8 Mistakes Older Men Make Trying To Look Young

Don’t Make Yourself Appear Older Trying to Look Younger!

Today, many men turn to fashion and excessively youthful clothing when trying to negate the implications of getting older. Dressing in a very modish way, however, doesn’t make you look like you’re still in your 20s or 30s, although it can, ironically, make you look older, and no one wants to look like a man in a mid-life crisis masquerading as a teenager. So, in a society and an employment market where youth is highly valued, what can you do as a more seasoned gentleman to look both youthful and authentic?

Whether you are in your 40s, 50s, 60s, or older, there are several approaches you can employ to make yourself look younger in a positive way. These methods won’t make you look too young, but rather, age-appropriate without appearing old or stodgy. The goal is to find clothing that suits your age but is also modern enough that it makes you feel updated and fresh.

By avoiding the following mistakes and incorporating our style alternatives into your wardrobe, you can achieve a look that balances the elegance of your age with a fun, youthful demeanor.

Do you know what it means to “dress your age?”

1. Wearing Athletic Clothing Outside the Gym

Gym Clothes Don’t Automatically Give You a Gym Body

Skip the athletic wear on a date unless you’re actually working out or doing some sports!Skip the athletic wear on a date unless you’re actually working out or doing some sports!
Unless worn when actually working out, athletic attire will rarely make you appear younger.

As part of Classic Style, we generally believe that athletic attire is best reserved for times when you are actually exercising and that no one should wear sweatpants, trainers, or similar garb as casual attire. However, many younger men tend to dress casually in athletic attire because they find it comfortable and suited to their lifestyles.

To a certain extent, this choice makes sense: young men tend to be more athletic and generally in shape, so exercise clothes can complement their physiques. Unless you have the body of a younger man, however, these same garments will instead emphasize the age of most older gentlemen.

Classic casual shirts are a staple piece to any gentleman's wardrobe.Classic casual shirts are a staple piece to any gentleman's wardrobe.

Why You won’t Appear Younger in

Casual Clothes

In general, the more casual an ensemble is, the more likely it is to be associated with young people: wearing overly casual attire when you are actually older makes this disjoint more obvious and draws attention to your advanced years because you are not wearing clothing typically associated with your age: maturity comes with the expectation that you are as mature as you look.

Instead: Wear Comfortable Clothes that Suit the Situation

So, if not sweats and athleisure attire, what can you wear instead that makes you look young but not too young? In hot weather, it can be as simple as wearing a polo shirt and a pair of shorts. More generally, you can go with a pair of longer pants and sports shirts. To keep cool, seersucker is a great material for pants. Linen is also a great material for older men because it has a certain element of casualness that makes you look younger; at the same time, it’s very sophisticated and classic.

How a sweater should fitHow a sweater should fit

Fore! Is Golf Attire For You?

Golf attire is a surprisingly versatile form of athletic wear that balances comfort and style and can be worn as casual attire in many circumstances. In particular, its reliance on soft lines and traditional patterns offers an unassuming look with some bold elements for visual interest.

Learn More About Golf Attire!

2. Wearing Sneakers Incorrectly

Other Casual Shoes Provide Superior Alternatives

Pair of sneakers that provide a more reliable sense of comfort.Pair of sneakers that provide a more reliable sense of comfort.
Sneakers have their time and place, but they should not become your “everyday shoe.”

As we age, our bodies are less able to acclimate to uncomfortable attire, especially clothing. Older men tend to avoid leather dress shoes because of the assumption that they are always uncomfortable and instead wear pliable sneakers at all times. Many young men also always wear sneakers as their primary shoe choice, leading to the assumption that wearing sneakers makes you more comfortable and appear younger.

The latter notion is disproven by the point made in the previous section: overly casual or youthful attire emphasizes age in everyone who isn’t young. The former point is also an incorrect simplification: while sneakers are comfortable shoes, they are not necessarily any more comfortable than properly fitted, high-quality dress shoes.

