Dressing Like An Adult: Casual Edition

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And make sure your pants fit correctly. That means getting them tailored and knowing what the right length should be.

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Also, have a nice pair of sneakers that you keep looking good at all times.

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A grey sweatshirt is one of the ultimate versatile casual staples.

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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Chime In

  • Nathan

    Brian, I noticed thecuff in your pants on this post which is something you don’t seem to do often. What are your rules or guidelines you follow when doing so?

    • http://hespokestyle.com/ Brian Sacawa

      Good question! We’re working on that article as I type this!

  • Tom B

    Great article and topic, once again! Living here in the sauna otherwise known as the Carolinas, I’d love to see a summer edition of this article. Or, simply – how to look decent in shorts. Any tips beyond the top obvious (no cargo shorts, mid-thigh and fitting well, wear a decent shirt, no blazer)?

    • http://hespokestyle.com/ Brian Sacawa

      Hey, Tom. Going to have to wait until next year for the summer version! We’re already shooting fall content. Give the Style Guide a look and search for summer. Glad to be of service, as always.

  • PeterK1

    I started thinking about this around my 50th birthday..

    A crash on my bike meant needing a new pair of glasses. So I asked myself, what glasses suit a 50 year old guy?

    From there I went on to upgrading my clothing to a better fit (I had been buying it to big) and more classic styles. My typical casual wear would be jeans, a henley and my black leather bomber (or shirt jacket in warmer weather) and a pair of suede brown sneakers.

    • http://hespokestyle.com/ Brian Sacawa

      Thanks for chiming in, Peter!

  • David J. A. Foster

    I recently turned 30, and I make an effort to “dress like an adult.” For me, that means casual wear is a flannel or oxford shirt, chinos and if it’s cold, a sweater. I think responsible adults – at least, in an urban setting – should not be wearing jeans or t-shirts. Remember, jeans were created as clothing for farm labour.

    • Joseph Padilla

      Just my two cents: If you think that “responsible adults” shouldn’t be wearing jeans or t-shirts, you are very much missing out.

      For me, there’s nothing like a slim-cut dark indigo or black jean that makes me look put together in a casual setting. Jeans have come a LONG way from farm labor wear. As for t-shirts? There’s nothing like a well-fitted tee, especially a henley, in a neutral color. And if you put it under, say, a leather jacket or bomber, all the better.

      As someone who is already thirty and a half years old, I’ll say that a life without t-shirts and jeans is a life of self-deprivation from the little joys of life.