Fashion for Men Over 40: The Ultimate Style Guide


As we all know, fashion is constantly evolving. We see new trends being introduced every season and naturally, people want to jump on board. But they’re not always good to follow, which is good news if you’ve become too lazy to stay updated. I’m looking at you, baby boomers. Trendy clothes may not be worth your time but keeping your appearance clean and respectable definitely is. 

This article will provide men over 40 with some style tips and a whole lot more. Without further ado, let’s start!

How Do Men Over 40 Dress?

Before we go over the do’s and don’ts, let’s do a quick background check on how men normally dress when they are over their 40’s. 

Older people tend to stick with their good ol’ reliables in terms of fashion. They dress with what they are comfortable with even if that look is no longer hip in the modern day. Ultimately, what matters to them is comfort over style. Some also go as far as wearing baggy and sometimes even worn-out clothes that have been with them over the years. Perhaps fashion is the least of their worries.  

What Not to Wear After 40

Especially if you are still trying to attract a mate at this age, you should maybe care a little about how you look. Really, any reputable adult shouldn’t let themselves go. Understandably though, you may not know the rules of the game. I got you. Let’s start with learning about what not to wear after the age of 40.

Don’t Wear Shiny Shoes With Jeans

A common mistake being made by dads and uncles everywhere is pairing their fancy shoes with their denim jeans. It gives off an overwhelmingly obvious contrast that makes your outfit distracting. Shiny shoes are designed for formal events to be worn along with a suit and tie. Jeans, on the other hand, are more of a casual, laid-back option. Combining those two is like wearing the sun as your shoes. It’s awkward and it hurts to look at.

Maintain a uniform look throughout your entire outfit. Jeans would look best when paired with sneakers, boots and loafers. If you are looking to wear those fancy shoes of yours then it is better to pair them with slacks. Always remember that the right combination makes for a great outfit.

Don’t Wear Cargo Pants or Shorts

We all know that cargos are so convenient with all those pockets, but when it comes to aesthetics, it’s a big no-no. It makes you look heavy and people might strike you as someone with poor fashion taste. If cargo shorts are long enough to cover your knees, are they even shorts at all? It looks awkward and unflattering, to say the least. 

Another thing is that cargos are bulky—literally and visually. The amount of pockets ruin the balance in your outfit, overpowering your top as the focus redirects to the chuck load of compartments in the lower area. Plus, having a lot of items inside them makes your pants heavier resulting in them being pulled even lower. In cases like these, it’s better to invest in a bag, which is also something that can elevate your style.

Don’t Wear Henleys or Deep V-neck T-shirts

Showing off your man-cleavage is a thing of the past. Young people might be able to pull this off, however, especially if they are fit. But as a man of age, you might not have those same bodily features that you had back in the day.

With this being said, this rule might not apply to everyone. We see a lot of people in their 40’s still maintain their buff shape through the years. If you are one of those people, then a henley still might look good on you. Although you must always avoid wearing those deep v-neck shirts no matter what because they just look ridiculous. We suggest sticking with the more traditional v-neck shirt.

Don’t Wear Too Much Jewelry

They’re not lying when they say that less is more. Yes, flashy looks may currently be a thing at the moment, with all those celebrities flexing their bling and their heavy gold chains. However, for a mature man such as yourself, it is best to tone down and—as the kids say— keep it lowkey. 

You don’t need to shine to look good, keep things simple by wearing a watch and a ring. A basic rule of thumb to ensure a classy look is only wearing two or three accessories at most in order to keep everything balanced.

Accessories are supposed to spice up your look and add a bit of a personal touch. Wear too much and you’re a gold chain or two closer to channeling Mr. T, whose taste is definitely not what we’re going for. 

Don’t Wear Shirts With Large Logos on Them

Wearing these types of shirts makes you look like a walking advertisement. The worst part is that you aren’t even getting paid to wear them. This design is a marketing strategy by companies that are taking advantage of the fact that people nowadays equate labels with quality. A key reminder is to never purchase clothes because of their brand alone.

It doesn’t mean you should stop buying branded clothing, you could still nab a few Versace shirts if you want. Just always make sure to choose clothes that suit you well and keep branding to a minimum. Again, keep it simple. The attention should be directed at the outfit, not at the logo.

Avoid Unusual Haircuts

At your age, your hair would probably be the least of your problems, but that doesn’t mean you should stop trying to maintain it. I also don’t mean you go overboard and experiment with wild cuts either. I suggest you go for timeless hairstyles such as the side part or if you prefer the clean and conservative look, you could opt for the classic crew cut. Either way, we highly discourage mohawks or other experimental cuts. Trust me, leave those to the young. 

