The Best Clothes For The Man-Child In Your Life

Learn how to break all the rules.

Winter's over. And so is all that "trying to wear serious coats and look like a professional grown-up" stuff.

What we're saying is, now that the weather's getting warmer outside, you have a little liberty to free yourself, to have fun with your style. Dress like a kid. Show your bratty youthful side.

One day a week, leave your blazer and tie at home and throw on one of these options. It'll make you happy, and when you're happy, you look better. We wouldn't recommend wearing them all at the same time, but hey -- do what makes you happy.

Overalls
ASOS
Who says overalls are just for toddlers or unsophisticated country people? These twill overall shorts are sharp enough to show your younger side -- and calves (maybe leave the banjo out of it). ASOS Short Overalls In Khaki Twill ($60, ASOS).
Cartoon Backpack
Herschel Supply Co.
Herschel Supply Co. collaborated with Disney for a line of Mickey bags and wallets -- and there's just enough abstraction to keep it out of kitsch-land ($79, Herschel).
Shoe Party
Converse
No shoe says you still play around better than Chuck Taylor, and Converse's online customizer lets you play along with the whole process ($74, Converse).
Baseball T
American Apparel
Do you coach a little league team, or do you still wish you played on one? Pretend you do with the classic baseball T ($28, American Apparel).
Smart Watch
Who needs Candy Crush when you can whip out your wrist arcade? The asteroids and ships of this tiny mock Galactic Defense game tell the time, and it makes a solid "pew" sound ($49.99, ThinkGeek).
Keith Haring Shirt
Uniqlo
Up your graphic t-shirt game with this print from Uniqlo's SPRZ NY department ($5.90, Uniqlo).
Galaxy Backpack
Jansport
Jansport is like the Chuck Taylors of backpacks, and this style is our favorite ($40, Journeys).
Hot Dog Pizza Hat
ASOS
The classic Kangol hat gets the improvement it so desperately needed with this hot dog/pizza print ($72, ASOS).
Classic Shoes
Bloomingdale's/New Balance
We're always into the retro feel of the New Balance Weekend Expeditions, but this colorway is just playful enough to stay sharp ($109.95, Bloomingdale's).
Umbrella With A Subtle Message
Artemy Lebedev
On a rainy day, your umbrella becomes as much a part of your outfit as your pants. Send a message to the weather with this subtle umbrella by Lebedev Studio in Moscow ($43, Lebedev Studio).
Ageless Jacket
Levi's
No other jacket bounces between casual and prep and youth and maturity than Levi's Trucker jacket, and the slimmer you go, the better you'll look -- we generally go for the lighter shade, but you do you ($148, Levi's).
Jewelry
Valley Cruise Press
It's OK to put jewelry on your clothes. In middle school, backpacks were more like vehicles for all the pins we could fit than for carrying books. While you don't need as many pins in your older years, one or two from Valley Cruise Press can only do your personal style favors ($10, Valley Cruise Press).
Huge Shades
Urban Outfitters
There's no need to get all serious with your shades. Why not throw on these huge red ones, with yellow-tinted lenses, every once in awhile ($18, Urban Outfitters)?
Prehistoric Socks
ASOS
When you're getting dressed in the morning, don't forget about your ankles. Dino socks are always a good choice, especially when you can buy three different pairs in the same pack ($14, ASOS).