Cool Clothes For Guys, No Matter What Age

Earlier this year, my middle-aged father sat down with me while I was visiting the family with an unexpected question for me.

He’s a lifelong business leader whose wardrobe up until just recently was composed mostly of stuffy wool suits from the 90s and merch from his favorite sports teams, but as he’s starting to enter the later part of his career, he decided it was high time for him to learn to dress better on a day-to-day basis.

I was really excited to help him start to develop a sense of personal style and to make some great additions to his wardrobe. But as soon as I started to go down my list of normal taste-building resources, the two of us quickly discovered a troubling theme.

Most of the really great fashion resources on the web -- especially the ones I knew about -- were targeted toward younger guys.

Obviously, it’s never too late to start investing more time, energy, and care into the way you dress, and it’s great for people like my dad to develop an interest in wanting to improve their style. But unless you’re in your mid-twenties and svelt, when it comes to online resources, your options can seem few and far between.

That’s why I felt inspired to write this guide up: no matter what age you’re currently at or your level of fashion knowledge, this article will compile some cool, simple fashion essentials that can help anyone at any age dress a little smarter without looking like they’re going through some kind of personal youth-related crisis.

Whether you’re still in your twenties or starting to enter your 60s, as long as you know what to look for and have a little guidance, there’s no reason why you can’t develop a strong sense of personal style that helps you make every outfit look great.

In Your Twenties? Try This Look: 

For those on the younger side of the age spectrum, now is a great time to experiment with more slim-fitting garments and sleek, trendy looks.

In this example, which is probably on the more conservative side of fashion for twentysomethings, you can see that a slim-fitting jean and suede Chelsea boot combination can make a pretty big impression.

photo via @rowanrow on Instagram

photo via @rowanrow on Instagram

Additionally, more streetwear and urbana-inspired garments can maximize your trendiness: adding hoodies, jean jackets, ripped jeans, or other such items to more traditional outfits can add a stylish flare and help make your outfit distinctive and memorable.

As always, proper fit is key, but as a younger person, you’ll have a little bit more room for experimentation: pairing a baggier top with slim pants, or a noticeably cropped ankle and no-show socks with sneakers can be fun ways to riff on traditional stylings as well.

Ultimately, this age range is a great opportunity to get creative with the traditional “rules” of fashion and bend them in potentially unexpected ways. That said, if you’re more comfortable playing along with the traditional standards as well, that’s totally fine as long as you emphasize fit first and foremost.

By focusing on slim fits paired with just one or few more experimental/trendy garments, you’ll be breathing fresh life into anything you put on.

In Your Forties? Try This Look:

(photo via Looktastic)

When it comes to fashion inspiration for men in this age range, Jeff Goldblum is (at least to me) the fashion legend to model yourself after.

He is a master at looking put-together and sophisticated in basically any situation.

For some guys, some of his fits and personal fashion choices might be a little too out there, and that’s fine -- just studying the way Jeff Goldblum puts an outfit together can help take your personal style up a level.

photo via  Looktastic

photo via Looktastic

If you’re trying to become more well-dressed and fashionable in your forties, you actually have an easily-overlooked advantage: while younger guys might have less flexible college student budgets, you’ve got the critical combo of a more flexible budget and less rapidly-shifting body dimensions working on your side. This means you can invest in quality, stylish garments that last you years, like the leather jacket Goldblum is sporting in the above photo.

Additionally, Goldblum is a master at picking the perfect fits and reincorporating minor details across his entire outfit to achieve looks that seem perfectly assembled.

Notice how the longer-than-normal collar on his shirt seems to reference the shape of the collar on his jacket, and how the length of the jacket’s sleeves is perfectly suited for his arms. This attention to finer details sets his outfits apart from the rest.

By focusing on simple, tried-and-true garments made with premium quality and exceptional fit, you’ll be looking both amazing and totally age-appropriate.

In Your Sixties? Try This Look:

(photo via @njp147 on Instagram)

For guys who are entering their sixties, especially if you’ve maintained a relatively slim physique, I’d recommend going with more casual, comfortable items made from premium materials and with a great fit.

photo via @njp147 on Instagram

photo via @njp147 on Instagram

A lot of the fashion I typically see styled for older gentlemen online tends to err on the side of formality, introducing garments like vests and ties into the majority of widely shared fits. There’s nothing wrong with these garments -- in fact, in many other cases, I love them -- but they’re a far cry from what I would consider to be “daily wear”.

Instead, I think moving away from the sorts of oxford shirts and narrow-toed boots I’d recommend for younger people toward styles that are simultaneously casual and sophisticated is a much better look.

In this example, the expertly fitted overcoat adds some slight formality to an otherwise casual look, creating an impression that screams confidence and wisdom.

Focusing on the details -- immaculate leather boots, nice watches, and built-to-last outerwear -- while letting the fit do most of the talking produces a look that’s understated, refined, and applicable in almost any everyday situation.

Ultimately, if you start with these examples, you’ll be able to put together awesome outfits that look totally cool no matter your age or personal sense of style.

Ready to find the perfect new addition to your wardrobe? Hellman Clothiers has you covered: drop by our store in Downtown Cincinnati or visit us online for a fantastic selection of leading American and European menswear brands.