I know you already got rid of your old I do all my own stunts shirt.
That was a good start.
But I know there are a few other clothing items in your closet that have to go. Now.
Listen, I’ve been there, too. You grow older, you mature more, you start dressing the part for success. But old habits and clothes just seem to hang on, don’t they?
Check through this whole list of unstylish clothes many guys have in their closet. If you’ve got one, toss it out now.
I’m not going to leave you without a few suggestions, either. For everything you take out, I’ve got a recommendation for a perfect replacement.
So let’s get started.
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5 Unstylish Things Men Need to Stop Wearing Now
1. Sweatpants
I understand that comfort is a priority for a lot of dudes. But that’s still no excuse to put on a pair of sweatpants and go into the world. And yes, I’m talking about even running errands at the grocery store.
When you’re wearing sweatpants, you’re basically saying, I give up. And that’s not a message you want to send. Even if you’re only sending it to the bag lady in the checkout line and you’re not worried about seeing her ever again.
Because part of your outfit is how it affects you. So when you head out for the day, dress like you’ve got a purpose—like you’re on a mission.
Now that doesn’t mean you need to put on a pair of stiff raw denim jeans or slip into a tailored suit every day.
If you prioritize comfort but still want to level up your style, something like a pair of sleek joggers will do the trick.
My favorite joggers come from Public Rec. I love their All Day Every Day Joggers in the fall and winter because the fabric is a bit thicker. They have all the comfort I would normally get from sweats, but because they’re tapered and have some structure to them, they’re much more stylish.
If you’re going to get joggers, choose quality. The minimalist slim fit design on these joggers hits an excellent balance between comfort and performance.
When the summer months roll around, I opt for the Stadium Joggers from Public Rec. They’re looser and the fabric is much thinner. To me, these make the base of my ideal Sunday afternoon outfit for chilling at the local brewery.
Of course, both of these joggers are at least as comfortable as sweatpants if you’re just relaxing at home. But the best part is that you can just pop up off the couch and cruise into the world and look sophisticated and put-together.
2. Boat Shoes
Maybe there was a time and place when boat shoes were a stylish choice, but they’ve been permanently ruined by the Margaritaville crowd in Las Vegas.
If a lady catches you wearing boat shoes, she’s going to think you lack imagination. And she’s not wrong—the style is played out.
I don’t mean to be harsh, and if you’re quietly tucking your boat shoes under your bed now, don’t worry—there are plenty of other footwear options that are comfortable and simple.
The key word in that last sentence was: simple.
Boat shoes are overcomplicated. What’s with that leather lace running down the side of the shoe? Does anyone know?
Instead of boat shoes, opt for a minimalist sneaker. One of my favorites on the higher end is the KOIO Capris. And if you want something a little more affordable, the GREATS Royale is another excellent choice.
The KOIO Capri Triple White is as loud as a white dress sneaker can get without leaving the minimalist realm. Go for these if you want a pair with a lot of details that aesthetically sits in between the dress and athletic sneaker worlds.
A minimalist sneaker is clean, comfortable, and allows the rest of your outfit to shine. If you’re a basketball fan, you can think of minimalist sneakers like the Tim Duncan of shoes. They’re not flashy, they don’t do any spins, but they’re damn-near impossible to beat. Because the fundamentals are solid.
If you want a lush sneaker that’ll serve you equally well at work and at cocktail hours, go for the GREATS Royale. They’re simple, no-nonsense, and designed to be trend-resistant.
If you want to branch out from sneakers and launch yourself into the next style stratosphere, I recommend a pair of Chelsea boots. Now if you’re used to boat shoes, Chelsea boots might feel like a huge leap, but a slim, sleek pair of boots is exactly the kind of thing that separates the stylish guys from the non-stylish guys.
3. Skinny Ties
Back in the early 2000s, skinny ties were all the rage. So I don’t blame you for still holding on to yours. In fact, I think I might still have a few in my closet right now, too.
Like with the rest of the items on this list—your not to blame for having some of these clothes. Trends happen. Fads happen.
But if you only have skinny ties left, it’s time to swap them out for more classic options. The trend toward skinny ties was just that: a short-term trend.
It’s the 20s now (doesn’t that sound weird?) and style is veering back toward the classic. And that means ties are getting wider.
Now you don’t want to go full 1980 and get the super wide tie—that was another trend that didn’t age well.
Instead, aim to match your tie to the width of your lapel. And if you didn’t already know, slim fit suits with skinny lapels are also out. As a rule of thumb, don’t choose a tie (or a suit lapel) under three inches.
