How To Dress Appropriately and Stylishly in Middle Age

My approach to fashion is about quality over quantity, having both style and substance. Style equates to confidence. It doesn't have to cost a lot of money either. It can be simple, clean, iconic, and sharp. Make the effort to make it look effortless. Develop a uniform, an understanding, and an appreciation for what works for you. 

Your style should get better with age. I’m 48 and quite frankly there are some things I can still get away with and many that I can’t. The ship hasn't sailed on looking good though. In fact just the opposite. 

However, if your gym clothes are still from college or HS then Houston, we have a problem. 

If the rest of your wardrobe is either chasing your youth in an effort to still look cool or so antiquated and ill-fitting that you look ten years older, don’t sweat it. It’s never too late to develop great style. 

 

Here are some tips and things I recommend for nailing your personal style. 

Keep it simple. Simple doesn’t mean boring. The best designers and best dressed men in the world keep their personal style simple. 

Fit matters. Even more so than the brand. I see lots of guys wearing very expensive top brands and look terrible because the clothes don’t fit them well. Find brands and items that fit your body. 

Go to a tailor and get all of your measurements done. Chances are you've been wearing things way too big. More than likely when you start wearing clothing that fits you well, it's going to feel a little bit tighter. It'll take a little getting used to, but it's worth it. 

It doesn't matter what's in, stylish or trendy. Clean, classic and updated basics with a great fit will always be appropriate and in style. 

Try things on. See what makes you feel good. Do you like collar shirts or do you prefer T shirts? Do you like V necks (And if you do, make sure they’re high V necks and not the cheesy chest hair bearing type) or do you like crewnecks? 

Look at fit guides. Are you short? Are you tall? Are you round or thin? What does the brand recommend? 

Look at magazines and websites and see how guys your age are styled and how they look. What do you relate to? Find a couple of guys whose look you like and emulate it. Do you like color? Do you want to keep it more monochromatic? I happen to like monochromatic, because it makes things very simple. 

I’m on the shorter side at 5’9 so I like joggers. I prefer things a little bit more fitted to make me appear longer and taller. 

I basically wear black, gray, brown and navy. I stay in the darker color palette because I sweat a lot and don't want to see sweat marks through my clothes. 

I prefer crewneck t-shirts to V necks and almost anything to a collar. So when I'm wearing light weight sweaters or anything, they're typically a crewneck and I will wear anything I can to get away from having to wear a button down shirt. In today's world, a perfectly fitted, high quality, crisp t-shirt with a great pair of slacks or joggers and an impeccable pair of shoes, watch, belt and sunglasses can get you in almost anywhere. 

Just as you can't out train a poor diet, you cannot out dress poor grooming, or health. If you want to look your best in clothing, be in shape and be impeccably well groomed. 

Start with the basics. I know when you're shopping online it can be overwhelming. Also, you don't know how things really fit and there are too many choices. Order a few things at a time. Use the Fit Guide and if you know your measurements. This will help you tremendously. 

If you like color, go for it. But, be responsible with color, particularly as you get older, follow the golden rule. Keep it simple. Don't mix a bunch of wild colors together. 

Use a tailor. I use a tailor on everything from T shirts to pants to loungewear, jackets, everything. A good tailor will make any item look better on you and like you paid a lot more for it. And, it’s not expensive. It costs me $10-$15 to get most items tailored. One tip - wash items first before you tailor them. A lot of times they’ll shrink and you don't want to over tailor or make something too small/tight/short to wear. 

My personal uniform is incredibly simple. For every day it’s Rhone Joggers and Element Tees. Rhone makes the best underwear and socks as well. I wear Greats brand sneakers and I can wear this out to almost any meeting. I can put a blazer over it, substitute a Reign Hoodie, or put a vest over it. I can dress it up, I can dress it down. 

Keep the accessories to a minimum. A great watch, belt and sunglasses. 

Looking good extends to the gym. You can and should look great when you train. The Mako and Versatility Shorts are my go to training shorts. If you're on the shorter side go with the seven inch. They’re cut perfectly. I prefer shorts with the liners in them, because I don't have to deal with underwear, particularly when I travel.

The Reign Tech Shirts fit me perfectly and I move very well in them. I tend to stick to the darker colors as I said, because I'm not that into showing visible sweat and I sweat like crazy. Again if you want to do color. Keep it on the top or the bottom, but not both. 

Ditch the high socks. The old school gym socks, RHONE makes incredible low cut socks.

Alright, let’s recap: 

  • Develop a personal uniform.

  • Nothing cheap or ill fitting. This doesn’t mean you have to spend a ton of money either.

  • When in doubt, go darker. It's more age appropriate. 

  • Get your measurements taken. How your clothes fit is as important as the brands you buy.

  • Loungewear counts! 

  • If you don't feel great, confident and at the top of your game in it, don't wear it.

  • Grooming matters. Can’t out train a bad diet, can’t out dress poor grooming.

  • Get in shape. The better shape you’re in the better anything you put on (or take off) is going to look.

  • Dress for your age. In your 40s/50s don’t dress like your teenage son or like a grandfather.

  • Package it up. After you've bought your splurge investment pieces and basics, your well-curated wardrobe deserves to be coordinated for maximum efficiency and effectiveness. Toss anything that no longer serves you or fits into your personal uniform. 

  • Accessories: he right watch, glasses, shoes and belt can elevate or ruin any outfit; Same principle applies here: Simple, iconic, quality. 

All the help you need in terms of looking appropriate, looking stylish and looking perfect for your age is out there. You can find it in The Pursuit, you can see it on the RHONE site, GQ, Esquire, Men's Journal, Men's health, etc. Just be observant. If your kids are really into it, it’s a hard no for you. 

In Health & Style - 

Greg

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