The 50 Douchiest Clothing Items Of All Time

Big Logo Polos

Do you have a favorite polo brand? Well, how the fuck is anyone going to know what it even is unless the logo is AT LEAST 4 inches tall and 3 inches wide? Now everyone will FINALLY stop asking you where your totally awesome shirt is from!

Bootcut Jeans

The origin of bootcut jeans is simple: Dudes who worked on ranches and wore cowboy boots needed a leg opening big enough to accomodate their pointy-toed, calf high footwear. Which is why it makes literally no sense that they became the staple fit of bros in low top tennis shoes and two sizes too small T-shirts. Abercrombie & Fitch basically domninated the bootcut scene in its prime, yet it made even less sense when labels like Seven For All Mankind made versions that cost upwards of $200 dollars. To this day, certain, New Jersey-based not-so-gentlemen still opt for the bootcut style because BRO, I DON'T FUCK WITH STRAIGHT LINES AROUND MY ANKLES, BRO.

Fleece Zip-Ups

If we're being honest, fleece zip-ups are pretty much the staple of the lady douche. You know, that girl that is really hot, but wears sweatpants, Uggs and a fleece pullover because she's "OMG SO FAT AND LAZY LOLZ! *takes kissy face selfie*" Thanks for my ex's body and image issues, boo.

Club/"Going Out" Shirts

What's the best way to get a woman's attention during a raucous night out on the town? Well, with a gaudy, high-end club shirt, of course! My own exhaustive research shows that the physics go something like this: The more rhinestones, cosmetic stitching and unfastened buttons you've got, the better your odds are for taking home some girl who's wearing a bandage dress.

Five Finger Shoes

It's an interesting, health conscious type of douche that wears sneakers with individual slots for each of his disgusting toes. He probably also loves himself some cargo shorts and tells you every Monday morning at the office how "sick!" his mountain climbing adventure was over the weekend. He'll also tell you how awful your Nike high-tops are for your knees because "the ride is so unnatural," while Kale chip crumb projectiles exploding out of his mouth, landing right in your fucking face.

"Casual" Bow Ties

Casual bow ties most recently rose to general prominence alongside "nerd chic," a genre of menswear riddled with try hard douchebags desperately seeking a shred of personality in irony. Typically a staple of formal wear, the bow tie was then issued in an array of prints and patterns, in turn lowering the bar for their appropriateness. This welcomed a whole new slew of Tumblr dashboard douchebags who decided that the casual bow tie was THE defining trait of the sartorially inclined gentleman, wearing them with short sleeve oxford cloth shirts and neckwear matching madras shorts. When the dust cleared, they ended up looking like the light version of the original douchebag whose casual bow ties announced their superiority to the rest of the world: rich preppy scumbags.

Seersucker Pants

Popularized by Colonel Sanders (I think), seersucker was long one of the staples of Southern Gentleman, looking to remain elegant and relaxed during the brutal summer months. And yet, somewhere along the line, douchebags decided that simply wearing seersucker, regardless of their debauchery, made them a respectable man. "Bro, so what if I just threw up in that chick's purse and then tried to fight her boyfriend? I'm wearing seersucker pants, so it's totally cool, right?!"

Suspenders

Before the advent of belt loops and because sizing wasn't as specific as it is today, people used suspenders to avoid showing their assholes to each other. Today, suspenders, often of the clip-on variety, are worn by douchers who think they purvey a certain level of sophistication and elegance. Newsflash homie, this isn't Savile Row. You look like an even more swagless Steve Urkel.

Shutter Shades

Anytime a rapper popularizes a garment, you can be sure that there will be an influx of douchebags chomping at the bit to get a piece of the action. People still don't seem to understand that just because a celebrity looks cool in something doesn't mean they will too and when it comes to Kanye West this point is especially resonant. There was a time when Shutter Shades were kind of a creative and influential fashion choice in pop culture, but they soon became the staple party wear choice of D-bags who treat STDs like Pokemon—gotta catch 'em all!

