Is Men’s Streetwear Attractive?

Streetwear can be a pretty divisive topic these days, it can look good but also can go really wrong.  While we always believe it’s important to cultivate a stylish essential wardrobe, it’s definitely good to also experiment with new trends and styles, especially as you’re on your journey to discovering your own personal style.

In this episode of 2 Minute Tuesday we’re weighing in on whether or not streetwear for men is attractive.

So, is streetwear attractive?  In our opinion, yes!  But it comes with a few caveats.

For The Right Person

Can streetwear look good? Yes, definitely.  But it has to work with your existing style and confidence.  If you’re the type of guy who can experiment with different styles and pull it off with confidence, then go for it.  It definitely takes a certain amount of swag to make it work.  If not, it can look fake and like you’re trying too hard.

Don’t Try Too Hard

Much like “Bad Boy Style”, streetwear is an overall look that can come off as really inauthentic if it doesn’t mesh well with your pre-existing overall look.  You can look like you’re wearing a costume and like you’re trying way too hard.  So, if you go for it, proceed with caution and give some consideration to when and where you’re adopting this vibe.

Does Well-Dressed Mean Boring?

We talk so much about an essential wardrobe and timeless personal style, it’s hugely important. A sharp timeless wardrobe is the foundation of great personal style and, ultimately confidence. This week on 2 Minute Tuesday we answer a great question from our reader/viewer Arthur.  He asked, “Does well-dressed mean boring?”

Tune in and find out what we think.

Timeless and Classic, Not Boring

Hopefully, we can help you reframe your thinking that dressing in a classic, stylish way might be boring. Rather, it’s always appropriate and timeless.  You never have to worry about being out of style or not being appropriately dressed, and you can feel confident that you’re always going to look great. Trends come and go at lightning speed and flash doesn’t equal substance.

Embrace Your Personal Style

As we’ve mentioned in previous posts, things like adopting a particular style (Bad Boy style, for instance) or popular trend just because you think it’s going to make you stylish or show personality isn’t the way to truly build your own personal style.  It’s going to feel inauthentic and like you’re trying too hard.  By starting with timeless essentials and building from there you’ll then be able to figure out what styles really speak to you as you gain more confidence and build on a solid foundation.

6 Men’s Fashion Trends Women Hate

As a stylist, I’m well-versed in all things menswear, including trends. While it’s great that more men than ever are trying new things with their wardrobes there are some trends that women just aren’t into.

Know that there is a difference between style (timeless, versatile) and trends (fleeting, extreme) and that a good essential wardrobe is not driven by trends. Here are our picks for 6 men’s fashion trends that women hate!

6 Men’s Fashion Trends That Women Hate

  1. Overly tight skinny denim – There’s a very fine line between trim/slim and tight. Don’t do the latter, nobody wants to see that.

  2. Overly distressed clothing – Speaking of denim, super distressed jeans with a ton of holes in them just isn’t a trend that looks good on men (especially when they’re skin tight too). Stick with dark to medium washes with no or very limited distressing.

  3. Margiela split toe boots – A very hard item to pull off, just keep it simple, these are too fashion forward for most men. Stick to versatile, essential shoes.

  4. Over accessorizing – A ton of stacked bracelets, a huge lapel flower, all these things just add up to way too much going on. Keep it to simple, minimal items and no fewer than one, maybe two at a time.

  5. Large logos or graphics – My stance on them is well-documented and most women will agree, those overly loud, aggressive logos just aren’t attractive.

  6. Dad sneakers – These bulky sneakers are really trendy now and just don’t look good on most body types nor are they versatile enough for different outfits.  Go with timeless and classic white or black sneakers.

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