A Man’s Guide to Dressing Sharp and Casual in His 30s

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A man’s wardrobe should undergo subtle shifts as he gets older and takes on different roles in life. To help you look great at every age, this year we’ll be offering guides to dressing sharp and casual in your 20s, 30s, 40s, 50s, 60s, and beyond.

In a man’s 20s, he does a lot of creating and experimenting with his career, habits, and relationships, as well as his style.

In his 30s, he starts to build and solidify the things he launched in the previous decade of his life.

While modern 30-something men aren’t always as solidly settled into adulthood as those in times past, it’s still a decade where guys are at least trying to pivot and head in that direction. You should largely know who you are by now — what direction you want to head, and, how you like to dress.

So this is a decade where you can start to build on the things you learned by experimenting with your personal style in your 20s. You’re going to improve the quality and fit of your favorite staples and cull your wardrobe into something befitting a man on the up and up.

Casual in Your 30s: Needs and Wants

As we discussed in the first installment of this series, a “casual” wardrobe isn’t necessarily short on formality — it’s simply what you wear outside of work for personal pleasure, whether that’s comfortable jeans or dapper suits.

What you wear when you’re just being “you” tells people a lot about you. It’s going to be one of the large determining factors in how your friends and peers perceive you.

So what should a man in his 30s be thinking about in regards to style, particularly when compared to men of other ages and generations?

  1. Fit

Unless you’re very lucky or very determined or both, your body has probably changed since you were 20. That’s not a bad thing, unless you’re fond of getting carded, but it is something you need to take into account when you dress.

The big three-oh is a good time to go through your closet and get rid of some old clothes. It’s a safe bet you’ve got some things in there that don’t actually fit, either because they’ve shrunk over time or you’ve grown, and you’ll want to remove the temptation to wear them out and about.

These are also the years when, if you haven’t before, you should be diving into the luxury that is custom-tailored clothing.

Depending on your means, you may not be able to afford a wardrobe made of bespoke suits and shirts, of course, and you can look great without. But you should at the very least establish a relationship with a tailor you like, and have him (or her) adjust your off-the-rack clothing to your specific measurements.

Your peers are increasingly going to be better dressers as you age, and a tailored fit in all your clothes — even the casual ones — helps you stay ahead of the curve. It also makes sure your body is looking its best at all times, no matter what shape it’s in.

  1. Identity

Your 20s were a good age for experimenting with looks. Your 30s certainly haven’t turned you stodgy, but it is time to have a little consistency in both your personality and its outward reflection. Dressing like a ripped-jeans grunge rocker one day and an ascot-wearing turn-of-the-century dandy the next just makes you look flaky.

You should have — or should work on developing — a look you’re comfortable with as your standard or “default” style. You don’t have to box yourself in, but you should probably know by now whether you prefer to wear jeans, chinos, or wool slacks as your off-hours trousers, and whether you prefer shirts with a traditional turndown collar (“dress” shirts) or something a little more relaxed.

This is also a good age to establish a few “favorites.” Own a couple beloved (and perhaps aging) garments that your friends know you for. Adjust and repair them as needed to keep them in your regular wardrobe for years. It’ll be a comforting touchstone for both you and everyone else.

Perhaps most importantly of all, this is an age where it’s crucial to have an identity — both an internal one and a wardrobe to represent it — that’s separate from your work life. Don’t be the guy who wears khakis and a blue shirt to the office, then puts on khakis and a blue shirt for a baseball game on Saturday as well.

It may sound like a minor concern, but having a “self” that’s separate from what you do for a living makes a big impact on your happiness and stress levels. Your clothes should be something enjoyable that you unwind in, not a reminder of your job (even if you love your work).

  1. Gravitas

We usually reserve the word “dignity” for older gentlemen (you’ll see it, for example, in our article on dressing for your 40s), but a man in his 30s wants his clothes to add a certain social weight as well.

There comes an age — and it almost always comes in the 30s at some point or another — where it’s no longer possible to be mistaken for a fun-loving 20-something out on the town. Rather than dressing even more relaxed and “funky” in an attempt to appear more youthful, accept that milestone with class, and even enthusiasm; exuding a bit of gravitas prompts people to take you more seriously and allows you to move into a more influential role.

This is an age where you should be comfortable wearing a jacket more often than not, wearing leather shoes instead of sneakers, and tying your own tie without thinking about it. You should have a haircut that can go before a board meeting or a judge with no more preparation than a quick combing. You should own a decent watch.

Little acknowledgments of adulthood like that are integral to looking like a man who’s comfortable being who he is, rather than a man who misses what he was.


Written By Antonio Centeno
Founder, Real Men Real Style