A pair of cordovan leather dress sneakers from Crown NorthamptonA pair of cordovan leather dress sneakers from Crown Northampton

What about a pair of

Dress Sneakers?

So-called “dress sneakers,” usually made of leather with simplified detailing and coloration, have become increasingly popular, even in the Classic Style sphere. While these shoes can be worn on certain occasions – as with chinos, jeans, or shorts in casual settings – they should not become your default footwear choice. As an older gentleman, you should employ more elevated options to reflect your elevated position in life.

Instead: Employ Sneakers Correctly, Plus a Range of Casual Shoes

When It Makes Sense to Wear Sneakers

Sneakers have a place in the wardrobes of older men, but that place is not as your primary footwear selection. Instead, pick and choose occasions for wearing sneakers: maybe for going grocery shopping, going on a walk , running some errands, or playing with your grandkids; these are all appropriate times to wear sneakers. Rather than full-on tennis shoes, go with a nice pair of neat-looking leather sneakers: they function the same as conventional sneakers but appear far more dignified and age-appropriate.

Casual Shoe Alternatives to Sneakers

For all other occasions, opt for a more elegant casual shoe. Consider a pair of driving mocs or boat shoes. If it gets a little colder, maybe an unstructured pair of chukka boots are the exact perfect mix between a casual and polished look. Loafers are one of the very best options for casual footwear, as they are easy to take on and off, are supremely comfortable, and still look dapper.

White foam found under the insole of the 2000s Allen Edmonds "Sanibel" loafers.White foam found under the insole of the 2000s Allen Edmonds "Sanibel" loafers.

What If I Have Foot Pains? A Cobbler Can Help!

If you have problems with your feet and you suffer from pain, you can go to your cobbler and have them glue in a leather sole that is backed by foam that makes your shoes a lot more comfortable. The shoe will wear similarly to a sneaker, but it will look considerably better and more age-appropriate.

3. Wearing Baseball Caps as a Casual Accessory

It Isn’t Always Time to Play Ball

Preston shrugs wearing a casual baseball capPreston shrugs wearing a casual baseball cap
Baseball caps are the hat equivalent of a tee shirt.

Like athletic clothes, baseball caps can work in a specific context, like if you are actually playing baseball or you’re going to a baseball stadium to cheer for your team. In all other circumstances, however, they have the same effect as wearing other examples of overly casual attire: they appear disjointed unless you really are young.

Raphael wearing a linen shirt, black baseball cap, and aviators.Raphael wearing a linen shirt, black baseball cap, and aviators.

Your baseball cap won’t hide

Thinning Hair

Many older men begin favoring hats as part of an effort to cover up their thinning hair or full baldness; because baseball hats are cheap, plentiful, and popular, the assumption is that they are serviceable as a good beginner hat. In fact, because of their youth culture and sports-affiliated connotations, baseball caps are poorly suited to this role: they draw attention to the fact that you are wearing a hat in unusual circumstances, which may get people thinking, “Is he trying to hide something, like the state of his hair?”

Instead: Employ Hair and Hat Tips Suited to Your Age

Make Sure That Your Haircut Reflects the Realities of Your Hair

Rather than obscuring your hairline with a hat, you should first select a haircut that suits the realities of your hair: the proper haircut will help any amount of hair look fantastic, whether your hair is full and rich or thin and sparse. This selection of classic hairstyles provides the ideal starting point for any gentleman, but if you are starting to lose your hair, never fear: these haircuts will flatter thinning hair, with suggestions suited to how much hair you have already lost. Your barber will be able to suggest haircuts to suit your hair type.

Find the Right Hat for You

When it comes to selecting a hat, there are a plethora of casual hats within Classic Style that maintain a youthful feel without appearing juvenile. Flat caps or a porkpie are ideal choices in cool and transitional weather, while nothing beats a Panama hat when the weather is hot.

Ensure that you’re wearing the right hat for your face!

4. Wearing Tight, Trendy Clothing

The Latest Fads Could Exacerbate Flab

tight clothingtight clothing
Cramming yourself into tight clothes wont’ restore your youth.

