5 Mistakes Older Guys Make When Trying to Dress More Youthful

This blog post comes from a comment that was left on one of my previous videos where I was asked to talk about this.  Now, personal style is absolutely subjective and my personal taste may not match yours and that’s totally okay.

Where is it written in stone that once we hit our 40’s, we have to wear corduroy, tweed and cardigan sweaters?  Actually, I love me a good well-fitting cardigan.  Anyway, society places labels on us older guys that once we reach a certain age, we have to dress a certain way.  I am 100% in the camp of maintaining a youthful edge with the clothes I wear, but also understanding what the boundaries are and what’s no longer appropriate.  Because, nobody wants to be “that guy” who looks like he’s trying way too hard.

So, let’s start at the ground and work our way up.  Mistake #1 is wearing your court shoes or workout shoes in public when you’re not actually jogging or working out.  We get it, you exercise and you want the world to know you’re still athletic.  That’s fine, but the problem comes in when guys default to their trainers over something a little classier.  Some alternative casual options are fashion sneakers (we’ve talked about this before), so if you’re a sneaker guy, there’s a ton of elevated tasteful fashion sneaker options out there for you.  Also, driving mocks or loafers are two more options which are still casual and comfortable.  It should go without saying that sandals and flip-flops out in public are bad, but I still see it all the time, especially in Southern California.
Mistake #2 is wearing jeans or trousers that don’t fit you.  This covers skinny jeans that are too tight, boot-cut or relaxed fit jeans that are too baggy and too long, as well as heavily distressed or destroyed jeans with rips everywhere.  Now this is where I teeter on the line somewhat.  Like I said before, I do try to maintain a youthful edge, but I don’t cross my self-imposed line of what’s appropriate. However, I do experiment and try stuff other guys might not.  Since I do spend a lot of time in this style space, I do create some opportunity to experiment and I’m absolutely not afraid to step outside the box a little.  Having said that, I still try to keep it classy.  Most mistakes happen when guys follow trends too closely or go with whatever they went with 10-15 years ago.  Skin-tight skinny jeans or baggy anything won’t look good on you.  Keep the legs slim (not skin tight) and tapered down to your foot, and keep the hem at about your ankle. Bunching or puddling pants at your shoes doesn’t fly anymore.

Mistake #3 is wearing the wrong shirts.  Graphic T-shirts with big branding logos, slogans or cartoon characters are no longer appropriate.  Instead go for simple solid colors.  Since we’re on the subject of T-shirts, nobody wants to see your chest hair sticking out of a deep V-neck or scoop-neck T-shirt either.  As for your button down shirts, they shouldn’t be oversize and your dress shirts shouldn’t be worn untucked.  Now, I’m okay with the untucked look, and I’ve wrote about it before, but not all shirts can be worn untucked. Dress shirts inherently have longer tails that look really goofy when worn untucked and it makes you look like you’re wearing a little dress. Your shirt tails shouldn’t hang below about mid-crotch when untucked. I would also try to stay away from the super bold patterns that can make you look like a clown.
Here’s another thing.. Unfortunately, our bodies start changing once we hit a certain age, and if you find yourself having to size up to accommodate a barrel chest or spare tire, finding a good tailor will benefit you more than you might imagine.  They can nip & tuck the extra billowing fabric and create a shirt that looks like it was custom made for you.

Mistake #4 is wearing sport jackets that are too big.  A super popular and classy look for guys is going with dark denim, brown brogues and a sport jacket. This is a great smart-casual date night outfit.  The problem is, this look can go sideways real quick.  If you’re noticing a trend here, it’s fit.  Everything should fit your body type.  If the fit is off, it can spoil an otherwise well thought-out outfit.  You should see about ½” of your shirt cuff when your arms are at down your sides.  If your jacket sleeves are too long, take it to a tailor and have the sleeves brought up.  Also, when the jacket is buttoned, you should feel a ‘slight’ pull at the button. Again.. slight.  If you can pull the jacket away from your body when it’s buttoned, it’s too big.  Try to size down, or if the fit is close, take it to a tailor and have the sides taken in.

Mistake #5 is trying to dress like you’re still 25. Look around, do you see 20-something’s wearing the same stuff you are?  Is the music at the stores you shop at getting too loud, and do the sales associates look like teenagers?  Chances are, you need to find a new place to shop.

Stick with the classics and make sure the fit is on point.  Feel free to leave me a comment and let me know some mistakes you see, and if you’d like me to take a deeper dive into this subject in another video, please let me know in the comments.  I’d love to hear from you.