Fashion Parody T-Shirts

In the history of garments it's hard to think of something that went from "cool" to "funny" to "the wackest shit of all time" as fast as fashion parody T-shirts. The fashion parody T-shirt douche is the douche who actually really loves fashion, but is looking to prove just how level-headed and self-aware he is. In reality, the fact that he cares at all about proving fashion things to other fashion people about his ironic fashion tastes are even worse than if he just rocked with the real shit in the first place.

5 Panel Hats

Hey, what's the best way to show everyone how uptown meets downtown you are and that you're totally with all the cool Tumblr brands? How about wearing a weirdly-shaped hat with the brand's logo on your head all day? Great idea! Throw in some leather and a few other exotic accoutrements and you've got yourself a reblogger's equally wet and trill dream.

Espadrilles

Espadrilles are for the socially-conscious douche who never misses an opportunity to talk about how socially-conscious they are all fucking day. Your buying ballerina shoes so that a kid in a third world country gets his own pair of ballerina shoes is stupid. Send some money to The Clean Water Project and leave us alone forever.

Aviators

Before aviators were appropriated by Le Douche, they were pretty much unimpeachable. Anything worn by jet pilots gets instant cool points, plus their minimalist design meant they were one of the true timeless items in men's clothing. Suddenly, aviators began appearing in all different sizes and colors on the faces of dudes who were "just lookin' to chill, man." Absent was their original metal frame, swiftly replaced by plastic for douche-efficient reasons. Gone were the flight jackets, twill pants and boots, replaced instead with board shorts and graphic-printed tank tops.

Deep V-Neck T-shirts

You're literally a walking male nip slip.

Trucker Hats

Ashton Kutcher : Douchebag Headwear :: Steve Jobs : Technology. Recognize the innovators.

Crocs

Crocs are worn by the type of douche who cares so little about his appearance that you figure he must either have totally given up on life prior to picking out his shoes or is just living in some other realm of cognition that you, as a normal human being, will never understand—so obsessed with his own comfort that he'll literally penalize everyone who happens to look at his feet.

Leather Shorts

Look, I'm not an anthropologist, but something tells me that when people first discovered leather, they probably used it for warm clothing. Now, of course, there's a entirely separate conversation on leather douche culture to explore, but we don't have time for that clusterfuck of impracticality. As per leather shots specifically, only the most careless of Internet cool guy douche could ever buy them, considering they typically price anywhere between $300 and $1000 dollars. That's A LOT of money to guarantee you'll always be sweaty.

Mandals

If you need a reason to not share your hairy toes and hairier feet with the rest of us, then you're already beyond convincing. You also probably don't have any friends to help you through this clearly tough time, so let's just drop it.

Critter Pants

There's a certain type of douche that 100% believes that wearing pants with embroidered bullshit motifs on them is the hallmark of the stylish man. They went to some uppity boarding school that costs more than your college's tuition and now make more money than your parents. During the work week their 9-5 kit consists of only the finest, ill-fitting Brooks Brothers suit, but on the weekends they love to re-live their glory days in some critter pants and boat shoes, pounding Natty Ice until they puke on the deck of the uncle's sailboat.

Short Suits

Are you Thom Browne? Do you perhaps work for Thom Browne? No? Then there's not a single reason under the sun, no matter how hot, for you to be wearing a suit jacket with matching shorts ever.

Manpris

Dude's in capri pants came dangerously close to having a moment a few years back and there's still guys in Europe and Asian trying to make them a thing. For the most part, capris are associated with the type of Euro-douche who travels to America on a wonderful, shitting all over everything-themed vacation. He will, somehow, sleep with your girlfriend before sleeping with your sister.

Mewelry

GUYZ, have you been to the #ArmParty? You know, that place where you put 20 colorful bracelets on your wrist and then Instagram them because didn't you hear? Colors and bracelets are FUN and, like, the "it accessory" for summer! Look, I get the nostalgic appeal of friendship bracelets. I'm Jewish so, duh, I went to Summer Camp too, but the way guys started some pussified #menswear arms race was both ridiculous and obnoxious to the point that it became not hard to imagine that the dude with the most friendship bracelets was, not surprisingly, friendless. If you must party with your arm, please do it in the privacy of your own home.

