Let’s talk a little bit about style mistakes that I see older guys make when they’re trying to dress a little more youthful.

Here’s a quote that I recently read from a French writer Victor Hugo. He said, 40 is the old age of youth, and 50 is the youth of old age.

So personal style is subjective. And my tastes may not match yours. And that’s okay.

So where is it written in stone that once we hit our 40s, we have to start wearing corduroy tweed and cardigan sweaters? Well, I’m a huge fan of cardigan sweaters but they have to fit well.

Society places these rules on us older guys that once we hit a certain age, we have to start dressing a certain way.

However, I’m 100% in the camp of trying to maintain a youthful edge with the clothing that I wear. But also understanding where the boundaries are and what’s no longer appropriate.

Because nobody wants to be that guy that just looks like he’s trying way too hard. Okay, so let’s start at the ground and we’ll work our way up.


So Mistake number one is wearing your running shoes or your workout shoes out in public when you’re not running or working out. I mean, we get it you exercise and you want the world to know that you’re still athletic, and that’s super fine. I think though the problem comes in is when most guys look a little more youthful. Just default to that athletic shoe over something a little more classy.

Some other casual options or fashion sneakers guys, we’ve talked about this before. So if you’re a sneaker guy, there are tons of elevated and tasteful fashion sneakers out there for you. So for example, instead of wearing this your athletic shoe out in public, why not opt for something like this nice, fastest sneaker or if you’re into white sneakers, they go with everything, something nice and streamlined, simple and classic like this, or even something in a sleek, stylish black and white.

Also, driving mocks and loafers are two more options for you that are still casual and comfortable.

And it should go without saying that flip-flops and sandals out in public are bad.

Buggy or skinny Jeans

Mistake number two is wearing jeans or trousers that are a little too trendy and don’t fit you. So this covers skinny jeans that are way too tight. This covers boot cut or relaxed fit jeans that are too baggy and too long. This also covers heavily distressed, destroyed jeans with rips everywhere.

Now, this is where I sort of teetering on that line a little bit. I mean, as I said before, I do try to maintain a youthful edge with the clothing that I wear. But I also don’t cross my self-imposed boundary of what’s appropriate.

However, I do experiment and I try some things other guys may not. Since I do spend a lot of time here in the style space, I do create some opportunity for myself to try new things and experiment and I’m absolutely not afraid to step outside the box.

However, I still try to keep everything classy. I think most mistakes happen when guys follow trends a little too closely or just go with whatever they went with 10 or 15 years ago. skin-tight skinny jeans or baggy, anything won’t look good on you. Keep your pant legs slim, not skin tight, and tapered down to your foot. Also, keep the hem at about your ankle bunching or puddling jeans down at your foot doesn’t fly.

Busy, sloppy t-shirts

So Mistake number three is wearing the wrong shirt. So graphic t-shirts with big branding, logos, slogans, and cartoon characters all over them are no longer appropriate. Instead, try simple solid colors. And since we’re on the subject of T-shirts, like nobody wants to see your chest hair creeping out of like a big v neck or some giant scoop neck t-shirt either.

As for your button-down shirts, so they shouldn’t be big and baggy and you should not wear your dress shirts untucked. It’s okay to have the untucked look. But not all dress shirts are meant to be worn untucked.

Dress shirts inherently by design have longer tails They’re meant to be worn tucked in. So they look goofy when you wear these shirts untucked, and it kind of makes you look like you’re wearing a little dress.

Shirttails shouldn’t hang below about mid crotch when you wear them untucked. And also try to stay away from super busy, bold patterns that can kind of make you look like a clown.

Here’s another thing, guys. So, unfortunately, our bodies start to change a little bit once we hit a certain age. So if you find yourself buying shirts or clothing, and you’re having to size up a little bit to accommodate your barrel, chest, or maybe your spare tire, finding a good tailor will benefit you more than you can imagine.

What they can do is nip and tuck all the billowing fabric and create a shirt for you that looks like it was custom-made for your body.

Sporty Clothes

Mistake number four is wearing sport coats that are too big. So a really popular and classy look for guys is going with like dark denim, brown brogues, and a sport coat, it’s a fantastic, classy, smart casual date night outfit. The problem is that this look can go sideways real quick. If you’re noticing a trend here is fit is king. Everything should fit your body type. If the fit is off, it can ruin an otherwise well-thought-out outfit.

So when wearing a sport coat, you should see about a half-inch of sleeve cuff with your arms straight down to your sides. If your sleeves on your sport coat or too long, take it to a tailor and have the sleeves brought up. Another thing is when your sport coat is buttoned, you should feel a slight pull at the button.

Now I said slightly. So if you can take your jacket and pull it away from your body when it’s buttoned the jackets too big for you. If you have a jacket that fits well on the shoulders, but maybe is a little too loose or too tight in the body.

Take that jacket to a tailor that can take the sides in or let the sides out and make it perfect.

Dress your Age

Alright, so Mistake number five is trying to dress like you’re still 25 look around a little bit, Do you see 20 somethings wearing the same things you are? Is the music at the stores that you shop out getting a little too loud? And are the sales associates in those stores? Are they kind of like teenagers?

If so, chances are you need a better place to shop. Let’s stick with the classics and make sure the fit is on point. guys feel free to leave us a comment let us know some mistakes that you see.


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