Clothing and style

How to Dress Well In Your 40s and 50s (and Beyond)

If you’re an over 40 years old male and want to dress better than most 20-somethings, this post is for you!

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@ericrnycstyle aging like top shelf whiskey

First off, a disclaimer: despite “old man style” being in the title of this post, being over 40 doesn’t mean you’re old.

Also, being an older guy doesn’t mean you have to dress a certain way.

The way you dress is influenced by your lifestyle. What kind of work do you do? Do you follow a specific dress code on a daily basis?

So it wouldn’t make sense to say “men over 40 should dress like this…” and “men under 40 should dress like that…”.

But for most older men, age does play a role in personal style. You don’t want people to think you’re trying to look younger.

This is even more complicated for older guys with non-average builds (like shorter guys). One of the big issues you run into is the difficulty of finding clothes that fit.

Unfortunately, many brands that really focus on fit are targeted at younger men – or even teenagers.

A sample of H&M’s Instagram feed (and overall aesthetic)

For example, brands like Zara, H&M and ASOS tend to carry fitted clothing in smaller sizes. But are these brands really appropriate for men over 40?

If you’re an older gent and want to wear “younger” clothing, that’s totally fine! But if you want to dress in a more traditionally “age appropriate” way, this post will help.

First off, here’s a quick list of specific things to avoid, assuming you don’t want people to think you’re trying to look younger:

  • Distressed jeans (any kind of tears, fading or stains)
  • Graphic tees
  • Sandals or flip flops
  • Baseball caps (at least worn backward)
  • Clothes with large logos or obvious branding
  • Hooded sweatshirts
  • Denim shorts
  • Basketball sneakers / tennis shoes
  • Overly trendy hairstyles
  • Tight fitting clothes
  • Baggy clothing

Come to think of it, most men should avoid most of the things on that list. But some things (like super distressed jeans) are especially inappropriate for older, more mature gentlemen.

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