance. He texted one of these girls to explain the the problem. When said hot girl showed up at the door with the birthday boy, he laughed. He said that not even HE could get this guy into his own party lookin' like that. Ouch!
Of course, there are times when you need to break some of these rules. These are guidelines for going out in grown-up situations.

Ask yourself, do they make this shirt in toddler size?
In today's casual society the bar is too low. Let's raise it up people.
Man-up already.