Dressing Sharp and Casual for the Men in Their 30s

You are no longer in your 20s and can't dress like a college guy anymore, but you are also not yet in your 40s so middle age hasn't caught up with you. You are in the middle years, the prime of your life, and need to figure out how to dress in your 30's.

If you dress like you are in your 20s, you may not be taken seriously. You'll be seen as immature or inexperienced. Conversely, if you dress like you are much older than you are, you may be seen as past your prime…. no longer an up and comer or worthy of being invested in.

This article is intended to help you find that perfect line between a young man and middle-aged, to teach you how to dress in your 30's.

You will discover:

1. The Best Look is a Varied One
2. Items Every Man in His 30s Should Own
3. Dressing for Specific Occasions

How To Dress In Your 30s #1. The Best Look is a Varied One

Do you know what doesn't impress anyone? Being “the _____ guy.” The guy who always wears sweaters. The guy with the one stupid fedora he wears everywhere, no matter what the rest of his outfit is. The guy who always wears suspenders, even with a belt. That guy.

And, less unique but equally unvaried, there's always the guy who just wears jeans and a non-descript shirt and sneakers whenever he's not required to dress up.

Don't be any of those guys.

The quickest way to impress people with your look is to vary it. Introduce new fabrics, new colors, and new styles and articles of clothing so that you're never a “that guy.”

Figuring out who you are and what kind of stylish man you are is just as important as figuring out how to dress in your 30's.

If you've never done much stylish dressing, your wardrobe is probably based on some simple staples right now. Let's take a look at those staples — and at some alternatives, you can wear that fill the same role, but add a little style.

• Blue jeans – There's nothing wrong with these, some of the time. Get them dark and close-fitted and they look great. But throw in some corduroys, khakis, colored chinos, and wool dress slacks too. So many men wear the same type of trousers every day that a man who varies his up always stands out. Check out our denim buying guide.
• T-shirts – Don't throw out the plain white undershirts, but get ready to move away from baggy tees with graphic logos or designs on them. Those are a younger man's game and you're learning how to dress in your 30's, not your 20's. Start wearing casual collared shirts instead: short-sleeved work shirts, polos, and patterned dress shirts. They give you a little more class without overdressing things.
• Sweatshirts – Ditch the college hoodies, and save performance fleece for actual mountain-climbing. Wear light sweaters and cardigans instead, or fall/spring outer layers like jean and leather jackets.
• Coats – Similarly, upgrade a generic canvas or nylon coat to a sturdy sportcoat or blazer. With a sweater underneath, they'll hold up until the snow starts falling. Own a good wool overcoat for when that happens.
• Sneakers – Gym shoes are for the gym. Outside its walls, wear leather shoes most of the time. Casual loafers, brogues, and boots all work well. So do leather work shoes. Colored canvas sneakers (think Converse All-Stars) have a fun, funky look, but unless you actually play in a rock band, you're pushing your luck with them at thirty-plus.

Make the upgrades you need to, a little bit at a time. It doesn't have to be an overnight transformation.

In fact, it's better if it's not — it gives your friends and co-workers time to adjust.

Remember, it may feel like a huge change to you, but the odds are no one is even going to comment if you show up for work one day in a pair of dark brown chinos rather than blue jeans.

How To Dress In Your 30s #2. Items Every Man in His 30s Should Own

So what defines a 30-something man's style?

He does, obviously. But if you're looking for a good starting place, here are some timeless staples that are never going to be a bad choice when you're figuring out how to dress in your 30's.

Jackets and coats

Your top layer, these tend to define your look at a distance, since they're the most prominent feature people see:

• Blazers – Own at least one traditional navy blazer. It's okay if it's a little boxy and stiff-looking, with the brass buttons and everything. You'll wear it when you want to look respectable, but a suit would be too formal. Once you have one of these you'll surprise yourself with how often you wear it.

• Sports jackets – The blazer's dressed-down cousin. A couple of these in textured weaves will keep you looking good all fall and spring. They're versatile, and can be made to work in almost any social setting.
• Sweaters and cardigans – Buy them in plain, solid colors and they'll be a versatile matching piece. You can never go wrong with gray and earth tones. When defining how to dress in your 30's personally, sweaters are a good place to find variety. They come in a multitude of colors and styles to help show your personality, without losing a lot of the versatility.
• Waxed field jackets – The Barbour brand is your icon here, although there are knock-offs and imitators. A good one is pricey, but it keeps you looking sharp in bad weather. Just make sure the fit is good — you don't want a baggy one making you look slouched and soft.
• Long overcoats – You can't throw a puffy nylon-shell parka over a good suit or blazer. Own a decent, dark wool overcoat that falls to near your knees. There are lots of styles — Chesterfields for severe formality, polo coats for upscale stylishness; trenchcoats for that rugged working class look. Pick your favorite, but own one.
• Leather jackets – If you find one you love and the quality is good, it's worth whatever the price tag says. If you don't love it, or the quality is cheap, or the fit is bad (leather's not adjustable), skip it. This is where learning how to dress in your 30's doesn't have to get stuffy. A leather jacket is the best way to keep the young and cool vibe, while elevating the looks.

