5 Men’s Shoe Styles Women Hate

It’s a fact that one of the first things a woman notices about you is your shoes.  So obviously it’s important to make sure your shoe game is on point. We always talk about how important it is to regularly clear out old and out of style items, and shoes are no different.  Shoes are a key part of your overall look, and a few wrong choices or out of date items can easily ruin an otherwise great look. 

Here are Ashley’s picks for 5 Men’s Shoe Styles That Women Hate!

5 Shoe Styles Women Hate

  1. Square toed dress shoes
    Out of date and out of style, get rid of them right now. Get yourself a proper pair of dress shoes instead.

4. White loafers or loafers with contrasting stitching
Your loafers should always have same-color stitching and white loafers are another out of date style nobody should wear. Try our Loafer Guide for better options.

3. Chunky basketball/gym sneakers
The gym or basketball court is fine but outside of that, these shouldn’t be worn with casual clothing. White sneakers or dress sneakers are a much better look.

2. Rubber flip flops
Unless you’re at the beach or pool these aren’t a good look.

1.Slides
Keep them to the bathroom or inside the house, nobody should see these!

10 Biggest Style Mistakes Young Men Make

As a stylist, my clients range anywhere from teenagers all the way up to men in their 60s and 70s, and these are 10 mistakes I’ve noticed with my younger clients when I first start working with them. The road to finding your own personal style is a long one but keep these in mind as you’re figuring out your own path!

10. Ill-fitting clothing

Whether you’re on the thin side or are a bigger guy, your clothing should always fit properly. A lot of times many young men try and over-compensate in either direction to make up for what their body type is, but don’t do it.  Big or small, proper fit is always king.

9. Oversized ties and knots

Buying a tie that’s too wide and using massive knots will only serve to make you look like a little kid, so make sure you use a knot that’s proportionally sized for your frame and suit.

8. Trying to be a hypebeast all day, everyday

Focusing solely on brands and labels plastered all over you is only going to send the signal that you’re dressing for the wrong reasons.  Be judicious in your brand choices and know that understated is always going to look good.

7. Dressing well means being uncomfortable

Thinking that you can’t dress well and be comfortable at the same time is something that I get all the time and it drives me crazy! A properly fitting shirt or jeans should always be comfortable and flattering.  Are they going to be as comfortable as baggy sweats and an old t-shirt? No, but ultimately if you want to be taken seriously you should always be cultivating and presenting a thoughtfully stylish appearance to the world, not one focused only on comfort.

6. Buying all statement items

This is a problem for most men looking to dress better, but more often with younger men because I notice they confuse fashion with style. Fashion pieces can be loud and make a statement, but that doesn’t make you stylish. Here or there, sure, it’s fine, but it’s important to always have basic, foundational items that are stylish and versatile as well.

5. Not having a foundational wardrobe

Speaking of the foundational basics, it’s critical to always start with the basics and get the right jeans, t-shirts, button-ups, shoes, and sweaters first. Don’t underestimate the style and power of a sharp, basic wardrobe as the building blocks of great personal style.

4. Dressing exactly like your friends and not trying different things

Going along with following hypebeast trends, I see a lot of men fall prey to dressing just like everyone else in their squad. You’re young, have fun with your clothing and style and embrace your individuality. Figuring out what looks good on you and makes you feel best is an important step in figuring out your personal style.

3. Looking good is expensive

One of my least favorite misconceptions about style is that unless you’re rich, you can’t look good, and that money matters in dressing well. This couldn’t be further from the truth! Looking good on a budget is absolutely doable, no matter how low the budget, and it just takes some knowledge and focusing on well-fitting, basic items.

2. Mixing too many patterns and colors

Just like focusing only on statement pieces, many younger men confuse being loud and wearing excessive patterns with being stylish. But in reality it’s just the opposite. Focus on more subtle details and cohesive pieces to give your outfits the best look.

1. Not caring how you look

This applies not just to clothing, but to grooming and hygiene as well. If you focus on looking relatively clean and well-groomed you’ve beaten a majority of young men out there.  Anyone that makes fun of you for caring about your appearance is a lost cause, so don’t even worry about the haters.

As I said earlier, don’t forget that personal style is a journey and like any journey, it’s bound to have a few bumps along the way, the important part is learning from your mistakes and figuring out what works best just for you.

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