8 Mistakes Older Men Make Trying to Look Young

Today, many men turn to fashion trying to negate the implications of getting older. By doing so, they end up looking like a man in a mid-life crisis masquerading as a teenager. But of course, aging is inevitable. 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?

In the HBO show Succession, for example, the character of Kendall Roy starts wearing Lanvin sneakers even though he’s in his 40s, and he just does that so he can be more accepted in the company he’s planning to buy–but people see right through it and it backfires on him. The same is true when you try to dress too young. It’s just not believable and it makes you look awkward.

Raphael looking young and stylish in his casual outfit.

Raphael looking youthful and stylish in his casual outfit.

The good news is, there are certainly ways that can make you look younger in a positive way because they don’t make you look too young, but somewhat age-appropriate without looking old or stodgy. Youthful clothing is generally trendier; bolder, more colorful, and you have to take it in the right dose to make it work for your age. The goal is to find clothing that suits your age but it’s also modern enough that it makes you feel updated and fresh.

Mistakes Men Make When Trying to Appear Younger

1. Wearing Athletic Clothing In Public

It’s not a good look to wear sweatpants or athletic attire in public when you’re actually not working out. However, younger guys these days wear a lot of sweatpants in public and it’s just part of their look. While this can emphasize a young man’s youth, on an older man it will just look more sloppy or even lazy. Being older means you have to try harder to look younger and you have to be more intentional about it.

wearing athletic clothes in public

Wearing athletic clothes in public will make you look sloppy or even lazy.

Keep in mind that the more casual the look is, the less likely it is to help you to look actually youthful. Maturity comes with the expectation that you are as mature as you look. Can you try to twist the perception in your favor? Absolutely. Let’s say you’re 60 and you want to look like someone in their early 50s, or that you’re 50 and you want to look like someone in their early 40s. However, it doesn’t work if you’re 70 and you want to look like you’re 25.

Alternatives for Older Men

So, if not sweats and athleisure attire, what can you wear instead that makes you look young but not too young? If it’s really hot outside, maybe just wear a polo shirt and a pair of shorts. If it’s not that hot, you can go with a pair of longer pants, and that’s even more dressy. During hot months of the year, seersucker is a great material for pants. Linen is also a great material for older men because it has a certain element of casualness which makes you look younger, at the same time, it’s very sophisticated and classic.

A linen shirt and a pair of chinos would be more stylish look than sweatpants and a hoodie.

A linen shirt and a pair of chinos would be a more stylish look for going out than sweatpants and a hoodie.

If you think about golf attire, it’s generally rather formal for casual wear but it has traditional patterns. It’s usually a little bolder and maybe it’s a look that works for you. In any case, it’s better than sweatpants and athleisure in public.

2. Wearing Sneakers At The Wrong Time

As we age, our body wears out and chances are, you may develop some arthritis or your feet hurt when you walk! So, sneakers may seem like a great idea because they’re more comfortable than dress shoes, for example. Right now, it is a youthful trend to wear sneakers with everything from your workout clothes all the way to your suits. As an older chap, wearing sneakers with everything doesn’t work because it looks like you’re just trying too hard.

You can pair your chinos with leather sneakers but don't make it your default choice.

You can pair your chinos with leather sneakers but don’t make it your default choice.

Any pair of leather sneakers, such as the one Kyle highlights in our guide to sneakers (pictured above) can work with a nice pair of chinos, maybe some jeans, or a pair of shorts–but don’t use it as your default choice in clothing. As an older man, you can’t get away with being sloppy but that also doesn’t mean you have to be dressed to the T at all times of the day.

What Should You Wear Instead?

First, pick and choose occasions for wearing sneakers: maybe for going grocery shopping or going on a walk or running some errands. Also, let’s say you go to the playground with your grandkids, that’s an appropriate time to wear sneakers. Rather than full-on tennis shoes, go with a nice pair of neat looking leather sneakers — they just suit your age much better. In other situations think about 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 casual and polished look. 

Raphael prefers loafers because they're dressy yet still comfortable (Shadow Stripe Ribbed Socks Dark Navy Blue and Royal Blue by Fort Belvedere)

Raphael prefers loafers because they’re dressy yet still comfortable (Shadow Stripe Ribbed Socks Dark Navy Blue and Royal Blue by Fort Belvedere)

Personally, I’m a big fan of loafers because they’re a dress shoe but they’re still quite comfortable and they just have a certain dynamic and a debonair look to them. If you have problems with your feet and you suffer from pain, I hear you. What you can do is 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 — almost like a sneaker, but it looks a lot better and more age-appropriate and it will still make you look young and fresh with a comfort that you need for feet at your age.