Trousers and Pants

Remember what we said about variety? It's true, and it's especially true about pants. If you can get out of the “jeans every day” mentality, you'll have a more defined look than the vast majority of your peers. Here are some great options:

• Corduroys – Basically equivalent to jeans in function, but less common and often more colorful. Leave the bright, primary colors to younger men, and work mostly in earth tones and deep shades with these.
• Chinos – They don't have to be boring. Keep them slim and fitted, in a nice light hue, and pair them with colors outside the office-casual staple light blue. These are one of those classic items that every man has that can also make you look a lot older if not done right. You want to discover how to dress in your 30's, not how to dress like your father.
• Wool slacks – If you only own one pair, medium-gray flannel is the timeless classic. But don't stop there. Wool slacks dress any outfit up, and you can get them in everything from severe charcoal gray to houndstooth checks.
• Jeans – Yes, they should still be in your wardrobe. But there should only be a few pairs, and they should be dark, fitted, and maybe contrast-stitched for a bit of visual interest. Plain ol' work jeans are fine for manual labor, of course — just change out of them once the job's done.

Shirts and Tops

Don't underestimate the power of a small shirt upgrade when discovering how to dress in your 30's. Just having a decent dress shirt with a light pattern shows people that you're thinking about your look, rather than wearing the most effort-free option. Here are some good starting places:

• Plain white dress shirts – Own at least one or two of these. They're not flashy, but they work when you need to be at your most formal — and the rest of the time you can use them as a neutral piece with your flashier pants and jackets. The versatility makes them worth owning.

• Patterned dress shirts – The bulk of your dress shirts should have some character to them. Think light, narrow striping instead of solids, check patterns over white backgrounds, and so on. A few button down collars are fine, but the majority should be point or spread collars — it's a dressier look.
• Work shirts – Long or short-sleeved, these are less structured than dress shirts, but still have the buttoning front and turndown collar. They're good for a casual, working-class look. Use them when a dress shirt would be too formal (but remember that you can “dress down” a dress shirt by rolling the sleeves and popping the top button).
• Polo shirts – A safe warm weather default. No reason not to own one or two. When you are discovering how to dress in your 30's, these can make you look younger and more fit if worn the right way, or older when worn too loose and tucked into jeans.
• T-shirts – If you own any, they should be closely fitted and solid-colored. Nothing wrong with wearing those with good, dark jeans — once in a while. It should be one look of many, not a daily default.
• Henley shirts – A slightly more fashionable alternative to the T-shirt, with a small buttoning opening at the top but no turndown collar. Good for when you want a relaxed look, but still want to stand out apart from other guys.

There are a whole lot of options for your shirts, so don't be afraid to do some mixing and matching, and exploring beyond these examples. Just steer clear of looks that are obviously for younger guys, especially T-shirts with graphics of any sort (yes, even the indie art ones from brands like American

Shoes

Never underestimate the transformative power of footwear. A guy in dark jeans and a tight white T-shirt wearing sneakers is an aging jock. The same guy in the same jeans and T-shirt with a pair of dark leather work shoes is a style icon. If there's one underrated wardrobe upgrade every aspiring dresser should work on, it's the shoes.

• Work shoes – Think Dr. Marten's for your example here. Plain, dark-colored leather with a solid rubber sole. Bam. You're done. Looks great with jeans. Contrast stitching is fun, but optional. Get them higher in the ankle and it's a work boot, which fills pretty much the same style role.
• Chukka or desert boots – Low, rugged boots with a crepe rubber sole and a distinctive two- or four-eyelet lacing system. A timeless classic. Works great with jeans, corduroys, khakis, chinos, or even some wool slacks.
• Dress boots – Smooth leather boots. Higher and dressier than chukkas, but a little more rugged and relaxed-looking than dress shoes. A great way to stay good-looking but dry in rainy weather without resorting to galoshes.
• Brogues – Tooled leather shoes with decorative hole patterns punched in the uppers. Your safe, default dress-casual staple. For a bit more flair, get them in wingtip (sometimes called a “full brogue”).
• Saddle shoes – Two-tone leather shoes. The highly-polished shine is a little 1950s rock n' roll — go with suede or a muted topgrain leather to keep them from becoming a costume piece.
• Loafers – Comfortable leather slip-on shoes. Lightweight, relaxed, and great for driving. You can wear them with or without socks, depending on the weather and the rest of your outfit.
• Oxfords – Your high-formality option. Wear them with suits and with your dressier slacks and blazers.

