Stylish Over 40

This is a guest post written by Style Crew ambassador, Eric Rodriguez.

At the ripe “old age” of 55, I can honestly say I wasn’t always “stylish”. Just a few years ago, I wore nothing but jeans, graphic t-shirts, and motorcycle boots. That’s not to say that this classic look isn’t considered stylish, but I can say the way I wore them was definitely not. My pants were too long, and my t-shirts were worn out. A few years ago, I purchased my first hat — a very dapper homburg.


Upgrading your look at the age of 40 or older can be a bit daunting. You don’t want to dress like your father and you definitely don’t want to dress like you’re still in a college frat. There are 3 main things you definitely need to keep in mind when striving to look stylish. What you need to focus on is having a proper fit, avoiding fads, and most importantly keeping it simple.

Watch the length

Proper fit, at any age, is always key to looking good, but as we mature ill-fitting clothes become incredibly less attractive. To combat this, avoid pants that bunch up at the bottom, short sleeves that reach your elbow, and long sleeves that are frankly too long.

Something as simple as having pant legs that are the proper length (slight break or no break) will go a long way to make you look stylish. Generally speaking, your clothes should be fitted, but not tight.

Avoiding Fads and Trends

Fads and trends are two different things. Examples of fads are wearing 20 beaded bracelets on one wrist or wearing jeans that are too skinny for your body. These should be avoided when you reach a more mature age (unless you’re a rock star like Steven Tyler from Aerosmith — that guy can wear anything!)

These trends may work for younger men, but on an older gentleman, they just look like you're either out of touch or trying too hard to hold on to your youth. Trends, which range from the current style of trousers, the width of your collar, the accessories you add on are what you need to stay abreast of.

Keeping It Simple

Keeping your look clean and simple is much more stylish than you’d think. A pair of dark wash jeans, white button-down oxford, a blue blazer, and a pair of loafers are more than enough to make you stand out as a stylish gentleman. 

Want to add a little flair to your outfit? Add a colorful pocket square or a tie. These simple touches will add some pop to your look and make you stand out in the crowd.

Finally, the main thing that will pull these 3 keys together is confidence. No matter how nice your outfit is, if you’re not wearing it with confidence, it will show. There’s nothing more appealing to people than a man with confidence.

Eric Rodriguez is a content creator based out of Brooklyn, NY focused on men's style. He enjoys food, watches and fashion and is an up-and-coming model, having been featured in several campaigns for various brands. Currently, he is an ambassador for Ash & Erie as well as Beckett Simonon, the shoe company. 

You can check out his page here: @ericrnycstyle

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