Photo Credit (Pixabay)
Helping a mature male styling client develop a passion for clothing is my favourite thing to do as Team SG’s resident dad style whisperer.
For guys over fifty, dealing in style is very fulfilling.
It can be difficult to figure out how to dress in your 50s (and beyond!), but I’m here to tell you that it’s completely possible. And because I can’t personally advise every man to find an AARP membership in his mailbox, this—a comprehensive guide on clothing for senior men—is the next best thing.
Now, if you’re new here, you may be wondering: Caroline, you’re a 29-year-old lady whose main interests are making homemade macaroni and cheese and watching Nordic crime programs. What could you possibly know about a man nearing early retirement and his style struggles?
To begin with, I adore older men who are well-dressed.
The Professor on Gilligan’s Island was my first crush! My hall pass is still Senator Sheldon Whitehouse of Rhode Island (shelly, if you’re reading this, let me help you choose some new connections!).
I’ve done the work beyond that. I’ve conducted interviews with some of the most well-known stylists, tailors, and costume designers regarding fashion for men over fifty.
Larry David’s dressmaker? She listed all of his necessities for me. The tailor who created every suit for the Billions cast? He revealed the methods that men employ to appear their best. I even interviewed male supermodels over 50 for two months to find out what they thought style meant to them.
…I understand that it’s a difficult job, but someone has to do it!
The elder men’s attire always catches my attention when I watch a show or a movie. How are their garments made? Which hues go well with their grey hair?
Here’s the problem, though. In actuality, age is simply a number.
Perhaps you’ve lost it all or your hair has turned grey. Your body may not look the same as it did in college—in fact, it would be insane if it did—but I’m willing to wager that you’re also not sleeping on a mattress on the floor any days!
You don’t have to lose your style or coolness as you get older.
And notice how a man over fifty needs to change his clothes. Perhaps you want to know where to shop in your 50s or are searching for casual clothing for older guys. Older men’s fashion can be just as exciting and diverse as that of men in their twenties.
Not sure where to begin? Do not be concerned.
- Hire a tailor
Good tailoring is one of the key factors that separates “a guy wearing clothes” from a “well-dressed man,” according to every single person I’ve spoken to who works in the style industry for men over 50 (and guys in general, for that matter).
One of the most crucial aspects of being a well-dressed, mature man is developing a relationship with a tailor.
Therefore, consider your tailor to be your clothing’s doctor. You have a dermatologist to examine that strange mole on your back, a dentist to take care of your teeth and an internist to monitor your blood pressure. To ensure that your wardrobe is in good condition, it’s time to hire a tailor.
And I understand your thought: I fit perfectly in the things I own!
No man, and I mean none of you, can fit into clothes that are brand new.
No, you don’t have to get all of your sweatpants or t-shirts adjusted, but what about the sleeves of the button-downs you wear with jeans or chinos every day? Make sure they are the proper length.
Or the blazer you wear each week to dinner with your spouse? Would it fit you a bit better if it were taken in or let out?
Once more, consider it similar to seeing the doctor: you don’t go every day for little issues, but for major ones? You should bring in an expert.
- Rather of following trends, try to elevate your own style.
The secret is that I also advise my younger clients to dress for themselves rather than to follow the newest and greatest trends. Older men, in particular, look their best when they do this.
By midlife, you’ve witnessed numerous trends come and go. Simply said, this will make it lot simpler to choose what trouser cut suits you the best and what hues and textures go well with your style.
For example, certain items of clothing don’t really fit a guy like you and which ones best fit your lifestyle.
Try not to view this rule as restrictive. After all, every man, be he a first-time grandfather or a muscular twentysomething, may think of clothes that suit him well and garments that don’t.
Rather, take this as a licence to ignore trends. What a luxury!
Men become more distinguished as they become older; there’s a reason why they’re called “silver foxes.”
One of the pleasures of dressing older characters like Robert and Sol, played by Martin Sheen and Sam Waterston, both of whom are in their eighties, is that they are men who have experienced a lot of life, according to Allyson B. Fanger, costume designer for Netflix’s (criminally underrated, in my opinion) Grace and Frankie.
The drama followed the lives of two lawyers who, once their children are grown, abandon their wives for one another. It’s spot on.
Fanger told me that the reason dressing Robert and Sol was so much fun was because their styles aren’t changing any more.
When it came to fashion, the two characters each had their own distinct style, preferred colour schemes, and brands.
Robert was a classic; a Brooks Brothers guy at heart, he enjoys wearing button-downs and chinos.
However, at its core, Sol was a hippie. He adores his comfortable Tommy Bahama linen trousers and Cubavera camp shirts.
The two truly serve as the ideal illustration of how anyone can achieve excellent personal style at any age, regardless of their preferences or sense of style.
