Casual Clothing for Men Over 40, 50, 60: 5 Rules for Clueless Guys


If you’re a guy over 40, there’s a high statistical probability that you have no clue about what types of casual clothes you should be wearing… the kinds of styles that will keep you from looking like an old dork.

Maybe you’ve just retired and you’ve finally had the chance to burn all your suits and ties. Or, maybe you still work, but you like to let it all hang out on weekends. Either way, I’m here to help you tweak your casual look, babe.

Of course, you don’t have to listen to me. All of the ideas in this article are just my opinions. There are no “fashion police” out there. However, I think you should keep reading and just… consider… that I might be onto something. (If you’re a Portland hipster, you already have your own set of fashion rules, so go away). The rest of you gents need to read this.

Clothing for Guys over 40, 50, 60 or Whatever

There are ways to look laid back without looking like a dufus, however you might need to get some new laid-back clothing for those times when you want to look casual, but polished… well, maybe not polished… but not like a 12 year old, either.
clothing for men over 40 50 60

No Baseball Caps over 40

Rule 1: Real Men Don’t Live in Baseball Caps

You think a baseball cap makes you look like a kid, but if you’re wearing a baseball cap, you might as well be wearing Mickey Mouse ears.

It’s time to man up and admit to yourself that you’re a mature adult and you’re probably never going to play left field for the Boston Red Sox. It’s time to put your baseball cap in the back of the closet. It’s time to be one of the big boys.

I don’t like telling you this stuff, but someone has to do it. Yes, there are times when a baseball cap is the right thing for a man over 40, for example, when you’re:

Playing baseball
Coaching Little League
Jogging… I mean really jogging
Playing golf
Washing your car
Watching a major league baseball game at Dodger Stadium
Playing poker with your buddies
Hanging out in your backyard
Watching NASCAR

The rest of the time, you’re going to look like a little boy who never grew up… a little boy who’s in a cranky old man’s body. And, if you won’t listen to me about losing the cap, promise me you won’t wear that bloody thing backwards.

If you want to keep the sun out of your eyes and cover your bald spot, you should consider wearing something groovy like a fedora or an English driving cap. Or, if you live Out West and you’re not in an overtly gay town, you might want to try a cowboy hat. Hey, almost any hat without a propeller will do.

shortsMature Men Don’t Wear Shorts

Rule 2: Adult Men Don’t Wear Shorts

Once again, I’m not talking about young hipsters and trendy metrosexuals. I’m talking about guys who are old enough to be totally clueless… guys who’ve never thought about style. Guys who let their mommies dress them, then let their first wives dress them, then let their corporations dress them, then just gave up and put on the easiest, most comfortable things in their closets after there was no one left to dress them.

I’m thinking of my husband. When I met him, he was wearing orange shorts. He was almost 60 at the time… and he’s lucky as hell that I didn’t turn around and walk out. If you look like the male model (on the left) in the shorts photo, you can wear shorts. Otherwise, save your short-pants ensembles for times when you are barbecuing in the backyard, hitchhiking along the North Shore, downing mass quantities of beer at NASCAR races, riding your bicycle, hiking the Cascade Trail, and things like that. Back in the olden days, wearing “long pants” was a sign of becoming a man. Let’s bring the concept back.

Rule 3: Beer Bellies and Bomber Jackets Don’t Mix

If you have a rotund, protruding stomach, you don’t want to wear anything that pulls in underneath your tummy. A bomber jacket has elastic at the bottom, so bomber jackets are a big no-no for most guys over 40.

A similarly bad look is a T-shirt (or any shirt) which draws in tightly under the belly when the shirt is tucked into trousers that are belted just under the man’s beer gut. (See middle drawing below.)

big belly
Cover Beer Belly with T-shirt and Overshirt

Rule 4: Overshirts and Long Jackets are Your Best Friends

If you look like you have swallowed a basketball, you need to cover your tummy. I don’t care what you looked like in high school or college. We’re talking “here and now”. Don’t be like the guy in the middle (of the above picture) who’s wearing a tee and a pair of jeans with a bright, shiny belt buckle in the worst of all possible places. Keep reading for better ideas.

When it’s warm out, you’ll have to suck it up and wear a cotton or linen shirt over your T-shirt like the guy on the right in the illustration. I’m sorry if you’re going to get hot and sweaty. (If you don’t like it, move to a desert island or have your stomach stapled, but don’t annoy the rest of the world with your poor diet and bad genetics.) The best shirt to use as an overshirt is a button-down style with a flat hem (not a rounded, shirttail hem), as in the illustration on the right. Make sure the shirt is big enough and long enough to cover your basketball tummy. Then, it’s up to you and your wife to decide whether you should button one of the buttons to finalize the camouflage.

When it’s warm, but not warm enough for a full-on jacket, the best overshirt is a denim shirt. You can roll up the sleeves if you want to be cool.

sleevesSleeves Too Long or Short? Go Hipster

When it’s cold out, you can wear a long leather jacket or a windbreaker or anything you can button or zip to hide your stomach. Make sure your jacket is big enough that it doesn’t pull through the midsection and draw attention to that big lump in your middle.

I’m not saying that you need to be uncomfortable. You can find drawstring sweatpants or jeans with stretchy waistbands to wear under your overshirts and jackets. I don’t think I’m being unreasonable.

Rule 5: Shoes Will Make or Break Your Outfit

I don’t know how many times I’ve been on a cruise or some senseless tourist excursion and I’ve had to get on the same bus as one or two older guys wearing black socks with white Nikes or white socks with leather sandals. Now, it’s bad enough that they were wearing shorts… but really… their footwear was the icing on the cake. Shudder. It was enough to make me hurl my croissants.

If you guys absolutely must wear shorts, please wear deck shoes or loafers or sandals without any freaking socks of any kind. I don’t care what your pals in Florida wear… I don’t care if you get blisters. It’s not my fault that you didn’t break your shoes in properly.

All of you older guys should dress like Europeans. Well, not like German tourists, but I know that asking you to dress like Londoners would be asking too much… if you grew up thinking that Europe and Epcot are somehow related.

What I am getting at specifically, is your white jogging-tennis shoes. There are sport shoes that are comfortable, but not ugly. Really. In Europe those white Nike things are called marshmallows… as in, “Why does that guy have marshmallows on his feet?” It’s a rhetorical question. We all know the answer… “because he’s a clueless American male with no taste.”

So, put on your blue suede shoes… or your Mexican Huaraches… or your old-school Hush Puppies… or go barefoot. Just don’t wear socks with shorts (unless you know what you’re doing) or ugly white Nikes with any activity that doesn’t involve hoops, bats, gloves, helmets, rackets, or wickets.

I understand that most guys are hopeless when it comes to fashion, but I don’t think I’m asking too much of you. It’s not like I expect you to learn to do the fox trot in stilettos… only women are that adept. We just want you to know that the coffee girls at Starbucks are not flirting with you… and if you’re wearing shorts and black socks, you’d better be standing on your freaking mega-yacht… or no one will be talking to you except the Chinese tour guide who expects a tip.

Guys need to learn that having witty reparte will get them nowhere if their everyday wardrobes don’t include a good dose of cool, casual style.

By: boomerinas

Source: Casual Clothing for Men Over 40, 50, 60: 5 Rules for Clueless Guys



This site uses Akismet to reduce spam. Learn how your comment data is processed.