3. Wearing Baseball Caps As A Casual Accessory

Like athletic gloves, baseball caps can work in a specific context like you’re going to a baseball stadium, for example, cheering for your team. At the same time, if you wear a baseball cap and you go out for drinks with friends it makes you look just as bad as if you would wear sweatpants with sneakers. It will certainly make you look like you’re trying to hide your hair and I get it, we’re all getting less and less hair. If you want to learn about ways to treat hair loss, check out our Top 5 Hair Loss Treatments for Men. It’s a hundred percent not sponsored and I’m honestly trying to figure out the treatments myself.

Wearing a baseball cap outside to hide your hair would make you look like your trying too hard.

Wearing a baseball cap outside to hide your hair would make you look like you’re trying too hard.

Hair and Hat Tips for Older Men

Firstly, you can get a haircut that is a little more youthful. That can be like an undercut inspired style and there are hundreds of great tutorials on YouTube. You can with classic hairstyles because sometimes if you go too aggressive on your haircut, it also doesn’t work for you. However, a new haircut can really refresh the entire look of your outfit and your persona.

Look dapper with a classic hat instead like this Panama hat that Raphael is wearing.

Look dapper with a classic hat instead like this Panama hat that Raphael is wearing.

So, if it’s really hot outside or you want some cover for your hair or for your head, go with a more classic hat like a Panama hat. Something in a lighter color or maybe a pork pie or something with a shorter brim — that’s a bit more youthful than something with a super-wide brim. That being said, a hat should first and foremost, fit your body and your face shape, which we discuss in-depth in the guide How to Get the Right Hat For Your Face Shape & Body Type.

4. Wearing Trendy, Tight Clothing

First of all, clothes trends come and go very quickly and it’s very expensive to keep up with them. Second, as a more seasoned man and a metabolism that’s not quite as strong as it used to be in your 20s, 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. It just makes you look ill-prepared.

Super tight clothes are unflattering and would make you look like you're seeking attention.

Super tight clothes are unflattering and would make you look like you’re seeking attention.

Also, the older you get, the more ridiculous trendy items will look on you. Just think about those really bold Balenciaga sneakers or maybe those La Martina polos or Ralph Lauren polos with huge logos. Moreover, wearing undersized clothes that are super tight such as skinny jeans or super slim-fitting suits, will make you the opposite of well-dressed because they just look like you want attention at all costs even though it doesn’t fit you well.

What Should You Wear Instead?

You can still harness the youthfulness of modern trends by just taking a more moderate approach to them. This means you have to incorporate the overarching trend. If the current trend is to have slim lapels and jackets, and have really tight and slim fit models, such as pants or jackets, you can go to the alterations tailor and have your pants slim down a little bit; have maybe a dart added to your shirt, and slim things down so you look more modern without being overly skinny and tight.

Ask an alterations tailor instead to slim your pants a bit.

Ask an alterations tailor instead to slim your pants a bit.

You can skip the pleats and go with a flat front or maybe shorten your pants slightly especially if you slim down the pant leg, so there’s no more break. Best of all, you should know how pants should fit, because, at the end of the day, it’s a very personal thing. If you have really big thighs like mine, something that’s very slim is just very unflattering.

5. Wearing Unflattering Jeans

Another mistake season gentlemen make when trying to look more youthful is to pick jeans or chinos they don’t flatter them in the color or the fit. Even though jeans or chinos seem very basic, they can really make you look very dated. For example, if you have a stonewashed pair of Wranglers from the ’90s, it’s just not a look that looks very advantageous these days.

Wear chinos or jeans that will compliment your body type.

Wear chinos or jeans that will compliment your body type.

On the flip side, if you wear the skinny jeans with the big holes and rips in your knees, it’s just not age-appropriate for you. The same is true for bold embroidery or acid washes or whiskering — it’s just something that’s super trendy and not something for a seasoned mature man. Why? Well, it’s a perfect example of a man in their midlife crisis, who is simply trying too hard.

Trouser Alternatives for Older Men

If you want to look younger but still tasteful, you have to fall somewhere in between the trendiest stuff and the very classic styles. It’s basically like goldilocks jeans, so you get the best of both worlds where it’s just right in the middle. It means jeans that are neither too tight, nor too loose and that is neither too light nor too dark. You want minimal details, you want no rips or staining, or aging on your jeans. Go for a pair with a proper length and if they’re a little slimmer, maybe skip the break altogether.

A mid or high-rise pants will flatter your physique more than low-rise pants would.

A mid or high-rise pants will flatter your physique more than low-rise pants would.

If you have regular slacks or pants, you may want to add 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 medium rise, maybe even a slightly higher rise because it will flatter your physique much more. Wearing those kinds of pants will make you look more intentional and younger and updated without looking outdated or over the top.

6. Dressing Like A College Boy

So, what do we mean by this? Just think about cargo shorts or flip-flops, graphic tees, sports jerseys or hoodies, and sweatshirts. While those garment choices will make a college boy look somewhat immature, they will make you look even worse.


While a sports jersey is appropriate when attending a game or party, it’s not ideal for everyday wear.

