Top 10 Style Mistakes Men Make

Over the years, I’ve been witnessing men make the same style mistakes over and over again so I put together a list of the top mistakes I consistently see. I also have a free ebook about the 10 Most Overlooked Men’s Style Mistakes that are completely different from this list and that I’ve never seen discussed before.

10. Skinny jeans or ripped jeans.

Quickest way to look like you’re trying to dress like a teenager.

Ripped Skinny Jeans Ashley Weston

9. Wearing dress shirts untucked.

Dress shirts are designed with long tails so that they stay tucked into your pants. You should never wear them untucked. By all means wear casual collared shirts untucked, like an Oxford button down, but never with a suit or sport coat and only if the tails of the shirt hit mid crotch/mid butt.

Untucked Dress Shirts Ashley Weston

8. Too much jewelry.

When it comes to bracelets, earrings (never!), necklaces, rings – keep it simple. Don’t wear more than 2 items, although I prefer only one item, not including your wedding band if you’re married. Thumb and index rings especially make me shudder the most.

Too Much Jewelry Ashley Weston

7. Too many patterns or statement pieces in an outfit.

A lot of men associate being stylish with wearing a statement outfit or wearing a ton of patterns. This is far from true and ends up making you looking ridiculous. A good rule of thumb is to choose only one item in your outfit that is a statement piece or has a pattern to ensure you look stylish and put together at all times.

Patterns Ashley Weston

6. Wearing old, worn out belts.

If you have quality belts, they might need to be replaced every decade or two. If you’re wearing a belt to constantly hold up your pants, you need to get the waist of your pants taken in. Belts are a stopgap solution to the problem of your pants just not fitting properly.

Old Worn Out Belt Ashley Weston

5. Wearing square toed dress shoes – including square toed slip on loafers.

I constantly see these shoes worn with suits, trousers, and jeans. It’s a tacky, amature look and can make an otherwise sharp outfit look terrible. Just want to point out: the square-toed slip on loafers that I’m talking about are not the penny loafers or driving mocs I listed in my Top 4 Men’s Shoes For Spring article.

Square Toed Dress Shoes 1 Ashley Weston

4. Ties that are too wide for your body type.

I see a lot of thin to average built men wearing 3.5″ wide ties. It really makes you look skinnier than you are, which sends a message to people that you’re not professional and might be sloppy in other aspects of your life and work. Think of the ‘Messy Bed, Messy Head’ mentality here.

Ties That Are Too Wide Ashley Weston

3. Wearing unpressed or wrinkled clothes.

It’s sloppy as hell no matter what you’re wearing.

Wrinkled Clothing Ashley Weston

2. Pants or jeans that are too long and end up with fabric stacked around your ankle.

Again, I see this problem at least a handful of times a day. This looks really sloppy and ends up making you look disproportionate as the stacking visually makes your legs look shorter.

1. Not wearing properly fitted clothing.

This applies to suits, dress shirts, tees, pants, jackets and sweaters. You want clothing to fit your body shape and not leave you swimming in fabric or showing off your mammal toe or the bottom of your stomach.

Clothing That Doesn't Fit Well Ashley Weston