The Worst Style Mistakes Men Should Avoid

These little details make all the difference in how you look.

It is a man’s responsibility to look good and dress appropriately for all kinds of occasions. Dressing well doesn’t necessarily entail the help of a professional stylist or a lot of sartorial know-how. It’s all about having a fundamental sense of style and getting those little details right.  

Even when you think people can’t tell, it makes a world of difference when you wear a shirt with a hole or when you switch out your dress shoes for loafers to go with your suit—the latter being a look that some men do get away with, but then again, breaking the style rules entails knowing them first.  

Below, the worst style mistakes you should stop doing right now.  

1| You're wearing a shirt that’s a size too large.

Photo by Roland Mae Tanglao.

Sure, we all did it in the '90s, but we also need to learn from our mistakes. Although today’s streetwear tenets make the case for this retro fit, the reality is that shirts, especially dress shirts, need to fit correctly.  


The right fit will always improve your appearance and make you look sharper. The armhole needs to begin exactly where your shoulders end; those buttons should be able to fasten without puckering against the fabric; the shirt should not puff around your torso, too. More important, shirts should have a neat, streamlined fit when you tuck them in your trousers—no billowing fabric or bunching up. Even if the oversized shirt comes back as a trend, having your shirts fit right will never go out of style. 

2| Your pants are an inch too long.

Photo by Roland Mae Tanglao.

A lot of men are still wearing the same fit from high school: pants with excess fabric gathering around the ankles. Wearing pants that are too long not only looks sloppy and juvenile, it can also make you look much shorter—not exactly an exciting prospect for a population of men with average height.

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Your pants, whether they’re jeans or trousers, should end just below your ankles, creating the slightest break—the fold that happens when the hemline meets the shoe. Shorter men can opt for a slightly shorter length, where the pant doesn’t break at all, to create a more vertical apperance. Meanwhile, taller guys can get away with a single crease in order to balance their stature. 

A word on ankle pants: While they can definitely be fashionable, there are nuances to pulling them off. To stay on the safe side, leave them to the advanced style enthusiasts. 

3| Your belt and shoes don’t match.

Photo by UNSPLASH.

First, put down that statement belt. That, in itself, is a style mistake. 

Now, generally speaking, the leather pieces in your outfit should match: brown with brown and black with black. That’s not to say that they need to be twins; your belt and shoes can vary in texture and, to some extent, shades, given that they’re in the same tonal spectrum. For example, a belt in medium brown paired with shoes in a darker brown can look rather sophisticated. When it comes to formal or black tie events, however, please keep them identical and preferably in black. 


4| You're sporting the wrong socks all the time.

Photo by UNSPLASH.

Socks are one of the most overlooked and neglected accessories that men should really pay more attention to. You don’t simply grab a pair from your sock drawer and call it a day; certain socks go with different kinds of shoes and occasions. It’s not appropriate to pair your gym socks with your dress shoes, especially when you’re at a black tie event. A general rule of thumb is to wear cotton socks for casual occasions, and silk ones for dressier and more formal events. 

Also, unless you’re keeping it strictly for exercise, ankle socks hardly go with any outfit, and especially not with your loafers (wear no-show socks). And please leave the white-socks-black-shoe combo to the late Michael Jackson. 

5| Your jeans are all skinny and ripped.

Photo by PIXABAY.

Something needs to be said about having any kind of rip or tear on your jeans well into adulthood, unless you’re an artist or musician trying to capture that bohemian vibe. It’s one thing to have a pair of ripped jeans for those dressed-down weekends; it’s another thing to keep several pairs of them in your closet.

Skinny jeans, for all its late-oughts glory, are particularly contentious: Aside from being rather tight and uncomfortable especially on warmer days, they don’t do much to improve a man’s silhouette. Men with stocky legs run the risk of stunting vertical length as their limbs will look unflattering in tight jeans. 

6| You're still wearing square-toed shoes.

Photo by PIXABAY.

Shoes make or break an outfit. They’re not just an afterthought to the mélange of fabrics draped on your body. There’s a reason it’s called “head-to-toe” and not “head-to-ankle.” Selecting the right shoes that are appropriate and stylish speak multitudes about your ability to put things together.  


Square-toed shoes are wide, clunky, awkward, and flattering to no one. You'd be hard-pressed to find a pair of well-made shoes with a square toe, which says a lot about the ones that are available in the market. If not for their cumbersome silhouette, then their other physical qualities are style mistakes that can ruin an otherwise sartorially sound ensemble.

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Sam Beltran
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