One last note on footwear: if you're in your thirties, you're old enough to have stopped listening to jokes about how only women own multiple pairs of shoes. Any guy needs at least three or four, and most of us can put twice that number to good use.

Accents

A very simple core wardrobe can turn into a distinctive personal style with the use of a few small accent pieces. Think about our earlier example of a guy in dark jeans and a white T-shirt. Add a broad brown leather belt with a rodeo buckle, and you've got a very different look than if you added a slim black leather belt with a narrow, rectangular buckle, now don't you? Find the accents that work for you and start building a collection:

• Belts – A plain brown one and a plain black one are a must. If they're designed to take interchangeable buckles, so much the better. Beyond that, add whatever suits your tastes — there are a lot of options here.
• Watches – Ideally, you should never look at your cell phone for the time. Have a dress watch and a more casual one, if you can.
• Pocket squares – Practically mandatory if you're wearing a suit/sports/blazer jacket. Leaving the breast pocket empty wastes an opportunity, and makes you look a little clueless. At the very least stick a plain white square in there, and as long as you're not in an ultra-formal business setting, don't be afraid to experiment with more color and pattern as well.
• Pens – You're old enough to own one nice, metal pen for tucking into the inside pocket of your suits and blazers now. It makes a statement when you pull it out to sign something. So does a cheap plastic pen…but it's not the statement you want.

How To Dress In Your 30s #3. Dressing for Specific Occasions

At this point, you've got the outline of a pretty comprehensive wardrobe. You don't need to own every single item that we listed — but owning most of them won't hurt.

Putting them together is its own separate skill. Fortunately, it's a skill you can master pretty quickly once you discover how to dress in your 30's. Just think about the standards or dress code (if any) of the setting you're planning for, and then about the look, you want to project.

Dressing for work: business attire

If you've climbed your way into a position of some respect or authority in your work life, it may be time to break out the business suits. When you are in your 30's, you are presumably more experienced than others in their 20's, and are working your way steadily up the ladder.

Not all men are going to end up in a job that requires these. In fact, the majority won't. But if you are a man of the suit-wearing class, don't be one of the ones in the same two off-the-rack suits from Men's Wearhouse.

At the point where you're wearing a suit multiple days each week, go ahead and save up to get two or three nice, tailored ones. Go made-to-measure if you can't afford true bespoke, or keep an eye for traveling two-day-tailoring events where you can score a bargain.

• Things you need for this look: Good suits in business style — dark colors with fairly restrained patterning or texture. White dress shirts (plain or lightly patterned) and some good silk neckties and pocket squares. Oxford dress shoes and matching belts.
• Things to avoid for this: Button-down shirts (too casual), mismatched leathers, and pretty much anything that's not the timeless business options listed above! Express your uniqueness in the quality of your suit and the accent pieces, rather than straying too far from the formula here.

Dressing for Work: Business Casual

Far more men are going to end up in a “business casual” work environment than a business dress environment. It may be called something else, like “smart casual” or “relaxed business attire,” but it all boils down to the same idea general range: anything from dark, neat jeans at the most casual end to wool slacks and blazers at the dressiest end, and collared shirts at pretty much all levels.

You have a lot of flexibility in a business casual setting. Make the most of it. Vary your outfits, so that you're not wearing the same “uniform” to work every day. Just because khakis and a blue button-down meets the dress code, for example, doesn't mean you can't throw on gray wool slacks and a dress shirt with a sports jacket some days.

Try to look a little sharper than the younger men at work, if there are any. You should probably be wearing jackets more often than not, and always a stylish pair of leather shoes. You can even throw a necktie on from time to time (assuming they're not required), just to exceed expectations a little. This outfit is essential when figuring out how to dress in your 30's to separate you from the younger men in the office.

• Things you need for this look: A good variety of trouser and jacket styles, with some lightly-patterned or light-colored dress shirts to complete the outfits. Casual leather shoes. Pocket squares for the jackets. Sweaters can work into the look too.
• Things to avoid for this look: Suits (too formal), brightly-colored shirts and trousers, blue jeans (even nice ones), cloth shoes.

Dressing for Work: Hands-on Labor

Not everyone works in an office. If you've got a traveling job or a hands-on job like factory work or home construction, do you need to think about your look during work hours?

