Style Mistakes Archives - Ashley Weston

10 Ways You’re Killing Your Style | Men’s Style Mistakes

Once you’ve got the basics of style down, it’s important to focus on those little things that can make or break your personal style and everyday look. Something as simple as a little mistake can totally throw off your look or ruin otherwise good style choices. Oftentimes its something as simple as how you present a particular choice. No matter what it is, focusing on the proper details and nailing those can save you from potential disaster. Some of these mistakes might be obvious but some you may not even know you are doing!

So, here are 10 ways you may be killing your style!

Being Overly Self-Conscious

Trying too hard can be as bad as not trying at all. Wearing trendy items that aren’t you or not wearing things that make you feel comfortable and confident are quick ways to ruin your overall style. People notice how you feel and if you’re feeling good about what you’re wearing and looking good, it will stand out.

Wearing Clothing That Doesn’t Work for your body type

Working with your body type is a huge part of getting well-fitting clothing. Choosing items that will flatter and fit well is crucial. Some easy items to avoid are henley shirts if you’re not fit or muscular, Chelsea boots if you’re a bigger guy, and classic straight-legged jeans if you’re a thinner guy. Check out all of our Fit Guides for tips about different body types and how things should fit.

Over-accessorizing

Yikes, this can go wrong so easily, over-accessorizing can be a huge problem. Johnny Depp, you are not. Go easy on rings, bracelets, and other flashy items and go for more subtle, refined accessories to show some personality or flair. Stick with 1 or 2 items max, like a pocket square and a watch.

Wearing too much cologne

A little goes a long way, and there’s nothing worse than smelling someone from 5 feet away. Nobody (especially women) wants that. If you can smell yourself, it’s too much.

Not paying attention to the details

Again, the little things matter, so take care to focus on them. Things like not lint rolling your clothing (especially dark shirts, suits, and jackets), wearing wrinkled clothing (just get our recommended steamer), and not tucking in your shoelaces really matter with your overall look.

Speaking of tucking in shoelaces (something Ashley is always super focused on as a stylist), our friends at Straight Laces have an ingenious shoelace set up that creates a clean, tucked look and basically turns all your shoes into slip on’s. It’s such a smart, useful product and we’re using them on all our shoes personally and with Ashley’s clients. Seriously, they’re that good. Just for our readers and viewers, we’ve got a deal for 40% off 3 or more laces! Shop here and use code AshWeston40.

Not dressing your age

We’ve discussed how to dress well in your 40’s before and a big part of it is embracing your age and wearing items that are classy and age-appropriate.

Wearing dirty, old shoes

Hopefully, this goes without saying, but a bad pair of shoes can absolutely ruin your entire look. Keep them in good condition and shined up.

Not Grooming Regularly

Overgrown hair, beards, and fingernails are no bueno. Make sure you’re taking proper care of your grooming and putting your best foot forward. Especially important in professional environments. We’ve got a ton of tips in all of our grooming guides.

Not taking care of your skin

Just like your grooming, proper skin care is an important part of your overall routine. It doesn’t have to be fancy or complicated but you should find a morning routine and an evening routine that works for you. Focus on moisturizing, good shaving techniques, and using the right products.

Wearing faded, ripped or pilled items

When items are faded (especially shirts, pants and sweaters), it’s time to send them off to the donation bin and get some replacements. If your sweaters are pilled, you just need to get a sweater shaver (we like this one best) to remove the little balls and get it back in good shape.

6 Ways You’re Wearing Your Jeans Wrong

Jeans are a staple in your wardrobe, and despite being a casual item, they’re probably the most important pair of pants in your closet, outside of chinos. So obviously it’s critical that you’re wearing them the right way and giving them the consideration they deserve. Because they’re so important, if you’re wearing them incorrectly you can be doing yourself a huge disservice, especially in the eyes of the opposite sex. After you read this and check out the video, make sure you take a look at our Jeans Fit Guide and our Dark Wash Jeans primer for how to do it right!

\We see all kinds of bad jeans-wearing these days and the worst part is these mistakes are easy to fix! So, here are 6 ways you’re wearing your jeans wrong!

Too Baggy

Obviously, it goes without saying that baggy jeans look awful. They aren’t flattering and just look sloppy. Baggy jeans only make slim guys look more skinny and bigger guys look more chubby. The right fit will be comfortable, so don’t think that you can get away with it because of comfort. Getting the right size and fit is a huge key, so make sure you’ve checked out our Jeans Fit Guide.

