The idea of “dressing your age” often feels a little cringe-worthy, with the implication that certain sartorial choices are better left to younger demographics. The idea that older women shouldn’t have long hair, for example, tends to raise my hackles. Frankly, the older you get, the less people should feel the need to police what you choose to put on your own body. Unfortunately, society expects certain things from those who are considered “old enough to know better,” and unless you want to be on the receiving end of some serious side-eye, you should keep up with what that entails.

It goes without saying that men often get the easier end of the fashion deal. The choices are more limited than women’s and there are less expectations about what is and isn’t appropriate. However, there are occasions when the “dad uniform” of light-wash denim with New Balance sneakers and a cozy sweatshirt just won’t cut it. If you still work in an office, or attend social events that require anything other than athleisure wear, here are some tips to help. 

Fit is Everything

A tailor measures the width of the shoulders in a suitcoat on a mannequinNo matter what your age, the difference between “a guy wearing clothing” and a “sharp-dressed man” is almost always tailoring. The fit of your clothing is everything, whether we’re talking about suits or jeans and casual wear. 

No one is expected to fit into an off-the-rack suit perfectly, and small tweaks can make or break a moderately-priced clothing item. By having a few of your items tailored — like pants, button-down shirts, and blazers — you can take your look to a higher level.

When it comes to casual wear, on the other hand, sometimes it makes more sense to find items that fit rather than tailor them. This may take a bit more effort than it did in your twenties, but it’s worth it. And — because you’re a man — you have the added bonus that once you find something that fits, you can usually buy it several in different colors and build the basis for an easy capsule wardrobe.

Quality Over Quantity

Mature man in sharp looking jacket with black shirt.
Well dressed mature man in stylish jacket and fitted black shirt.

Young men can get away with wearing torn jeans and vintage tees, because it’s assumed that they’re sleeping on a mattress without sheets and drinking cheap beer out of kegs. Older men, on the other hand, should exude a look that says, “I enjoy expensive wine and aged cheese.” 

You can achieve that look by having clothes that fit well (tailoring isn’t cheap, after all), and by investing in a few staple items. Many fashion blogs for men of this age emphasized the versatility of quality knitwear; for example, a sweater can be dressed up with a button-down underneath or worn casually with a pair of jeans. A quality sweater will last for years with the proper care, so it’s best to have a few in your regular rotation. 

If there’s a “statement piece” you’ve always wanted to have, now is the time. Buy the expensive leather jacket that can be worn with everything or spring for a cashmere pullover. The idea is that you are finally established enough that you can afford a few expensive pieces, and old enough to know how to take care of them so they’ll last.

Stay Current

If you’re at all worried about looking fashionable, then it is important to be aware of when things go out of style and update your wardrobe accordingly. Alternatively, you can try to curate a closet filled with items that are more timeless, and then you won’t have to waste another thought on fashion trends. Take jeans, for example. Opt for slim or straight-fit, and darker hues are safer (and slimming.)

Man with grey hair is smiling at the camera and walking with one hand in his pocket.Color-blocking is another easy way to keep things simple; try to buy tops in classic colors like camel, dark gray, navy, or forest green. It may seem boring, but it establishes a solid base for a capsule wardrobe so you can mix-and-match at will. The added bonus is that unlike prints, solid colors never really go out of style (although be careful of pastels or neons.)

Finally, go through your suits every couple of years and swap out the ones that look really dated. Try to get a suit that has subtle touches without going whole-hog into the latest fashion trends. GQ magazine advises playing it safe by opting for a trim, two-button jacket with wider lapels and well-tailored flat-front trousers, for example. 


shoes are displayed on stepsStop it with the tennis shoes, fellas. If you’re going to dress your age, then running shoes are for exercise. You can still wear comfortable shoes; they just need to be more stylish. You should aim for smart, casual shoes, like loafers, deck shoes, or even just sneakers in a solid color that don’t have a logo emblazoned across them. This rule applies to other accessories like hats or scarves as well; Go for less branding and more personal style. 

Final Tips:

By this point, you should know who you are and what you like to wear, and fashion is ultimately about being true to yourself. People can tell when you’re uncomfortable, but won’t give a fig what you’re wearing as long as you wear it with confidence. 

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