In an effort to appear young and hip, some men adopt the latest clothing trends to emphasize that they are still “with it.” In general, we feel that chasing trends is a losing proposition for anyone: by definition, fads come and go, and it can be very expensive to remain on top of what is trending.

Chasing trends is a particular pitfall for older gentlemen as most trends are based around the physiques of the young, with cuts and lines intended to flatter fit, athletic bodies. Unless you have the build to pull them off, these tight-fitting clothes that are super trendy will show every imperfection and every extra pound you have, which is not advantageous and doesn’t make you look younger.

Photo of Thomas MannPhoto of Thomas Mann

“One fellow, in a bright yellow summer suit of ultra-fashionable cut, with a red necktie, and a rakishly tilted panama, surpassed all the others in his crowing good humour. But as soon as Aschenbach looked at him a bit more carefully, he discovered with a kind of horror that the youth was a cheat. He was old, that was unquestionable. There were wrinkles around his eyes and mouth. The faint crimson of the cheeks was paint, the hair under his brilliantly decorated straw hat was a wig; his neck was hollow and stringy, his turned-up moustache and the imperial on his chin were dyed; the full set of yellow teeth which he displayed when he laughed, a cheap artificial plate; and his hands, with signet rings on both index fingers, were those of an old man.”

From Death in Venice by Thomas Mann

Furthermore, as an older person, the social assumption is that maturity should cause you to feel secure and confident with yourself and your personal style and that you have no need to seek validation or approval from others by wearing the latest trendy clothing. Wearing particular clothes to fit in is usually associated with high school students and is, generally speaking, not considered becoming of an older gentleman.

Naturally, you should feel free to wear what you want, but obviously chasing trends will usually cause others to assume that you are trying to dress like something you are not because you lack confidence in who you really are.

How to Dress Up When Others Don’t

Instead: Moderate Trends To Suit Your Age and Style

Photo of Trousers legs medium fitPhoto of Trousers legs medium fit
Proper tailoring helps your body appear slimmer without sacrificing comfort.

There are, however, several ways that you can adapt contemporary trends to reflect the realities of your body and your age; it simply requires a more moderate approach to them. This means you must incorporate the overarching trend, if not each of its particulars. If the current trend is to have tightly fitted jackets and trousers, you can go to the alterations tailor and have your trouser legs tapered and a dart added to your shirt: these alterations will give you a slimmer profile without making it look like you have been stuffed into your clothes.

5. Wearing Unflattering Jeans

Don’t Let Every Jean Genie Out of the Bottle

Cheap jeans are usually only available in mid or low-rise.Cheap jeans are usually only available in mid or low-rise.
Not all jeans suit all body types.

Jeans are considered an iconic emblem of youth and have been favored by young men for decades, ever since subcultures in the 1950s first popularized them as casual attire. In many ways, however, the wrong jeans are a minefield of issues that can actually make you look older than you are.

Many Jeans Styles Can Appear Dated

The distinctive trendiness of jeans means that many cuts, colors, details, and treatments are closely associated with particular fashion epochs: think about the bellbottoms of the 1970s or the boxy stonewashed jeans typical of the 1990s. Wearing these jeans today can make you appear dated and like a fashion fossil come to life.

Hyper-trendy jeans are also unlikely to flatter you, as they tend to be extremely skinny jeans and, therefore, inappropriate for anyone without the build of a model. They also tend to feature faddish detailing, such as faux distress, holes, and rips that are not consummate with the demeanor of a mature, classic gentleman.

Instead: Find the Proper Jeans for Your Body Type

In order to appear younger but still tasteful, you should seek out a pair of jeans that falls in the midpoint between what is trendy and what is timeless. Such jeans should be neither too tight nor too loose and neither too light nor too dark. You want minimal details, with no rips, staining, or aging on your jeans. Go for a pair with a proper length and if they’re a little slimmer, it is usually best to avoid a break altogether. This “Goldilocks” approach allows you to enjoy the best of both worlds with jeans that aren’t dated but are also comfortable and flattering.

Find the right pair of jeans for you!

