Does dressing your age make sense?

March 16, 2024
A razor-thin line separates looking stylish and looking foolish regarding dressing your age. 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 those 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.

For everyone, if you start with mediocre style and add one or two trendy, edgy, or classy items, the look is bad and is ‘trying too hard.’ But if you’re dressing purposefully, consistently, and authentically, you can make strong style statements at any age. I’d caution against a lot of trend hopping after a certain age, as getting a firm handle on your tastes the older you get is more genuine than chasing pop culture’s changes. Sure, everyone can try new stuff; however, the older you get, filter trends through a more mature sense of understanding and preference.

A great rule is fit, fitness, and style — in that order. With fit, ensure your clothes fit you. Fit means no extra material or not too tight. Avoid big and baggy anything. Big and baggy clothing doesn’t look great on anybody and is a trend more suited to 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. Likewise, 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.

Take your measurements, measure the clothes that fit you best, and then buy clothes that match those measurements. You can also get items tailored as 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 pull, bagging, and bunch 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.

Regarding fitness, clothes look and fit better if you’re in shape, regardless of age. Physique makes such a big difference. I find that the difference between people who let themselves go and people who maintain fitness snowballs as you age. If you’re a fit middle-aged guy, you’ll have more style latitude than an overweight, out-of-shape man of the same age.

Many people keep the same style from their twenties, so when they hit their forties, they look dated and out of style. The issue is not age so much as not adapting to current styles (an older guy still wearing JNCO jean shorts rather than Nike shorts, DC skate shoes rather than Chuck Taylors). But there’s a fine line between adapting to the styles of the time and being trendy.

Sure, younger guys can pull off wearing trendy items, but they need to understand the financial impact of trends — they come and go quickly. However, when the older gentlemen go trendy, they look like they’re trying too hard. If you’re more mature, avoid trends and go to more classic styles. Look around you and online at what men are wearing that you like for inspiration.

All ages need to know where they’re shopping. 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.

Brand doesn’t really matter when dressing age-appropriate as long as what’s being worn is the right fit and style. Remember that non-brand name items may not last as long due to less quality construction. But don’t have brands and logos plastered all over your clothes. One of the mistakes that many younger guys make is thinking flashy logos are stylish. Logos can make men look youthful. Conversely, if an older guy wears the same thing, it can make him look ridiculous.

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 under-dressed, which a simple solution is being overdressed. You’ll look better than everybody else in the room.

Conversely, 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.

And for anyone, whether young or old, you look stupid with too many accessories. Chains and necklaces should be limited to one or two, which also applies to bracelets. Wear one ring, maybe two. And Apple watches are a big thumbs down.

The bottom line is that you never get a second chance to make a first impression. Clothes that don’t fit properly, have bumper sticker slogans, or look like you stole them from your deadbeat uncle will make you look less appealing. Further, keep your temple in tip-top shape no matter how old you are. Clothes look better on a well-cared-for body.

And dress stylishly. Adapt outfits for the setting, and invest more in good items, as they’ll last longer. Over time, your wardrobe will grow. Buy classics such as plain tees, Polos, button-downs that fit well, and pants that don’t sag or are too skinny. Unfortunately, the world will judge you based on your attire, which may impact potential dates and employers. Zero in on fit, fitness, and style as appearances go a long way, gentlemen, regardless of age.

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