Cargo Shorts

These are the de facto summer bottoms choice of classic American douchebags everywhere. Now, to be clear, of course we're not talking about these new wave, slim cargo jams—those are literally and figuratively tight. No, we're talking Hollister-era baggy burlap sacks with drawstrings longer than your wang and gigantic pre-wrinkled pockets large enough to carry even the most methodically put together dickhead survival kit.

Ribbon Belts

Ribbon belts, the sign of the man who needs to present his package like it's some sort of birthday gift, lest it goes untouched forever.

Non-prescription Eyeglasses

As someone who actually wears glasses, I take genuine offense to the fake glasses trend. For the most part, wearing glasses is a pain in the fucking ass and those of us who need them choose a pair based on a very simple criteria: What will make us look the least stupid? Notice how I didn't say, "What will make us look the best?" If you are so confident in your looks that you willingly wear glasses even though you don't need them, then maybe you actually do need glasses because no one is that good looking.

Oversized Belt Buckles

In case there was any confusion that you want everyone to be staring at your mildly racist, Kenny Chesney concert attending dick all day, there's the oversized belt buckle.

High-Fashion Motorcycle Jackets

Nothing says "rebel style" quite like ponying up several THOUSAND dollars to a Parisian fashion house for a leather jacket that will never, ever be born on a motorcycle.

Loud Pants

Overly loud pants, such as those worn by professional golfer and semi-professional alcoholic clown John Daly, are the type of pants worn by the man that's so wealthy that he has no zero reservations throwing his money at shit that he knows looks terrible.

Pre-Distressed Denim

Pre-ripped jeans are the perfect example of taking something authentic and genuinely cool and sucking all of the life out it. At one point in time, people actually worn raw denim until they ripped and wearing these otherwise-would-be garbage pants became a symbol of youthful rebellion. But at a certain point in time, all of that became too much effort. Why wait 3 years for jeans to rip when you can just beg your Mom for a pair for Christmas and then when she gets you the wrong brand call her a dumb, stupid bitch?!

Earrings For Men

Man earrings aren't douchey because men shouldn't wear jewelry, but, anyway you slice it, putting something decorative in your ears is either a cry for help (gauges) or an overly obvious display of riches (diamond studs).

Vintage Band T-Shirts

Because how will anyone know you're Metallica's biggest fan unless you spend a couple hundred dollars on a vintage T-shirt from their '88 Tour? Rocking on, forever alone.

Fitted Hats With The Stickers Still On Them

Even when this trend was popular with rappers a few years back I never understood it. Like, is your hat supposed to look brand new just because it has a sticker on it? 'Cause, like, I can clearly see the sweat stains. Or are you seriously flexing that your head is not just figuratively big, but literally big?

Fedoras

Fedoras were once the staple headwear of businessmen and classy gentleman across the world, worn as a sort of helmet before heading out into the thankless and cutthroat concrete jungle. Nowadays, you're more likely to see a fedora on some B-level chef in a commercial for tortilla chips than you are on the streets of your city. Fedoras were appropriated by douchebags attempting to conceal their natural behavior and, unfortunately, it appears that too many women fell for this schoolyard trickery. Of course, there are still appropriate ways to wear a fedora, but, just to be clear, with a tank top and tribal tattoos is not one of them.

Colorful Shoe Laces

While a fairly recent trend, neon laces in footwear quickly rose through the douchey clothing ranks to earn an illustrious spot amongst our top 50. Lauded by wack bloggers as a way to "liven up any pair of shoes for less than $5," laces that pop were seen as a "fun way to turn any old pair into something completely new!" In reality, you're turning your footwear in billboards for how super thirsty you are for acknowledgment.

Pocket Squares

The modern pocket square arrived as a perfectly creased Mad Men-esque fold before morphing into a flamboyant, oversized mess almost overnight. It has since become one of the premiere symbols of the try hard #menswear douche. When mistreated, a pocket square becomes the quickest way to identify the most pretentious man in the room because, in his mind, you aren't shit unless you spend 10 minutes in the mirror adjusting a silk piece of fabric.