An easy way to pick up new ties is through, Gentleman’s Box. They send through a new tie (plus other accessories to match the tie, like socks, lapel pins, etc.).
Gentleman’s Box packs impressive value in their Classic subscription.
While I’ve had experience with tons of other subscription services, GB is at the very top of the list for building a theme and delivering quality with nearly every item.
Floral ties are currently in style, but they certainly have a bit of that fad-aura about them. You’ll never go wrong with solid matte ties, so if you want to stick to classic style that never gets old, that’s your best play.
4. Ratty Sweatshirt
There’s a fine line between well-loved and raggety. And guys love to push the boundaries with their sweatshirts.
Trust me, I’ve seen it countless times: good looking guy, nice crisp jeans, and a good pair of sneakers. This guy has it together—except for his beat up old sweatshirt.
Outerwear is one of those things you never want to skimp on. It immediately becomes the focal point of your outfit because it tends to be the bulkiest item you’re wearing.
Honestly, you’re better off wearing beat up jeans and sneakers with a nice coat rather than the other way around.
That ratty old sweatshirt is still good—like for when you’re cooking pasta at home and you don’t want to ruin a new shirt. Or for when you’re out for a run in winter. There will always be a time and place for the beloved beat up sweatshirt. But it’s not when you want to look stylish.
If your old sweatshirt is your go-to for chilly days, it’s time to make a swap.
I’d start by looking at the Public Rec Better Than Down collection. They offer a vest and a bomber jacket. If you run a little warmer and want something for brisk fall days, the vest might be your speed.
Feels like a down vest. Looks like a down vest. But Public Rec decided to let the geese keep their hair. Kudos, Public Rec. The result is a warmer, lighter, and less-pokey vest that keeps its shape all fall and winter long.
Or if you want a lightweight jacket that can keep you warm through fall and winter, then the Better Than Down Bomber is the way to go.
Made with water-repellant Thinsulate, which is proven to beat down as an insulator in study after study. What do you get when you mix science and style? Pure dopeness.
The fit is modern and stylish, and even though the Better Than Down collection is puffy, they don’t add any “visual” weight because of the slimmer torso.
5. Baggy Shorts
Are you still wearing shorts that go below your knees?
I’m not about to suggest that everyone here starts wearing Daisy Dukes and short shorts: nobody needs to see that.
But it’s time to ditch the baggy shorts for good (and cargo shorts, too, if you have those).
My favorite length for shorts inseams is seven inches. That should fall a few inches above your knee, and the style is mature and modern.
This might surprise you, but the fashion trend is toward even shorter lengths, like five inches. I think this style looks great on guys under 30 and physically fit gents, but a seven inch inseam is a safer play for any dudes 30 and above.
A nine inch inseam is ok, and might be a good stepping stone for you if you’ve always worn your shorts below your knee. At nine inches, the hem of your shorts will fall just above your knee-cap.
When swapping out the baggy shorts, there are several options: if you want comfort, I’d go with the Public Rec All Day Every Day Short. To me, this is the ideal backyard barbecue short as it’s relaxed and stretchy, but still has a slimmer, tailored fit.
It's hard to get more comfortable than Public Rec's All Day Every Day fabric. The drawstring and uber-stretchy fabric make this comfortable enough for a backyard barbecue, but stylish enough for a trip into the city.
If you want something a little more traditional, check out the Everlane Performance Chino Short. It’s a more classic looking short than the Public Rec ADED, so it dresses up a bit better (not that you can really dress shorts up a whole lot—they’re better off strictly casual), but they’re also a little less comfortable.
Do You Have Anything That Needs to Go?
If you’re reading this and you’re red in the face, don’t worry. Unless of course you’re currently wearing sweatpants, boat shoes, a nasty sweatshirt, and a skinny tie. If that’s true, you have some serious fashion homework to do.
Like I said, I even went and found a few of these items in my closet, and I stay up to date on classic fashion and the latest styles for a living.
There are two basic ingredients to perfect style: fit and confidence.
Try swapping some of these unstylish clothes for the more fashion-forward alternatives and see how the fit boosts your confidence.
Ditch the sweats and put on a modern fitting pair of joggers: now you’re starting to get it.
Donate your boat shoes and pick up a pair of sleek leather sneakers.
Save the old sweater for pasta night only and layer a sophisticated coat on top.
Ditch the fashion-fads: no more skinny ties, or baggy shorts.
Swap them out for something more timeless.
