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Style advice

How to Dress If You’re Over 40

Ever wondered why older men seem to dress better while others seem to dress even worse than when were younger?

It’s a paradox, which has nothing to do with age and everything to do with each individual’s mindset and life choices.

When we’re young, we’re much more inclined to take care of our looks. After all, we’re energetic and in a permanent competition to attract the opposite sex.

But after a certain age, something amazing starts to happen. Some men become more and more comfortable, while the rest go into the opposite direction: they feel life passing them buy and, in an effort to look and feel their best, they start to learn everything there is to know about style.

If you’re in the first category and you’re looking to jump into the second one, you’ve come to the right place.

Style is for everyone, no matter how old you are. Its rules are timeless and, more importantly, they are easy to read and apply. So let’s help you find a style that suits your age while avoiding to look like a youngster or like someone who’s trying too hard.

Avoid fashion fads

Older men are often associated with certain qualities, such as wisdom, stability and class. Which is why the last thing you want to do when improving your style is to embrace fashion.

Forget funny t-shirts, forget what you see on the runways, even if some of the things you see there look like something you’d like to try. Start dressing a little more formal.

The absolute first thing you want to do is to start wearing shirts. Avoid t-shirts with logos or funny messages on them, such as this one:

Please, no matter how old you are, NEVER wear something like this! Take a look at the Very store to find some great clothes, not too flashy, at affordable prices – perfect for someone in his 40s.

If you’re already hooked on shirts, the next step is to make sure they fit you properly. A lot of older men wear over-sized shirts, most likely because this was cool when they were young.

Now I’m not advocating you should go for slim fit or, heaven’s forbid, skinny. Regular fit is fine for guys over 40. In fact, regular fit is cool for guys in their twenties as well.

I strongly suggest you take all your shirts and pants to the tailor and have him or her make adjustments to all of them. You’ll look a lot younger by wearing clothes that fit, and you don’t even have to make a new purchase!

Leave the past behind

Ok, I bet you’re probably a little confused. On one hand, I told you you shouldn’t wear all those baggy clothes that were trending when you were young, while, on the other, I told you that style is timeless, that it has old rules that still apply today.

Both of these pieces of advice are true. The thing is, you have to be able to distinguish between what looks good in terms of style and what doesn’t.

I already told you that baggy clothes are a no-no and that all your clothes should have a regular fit.

But that’s just the tip of the iceberg. You have to know each and every clothing item that is considered timeless and cool, at any age. So here’s a small list to get started:

– sport coats
– chino pants
– classic leather jackets
– v-neck and roundneck tops
– cardigans
– overcoats
– and, of course, the omnipresent shirts

You can assemble an entire wardrobe with just these items and, if you make sure they all have the right fit, you’re already ahead 90% of all men your age.

Don’t be afraid to accessorize

Older doesn’t have to mean boring. Watches, scarves, sunglasses, pocket squares, ties, hats, caps and so on – these are all excellent for when you’re 40, 50 and beyond. SO go ahead, stop being afraid of what others might think and try a few of them on.


Don’t wear your work clothes outside of work

If you’re used to wearing a suit every day for work, you have to learn to relax your outfits when you’re NOT doing your job. Try something a little more casual, such as chinos, jeans, leather jackets. This isn’t something specific to men over 40, it’s something every man out there has to keep into account.


Instead of wearing your best office suit to dinner, why not couple a blazer with a pair of modern, straight leg jeans, a simple dress shirt, and a pair of casual boat shoes?

Blazers and sport jackets also work fine (I’ve also written an article about those two – please read it).

Keep it simple

Don’t try to be very flashy. Leave the loud patterns and flashy ties to the young generations.

For instance, wear simple designer jeans instead of rugged ones.

Notice how the pair of black jeans below fits the person perfectly. Notice especially the bottom of the jean and how it “follows” the legs.

Tip: try to shave often… a beard will make you look older.

George Lavas

George is dedicated to fashion and style for men. Based in the UK, George enjoys writing about lifestyle and fashion from both sides of the pond. George created BeStylish.org to help readers create a strong sense of style with minimum effort believing that everyone can look and feel good, all day, every day.

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