Fur Coats

Unless you're an actual Pimp or Killa Cam himself, wearing a fur coat just makes you seem like you're trying to be either of those things, which clearly you're not. Oh, and killing helpless animals for purely aesthetic reasons is fucked up regardless of how douchey PETA happens to be too.

College Sweatshirts

We actually have to give credit to the assholes who still wear their college hoodies for making it so easy to spot their douchiness. It's real nice of them to not only let us know where they get their communications degree, but that they live in Murray Hill and still go to Dave Matthews Band concerts.

Raw Selvedge

Listen, raw selvedge is douchey because it somehow became the only acceptable type of denim for menswear heads. Yo, some of us don't enjoy walking around like our legs are broken are we're wearing full leg casts, but, evidently, if you don't take it raw, then you're not a "real man". See what I mean?

Wife Beaters

When the name of a clothing item is an assault and battery charge, there's nothing else to be said.

Expensive Underwear

It's hard for us to spot a D-bag for this one because we'll never see it, but we can usually guess based on, oh, I don't know, 49 other things come to mind.

Meggins

The first cousin of the leather shorts douche, the meggings douche is the guy who only follows Tumblr's that features the word "trill" in the title and buys things just so he can post them on his own Tumblr, the name of which features the word "trill" in the title.

Giant Scarves

Hey Douche, I'd like you to meet The Law of Diminishing Returns.

Carabiner Keychains

This is the definitive accessory of the overly practical douchebag. He drives a Honda, has a real healthy 401K, keeps his cellphone in a holster, fucks his girl exclusively in the missionary position and on the weekends loves to let loose with a few Miller Lights and a PACKED DVR.

Puka Shell Necklaces

If you were alive during the '90s and early '00s, you know EXACTLY who the puka shell necklace douche is: the lead character in any teen movie's best friend. He is much less concerned with real world problems than the film's hero, is the facilitating factor in any and all hijinks and loves the slang du jour. His parents might have given him everything, but he's rebelling against the system to make sure this is a summer to never forget.

Velvet Slippers

Velvet slippers are the fastest way to show the world that you love conscpicuous consumption, medival symbolism and sweaty feet all at once. When worn with a tuxedo, velvet slippers are not just acceptable, there fantastic. Yet, over the past few years, the footwear has abandoned its roots in favor of everyday wear and has become the dirty laundry of menswear trends. Is camo popping off right now? Put that shit on a slipper! Is subversive messaging the new thing? Slipper it!

Pinky Rings

The stereotype of the pinky ring wearer skews heavily towards film villainy—some bald headed asshole with a scar, scheming some terrible act whilst gently twisting and turning a bedazzled ring on his little finger. In reality, pinky rings are worn by dudes who just recently got divorced. Hastily diving back into the dating pool, they switch out their wedding band for a pinky ring before heading down to the nearest strip club where they hope to find the pair of tits they've always wanted.

Tank Tops

If you're heading to the beach, tank tops make perfect sense. If you're in the city and trying to show the world that you go to the gym, then ding, ding, ding! *Audience yells in unison* YOU-MIGHT-JUST-BE-A-DOUCHEBAG! Do we really have to explain why you're disgusting, you filthy animal?

Varsity Jackets

The staple garment of the prototypical jock douche can not go unnoticed. While nowadays you're more likely to spot a varsity jacket on some completely nonathletic virgin waiting in line for a new sneaker to drop, the varsity's place in douche history is evergreen.

High-Fashion Sneakers

Nothing is quite as low on the practicality totem pole as sneakers that cost hundreds of dollars. The douchebags who wear them can try their hardest to justify this insane garment with claims of quality, but at the end of the day, sneakers are pretty much all made the same way and are comprised of the same exact ingredients: rubber, leather and fabric laces. The high-fashion sneaker wearing douche does not want you to know this.

Sports Jerseys (In Non-Sports Settings)

If you're not playing in some sort of sporting event and not spectating some sort of sporting event and still wearing an athletic jersey, then do you really think anyone even remotely cares where your allegiances lie? Actually, even if you are attending a sporting event, is it necessary to inform the other people in the stadium which team you're rooting for? Doesn't your drunken yelling already do that?