The most crucial aspect of any man’s style is knowing and being confident in who he is, and it’s much simpler to accomplish when you’ve spent decades getting to know yourself.
- Purchase pieces that will last a lifetime.
You can spend more on your clothes if you don’t follow fads. Why? Because you are aware that you will wear whatever you purchase for more than one season.
This implies that you should get one or two of each essential piece for your wardrobe rather than a large quantity of cheap shirts and pants. After that, have those things expertly fitted. The final action? Accept the simplicity and ease of having a distinctive unique style!
Seek out companies that value quality and craftsmanship.
Spend your money wisely because you may not have enough cash on hand to buy everything in your closet.
Consider the things that you use the most. If, like a post-presidential Barack Obama, you live in blazers and only wear sweaters on occasion, set priorities appropriately when creating your budget.
- Create a uniform for your wardrobe
76-year-old Larry David loves wearing uniforms. David provides us with a fantastic illustration of how adaptable and liberating adding this type of sartorial structure can be, even though we typically think of males adopting a daily uniform as the classic suit and tie.
He is the epitome of casual style; in fact, the Curb Your Enthusiasm star provides a fantastic guide if you’re looking for casual attire for guys over fifty.
Soft shoulder jackets, AG 5-pocket chinos, and crewneck sweaters and zip-ups are his go-to pieces.
You’re a perfect fit for this style of clothing if you’re the type of guy who finds the idea of choosing clothes every day overwhelming.
Using a few items that you adore, create a capsule wardrobe. A jacket, some knitwear, your favourite pair of trousers and a couple shirts that make you feel your best.
Additionally, don’t be scared to purchase your favourite goods in a variety of colours! (This is another activity David engages in.)
In this manner, you can know that whatever you take out of your wardrobe each morning will probably go together.
- Adopt a Monochrome Colour Scheme
To achieve a unified style, monochromatic dressing entails matching items that are all in the same colour family. Wearing clothing like this lengthens your figure and keeps you looking put together, sleek, and contemporary with little work.
Steve Martin, 79, plays a character on Only Murders in the Building who frequently rocks a monochromatic outfit. Imagine wearing a blue knit jumper or overcoat with white shirt and blue jeans.
These kinds of outfits are simple to put together and even easier to look amazing in when it comes to guys over 50 fashion.
There are several ways to go monochrome, but at Team SG, we prefer the black and blue combination. Stick to earth tones, like tan chinos with a thick oatmeal rollneck sweater, or go for rich deep blues, like navy.
- Pay attention to the final details
One of the things that sets men apart from boys when it comes to presentation is their extra attention to detail, which may not be apparent at first but becomes crucial once you see it.
The last touches are just as important for things like a well-groomed beard (and nose hairs!), clean cuticles and nails, and ensuring that you smell good as they are for your attire.
Similar to the chic tie and matching socks shown above by Stanley Tucci, who Style Girlfriend users voted the most stylish man of 2023!
For men over fifty, accessories are a terrific way to add flair.
A plain blue overcoat can be made more elegant with a lovely scarf. Just as the wrong shoes may ruin an ensemble, the correct ones can make it.
Investing in accessories is another excellent way to upgrade your wardrobe. A classic pair of glasses will never go out of style, and if you invest in long-lasting ones, you’ll wear them for many years to come.
Since it’s one of the first things I notice about a man, I want to pay a special mention to timepieces. If he wears one, tell me what it is.
Let me clarify, though: A fine watch is one of the few things worth investing in if you have the money, but you don’t have to spend it all on it.
Even a reasonably priced tank top from Seiko will give you a more refined and upscale appearance.
- Be yourself: An article about style for guys over fifty features an older male model getting retouched on set.
I realise it seems strange to say, “Oh, and just accept you for who you are,” at the conclusion of a list of style guidelines. Because you may think, “Well, I’m wearing Crocs and a torn sports jersey.” I respond, “Okay, please change yourself.” (I’m kidding.) (Or do I?)
In reality, though, I’m saying that you shouldn’t obsess with dressing a specific age. These style advice are excellent if you’re unsure of where to begin or want to up your style ante. However, if you already have a distinctive look or want to dress unconventionally, don’t let the fact that there’s a 5, 6, or 7 before your age make you feel that you can’t.
Presenting yourself as the greatest version of the man you truly are is the best approach to look well.
As we’ve already established, growing older simply means that you become more aware of who that is with each year that goes by.
Consider a male model. Above is Lono Brazil. Brazil is currently ruling the mature model game, and when he’s out and about, he’s the complete opposite of a Brooks Brothers dad or a Larry David impostor. He like wearing avant-garde and architectural pieces from leading designers. And you know why it works? Because he is that person.
You will therefore always be in style if you dress for who you are.
Where to buy clothing for people in their 50s and older
Here are some of the brands I frequently recommend to my clients who want to seem more stylish for guys over 50: