Attempting to unpack what it means to dress your age in a casual context

I’m coming up on a birthday next month. And it’s not just any birthday: it’s the big one. That’s right, believe it or not – and I certainly hope you don’t believe it – in a couple weeks I’ll be turning 40.

“Dressing your age” is a topic that I’ve gotten a lot of questions about over the years and it’s a topic we’re planning on tackling in a bigger way in the next month or two. But as I’ve been thinking about it recently – how can you not when you’re turning 40? – I’ve realized that there are some situations where it’s really pretty simple and some that it’s more difficult.

dress like man casually

Regarding the former, it’s really easy to put a suit on and look like an adult. Of course, there’s a lot that goes into making sure it looks right. Is the suit tailored properly? Are your trousers the right length? Have you tied an acceptable tie knot or a ridiculous one? But when you get down to it, as long as you’re paying attention to some key details, it’s pretty easy to suit up and look grown up.

dress like man casually

| WEARING | Jacket c/o Reiss, Levi’s sweatshirt, Brooks Brothers shirt, Ring Jacket pants, Piaget watch, Common Projects sneakers | PHOTOGRAPHY | by Rob McIver Photo

Casual wear is a completely different story. How to do you take universal casual staples such as a t-shirts, denim jeans, sweatshirts, et. al and make them “age appropriate” when they’re worn by all ages pretty much across the board? It’s a question that’s honestly a little difficult to answer.

Does Alessandro Squarzi, who is in his early 50s, not look like the perfect early 50-year-old in his trademark denim jeans and olive-drab military-inspired jackets and waistcoats? Even our usually-suited dapper Italian friend Giampaolo Alliata knows a thing or two about rocking a leather bomber, hoodie, jeans and white sneakers. So as much as I’d love to tell you that there’s a formula you can follow, I’m afraid there really aren’t any hard and fast answers.

dress like man casually

However, what I can tell you is how I personally approach this issue. And, to be honest, it’s tough! What it really comes down to for me is exactly the same as what I was talking about in the beginning in terms of suiting up – you’ve got to pay attention to the details, especially fit.

The easiest way to look like a 40 year old who’s still living in haze of nostalgia for his college years is to have baggy (or worse, carpenter) jeans or chinos that are pooling around the ankles. Grow up and get them tailored or do some due diligence and spend some time finding a RTW option that works for you.

Beyond that, I have two other pieces of advice to give. The first is to invest in at least one classic casual jacket. If you’re going to have just one, make it a leather bomber – though don’t discount other versions such as corduroy, wool or suede.

Next, have a pair of sneakers that you keep looking nice. Maybe during your early to mid-20s hipster days, it was de rigueur to have dirty Chucks, but if you want to look like an adult, it’s important to keep those sneakers looking clean.

dress like man casually

Chime in: What does dressing casually like an adult mean to you?

Thanks for reading.

Stylishly Yours,

Brian Sacawa
He Spoke Style


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