Sit outdoors at a cafe or have a drink at a bar with a view of passersby and you’ll quickly notice something strange -- grown-ups in children’s clothing. While women are guilty of this sin too (pigtails anyone?), men tend to be particularly prone to wearing clothes they should have thrown out a decade ago. Most men don’t live to shop, so it’s natural to not feel like your wardrobe needs to be revamped every season. However, every so often, it’s necessary to take a cold hard look at the garments in your closet and determine what’s out of style, and more importantly, what you’ve matured out of wearing.

If it’s time for you to clean out your closet, read on for our suggestions on the items you should quickly donate to your favorite charity.

Oversized clothing
One of the greatest crimes committed against fashion by men is wearing oversized clothes. While big and baggy might have been a cool look in high school, if you’ve reached the legal drinking age, it’s no longer hip. Though some of the stars who helped popularize this look, such as Jay-Z, continue to occasionally sport baggier jeans and shirts, they compensate by accessorizing their look with a Ferrari. So unless you plan to turn up in front of Madison Square Garden in a Maserati, it’s time to shift your style mentor from Coolio to Kanye West.

Also, know that no one wants to see your ass hanging out of your clothes, and it’s high time for you to admit that fastening your belt around your butt is just plain uncomfortable. Take a cue from John Legend and purchase some slim-fit shirts and pants that don’t look like you’re wearing a soggy diaper. If you’re a little on the heavier side and you’ve been wearing baggy clothes to conceal your figure flaws, you should be aware this tactic also qualifies as a fashion misstep. Larger men should choose clothes that skim over the body, creating a smooth-looking shape, and choose darker colors to appear slimmer. Avoid baggy, shapeless garments that make you look like a balloon.

Replace with: Form-fitting shirts, knee-length or just-above-the-knee shorts that fit well, and pants that suit your body type.

Backpacks
If you’ve successfully managed to make the transition from school to work, your daily carryall should reflect your entry into the adult world. While stylish backpacks are certainly available, they are best suited to students. Many men persist in wearing backpacks because these allow them to fit all their daily necessities into one bag, but a messenger bag offers the same convenience, and so much more stylishly. So if your day is no longer filled with the pursuit of academic knowledge, it’s time to trade in your rucksack for a more fashionable, adult alternative. Avoid looking like a tourist or a conference attendee, however, and go for one in slick black leather or a bright color. A messenger with handles and a detachable shoulder strap is a great option for those who find themselves frequently traveling to business meetings, since it can double as a briefcase.

Replace with: Messenger bag.

Baseball caps
Wearing a baseball cap is acceptable only in either of two situations. One of these, of course, is during a sporting event or while engaging in athletic activity. The other scenario in which a baseball cap is passable fashion-wise is when the cap is merely a planned, complementary component to a cleverly put-together ensemble. Unfortunately, too many men wear baseball caps everywhere they go, with many using it as a strategy to avoid grooming. Moreover, women are biologically predisposed to read baseball caps as a sign that says, “This person is unsuitable for mating.” To a female, baseball caps signify an adolescent attitude, so if you’re attempting to attract a woman of legal age, forgo the cap in favor of more fashionable headgear or a stylish haircut. Hats can be a fun way to add flair to an outfit, and since bad hair days are a reality for everyone, try swapping your cap for a more au-courant cover-up, like a trilby.

Replace with: Other fashion hats, like trilbies or driving caps.

Jeans with holes
Yes, it’s true that distressed denim is everywhere these days, and a lot of it looks pretty hot. While we endorse the purchase of such artfully destroyed denim, should that be your thing, we cannot condone wearing a $30 pair of jeans that you’ve beaten to death over the course of the last 10 years. Sure, they’re really comfortable, which is why you keep wearing them, but if they feel like a second skin, it’s probably because they’ve started to look like one. If your wardrobe is filled with only this type of jean, you are strongly advised to go shopping immediately and not come back until you’ve found a pair of dark blue jeans that fit you perfectly, with no stylized flaws; you’ll wear them everywhere for the next two years. And don’t worry: You can still wear your old favorites around the house.

Replace with: New jeans that fit your body properly.