Again, your 40s and 50s aren’t old. We’re using the term incredibly loosely. However, since your closet is a living, breathing, ever-changing being, why not start early? Here are some things to consider.
Find Your Older Gent Look (Or Looks)
I live on the Upper East Side of Manhattan. When I get up early enough to see the early bird special crowd, I see a lot of chic Brooks Brothers blazers paired with vintage Ivy League baseball caps. I have a feeling that’ll be me if and when I get to be a senior citizen.
I’m not saying to box yourself in. But you probably already had a style going by the time you were in your late ‘30s and into your early ‘40s. What is the more grown-up version of that?
If you’re a rocker type, maybe instead of ripped skinny jeans and leather platforms, you pair vintage band tees with some Americana. If you’ve always been a highly-formal suit guy, you’ve earned the right to ease up a bit. Throw some man-of-leisure components into your outfits, like cardigans, loafers, or sun-faded vintage baseball caps.
Those are just a few possibilities, but you’ll have to figure your path out for yourself. Fortunately, we’ve got some visual examples momentarily to give you inspiration.
Consider Your Lifestyle
Often, style and practicality go hand in hand. If you couldn’t figure out what your older gent look is, then your lifestyle is a great north star. Perhaps you’re a logger or construction worker. Or maybe you were and now are retired. Workwear, as a category, is a menswear classic and staple. The jeans, cargos, denim, and utility outerwear that you wore to work can easily be incorporated into classic, casual combinations.
If you’re a country guy, perhaps you live on a farm. English countryside style is a good place to find inspiration. Of course, you can’t go wrong with suit separates, military wear, and nautical pieces. So, how do you turn these practical pieces into fashionable, flattering garments? Well, it’s all in the fit.
Choose Your Fits and Cuts
Okay, so I’m a proponent of really just wearing what you want. But, as an older gent, particularly if you’re one of modest height, you’d do well to just go with a classic fit that accommodates your body type. Moreover, when the fit of your clothes is timeless and flattering, you can basically get away with any personal style. Classic fits range from slim, not skinny, to relaxed, not baggy, but clean-lined. The latter means that if you go for looser-fit pants, say slacks, the waist should be just a bit higher. The difference between practical workwear and stylish workwear is the fit.
Imagine big-pocketed cargo pants that’ll fit the gear you need on the worksite. Now imagine a slimmer version paired with a button-down and an unstructured blazer. The latter is an example of how fit can transform your lifestyle pieces into everyday style.
You Don’t Have To Let Go of Everything From Your Youth
Listen, if you’re over 40, you should probably get rid of your distressed skinny jeans. Do the same with any t-shirts with cartoon characters on them and most graphic tees in general. Baggy hoodies and brightly-colored high-tops aren’t a great idea either. That is, all things considered. However, you can usually get away with more youthful things if they’re subtle, well-fitted, or if they’re vintage. I already mentioned sun-faded baseball caps and classic vintage tees. A well-worn, patinated leather jacket is another example. You just have to contextualize them and balance them out with more neutral pieces.
Just because you’re at an advanced age doesn’t mean you can’t be yourself. I used to love wearing primaries, but as I got older, my stylist recommended I go for more grown-up versions of them. Burgundy, crimson, and oxblood instead of red, dark navy or slate blue instead of overly bright blues, and mustard or honey instead of yellow. Relatedly, go for sneakers that aren’t too sporty or too fashion-forward. Models like the Nike Internationalists or Waffle Nav, in neutral colors, are retro but relevant. Anything slightly retro eases the inherent youthfulness of pieces like sneakers because you’re sort of hat-tipping to your generation. You’re not trying to keep up with the kiddos. Basically, you want to find more mature expressions of the styles you liked at younger ages.
Always Follow Dress Codes
You may have thought it was charming to wear patent leather Air Jordans to your prom. But regardless of your personal style, anyone past 40 needs to invoke his inner gentleman when needed. If a host, whether they’re a friend or an establishment, was kind enough to invite you to an event, you want to be respectful. Dressing the part is part of that respect.
Embrace Your Changing Hair
Don’t be ashamed of going gray or balding. Both can look absolutely distinguished. Yes, the hair plug industry has come a long way. And yes, with the right hairdresser, you can get a natural color on you (if they don’t color match your eyebrows, find another hairdresser). However, from what I’ve seen, only the very best of the best treatments ever come out looking good.
I’ve seen wildly wealthy people come out of super expensive treatments looking unconvincing. And we don’t all have access to the best of the best. Embrace your changing hair with dignity, go for flattering cuts, and take care of your beard.
Quick Effortless Style Hacks From Experts
Hey, don’t just take my advice. We at The Modest Man also crowdsourced some great tips from style experts.
Dark Colors Are a Safe Bet
John Galfano from 40 Over Fashion believes that dark, solid colors are one style tip that works universally. You don’t have to think about patterns and, as Galfano says, it makes you look more expensive. And even if you go for patterns, he recommends dark-on-dark compositions versus a dark fabric with high-contrast white stripes. Even as someone who prefers lighter colors, I fully agree with him. There’s a reason why darker suits are considered more formal than lighter ones. Even a black T-shirt looks way chicer and more intentional than a white one.
When You Aren’t in Dress shoes, Go For Simple Leather Sneakers
I mentioned this earlier, but I’m glad the brilliant fitness guru Dr. Bret Hoffer cosigns. Hoffer advises avoiding actual running sneakers and going for minimal leather sneakers. Go for one in plain white and one in plain black. That alone will make your T-shirt and jeans outfit look that much more grown-up. You might go for low-tops or high-tops. High-tops look a bit more youthful, and low-tops slightly more versatile. You can even wear a pair of white or off-white minimal leather sneakers with a suit.
Be Aware of Trends, but Anchor Your Closet in High-Quality Classics
Jeff Morgan, or The Style OG, recommends investing in classics. Get some good dress shoes, a blazer, and a nice pair of jeans that you’ll wear before ever wearing them out. I agree with this quality-over-quantity approach. However, don’t completely ignore trends. By paying attention to them, you can add slight, subtle changes to your outfits that aren’t consequential in the long run. He says, “Adopting the subtle fluctuations of silhouettes, colors, and small details will have you looking well-seasoned and in season.” Knowing the trends isn’t about blindly following them. It’s about expressing your personal style and making sure you aren’t irrelevant looking.
Old Man Outfit Ideas
Conclusion: Old Man Style — Not Just for “Old” Men
I’ve always admired the way my grandfather dressed, so perhaps I was an advocate for “old man style” at an early age. Now you know that with a few tips, tricks, and hacks, your style can age like excellent whiskey. Even more, you can enter your prime years a more sartorially together version of who you always were and are. You can even take elements of your youthful style with you. Did I say prime years? Yes. If you’re over 40 and reading this, I fully believe that men and women are at their best past 40 and get better and better even after that!