The answer is a qualified yes. Dress with safety and function in mind first! But within that framework, it's not a bad idea for a man to make his work clothes clean and fairly sharp-looking.

Be thinking in business terms. Customers are going to be more impressed by a guy in brown cotton pants and a polo than a guy in jeans and a T-shirt (especially if he holds a clipboard and looks busy while he's talking to them). If it's worth your while to make that extra impression, do it.

• Things you need for this look: Clean, damage-free jeans or sturdy cotton trousers. Soft collared shirts like polos or work shirts. Leather work boots (or plain, dark-colored synthetic ones if leather isn't a viable option).
• Things to avoid for this look: Coveralls or overalls (where they aren't necessary for protection). Anything badly ripped and stained. T-shirts.

Dressing for Yourself: Daytime Errands

A big part of the reason to upgrade your wardrobe is so that you look your best when there isn't a specific event demanding it.

You never know whom you're going to run into — and there's a certain amount of pleasure in the respect you get when you're dressed better than most of the men around you, too.

For the man discovering how to dress in his 30s, a style that's relaxed but a touch dressy makes a good off-hours outfit. Stay away from anything sloppy or careless-looking (especially anything with a loose, slouched fit). Trim jeans, tight lightweight sweaters, and casual collared shirts all work well, as do casual jackets.

• Things you need for this look: Almost anything neat and well-fitted. Sweaters, jackets, and light coats for top layers. Casual dress shirts or solid, dark-colored T-shirts, henleys, and other relaxed styles. Trousers in a variety of styles (jeans are fine, but keep them dark and fitted). Casual leather shoes.
• Things to avoid for this look: Suits and sharp blazers. Neckties (dress shirts are fine, but keep the collar open, and maybe roll the sleeves if it's warm). Sweatshirts, hoodies, and puffy performance fleece (thin, lightweight performance gear is fine for outdoor activities). Gym shoes (unless you're going to the gym).

Dressing for Yourself: Evening Socializing

Going out at night, you want to look a little sharper and a little more dressed-up than you do during the day. That doesn't mean business dress, though — your clothes need to say “social” as well as “dressy.”

In fact, it's better to be wearing regular old jeans and a T-shirt in most social settings than it is to be wearing a business suit and tie. While there are certainly some higher-formality events where men do wear ties in the evening, the basic rule of thumb is that you take it off once you leave work, and only put it back on if you're going somewhere that expects it (like the symphony or the theater — and even there, plenty of men go without neckties these days).

Casual evening suits are something of a rarity these days, but if you have one (and if it isn't an awful 1970s polyester lounge suit), social events at night are the time to wear it. Slacks or dark jeans and a casual jacket work well too. Here's where your look can get a little funkier — a T-shirt under a suit jacket or a pair of canvas sneakers with nice wool trousers aren't out of the question, though you want to be careful not to overdo it.

• Things you need for this look: Simple, dark jackets (suit or sports). Dark, fitted jeans and other trousers. A variety of shirts, both collared and non. Casual footwear that's in good shape.
• Things to avoid for this look: Conservative business dress. Plain collared shirts with khakis or other “bland” dress-casual trousers. Gym shoes or other colored rubber/cloth footwear. T-shirts with logos, school or brand names, or other non-artistic graphics.

Dressing for Romance: Dating or Date-Seeking

Turns out the things you wear to look nice for a date are just about the same things you wear when you're looking for someone to date! (Or at least, they are if you're representing yourself honestly.)

When learning how to dress in your 30's, a lot of guys on the dating scene — and a lot of married or otherwise committed guys — have let their standards slip a bit. Try to stay out of that trap. Dress like the other person's opinion matters to you, because if it doesn't, you really shouldn't be pursuing them.

Aim to look dressy, a little dark and sleek, and not too over-the-top “sexy.” You don't need to be popping the first four buttons of your shirt or wearing massive, floppy collars and chunky gold pinky rings to be romantic. If anything, strive to be a little on the minimalist side. Understated elegance is very attractive (especially in a tailored fit).

• Things you need for this look: Dark, fitted trousers and jackets. Light-colored collared shirts (white with light patterning works well). Nice leather shoes and matching belts. Some modest jewelry if it's your thing. A splash of decent cologne (nothing cheap, and no more than a dab on the back of the neck).
• Things to avoid for this look: Boring work clothes. Jeans and T-shirts. Gym shoes. Too much pink, too much cologne; too much anything, really. Keep It Simple, Stupid.

Follow these simple rules to master how to dress in your 30's and you will conquer your prime years.

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