Smarter Choices for Older Men

Instead of khaki shorts, wear a nice pair of cotton chino shorts that just end slightly above the knee for a more modern youthful look. More tips on shorts can be found on the Men’s Shorts Guide For Summer. Also, instead of flip-flops, which are fine by the pool or at the beach, you can go with a nice pair of boat shoes or a pair of loafers, maybe with some woven leather. You can also go with some driving mocs that make everything a little more relaxed, youthful, and modern all the while still staying true to your age.

Cotton chino shorts that are just above the knee gives a modern and youthful look.

Cotton chino shorts that are just above the knee gives a modern and youthful look.

You can ditch the hoodie sweater for a sweater that you can also wear around your neck or you can go with a Harrington jacket, maybe even a denim jacket or a nice leather jacket. Instead of having graphic tees, go with solid t-shirts and definitely avoid the v-neck because it highlights your wrinkles in your neck area so always go with a crew neck.

Henley shirt

A henley shirt is a great choice for men transitioning from t-shirts to polos and other formal styles.

Personally, I’d advise you from moving on from t-shirts in general and maybe going with a polo shirt. If that’s too formal for you, think about getting a Henley shirt; it just adds a bit more detail and more maturity to your outfits. Color-wise, I’d say, stay away from plain white or plain gray because they look more like undershirts. Also, don’t wear wife beaters. Instead, go with other more subtle colors. Again, upgrading to polo shirts is always a good idea in my mind. When it comes to sports jerseys, they’re fine to wear them on game day or when you’re at the bar but outside of that, leave it in your closet.

7. Wearing Excessive Colors And Patterns

Bold colors and patterns are certainly a way to catch someone’s attention but on an older man, it almost looks like you are very insecure and that’s not something you want people to think about you.

Hackett Flamboyant Outfit in Madras and Paisley

Hackett Flamboyant Outfit in Madras and Paisley–bold even for a young man!

What Should You Wear Instead?

Just because you should skip the pink pants paired with a bold flowery or paisley shirt, doesn’t mean you can’t incorporate color or patterns at all. What you can do is to use bold pops of colors or patterns in small doses so it could be a bold striped shirt, maybe a louder tie, or a pocket square or 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.

Keep the rest of your outfit more muted if you already have one bold item.

Also, it’s always good to pair either a loud pattern or a bold color. Just imagine I would wear a shirt with a bold pink and white stripe; it would just be over the top. Instead, a brown and white are bold because of the pattern but the color scheme is very classic. The same is true for socks. 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. They make you look modern, but not childish.

You can go for two-tone socks if striped socks are too much for you.

You can go for two-tone socks if striped socks are too much for you.

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. I know a lot of older gentlemen who are vehemently against that, you can achieve that same look and protect your hygiene by going with no-show socks. Curious about pairing them with your pants and shoes? Our guide on how to combine socks, shoes & pants can surely help you!

Paper test to determine your skin undertone

Paper test to determine your skin undertone

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 it just makes you and 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 your skin tone or if you’re black, you should pick colors that best flatter your skin tone, which we discuss more in this guide.

8. Using Young and Bold Scents

You may have realized by now that using Old Spice day in and day out has put you at a certain age category, even though you may not like it. In a push to be more youthful, you went out and tried to get a really young, bold, and kind of light scent in the hopes that people think of you as younger. Sadly, an older gentleman that smells like he just spent all day in an Abercrombie and Fitch store sends different signals. Yes, it’s overpowering but it also just doesn’t suit the style and the maturity level of that person.

Find a scent that works for you.

Find a scent that works for you.

Choose Age-appropriate Colognes

So instead, get a quality scent that’s based around the season, such as lighter fragrances for summer. You can also find something that you just like, it works for you, and that’s classic, but not old and stodgy. If you haven’t yet found your classic scent, check out the list of  8 Classic Fragrances for Gentlemen we like and that may work for you.

Mont Blanc Individuel

Mont Blanc Individuel

Sometimes, you can also rely on brands. For example, 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. 

Bonus Tip: Avoid Body Odors & Bad Breath

While you probably know that sensory experience is very important, sometimes what we forget are body odors. So, yes, take a shower and use your deodorant, but bad breath is something that makes you look very old. People don’t want to have anything to do with you, the worst about it is that most people will never mention that you have bad breath even though you do and so maybe a loved one or someone who’s very close to you can give you an honest answer.

Various types of deodorants and antiperspirants.

Various types of deodorants and antiperspirants.

At the same time we all have bad breath on occasion, not just because you get up and don’t brush your teeth but maybe because you drink a lot of coffee, you have some stomach issues, or whatever. For example, I recently had issues with bad breath and I realized it came from a water bottle that was reusable but I had to clean it every day otherwise, I had bad breath.

Raphael swears by TheraBreath

Raphael swears by TheraBreath

The one thing that got rid of my bad breath right away and let me think about the causes was a mouthwash called TheraBreath. Before that, 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. Take these tips to heart, and you’ll be able to look secure in your age while maintaining a youthful edge!

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

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