7 Sneaker Mistakes That Make Grown Men Look Like Try-Hards
6 Video Views·Sep 16, 2026
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Video Summary
AI GeneratedThis video provides a comprehensive guide for men on how to pair sneakers with various types of trousers. It covers the different categories of sneakers, the importance of proper pant proportions and hemming, and advice on maintaining a timeless, age-appropriate style without overdoing it.
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And so, the rule to follow here is you just want to update your style. You don't want
to rewind your age. Mistake number one. You're wearing the wrong
type of pants with the wrong type of sneaker. Seriously, great sneakers plus bad pants equals
bad outfit. So, how to fix this? Well, here are the quick rules on how to match the right
type of sneakers with the right type of trouser. So, first up, the four families of sneakers.
We've got our dressiest styles. We're talking the minimal leathers, often made in suede
or leather in a variety of colors from white to brown to black, aka the neutrals. And in
general, these are going to be clean, restrained. They're going to give off a low profile.
Next up, we've got court and retro sneakers. These are going to have a little bit more
paneling, textures. We're going to see a mixing of materials, maybe a little bit of color,
a striped pattern. And for the most part, still made from leather and suede, but just
a bit more casual. Next up, we've got canvas. We're keeping
the silhouette, but we're going with a lighter weight material, also usually more affordable.
And finally, we've got the most casual, the sport lifestyle sneaker. Inspired by training
and running shoes, overall still it keeps a simple clean silhouette and therefore, it
can still be worn with casual clothing. So, how to match? Well, some items like dark
denim, it's pretty much going to work with any of those. Yeah, that's why we love dark
denim. It's going to work with pretty much any of those four styles you throw at it.
Now, of course, some of those shoes are going to give the overall outfit a more casual vibe,
some are going to dress it up just a tad. But, it's when we get into that mid-wash
light wash denim that all of a sudden we got to be careful because those dark colored minimal
leathers, they don't work as much. Yes, white will work with them, but black, dark
brown, not so much. Yeah, the court sneaker is about as dressy as you want to go there.
Now, chinos and khakis look great with the top, too, but you want to be careful of trying
to match chinos with canvas sneakers. Although, interestingly, the sport lifestyle sneakers
can work if you're going with a casual outfit, maybe just wearing those khakis with a t-shirt.
Yeah, that look can work. Next up, we've got performance pants. What
I like about this is in general, all four styles can work with performance trousers,
but it really does depend on the cut and color. Now, what about linen? What about lightweight
summer trousers? Well, for this type of pants, sneakers in category 1 and 2 are going to
work best. While for cargo or utility pants, categories 2, 3, and 4 with sneakers are going
to be right at home. And when it comes to shorts, again, categories 2, 3, 4 are where
it's at. Unless the shorts are a little bit dressier, you're going with no-show socks
and maybe wearing it with a polo. Then, yeah, in that case, you could pull off category
1, especially a pair of sneakers in white leather.
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the best deal out there on the web. Now, the next sneaker mistake a lot of guys
make is they get the proportions all wrong. Seriously, too wide of a hem, too much bunching
at the bottom makes your shoes disappear. Or, skinny taper that's cut too high all
of a sudden can make your shoes look large and clownish.
So, the rule here is to make sure your trousers are hemmed properly to work with that type
of shoe. Now, for most of you, you can avoid this issue by generally sticking with slim
or straight cut trousers. Most slim or tapered openings are going to be at about 13.5 to
15 inches in circumference. Straight trousers, on the other hand, are going to have a circumference
of about 15 to 16.5 inches. Now, an issue starts to arise when you start
to wear baggy, loose, or boot cut trousers because all of a sudden we're starting to
see openings go well beyond 16 inches. We'll see 17 inches, 18 inches. And the reality
is those type of openings are not made to look good with sneakers. It will work with
boots because they're simply larger, but it won't work with the sneaker silhouette.
Same thing with overly skinny trousers. Anything that starts to fall below 13 inches will start
to make your sneakers look comically large. Now, the second part of this that leads to
the next mistake is that your trousers are puddling on your sneakers.
Yeah, you know what I'm talking about, all that excess material that bunches down at
the bottom. And here's the deal, on a pair of boots, this could look okay to a degree,
but with sneakers if they're more than an inch too long, it just starts to look sloppy.