Too tight

The right taper is important but overly tight is definitely really bad. It can be super unflattering especially if you don’t have a butt which most men don’t have. It also makes you look very juvenile if your jeans are way too tight and it’s definitely not professional, regardless of how casual your work environment may be.

Bad washes

Washes that are too light (very light blue or grey/white) or acid-washes are neither timeless nor versatile. They just make you look like you’re trying too hard to be trendy. We recommend keeping your jeans in a clean, dark wash or check out a few of our other recommendations for jean colors.

Distressed or Ripped Jeans

It’s a fine line between good and bad but for 95% of men over the age of 25, this just isn’t a good look. Like some of the lighter washes, it makes you look like a teenager/fuccboi who is trying hard to be trendy. Sometimes a little bit of distressing is fine, but again only if you’re under the age of 25.

Too Long

Such a bad look and such an easy fit. Find the right length or got to a tailor, it’s a simple $5-10 fix. It just looks sloppy and can ruin an otherwise good fit. Also, it can make you look really short; not flattering at all.

Saggy Butt

Yikes, this is super unattractive. Find the right fit in the seat – proper rise (the length from the bottom of the crotch to the top of the waistband) is crucial. Here’s a handy reference image for what the “rise” is. The key is to not have a ton of excess fabric in the booty area. You want a trim fit but not overly tight.

What NOT To Wear If You’re Over 40 | Style Tips For Older Men

As we discussed in our previous video about Dressing Well When You’re Over 40, style and confidence as you age is all about embracing what you have and presenting a classy, refined look. Now, it’s worth mentioning that nearly all of our style advice, from Essential Wardrobe items to Fit Guides, applies to all age ranges. But, dressing well later on in life is just as much about what NOT to wear as it is the exact items you are wearing.

So, we thought we’d answer a few of the most commonly asked questions about what not wear if you’re over 40.

Q: Can an older man wear white sneakers?

A: Absolutely they can. In fact, we did a whole video about it. White sneakers like Adidas Stan Smiths and are a classic casual item for any man, regardless of age. That said, if you’re not comfortable wearing white sneakers or you feel like they’re a bit too young, we recommend going with a nice, clean leather sneaker in any color of grey or navy blue. Suede versions are excellent too as the added texture is a nice look.

Picks:

Common Projects

Koio

Beckett Simonon

Q: Is it really important to wear fitted clothing?

A: Yes, it’s critical to wear well-fitting clothing, no matter how casual or dressy. That said, this doesn’t mean tight! There is a HUGE difference between slim, well-fitting, clothing that’s proportional to your body type and something that’s overly tight. A lot of older men end up skewing overly large or baggy due to comfort or fears that they aren’t dressing their age but having a wardrobe that fits you well is something every man should have, regardless of age. For mode insight, make sure to check out all of our fit guides for in-depth info on all types of clothing items.

Q: What can I do to give my wardrobe some personality?

A: The most simple and cost-effective way is the right choice of accessories. So watch bands, ties and pocket squares, a ring, or a fun patterned sock are all great ways to add a bit of personality in an age-appropriate way. Being age-appropriate is the key thing, and over-accessorizing is a quick way to kill your style by making it look like you are trying too hard.

Q: What items should I avoid if I’m over 40?

As we mentioned in a previous video, leather jackets are a big one for men over 40 to avoid, with one exception. We do like leather or suede bomber-style jackets for men in this age range, but other types like moto and biker-style jackets just make you look like you’re having a midlife crisis. T-shirts with logos are another huge no-no, they just make you look juvenile. Additional types of t-shirts to avoid include henleys and deep v-neck t-shirts. They just aren’t the right look for an older guy. Stick to polos and well-fitting crewneck t-shirts. On the denim side of things, jeans that are light-wash, or ripped and distressed fall into the same category, they just look too young. Keep your jeans well-fitting and in a dark wash.

How To Dress Well When You’re Over 40

Just because you’re over 40 doesn’t mean you shouldn’t be giving some consideration to how you dress. While the majority of our style tips are applicable no matter what your age is, for you older guys out there there are a few extra things to keep in mind. Above all else, it’s about both embracing your age and confidence, and crafting a style and wardrobe that enhances everything you’ve got going for you.

