Dressing Your Age: How to Dress Like a Man (and Not a 40-Year-Old Teenager)

Getting older doesn't mean sitting on the rocking chair in your grandfather's cardigan. Dressing your age means wearing clothes that make you the most polished man in the room. And it doesn't have to ebb and flow with what the twenty-somethings wear. Keep reading to discover how you can dress like a man (and not a 40-year-old teenager).
Image Credit@giorgiogiangiulio by @ChillaxingROAD

Dressing your age means something different to everyone. After all, age is just a number. Yes and no. We'll defend your right to dress how you want. But we won't help you leave your door looking like a meme.

You want to be the most polished man in the room. You don't want to be the ridiculous-looking 40-plus-year-old man trying to dress like a teenager.

No matter your age, always aim for refinement and polish. Here's what you need to know to make being stylish in your 40s and above effortless.

(Shout out to our email subscriber, akgordon, who suggested this topic.)

Spend it Because You Got It

Getting older means you're farther along in your career and have more cash in your bank account. Put it to good use and invest in high-quality clothes. Go for natural fibres, sturdier buttons, and stitching that doesn't come loose after a few turns in the washing machine.

Find out more about how to spot high-quality clothes in our article: Sharp Eyes = Sophisticated Style: How to Spot High-Quality Clothes.

Don't Go After Trends. You're a Classic. Dress Like It.

It's ok if you're not trendy. You're a classic. Dress in classic pieces, and don't chase the trends you see online. Keep it simple and collect foundational tops and trousers in neutral colours, making it easy to assemble stylish outfits every day. And you absolutely must follow our next advice for dressing your age.

Say Goodbye to Tight and Oversized

Let's be honest. We don't have the same body we did in our 20s. Don't try to squeeze into tight-fitting clothing. And don't hide your body by "dressing younger" in oversized clothes. Clothing that fits is always in style. Focus on clothes that complement your body type; you'll always look polished and not like someone trying to hang on to their youth.

Rein in the Colours and Patterns

We're not saying to avoid wearing colours and patterns altogether. But dressing your age means you must be more mindful of how you wear them. Loud prints and colours scream for attention. Show the younger guys how to use subtle colours and patterns to build refined outfits where the whole is greater than the sum of its parts.

How to Dress Your Age? Find a Style Role Model

Figuring out how to dress your age can be tricky. Youthful but mature style is a challenging tightrope to walk. It gets easier if you have a role model. Find someone whose style you want to emulate. Search images online and put together some outfits that speak to you.

It doesn't have to be one person. You may grab Cary Grant's classic grey suit and grey grenadine tie for date night. Or you can borrow from Paul Newman's rugged but stylish aesthetic for the weekend.

Dressing Your Age in the Office: Crush Your Professional Look

How about you pull Steve McQueen's navy blue suit from The Thomas Crown Affair and wear it to the office? Talk about giving the younger guys something to aspire to.

Upgrade your work wardrobe to reflect your place in the company. Wear higher quality dress shirts and suits tailored to your frame. Find leather Oxford or monk-strap shoes and give everyone coming up more reasons to follow in your footsteps.

Dress Up, Don't Dress Down

You have plenty of reasons to dress up in the office. Take the same mentality outside the office. You can get away with sweatpants or overly distressed jeans in your 20s. Go for slim-fit dark wash jeans or chinos in your 40s and 50s. Treat every outing as a chance to flex your style and show everyone how it's done.

Accessorize Like You Know What You're Doing

Accessories can say a lot. Too many (or the wrong) accessories signal someone lacking experience. Updated and tasteful glasses can make you look modern and stylish. A pair of Steve McQueen Persols evoke a rugged elegance. Understated neckwear for office and formal events shows you're a seasoned gentleman who knows what they're doing.

Stay on Top of your Grooming

Dressing your age (and looking great) includes getting fresh haircuts and keeping your hair in check. Don't let your hair and beard go, but don't go too crazy, either. You may be tempted to dye your hair or try a new "younger" hairstyle. Beware: it's a decision that can make you look like a 40-year-old teenager or someone trying to hang on to their youth.

We're not saying don't try anything new. We're saying proceed with caution. Celebrate who you are today. You earned it. It's time to look ahead, be yourself, and show those youngsters how to age gracefully.

Discover more ways to age like a fine wine. Read: 4 Ways to Dress Better as You Get Older.

Refined accessories for the seasoned gentleman.