10 of the Scariest Men’s Style Trends from the last 10 Years

Here’s what we don’t like doing on this site: lobbing criticism at what others want to wear. Because really, who the hell are we? Yet today is Halloween, and… it was either this or a “Best of Orange!” post. Now mind you, the below are limited to the last decade. So, by 2006, it’s probably fair to say that classic punching bags like square toed Frankenstein shoes and frosted tips had already fallen out of favor. So keep that in mind. Meanwhile, there are always exceptions. Context is important. Russell Westbrook, who is awesome, could probably wear all of the below at once and still somehow pull it off. So with all that in mind, let’s get weird. 

 

Super Skinny Men’s Jeans

Bending over to tie your shoe should not bring with it the risk of castration by denim. Look at those things. Where, precisely, am I going to stash the Mighty Excalibur and his loyal pals Mario and Luigi? There’s no room in that inn.

 

Outerwear worn under a Sportcoat or Suit Jacket

If you walked down the street with your underwear over your jeans, they’d call the cops.Want to extra insulate your topcoat? Fine. Of course. Put on a vest under your topcoat. But a puffer vest or a denim jacket under a sportcoat or blazer is like sticking a single piece of bread in between a bunch of lunchmeats and calling it a sandwich.

 

Purposefully Destroyed Casual Clothes

You want a paint splattered t shirt? Put on a t shirt, and paint something.

 

Enormously Oversized Watches

Unless you’re the size of Shaq, anything over 45mm is pushing it (and plenty would argue the classically sized wrist watches of decades past, say, 40mm or under, look best). A rule of thumb for your wrist: The lugs shouldn’t stick out over/past the edges of your wrist when viewed from above. Dress watches should be even slimmer/more subtle (although some of us like a nice dress chrono with some heft to it).

 

Stripes on Stripes on Stripes

Think Keith Olbermann back when he was doing Countdown. (And 100% understood if you didn’t have the stamina for Keith and his… style. After a while it was like throwing an entire bouillon cube in your mouth. If that makes any sense. Which I’m sure it doesn’t.) More lines than a bar code. This can actually be done successfully, sometimes, but there’s got to be plenty of difference in terms of those stripes (width, spacing, etc.) And it helps, a lot, if at least the suit or shirt is more of a check instead of all vertical stripes.

 

Drop Crotch Pants

This needs no further explanation.

 

Stacking Bracelets upon Bracelets

This sadly gave birth to the term “wrist game” and poof… there was a Captain Jack Sparrow on every corner. Wearable knick knacks. That’s all it really is. At least true hoarders don’t take their collection of porcelain hippopotamus figurines out into public with them. (Photo Credit)

 

The Deep, DEEP V-Neck T-Shirt

Man cleavage. Beats me.

 

The Jimmy Fallon “Pocket Dial”

A solution to a problem that didn’t exist. True, carrying a smartphone in your slim pants pocket can bounce around a bit. But instead of sticking a fake pocket square on your phone, why not just put the phone in the inside suit jacket pocket? Credit to them for donating proceeds to charity at least. But still. A toupee for your phone?

 

Constantly Sharing your Outfits on Social Media

Congrats. You dressed yourself!

Again. There are always exceptions. And many of us have fallen victim to one or more of these in the past. That’s the thing about trends. They ignite, they spread, they burnout. And that’s just fine.