Here’s how to dress well when you’re over 40!

Dress Your Age

The older you get, the more important it is to dress your age. There’s nothing sadder than an older guy trying too hard to look young. Embrace your age and all the great things that come along with it. We’ll discuss further in a minute but this doesn’t just go for the items you choose, it has to do with the fit and how you wear your clothes as well. It’s important to always strive for a tailored fit. In terms of specific items we recommend, suede bomber or collared jackets, wool or cashmere blend sportcoats paired with chinos, dark wash jeans, or wool trousers are all excellent places to start. You can easily dress these items up with a collared shirt and dress shoes or dress them down with a sweater or t-shirt and sneakers.

Stick To The Classics

Just like dressing your age, as you get older it becomes even more important to stick to classic, timeless items. Leave the trends to the younger guys and embrace the distinguished style that you can pull off. For example, some classic items that should be the foundation of your wardrobe are: suits /blazers, oxfords, dress boots, chinos, Harrington, bomber or standing collared jackets, and polo shirts.

Class It Up

Many men mistake getting older and trying too hard with dressing too casually. Yes, there’s always a place in your wardrobe for well-fitting basics, but take your casual wear up a notch. A polo shirt instead of a t-shirt works well, leather loafers or driving mocs instead of sneakers instantly adds class to a casual outfit. And if you want to add personality to your outfits more, that’s always done through accessories – not the main items in your wardrobe. Understated, distinguished and in-control is what we love to see older men doing. Screaming “Look at me!” with crazy outfits or “funny” t-shirts is just immature.

Nail the fit

We talk about it all the time and have an entire series dedicated to its importance, because, above all else, this is key. Many older men tend to wear clothing that’s one or two sizes too big to hide problem spots on their bodies or for pure comfort. Big mistake – it actually starts bringing attention to you hiding something and being insecure about it. Wearing-tailored clothing will always allow you to present your best self as opposed to wearing too tight or too baggy of clothing, which is just unflattering.

Back To School Style Mistakes Men Make

You’re headed back to campus and we’ve got some style tips to help you look your best this Fall. We see a lot of these common mistakes young guys make by either trying too hard or not trying enough. You want to find a balance between effort and casual dress, all while staying comfortable.

The good news is a little birt of effort in the style department goes a long way, so all of these back to school style mistakes are easily avoidable.

Socks and Slides

There’s no excuse ever. Pick up some Vans slip-ons, they’re just as comfortable and low-maintenance, plus they’re much more stylish.

Slip-On Picks:

Vans

SeeVees

Sperry

Too many logo tees

Leave that for all the annoying kids who are decked out in their logo tee, pants, and socks. They look ridiculous, don’t join them. Stick with the basics and go with something from H&M and Uniqlo, they make our favorite t-shirts that Ashley uses all the time with clients.

Not Putting In Any Effort

Your wardrobe doesn’t have to be fancy but you should care about what you’re wearing. That’s why we made it easy on you and put together a list of all the essentials you need for a stylish back to school wardrobe.

Basketball Shorts All The Time

Why? Unless you’re on the court or on the couch you shouldn’t be wearing basketball shorts. Grab some dark joggers instead, they’re just as comfortable and look a lot better.

Jogger Picks:

Too much hypebeasting

It reeks of trying too hard. If you want to sprinkle it in here and there, totally fine. But don’t jump in with both feet and wear all the trends at once, all the time. Again, we did a back to school essentials article that sprinkles in just the right amount.

Not caring about grooming

Look, there might be days you don’t want to style your hair. Fine, no problem, throw on your favorite baseball cap. But, here’s no excuse to have overgrown, unwashed hair or neglected skin. Your overall appearance, especially when it concerns hygiene, will be a huge make it or break it situation when it comes to people wanting to hang out with you. Check out all of our grooming tips in our grooming section. From haircuts to skincare, we’ve got all the tips you need.

Wearing only workout gear

Unless your an athlete and it’s absolutely necessary because of your schedule, then there’s no excuse. It’s lazy and looks like you might be hiding a less than desirable physique. You wanna feel just as comfortable? A pair of some Adidas Ultraboosts, black joggers, a tee or a hooded sweatshirt, and a bomber jacket will look 100 times sharper. All of our picks are right here.

