How to Dress Casually for a Man in His Sixties

Photo Credit (Pixeles)

If you wait, good things will arrive.

Now that you’ve waited, enjoy the good times.

Let’s be clear right away: your style will not be defined by the clothes you purchase when you turn 60. Imagine writing an article for a thirty-something man and expecting him to stick to that plan till retirement—that could be more than thirty years!

We therefore approach this knowing that “sixty-plus” is a wide age range. Like every other month, year, and decade of your life, your style will develop and change at that period.

However, sixty is a fantastic starting point for when a man can start to transition from middle-aged dress to older gentleman fashion.

There is nothing wrong with this. Silverbacks have been among the most iconic pieces of fashion. As they grew older, they simply improved. Over time, both wealth and taste tend to accrue, creating a completely separate fashion school from that of the younger generations.

60s Casual Style: Needs and Desires
If you’re lucky enough to be retired by your 60s, your whole wardrobe consists of “casual” clothing because you don’t have any professional obligations and are only dressing for yourself.

Until you reach the “sweatpants and hoodie” level, resist the urge to go straight down. No one is being helped by that.

Men of all ages ought to treat their leisure attire with the same level of care as their professional attire, if not more. When you are on your own time, your attire speaks most about who you are as a person; it displays your personal preferences, beliefs, and disposition before you even speak.

Men in their sixties and beyond are capable of making a statement that carries the weight of decades. Take advantage of that and dress to accommodate an elderly gentleman’s needs and preferences:

Fit is supreme.
A black man in his 60s wearing a perfectly tailored suit with a pocket square
A perfect fit is essential for any man. By your sixties, you should not only grasp the value of a competent tailor, but you should also have one or more of your own knowledgeable men who know your preferences and have your measurements on hand.

It goes without saying that not everyone is lucky enough to have a good relationship with a good tailor, but try your best to develop one in your general region. Additionally, if you come across someone who does well, keep him on board!

Many of the finest tailors are also elderly guys, and you never know when they’ll decide to hang up their shears.

Essentially, the purpose of a customized fit is to enhance the appearance of your body. If your body is changing in weight or proportion, which is common in older men, it can be crucial to keep your adjustments current. Keep an eye on your sizes; if something is beginning to sag or pinch, have it altered by a tailor.

Not only can well-fitting apparel improve your appearance, but it also increases comfort and confidence. Our bodies may shift slightly as we age, and tailoring is a crucial ally in keeping a put-together appearance.

Clothing that fits well highlights your best features and creates a gorgeous silhouette. To maintain a classic and elegant look, make adjustments to suit any changes in body shape.

Beyond appearance, the comfort that comes from wearing well-fitting clothing promotes mobility and an active lifestyle, confirming the idea that, even in your 60s, fit is still the most important factor.

Any man would benefit from this counsel. For older guys, however, it can make a big difference. According to some deeply ingrained cultural conditioning, an elderly man wearing a poorly fitted suit is “sad,” “poor,” “lonely,” and many other unfavorable adjectives that are most likely untrue. All that exists is the impression.

Avoid it and stay on top of your tailoring requirements.

An elderly man wearing a vest and a nice suit
Younger guys use strong color contrasts and aggressive cutting to convey dominance. That’s a losing game at your age. Dress like the elder statesman, not the young gun, and make an impression by showcasing your years rather than your personality.

This typically translates into conservative cuts and dismal hues. In this case, high-quality materials are also quite important; a younger man wearing a thinner, less expensive jacket can be completely intimidated by an older man wearing a thick, luxurious wool coat.

Develop a little distance. Just a little, not much. Wear something that lets them know you’ve been around and witnessed a few things. You should use opulent textiles, use a variety of muted colors, and have a classic style.

Also, it’s not a terrible idea to adopt some of the “elder statesman’s” accents. Put on a nice felt hat in a traditional style, such as a homburg or porkpie. Even if you are not in dire need of one, carry a stylish cane. Always keep a clean handkerchief in your inner pocket and a neatly folded pocket square in your outer breast pocket. You should use the latter for practical purposes, such as wiping your nose and eyes, rather than the former.

Put simply, act like a gentleman of some caliber.

Ability
An older Asian man in a great suit, dark shirt, and tie
Elders are not often treated with generosity in our culture.

Be prepared for others to treat you with a little more contempt or dismissal as your hair turns gray (or disappears), and particularly as your body becomes more rigid.

Although it’s annoying, realists should prepare for it. The older man in retirement must still look like someone with places to go and people to see, just as the younger man must dress a bit sharper and a bit more aggressively in his business outfit if he wants to be taken seriously at a firm full of middle-aged men.

The dismissive (disrespectful waiters, counter employees, etc.) and too sympathetic (“help you across the street”) types are avoided by upholding high clothing standards.