Seriously, sneakers look best when there's a full break, aka just a tad of bunching at
the bottom. And for certain trouser types like chinos, you could even go with a clean
one, no break. That's where the hem just barely kisses the top of the shoe.
Now, the solution here is pretty easy. You can actually get those trousers hemmed for
a relatively inexpensive amount. It's an easy fix that any tailor or seamstress can
do. Or if you just want to do it yourself, 100% possible you can either stitch it yourself
or go with the easy fix, aka hemming tape. Seriously, with an iron, a little bit of heat,
you can hide that excess material folding it in on itself.
And, of course, the best option is just to buy trousers that fit you properly, which
you think would be easy, but, yeah. Now, this next mistake is one I think a lot
of guys in their 30s, 40s, 50s really fear doing and that is they look like a tryhard.
They look like they're trying to look young. And so, the rule to follow here is you just
want to update your style. You don't want to rewind your age.
You see, the reality is you don't need those trending sneakers that all those 19-year-olds
are out there trying to buy. Now, if you're 29, 39, 49, 59, what you're looking to do
is refine your look. And because you know your history, you know that sneakers have
been around since 1917 and then were made popular in the 1960s by the tennis courts
and the basketball courts. Yeah, you know the simple court sneaker silhouette is not
going to go out of style. So, knowing that, you choose a style, you
choose a material, you choose a particular shoe type that's timeless in design and works
with your lifestyle because that's the key because I don't know what you do, I don't
know what type of trousers you normally wear. But, so far in this video, I've armed you
with the information that you can now with confidence go out there and choose the right
sneaker for you. But, should you go with color? Should you
go with a fun pattern? Guys, the next mistake you want to avoid is don't let the sneakers
hijack your outfit. And I'm not saying to be boring. You can have color, you can have
texture, you can have contrast, you can bring in something fun. But, remember this rule,
one hero per outfit. So, if you're going to go with some loud
sneakers, then you want to keep the rest of your outfit simple. A simple solid colored
shirt, solid colored trousers, yeah, you can have fun with the shoes. But, honestly, I
think for most guys since they're spending good money on their footwear, they oftentimes
want to keep it. For versatility reasons, you want to keep your shoes a bit more muted.
Go with neutral colors. Solids are great, subtle patterns are very stylish and an easy
way to incorporate them. But, yeah, when it comes to your first couple pair of sneakers,
keep it simple. And, notice I said couple pairs because another
mistake a lot of guys make is that they buy one pair of sneakers and they wear them to
death. Seriously, they go with that white pair and they wear it with everything. They
wear the hell out of them. And all of a sudden, they start discoloring.
Gents, there's nothing wrong with having a couple pairs. We talked about those four
categories. Find the sneaker styles that work with your lifestyle. And don't be afraid
to have a couple pairs that you can rotate through, that you can take care of, you can
clean, that you can choose to wear in the different situations that call for them. Dress
up a bit when the opportunity arises. But, yeah, don't be afraid to give yourself
options. Now, this next mistake is one I wrestled with
and that is when you first start to wear sneakers, well, it's easy to confuse being unfamiliar
with being uncomfortable. And by that, I mean when you're stepping up your style, sometimes
you start wearing an item that you're just not used to wearing. Because let's face it,
you've been wearing those worn out running shoes. You feel good in them because you're
used to them. So, when you put on a pair of nice sneakers, you feel conscious about this.
You perhaps think people are looking at you. Well, the good news here is pretty much everyone
else is focused in on themselves. Most people don't even notice you. I know, hard truth.
But, the good news there is that you can wear whatever you want. And, again, not only are
you going to be comfortable wearing these when you get used to it, but also they allow
you to step up your casual style because, yes, not everyone is paying attention to you,
but people do judge a book by its cover when they meet you for the first time. And shoes
like this easily allow you to step up your casual game.
And, speaking of stepping up your casual game, guys, I've got a video for you right here.
You want to learn how to dress like a man, I got you covered, boom, right here. Go check
it out, solid video. And, yeah, let me know what you guys thought of this video in the
comments below. I will see you later.

