How to Ace Fashion for Men Over 40

Fashion for men over 40 shouldn’t be complicated, but we all know it’s not that simple, either.

Based on experience, forty-somethings tend to fall into one of the following categories when it comes to fashion:

  • Those who know what they’re doing
  • Those who try to cling to their younger years by dressing like a 25-year-old
  • Those who simply DGAF about dressing well

Ironically, men who are in their 40s tend to be more successful and confident than those who are younger than them. They have every means necessary to invest in good clothes. They also have that unmistakable glow of quiet confidence that can only come from multiple decades of life experience.

In short, if you’re over 40, you probably have enough money and self-assurance to dress impeccably. Unlike when you were a broke young man who’s still figuring things out, there’s no reason for you to dress sloppily this time around!

Different rules for different decades

Notice how clothes, shoes, and accessories typically associated with older men are getting so popular lately? Dad jeans, grampy fanny packs, dad sandals… And of course, who could forget the “dad shoe” trend that took the fashion world by storm a couple of years ago?

But no matter how in-demand these pieces are in mainstream fashion, the fact that these terms still carry negative connotations remains. Fashion and style can be funny like that. A 23-year-old male model wearing dad jeans and chunky sandals (and with socks, nonetheless!) is seen as cool and trendy. An actual dad wearing this combo, however, earns the reputation of being a terrible and uninspired dresser.

Remember, the “dad shoe” trend is also known as the “ugly sneaker” trend for a reason.

That being said, when it comes to fashion for men over 40, it’s a good rule of thumb to stay away from trends, especially those that explicitly make a caricature out of old-age fashion. Here’s the number-one rule: Classic, well-fitting outfits are always a great choice. Check out more tips below!

Fashion for men over 40: Our top tips

Dress like an adult

When we say dress like an adult, we don’t mean dress old. We mean dress sensibly so it doesn’t look like you’re trying incredibly hard to look like a youngster. 

So no matter how cool graphic tees seem to you, it’s best to retire them and stick to classier alternatives. The same goes for other items that are prone to screaming juvenile, like skinny jeans, ripped pants, and varsity jackets.

That said, the best way to refresh your style in time for your 40s is to edit your existing wardrobe accordingly. Let go of pieces that aren’t flattering anymore, and replace them with high quality classics that are both stylish and versatile.

Comfortable doesn’t have to mean oversized

Lots of men in their 40s and beyond fall victim to ill-fitting clothes. They either wear clothes that are too snug (likely from their younger, fitter years), or seek comfort a little too much by going for oversized pieces. 

But one thing you have to remember is that comfortable doesn’t have to mean loose and shabby. Well-fitting clothes will give you that perfect balance of comfort and style. Granted, finding perfectly-fitting items can be harder when you’re older, especially if your body has changed a lot since your 20s or 30s. However, it’s nothing a competent tailor won’t be able to fix.

The devil’s in the details

Curating your wardrobe to suit this new stage in your life requires you to pay attention not only to the general styles and shapes that work well with a man in his 40s, but also to the tinier details that make a big difference.

For example, regardless of the jean cut you pick, dark wash denim will always look classier than light ones. Plain or muted t-shirts made of thicker material will also go a long way compared to statement tees with loud colors. And when it comes to shoes, we recommend sleek silhouettes made of leather or suede over bulky canvas or mesh sneakers.

No, it’s not about blending in

As much as we preach about the virtue of going for classic pieces, we also want to stress that it’s not about blending in with the crowd. In fact, separating yourself from the herd is probably more important in your 40s, but remember to do it in a tasteful way.

Play it too safe and you risk looking like every other boring middle-aged man in America. Aside from wearing only well-fitted, high quality clothes (which will help you stand out in a sea of forty-somethings in ill-fitting suits), you can also substitute more “expected” pieces with something unique but graceful. For example, instead of wearing the usual long-sleeved shirt tucked into slim-fit pants, you can opt to wear a more casual linen top untucked — giving you a more relaxed but still put-together look.

Get fit

You can buy the most stylish clothes in the world, but nothing will make as big of an impact on your overall look as a fit physique. Make sure you’re making time for your fitness routine, ideally at least three times a week. And of course, fitness is mostly about eating the right food and nourishing your body from the inside out. Losing weight tends to get more difficult the older you get anyway, so you might as well establish a solid routine now if you haven’t already!

The bottom line

No matter what your age is, well-fitted classic pieces will always be a great investment. But while loud, creative clothing can be fun in your 20s, wearing them two decades too late can result in fashion mishaps. 

If you’re over 40, fit and proportion are king. So is dressing appropriately. With the tips above in mind, you’ll be able to curate an envy-worthy wardrobe that will highlight your best assets while making the entire process look impossibly effortless. Best of luck!