Men’s Back To School Essentials

You’re headed back to campus and we’ve got some picks to help you look your best this Fall. We know that school can be stressful and the last thing you have time for is thinking about what to wear. However, we can all agree that you still want to look your best which is why picking up these pieces will take the guesswork out of what outfit you should wear because they all can go together easily and stylishly.

The key to solid back to school items are ones that are comfortable, stylish, inexpensive, and versatile, and these back to school style essentials will have you covered for the entire year.

Sneakers

You need a good everyday sneaker that’s comfortable, stylish, and affordable. We’re huge fans of the Vans Old Skool sneakers which come in a bunch of different colors and patterns, though I love the black and white ones the most. If you’re going to get a pair of white sneakers, I’d opt for leather like the Stan Smiths which are easier to keep clean than canvas kicks.

Picks:

Vans

Stan Smiths

More Sneaker Picks

Jason Markk sneaker cleaning wipes

Like everyone, you need something to carry your notebooks, laptop, and gear every day and just like your clothes, it’s important to pick up a backpack that keeps you organized, looks sharp, will last you all year, and won’t break the bank. We’ve discussed the ins and outs of our favorite backpacks before, and the key is finding the right size and style.

Picks:

Sunglasses

The right shape can instantly up your style game, but the wrong shape can really work against you. Stick with a classic style that compliments your face shape. Check out this article for more on how to choose the right sunglasses for your face shape.

Picks:

A Second Pair Of Pants

A man can’t live on denim alone so it’s wise to consider a few more options. We definitely recommend chinos, they’re comfortable, stylish, and affordable. If you go for chinos, go with navy or charcoal grey as that’ll go with everything. If chinos aren’t your style grab some sharp jogger pants for a different option. Go with black or charcoal as they’ll not only look the best but it will keep them from looking too much like your workout gear.

Chinos:

Joggers:

Why Older Men Shouldn’t Wear Leather Jackets

If you’re an older guy, dressing your age can be tricky. As we discussed in a previous 2 Minute Tuesday, there are things you should, and maybe more importantly, shouldn’t do as a stylish older guy. In addition to cultivating a timeless Essential Wardrobe, some items just don’t work. We’re revisiting some style tips for older gentlemen in our audience after some feedback and questions about leather jackets in particular.

They Make You Seem Like You’re Trying Too Hard

The style and bit of rock n roll edge that a leather naturally has just read too young for an older guy. There’s nothing wrong with having some cool factor in your wardrobe, but there’s a line where something like a leather jacket doesn’t help this, it just hurts it.

It Doesn’t Complement Your Age

At a certain point, we encourage you to embrace your age, whether you’re 40 or 70. This doesn’t mean dressing in a way that feels old or stuffy (no matter what your age is), but rather you want to cultivate a style that’s distinguished and age-appropriate. You want a look that doesn’t detract from your natural stylishness as an older guy.

There Are Better Alternatives

As we mentioned, there are a ton of better alternatives available for you older gentlemen. A bomber jacket in a different material like suede or cotton is a great place to start. You can also try a Harrington jacket for something equally as stylish.

Suede Picks:

Other Picks:

Women’s Fashion Trends Men Hate

We talk a lot about men’s clothing items and trends that women hate, but now it’s time to flip the script. We thought it was about time that Dorian shared some of his opinions on some of the biggest women’s trends happening out there. Fashion can be a crazy place, so here are Women’s Fashion Trends That Men Hate!

1. Low-Slung Sunglasses

Both of us can agree that this trend not only doesn’t make practical sense, but it just looks weird and unapproachable.

2. High-Waisted Cropped Bell Bottom Jeans

I’m a fan of these but Dorian definitely thinks they look weird and unflattering, no matter what type of woman is wearing them.

3. High-Waisted Cutoff Jean Shorts

Another take on the unflattering high-waisted jean trend, these just look sloppy and like women aren’t really trying.

4. Ugly Fashion Sneakers

Something both of us completely agree on, the ugly sneaker trend needs to die immediately.

5. The Hobo Tomboy Look

Definitely a major overall trend, we’re not feeling the oversized, trashy looking vibe, no matter how attractive the woman is underneath all the layers. Just like we say with men, your clothes should always fit your body.

6. Bicycle Shorts

Speaking of unattractive looks no matter how attractive the woman, the bicycle shorts trend isn’t doing anyone any favors. Despite what you may think, nobody wants to see a woman’s camel toe in public.