Fashion for Men Over 40

Now that you know what not to do, let’s proceed with getting to know what to do to elevate your wardrobe as a dignified middle-aged man. Get ready to boost your confidence and get a more positive outlook in general with these tips on how to stay on fleek, as the youngsters say.

Wear What Makes You Feel Good

The famous phrase “look good, feel good” should be in everyone’s mind when picking an outfit. You should always prioritize how you feel rather than worrying too much on how others might think. But in some cases where you need fashion guidance, asking for a second opinion also wouldn’t hurt and will probably help a lot.

 Just always keep in mind the basic rules, make sure the clothes you have are comfy and well-made, and lastly, remember to wear them with confidence. Your attitude also really sells the outfit, so wear what makes you feel like your best. 

Dress in Well-fitted Clothing

Understanding your fit is a key factor in looking good. Your clothes must not be too baggy nor too skin-tight. Instead, it must hug your figure snugly to achieve that perfect fit. A well-fitted suit highlights your body shape and makes you look professional and neat while a poorly fitting suit will give you opposite results.

By now, you should be able to know the perfect fit for your clothes. Also, a great way to up your style is to alter your clothing accordingly. It is always good to invest in experienced tailors that will fix your clothes and make you look good.

Sneakers Must Be Plain and Classy

In terms of footwear, sneakers are the best option because of their flexibility and variety in style. You could pair them with jeans, chinos and if done right, you could even pair them with business clothes! They don’t only make you look good, but they’re also very comfy and convenient to wear. However, the sneakers you should be looking for must be sleek, simple and stylish.

The best example for a quality pair of sneakers are the famous all-white Air Force Ones. This style remains a classic, they’re versatile, and they always look neat which is a big factor in elevating any outfit. If you’re on a budget, any all-white sneaker alternatives from other brands would do just as well. With that being said, avoid the flashy neon-colored sneakers or any other styles that stray away from the plain and classy theme.

Wearing a Watch All the Time

Watches, just like sneakers, are one of the most flexible types of accessory out there. It functions not only as a timepiece but also as jewelry. They are works of art that never go out of style and make you look elegant and suave. 

It’s great to have classic analog watches rather than digital watches as these types are flexible and timeless—no pun intended. Analog watches look good in not only business attire but also casual attire as well. It doesn’t have to be a Rolex, just go with an alternative but still high-quality classic analog watch and it would definitely up your everyday style.

Rock Those Shades

You can never go wrong with sunglasses. It makes you look more stylish by just putting them on. There are various types of sunglasses that could go with different styles so the possibilities are endless!

Make sure you choose the right type of eyewear for the style you are going for and also keep in mind the shape of your face. Wearing one will definitely give off that cool, laid-back factor and will upgrade any plain outfit. Aviators, for example, look good when worn with a suit and tie or even with denim, while cat-eye sunglasses are ideal for those with more adventurous tastes. 

Always Know What Socks to Wear

Shoes and socks always go together like hand and glue. It all boils down to which socks you should wear with a specific type of shoe. This is an important tip as making a mistake could ruin the outfit as a whole. 

Older men look better sockless or with foot socks with neutral colors when wearing loafers or driving shoes. This gives a casual look to it. Dress shoes on the other hand should always be paired with dress socks. Never wear athletic or crew-cut cotton socks with shoes other than sneakers, or else they would look out of place. 

Frequently Asked Question about Fashion for Men Over 40

What should I wear in my 40s?

It is recommended by the fashion police that you wear well-fitting clothes, plain-colored sneakers, and quality accessories. Plus, you should probably invest in a good tailor, too. At the end of the day, only you know what’s best for yourself though, so wear whatever makes you feel good.

Are there any clothes over 40 you shouldn’t wear?

There are a few clothes that people over 40 are discouraged to wear. Cargo shorts and pants, for example, are impractical and do not look good at all. They alter your shape in a weird way and nobody really needs that many pockets. Shirts with huge logos are a no-no as well unless you prefer to look like a walking billboard ad. Keep things simple and go for good shirt designs rather than branding.

What can a man do to look good at 40?

Having regular exercise, maintaining a good diet, and good hygiene are just some of the ways a man can look good at 40. But besides those, having great style and wearing clothes with confidence is the secret ingredient to looking good. Just make sure to invest in great-quality clothing and well-fitted shoes. Overall, taking care of your health and well-being is the key to looking your best at 40, and that includes your choice of clothing. 

A Final Word From The Trending Man

As repeatedly said throughout the article, simplicity is key. Keeping things lowkey is the best way to stay chic and timeless. Going for a casual shirt along with an analog wristwatch, jeans and white sneakers will give off an effortlessly cool vibe. You are 40 now, you’ve done so much, so there’s not much pressure to prove yourself. At this age, life may throw problems your way, but it’s always better to wear nice clothes when facing them. 

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