30 Men Who Failed So Hard at Fashion That You'll Cringe

By Thalia Shepherd - Mar 23, 2025

If you think men’s fashion is simple, think again! There are many ways that men can step out of their comfort zones, but not every look is a hit. In fact, some are so bad that we can’t understand the thought behind them. For many men, fashion remains a mystery, and the results can be incredibly embarrassing! We’ve amassed some crazy images of men’s worst fashion fails that will definitely make you cringe.

Short Shorts

Some people may say that shorts can never be too short, but, in this case, they’d be wrong! This man’s bold choice of short white shorts certainly draws the eye but also raises an eyebrow. They’re a far cry from the typical knee-length shorts that men usually wear.

Short shorts have been making a comeback recently, but there’s a time and a place for them. In this case, the shorts are simply ill-fitting, which makes them quite unflattering and certainly a questionable fashion choice. Perhaps they’d look better with improved styling.

Clashing Prints

Sometimes, mixing and matching different patterns and prints can work. However, other times, like this one, it simply doesn’t work. Individually, these items could work, but together, they’re excessive. The polka dot pants look almost like pajamas, and the Pink Floyd t-shirt doesn’t work with them.

This could be a case of prioritizing comfort over style, but it’s possible to wear casual clothes without looking like you’ve made absolutely no effort. Though we appreciate the Pink Floyd representation, the shirt would definitely work better with different pants.

High-Waisted Leggings

Leggings were all the rave in the 1960s, but they don’t have the same chokehold on fashion nowadays. However, that didn’t stop this man from embracing these shiny, high-waisted leggings, which have us captivated for all the wrong reasons! They’re certainly a bold choice.

The shimmery pattern instantly captures attention, but the leggings stand out even more because they’re so exaggerated compared to the rest of the outfit. We’re not sure they’d even be comfortable company for dinner, so we can’t imagine what happened after this photo.

Tiny Tee

Though we appreciate the witty slogan, “This is my party shirt,” printed across the chest, we have to admit that this tiny tee is a huge no-no. Oversized shirts are in, but it’s very tough to make an undersized shirt look good in the same way.

In this man’s case, it looks like he’s wearing an old shirt that no longer fits. The sleeves are so short and tight that they look painful. Constricting the body like this is as unflattering as it is uncomfortable, so we’ll have to pass on this look.