That does not imply business attire, but wearing your most intimidating dark suit and necktie for a stroll around town or some afternoon errands is harmless (and occasionally rather enjoyable). It does, however, entail making sure that everything you wear is well organized, with a purposeful style that culminates in a clearly structured “outfit” as opposed to merely a collection of haphazardly assembled clothing.

Naturally, you will be given more power if your clothing fits well and is of higher quality (see points #1 and #2). If you put it together carefully, you’ll escape a lot of the trouble that comes with interacting with folks half your age, who can occasionally be jerks.

Casual Outfits for People in Their 60s and Over
An elderly man with an unbuttoned dress shirt and jacket
What, then, suits an elderly man?

The garments fit and are comfortable, just like any other man’s. It goes without saying that classic fashions will look better than cutting-edge runway experimentation since they are “timeless,” which is a nice phrase to have as you age.

However, the level of formality can vary from wearing a full suit to wearing jeans and a T-shirt (only make sure they fit well, and maybe only if you’re still in reasonably good shape).

If you’ve been diligent about adding high-quality pieces in your 40s and 50s, you should have a rather large wardrobe to deal with. As often as necessary, have items adjusted by your tailor. Continue adding new pieces while keeping a lookout for high-quality purchases; when you find the greatest, don’t be scared to spend money on it.

The Saddleback Leather Company’s tagline, “They’ll fight over it when you’re dead,” is a terrific attribute to seek for in apparel at this age. In light of that, here are some styles that are sure to make your friends and children envious:

The Double-Breasted, Casual Jacket
A double-breasted jacket works well for a more laid-back style.
“Casual” and “double-breasted” are two words you won’t encounter very often before you’re sixty.

Compared to its single-breasted relative, the double-breasted jacket is perceived by most men as more official and stodgy. They are partially correct, but only partially so.

The respect required to wear a double-breasted jacket well is innate in an older gentleman. Choose a hue or pattern that isn’t appropriate for a boardroom, such as heather gray, chocolate brown, or forest green, to defy the conventions of business attire. If you feel like it, add some pinstripe. Add enough flair to make it impossible for anyone to mistake it for anything other than casual, pleasure-only clothing.

This goes well with blazers and matching outfits. You exclaim incredulously, double-breasted blazers? Indeed. They’re out there and don’t have to be limited to brass-buttoned navy blue. Try on a plaid or one in a deep, rich hue.

It’s a good thing that you’ll be the only person wearing something similar in the room.

The Gentleman from the South
Casually search the Pacific Highway for an older male.
For the warmer months, take inspiration from the classic style of the South in America: white pants, striped suits and jackets, straw hats, and of course, the red-soled white buck shoe.

The core concept has hundreds of variations. Select your favorite. Light-colored, airy cotton and linen are the most dignified way to combat heat and humidity. When everyone else is pulling up their shirtsleeves, you’ll still be wearing your jacket and feel perfectly great.

You can’t get away with wearing anything other than a shirt made entirely of cotton for this appearance; it must also have a light, breathable weave, ideally from long-staple cottons like the Egyptian, Sea Island, or Pima types.

To finish the appearance, experiment with adding colorful touches to your light-colored attire. The attention is drawn, respectfully, of course, by a bright red pocket square puffing up casually from a white or white-and-blue-stripe jacket. This style is Southern.

Gentle Tweed
An older man with a cap and tweed suit
Tweed is a fluffy, wooly material that has long been associated with British country gentlemen and Oxford professors. In addition to the cloth’s obvious roughness, it frequently combines threads of various colors to create a subtle pattern.

Have a few tweed things. Overcoats, matched suits, jackets, and pants—it’s a man’s three-season leisure garment.

Older guys look very nice in jackets with lots of pockets, usually flap pockets, and a moderately high front. Any shade of earth or gray works well. Plaid and check patterns are rather popular. Browse until you discover a style you like; there’s virtually no limit to what you can find.

For a subtle equestrian touch, mix a tweedy ensemble with dress boots or casual leather shoes like monkstraps or brogues. You can wear a soft rollneck shirt or a dress shirt and tie with a tweed jacket. For a truly rustic esquire vibe, you can even wear a mismatched vest underneath.

Three Items of Clothes Every Man Over 60 Should Own
The Ideal Overcoat
A man in his 60s with a scarf and an overcoat
The senior gentleman’s best friend is a wool overcoat that is full or three-quarter length. Though some guys prefer a little curve at the waist or flare at the hem, it’s well worth having one custom-made to get the ideal fit in the shoulders. With a straight coat, everything else falls into place.

Avoid limiting yourself to just one. While a basic overcoat in dark gray or navy blue is an excellent place to start, men in their sixties (and beyond) can also get a lot of use out of an olive or camelhair overcoat.

Getting nice, sober coats made of rich wool is crucial. Avoid plastic-like synthetics and loose trenchcoats with plenty of buckles and flaps. A duffel coat or a shorter coat, such as a blouson, are good choices if you want a more laid-back look.

