How to PROPERLY Dress Your Age | Top 10 Age Appropriate Do’s & Don’ts

December 5, 2023
A razor-thin line separates looking stylish and looking foolish regarding dressing your age. I want to review a few age-appropriate dressing dos and don’ts to make sure you always look amazing. When it comes to dressing age-appropriately, taking style risks to evolve stylistically. The problem arises when older dudes try to dress too young or aren’t consistent. It’s about what you do and what you wear consistently. If you’re a young guy, always dressed up and looking polished & presentable, you’ll be respected more than young dudes wearing baggy sweatpants.

Young guys’ biggest complaints are that they aren’t respected, and a quick solution is to upgrade and elevate their style and aesthetic. Wear clothing that fits, get rid of logos and graphics, and wear clothing that’s timeless and elegant. It doesn’t matter how young you are; you will look better than your peers. On the flip side, if you’re an older dude ready to embrace a better aesthetic, take some chances and wear clothing that fits you, play around with colors, and find clothing that makes you feel like the man.

How to look your best AT ANY AGE!

Overdress. It doesn’t matter if you’re 14 or 44; get into the habit of always dressing above the level of dress in the room. If you do, you will always look appropriate and stylish. One aspect that makes young men look immature is being underdressed, which a simple solution is being overdressed. You’ll look better than everybody else in the room.

Know where you’re shopping. Don’t wear clothing that is made for the younger generation. Certain stores are designed specifically for teens and young 20-year-olds. Some stores skew older, like Brooks Brothers, which is a great store but will look more old-money aesthetic that lends itself to an older generation.

Don’t plaster brands and logos. One of the mistakes that many younger guys make is thinking flashy logos are stylish. Actually, they make men look youthful and young. Conversely, if an older guy wears the same thing, it will make him look ridiculous.

Avoid wearing overly-distressed anything. Overly distressed or even overly stylized will make you look youthful. And if you’re an older gentleman, but bling on your denim looks stupid. If you’re wearing super tight jeans, you also look silly. But lots of holes or distressed anything will make you look foolish.

Consider trends carefully. Younger guys can pull off wearing trendy items but understand that trends will come and go quickly. When older gentlemen between 30 and 50 go trendy, they look like they’re trying too hard. If you’re more mature, avoid trends and go to more classic styles.

Understand different levels of casual dress. You can dress as an older gentleman and look fantastic, timeless, and sexy wearing a simple hoodie and joggers. But there’s a difference between that and even more casual options that a younger guy could get away with wearing, such as an everyday hoodie and sweatpants. Super casual clothing looks better on younger men, but that doesn’t mean younger men wouldn’t look better and more mature in more refined, elevated-quality casual clothing.

Do not wear striped shirts. More specifically, do not wear striped Polo shirts. Polo shirts can make a lot of guys look ridiculous, even young dudes. A worn-out Polo especially looks stupid. Elevate and upgrade your Polo with Collar and Co. polos, designed to look like dress shirts. They solve the problem with Polo collars, as theirs are rigid and not floppy. This makes them more dressy and sexy — perfect for layering. Check out Collars & Co. and use code ALPHAM for a special limited-time discount on your order!

Avoid big and baggy clothing. Big and baggy clothing doesn’t look great on anybody. It’s a current trend more suited toward the younger demographic. First, baggy clothing makes everyone look short. Also, big and baggy clothing is sloppy. The general rule is always to dress in clothing that fits your body, which goes for shirts, pants, and outerwear.

Tailored looks amazing. An item will look fantastic regardless of age if it is tailored correctly. Tailoring is one of the quickest ways to make yourself look badass. A cheap suit looks crunchy, the shoulders are big & bulky, the lapels are super thin, and the pants are pulling, bagging, and bunching at the ankle. When tailoring a suit, address the jacket as well as the pants. Make sure the pants get tapered down by the ankle.

Too tight is too much. Regardless of age, you must ensure your pants are not too tight. Also, make sure your pants don’t bunch at the pockets and pull with a lot of whispering. Tightness in the crotch indicates that the pants are too tight and need to be sized up.

Avoid too many accessories. Whether young or old, you look stupid with too many accessories. Most older dudes cannot pull off earrings. Chains and necklaces should be limited to one or two, which also applies to bracelets. And wear one ring, maybe two. Last, Apple watches are a big thumbs down.

Consider your shoes. Younger guys look amazing in more stylized shoes because they’re more trendy. Conversely, older dudes wearing running shoes with anything other than athletic gear look horrible. Upgrade the quality of your sneakers to a bit more stylized and avoid big bulky trends that look bad on everybody. Ensure the toe box is natural and the shoe has a simple, clean aesthetic.

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