1. Do Not Try to Dress Like a Young Man
Styles that play off the insouciant look of youth — tousled hair, untucked shirts, undone shirt buttons, and so on — don’t wear well on an older man. It makes you look like you’re trying too hard to pretend that you’re young.
Does that mean it’s time to switch to high-rise sweatpants and orthopedic loafers? No. But you shouldn’t be sporting cherry-red chinos with the cuffs rolled up to show off your ankle tattoo, either.
2. Find Brands That Suit You
Don’t be afraid to change brand loyalties as you age, especially once you hit the point where your body is changing in size and posture. Things that fit well when you were younger may stop working as you age.
If you don’t have a couple of good, reliable brands that you know you like for things like dress shirts and slacks, swing by an upper-end menswear store and ask the staff for some recommendations. Try a few different brands on and see which ones sit the best on your body. You don’t have to actually buy anything — just start gathering a few brand names that work well for you.
3. Be Aware of Societal Expectations
Stereotypes are, unfortunately, quite real, and they can have an effect on your life.
The good news is that you can dress to control the stereotype people see.
If you’re not really taking care of your appearance, it’s easy for an older man to look like a “senior citizen” — shuffling along to the early bird special at Denny’s; forgotten and inconsequential.
If you’re looking sharp, on the other hand, people see the gray hairs and the good clothing and automatically think of leadership, wisdom, and maturity.
4. Own the Latest Technology
This isn’t quite a menswear issue, but it sort of falls under the category of accessories, and it’s important: make sure you’ve got a good smartphone, and that people see you using it. Other small consumer electronics like tablets are good, too — the point is to make sure people see you with the same access to the digital world that they have.
It’s a way to visually show younger men (and women) that you’re a part of the same community. You don’t even really have to use it for much, in most cases — unless you’re applying for a social media job or something like that, just having the phone is enough to convince people that you’re still with the times. Whether you’re actually checking Twitter every five minutes or not doesn’t matter, so long as they know you could if you wanted to.
5. Experiment with the Classics
To avoid looking stuffy, you do want to develop your own personal style. That means adding some unusual elements and experimenting a little — but do it like an older gentleman.
When young men want to stand out they generally turn to counter-culture symbols: long or spiked hairstyles, tattoos, deliberately low-formality clothing, and so on.
For older men, look toward classic but underused style elements instead. Throw on a fedora or a Panama straw hat, swap a polo for a Guayabera, wear a light plaid suit as social wear on the weekends — things that nod toward traditional menswear, but that you don’t see on a lot of people these days.