His Personal Tuxedo
A black man in a restaurant wearing a tuxedo, bow tie, and boutonniere
It is reasonable to assume that a man in his sixties will occasionally be attending at least a few black tie occasions. There will be business or charity functions, award shows, weddings, and maybe even a New Year’s Eve gala or something similar.

Eventually, having a good tuxedo tailored to measure (or entirely bespoke) becomes more economical than renting one every time. Additionally, you get a garment of far superior quality and an unparalleled fit, which makes you stand out from other visitors who are still confined to rentals.

A classic black tie dinner suit should consist of the following: a white formal shirt, a tuxedo jacket with either shawl or peak lapels, plain-front trousers with the appropriate braiding, and all the required accents (black bow tie, shirt studs and cufflinks, dress pumps or highly polished black oxfords, etc.).

Invest in the appropriate shirt, tie, and tailcoat if you find yourself attending white tie events instead of black tie ones, such as cruises. However, these events are far less often than black-tie ones.

It’s an investment that is only utilized a few times, but after just one or two usages, it proves to be worthwhile.

Some Excellent Waistcoats
An elderly man with a waistcoat and a formal shirt with rolled sleeves and a tie
Another style that seems to be designed for an older man’s dignity is the waistcoat. Naturally, one of their original purposes was to cover the crotch of guys who had slipped a little, but the nappy look isn’t just for those who are becoming bigger around the waist.

Making yourself a three-piece suit is the simplest approach to obtaining quality waistcoats. In addition to a few “social” suits, casual hues and patterns also provide vests that go well with contrasting jackets or pants for a more striking ensemble.

Once you get the idea of switching vests, you’ll have access to a look that most guys never try. However, if you get too many patterns and colors going on, you may end up with some ugly combinations.

Waistcoats that are not a part of a suit can also be purchased; they are frequently more flamboyant, with high-sheen facings or intricate “wallpaper” designs. If you like these, don’t be afraid to wear them; just wear them sparingly and only with rich, sober jackets and pants that will balance them out.

Searches for the Over-60 Man You Must Never Date
We’re going to do it anyhow, just for one or two of the most heinous looks that should never, ever be seen on a man over sixty, even though you’re old enough that you don’t need anyone telling you what you can and can’t wear. You are most likely not the exception to any of these principles, if you believe you are. Or perhaps you’re simply an undiscovered fashion genius. You make the decision.

T-shirts with a logo. Okay, if you’re doing anything like cleaning the car. No logo T-shirts else. Nothing—no corporate brands, no band names. Generally speaking, younger guys should wear T-shirts. If you must, wear one that is tight-fitting, dark, and only one color. One potential outlier? You want to make younger men envious if you have a very rare and amazing vintage shirt from at least thirty years ago, such as one from a Who performance or something like that. There are benefits to getting older.
unique neckbands. Your ties should be pricey, silky, and sophisticated at this age. You’re not doing it correctly if it has Mickey Mouse or Star Wars.
camouflage and Hawaiian prints. Like the neckties, novelty prints don’t really suit you anymore because you’re too old. Will you continue to see elderly, retired men wearing garish Hawaiian shirts on the beach? Of course. Are you supposed to be those guys? Most likely not.
Additionally, you should avoid all of the typical suspects with poor attire, including sportswear (including sneakers) and anything with an elasticated waist. Wear these exclusively at the gym.

Men over 60 can up their style ante by avoiding these trendy choices. Excessively tight or baggy clothes might throw off proportions, so say goodbye to it. Instead of using gaudy logos, use classic patterns. Avoid overdoing the accessories; a minimalist look conveys refinement.

Give preference to timeless artifacts that stand the test of time rather than fads. Last but not least, strive for a unified and elegant look rather than mismatched colors and patterns. Men in their 60s can easily project a classic, refined look by avoiding these traps.

Last but not least, elderly men occasionally worry about what to do about clothes that are required by a medical condition. In other words, can you wear velcro pants, for example, if your hands aren’t working well enough to button things?

The answer is straightforward: “Yes.” You do what you have to do, don’t you? We are all affected by age and illness in different ways and at different periods. We do the best we can. If you require a cane, bulky orthopaedic shoes, or an extra-long jacket to cover a curved spine, you acquire them, wear them, and don’t waste anyone’s time on them.

Developing a relationship with a tailor could be worthwhile. Work with them to make any necessary medical adjustments discrete. Some tailors do amazing work for people with motor issues, partial paralysis, and other similar conditions, and a lot of their creations are difficult to distinguish from “normal” menswear until you look closely and see that they lack buttons and zippers. It’s an excellent strategy to maintain your sharp appearance if you could use that kind of tailoring and you can locate someone who specializes in it.

However, if you are unable to, make sure your wardrobe is well-stocked and wear your fine clothes with whatever modest accommodations you must make for necessity. Life is like that. You still have a nice appearance. Don’t worry about it.

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