Drape of Fort Belvedere pantsDrape of Fort Belvedere pants

The key to looking great in

Any Pants

No matter what type of trousers you wear, consider adding a a cuff but keep it slightly on the shorter side and avoid any puddling at the bottom of your pants. Avoid super low cut pants because they will really highlight your love handles. Instead, go with something like a mid or high rise because it will flatter your physique much more. Wearing those kinds of pants will make you look more updated and younger without looking outdated or over the top.

6. Dressing like a College Boy

Parodies of Collegiate Attire Don’t Make You Look Younger

Active wear should be worn in the gym or when you're actually working out, but not as an everyday wear.Active wear should be worn in the gym or when you're actually working out, but not as an everyday wear.
Do you think anyone is likely to mistake Raphael for a college freshman?

Some men explicitly ape the clothing habits of young men in an effort to be associated with youth. Nowadays, this endeavor consists of crafting ensembles that parody the looks of young college men, replete with cargo shorts, flip-flops, graphic tees, sports jerseys, and hoodies or sweatshirts. Adopting this costume of youthful culture won’t fool anyone into thinking you are young; in fact, on actual college men, this look usually appears immature, and on anyone else, it tends to look downright silly.

Instead: Emphasize Dynamism Suitable to Your Age

Many elements typical of the youthful look of a college boy can be tastefully updated to suit the needs of an older man. These upgrades are age-appropriate while still capturing some of the whimsical effects of more youthful attire.

Instead of … Consider …
Flip-Flops Boat shows, driving mocs, or woven-leather loafers
Khaki Shorts Cotton chino shorts that end slightly above the knee
Hoodie Knit cardigan
Sweatshirt Casual jacket, like a Harrington or Trialmaster, or leather jackets
Graphic Tee Solid-color tee, henley, or polo shirt
Kyle showcases how a classic white t shirt should fitKyle showcases how a classic white t shirt should fit

Should you just ditch

Tee Shirts?

If you are interested in cultivating a Classic Style look as an older man, there are few circumstances, outside of chores around the house, when you are likely to be wearing a tee shirt (except as an undershirt). Instead, consider wearing a Henley, a polo shirt, or a sports shirt. They are just as comfortable but appear far more structured and dignified.

Learn more about tee shirts and Classic Style

7. Wearing Excessive Colors and Patterns

Bold and Young-Looking Aren’t Always Synonymous

Raphael in a summer-appropriate outfit featuring pastel tonesRaphael in a summer-appropriate outfit featuring pastel tones
Bold ensembles are lots of fun, but they don’t always make you appear younger.

Colorful plumage is a sign of youth and virality in many species of birds, but unless you’re a peacock, excessively loud patterns and colors aren’t likely to trick anyone into thinking that you are still young. On older men, these distracting details can make you appear insecure as if your clothes were wearing you and not the other way around.

Instead: Incorporate Bold Detailing Sensibly

Orange boutonniere and silk pocket squareOrange boutonniere and silk pocket square
Bold accessories provide visual interest without becoming overwhelming.

Selecting the Proper Accessories

When done correctly, the incorporation of color and pattern can be utilized to make you appear more youthful without seeming affected or fake. This is best achieved with bold pops of colors or patterns in small doses: consider a bold striped shirt, a louder tie, a pocket square, a boutonniere, or maybe even your pants. But if you have one bold item, keep the rest more muted so it doesn’t overwhelm your personality.

Finding Balance Between Bold Colors and Patterns

Subtlety can be maintained by opting for either a bold pattern or a bold color. For instance, a shirt with very broad pink and white stripes could be overwhelming, but if only one element is bold – like a very broad stripe – while the color element is more sedate – like brown and white – the result is a unique garment that remains classic and versatile.

Kyle being unsure how to Pair his Hawaiian Shirt with the rest of his wardrobe.Kyle being unsure how to Pair his Hawaiian Shirt with the rest of his wardrobe.

Consider color choice and

Skin Tone

If you have gray hair and your hair is getting whiter, and you have a lighter skin tone, pastel tones are really your friend because they make your face pop and your wardrobe doesn’t overpower the rest of you. On the other hand, if you have a high contrast between your hair and darker skin tone, you should pick colors tonally comparable for the most harmonious effect.

Find the colors that suit your skintone!

The Value of New Socks

Fort Belvedere Shadow Striped SocksFort Belvedere Shadow Striped Socks
Socks provide ideal, understated visual interest.

Socks provide the perfect opportunity to introduce a bold color or pattern without the risk becoming overwhelming. Rather than wearing those bold, crazy socks that a lot of people wear with pizzas on them or football teams or dinosaurs, get a pair of two-tone striped socks that have subtle color variations; they work well with your pants, they look modern and fresh, but not to the extent that a pair of football socks would.

If striped socks are too much for you, maybe get a pair of two-tone solid socks that are a little more subtle but just visually interesting and they can even be a conversation starter. Or, during the summer, when you wear loafers, you may even want to skip your socks altogether, or you can achieve that same look and protect your hygiene by wearing no-show socks.

Learn to combine socks, shoes, and trousers

Exceptional Socks from Fort Belvedere

8. Wearing Extremely Youthful Fragrances

Overly Juvenile Fragrances Don’t Pass the Sniff Test

It is very important to try first your chosen fragrance to know if it would last long on youIt is very important to try first your chosen fragrance to know if it would last long on you
The right fragrance improves any ensemble.

Fragrances are an often overlooked component of your wardrobe, but in an effort to smell, as well as appear, younger, some men ditch their Old Spice and select a very saccharine, overwhelming, youthful scent. Such overpowering smells, however, create a disjointed effect because the odors are not associated with the style and maturity of an older man; they are often better suited to a middle school locker room.

Instead: Utilize Age-Appropriate Fragrances

Fragrances tend to have fewer hard and fast rules regarding age appropriateness than casual clothing. As a result, any fragrance that is timeless, elegant, and versatile should serve you very well, especially if you take the time to make selections that take into consideration the season, such as summer, or the occasion; failing to do so is a mistake that fragrance experts avoid.

Photo of Raphael wearing an Irish tweed red and orange regimental tie and a blue tweed vestPhoto of Raphael wearing an Irish tweed red and orange regimental tie and a blue tweed vest

Raphael Says:

“Creed has a nice set of fragrances for seasoned gentlemen that make them smell young and modern or classic, whatever you like. While those scents are a little more on the expensive side, you can also find other colognes, such as Montblanc Individuel which has been a favorite of mine for years. If that doesn’t float your boat, maybe check out Eau Sauvage from Dior. It’s just a very nice scent; it doesn’t cost the world, and it will neither age you nor make you super young; it’s just right.”

Which Roberto Ugolini Fragrance is Right For You?

Photo of Oxford decorative layflat with fountain pensPhoto of Oxford decorative layflat with fountain pens

I want to seem mature, dignified, and in charge


Photo of Kitten Heel with Decorative ElementsPhoto of Kitten Heel with Decorative Elements

I want to seem romantic, mysterious, and exotic

4 Rosso

Photo of Azzurro with Decorative ElementsPhoto of Azzurro with Decorative Elements

I want to seem fun, playful, and youthful


Bonus Warning: Neglecting Body Odor and Bad Breath

Don’t Be Oblivious to the Olfactory

Raphael taking a whiff of his cologne.Raphael taking a whiff of his cologne.
Never again worry, “Is that smell me?”

Because of negative associations between old age and odors, many people erroneously assume that all older men smell bad. This prejudice means that people will be expecting bad smells when encountering more mature fellows, so it is essential that you take proactive steps to prevent even the perception of foul smells. Fortunately, this endeavor is fairly simple.

Avoid using bar soap as it could make the stain worse.Avoid using bar soap as it could make the stain worse.

Body Odor

In most cases, the elimination of body odor requires little more than regular showering and the use of a deodorant or anti-perspirant. Determine what shower routine suits your lifestyle best and check out our recommendations for the best hygiene products to improve your daily cleaning regimen.

7 Products to Boost Personal Hygiene!

Photo of Raphael incorrectly eating with his elbows on the tablePhoto of Raphael incorrectly eating with his elbows on the table

Bad Breath

Bad breath can be a more difficult issue to tackle because it can be caused by a wide variety of sources, including dental health, diet, and lifestyle choices. Raphael, for instance, discovered that his bad breath was being caused by a dirty water bottle.


Raphael swears by


“Before Therabreath, I used Listerine and Odol, and I wondered, what can a mouthwash really do for bad breath? But honestly, this TheraBreath stuff is really, really good. This is 100% not sponsored; it’s just something that I learned from a friend, and I want to pass it on to you because nothing makes you age as quickly as having bad breath.”


Photo of Group shot of Jack Nathan Preston EbPhoto of Group shot of Jack Nathan Preston Eb
No matter what your age, we hope that you found this advice helpful!

Getting older can be a scary and disheartening experience, but we hope that by considering the pitfalls highlighted in this video, you will have the confidence to avoid sartorial mistakes that age you, embrace clothing tips that help you look as young as you feel, and love every minute of your life. The autumn of your years can be one of the most rewarding, fun, and invigorating periods of life; don’t waste it trying to dress like something you’re not!

Are you guilty of any of these mistakes? How do you account for your age when dressing? Share with us in the comments!

Outfit Rundown

Raphael wearing a brown loafer, stripe dress shirt and off-white pantsRaphael wearing a brown loafer, stripe dress shirt and off-white pants
Raphael sports a casual gentleman look fitting for summer

Today Raphael is wearing an outfit that is perfect for an older gentleman during the warmer months of the year. It consists of a linen shirt in a bold white and brown stripe and I got it from a company by the name of Spier & Mackay.

His pants are a pair of classic chinos from Polo Ralph Lauren. They have pleats in the front because he has big thighs, and they also have cuffs because he prefers the added weight; they’re a little shorter, and they’re neither super-wide nor super slim but just in the middle.

Raphael pairs this look with a pair of dark brown loafers from Scarosso, which is a German brand, but the shoes are made in Italy. They have this woven leather, which is a bit more casual. Color-wise, it works well with the brown in my shirt. He is combining it with a woven belt that picks up the brown leather color and the casualness of the shirt and the chino.

Overall, the look relies on very earthy pastel colors that work well for Raphael’s age or for someone who’s 10 or 20 years his senior.


What are typical fashion errors older men commit when trying to appear younger?

Older men often fall into the trap of wearing clothing that is too tight or too loose in an attempt to either show off their physique or hide it. Another common mistake is opting for overly trendy items that don’t match their personal style.

Is wearing bright colors a misstep for older men aiming to look youthful?

Not necessarily. While incorporating bright colors can add a vibrant touch, it’s crucial to blend them tastefully with neutrals. The error lies in using too many loud colors at once, which can come across as forced.

How important is fit for older men trying to achieve a younger look?

Fit is essential. No matter your age, well-fitted clothing flatters your body shape and creates a polished look. Older men should avoid extremes—nothing too baggy or too tight.

Should older men follow the latest fashion trends to look younger?

It’s better to focus on timeless pieces that suit your body type and personality. Chasing every new trend can lead to a disjointed wardrobe that feels inauthentic.

Can accessories help older men look more youthful?

Yes, accessories like watches, glasses, or a stylish pair of sneakers can add a modern twist to your outfit. However, it’s about balance—too many accessories or choosing ones that are meant for a much younger crowd can backfire.

What role does hairstyle play in an older man’s youthful appearance?

A contemporary haircut that suits the shape of your face can take years off your appearance. But beware of hairstyles that are too “young”—they can have the opposite effect. Your haircut should reflect the realities of your hair, whether it is thinning, salt and pepper, gray, or white.

What else can I do to avoid appearing older?

Proper skincare is a vital tool in preventing the appearance of premature age. Even adding a simple moisturizer to your daily regimen will go a very long way toward making you appear younger in a subtle and refined way.

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