What Shoes Does the Well Dressed Man Wear With Shorts

Good things come to those who wait.

You've waited; now let the good things roll.

Let's be clear up front: the clothes you're buying when you turn 60 aren't going to define your style for the rest of your life. That could be thirty-plus years — imagine writing an article for a man of 30 and expecting him to follow that plan until retirement!

So we're going into this with the understanding that "sixty-plus" is a big age range. Your style will grow and evolve during that time the same as it has every other month, year, and decade of your life.

But sixty is a good benchmark for the time when a man can start really shifting from the fashion of middle age to the fashion of the elder gentleman.

This is not a bad thing. Some of fashion's greatest icons have been silverbacks. They just got better as they aged. Both money and taste tend to accumulate over time, and the results make for a whole different school of fashion from the younger generations'.

Casual Style in Your 60s: Needs and Wants

If you're fortunate enough to have retired by your 60s, your whole wardrobe is effectively "casual" clothes — you're just dressing for yourself, now, with no professional needs to meet.

Resist the temptation to slide promptly downward until you hit the "sweatpants and hoodie" stage of things. That's not doing anyone any favors.

A man of any age should take just as much care with his casual clothes as he did with his work wardrobe, if not more. What you wear when you're on your own time says the most about you as a person — it's your own taste, opinions, and attitude, on display before you ever open your mouth.

Men in their 60s and older have the ability to make a statement with the weight of years behind it. Use that to your advantage, and dress to meet the needs and wants of an elder gentleman:

Fit

Every man needs a great fit. By your sixties you should not only know the importance of a good tailor, you should have one — or several — of your own, experienced men with your measurements on hand and a good understanding of your preferences.

Obviously, not everyone's fortunate enough to have a good relationship with a good tailor, but do your best to cultivate them in your general geographic area. And if you find someone that does a good job, keep him in business!

A lot of the best tailors are also gentlemen of advancing age, and you never know when they're going to decide it's time to hang up the shears…

Fundamentally, the function of a tailored fit is to make your body look good. Keeping your adjustments up to date can be important if your body is changing in weight or proportion, which isn't unusual in older men. Stay on top of your sizes — if something's starting to pinch or to sag, get it in to the tailor.

It's good advice for any man. But it can matter a lot for older men. There's some deep cultural conditioning that thinks of an old man in an ill-fitting suit as "sad," "poor," "lonely," and lots of other negative things that probably aren't true. It's just the impression that's out there.

Stay on top of your tailoring needs, and dodge it.

Gravitas

Younger men project authority with aggressive cuts and bold color contrasts. At your age, that's a losing game. Impress people with the weight of your years rather than the force of your personality — dress like the elder statesman, not the young gun.

That means, for the most part, somber colors and conservative cuts. Top-notch fabrics also go a long way here; an older man in a thick, rich wool coat can intimidate the hell out of a younger man in a cheaper, thinner jacket.

Cultivate a little aloofness. Not a lot — just a little. Dress to remind people that you've been around and seen a few things. Your fabrics should be luxurious, your colors varied but restrained, and your style full of classic elements.

It's also not a bad idea to indulge in a few of the accents of the "elder statesman." Wear a good felt hat in a classic style like a porkpie or homburg. Carry an elegant cane, even if you don't strictly need it. Always have a neatly-folded pocket square in your outer breast pocket, and a clean handkerchief in an inner pocket — and know to use the latter for utilitarian needs like wiping your eyes and nose, not the former.

In short, carry yourself like a gentleman of some stature.

Capability

Our culture is not always generous to its elders.

Be aware that, as your hair silvers (or vanishes), and especially once your body starts moving more stiffly, people are going to start treating you a little more dismissively or condescendingly.

It's obnoxious, but it's something that realists should plan for. Just as the younger man needs to dress a little sharper and a little more aggressively in his business attire if he wants to be taken seriously at a firm filled with middle-aged men, the older man in his retirement needs to still dress like someone with places to go and people to see.

Maintaining high dress standards keeps off both the obnoxiously sympathetic ("help you across the street" types) and the dismissive (negligent waiters, counter staff, and so on).

That doesn't mean business dress, though there's no harm (and sometimes quite a bit of fun) in slipping on your most imposing dark suit and a necktie for a walk around town or some afternoon errands. It does, however, mean making sure that everything you wear is well put-together, with a style that's deliberate and adds up to a clearly-structured "outfit" rather than just some random clothes thrown together.

The better your fit and the finer the garments themselves, of course, the more authority it'll lend you (thus our points #1 and #2 here). Put it together with some deliberate care and you'll avoid much of the hassle of dealing with people half your age — who can, let's face it, be jerks sometimes.

Casual Looks for Your 60s and Older

So what looks good on an older gentleman?

Comfortable, well-fitted clothes, same as on any other man. Classic styles are going to work better than fashion-forward runway experiments, of course — they look "timeless," which is a really great word to have associated with you as you get older.

But the formality can range from a full suit on down to jeans and a T-shirt (just make it really well-fitted jeans and a T-shirt, and maybe only if you're still in pretty good shape).

You should have a pretty extensive wardrobe to work with, if you've been good about adding quality pieces in your 40s and 50s. Get things to your tailor for adjustment as often as you need, and keep on adding new pieces, with an eye toward quality purchases — don't be afraid to spend on the best stuff, when you find it.

"They'll fight over it when you're dead," the slogan of the Saddleback Leather Company, is a great quality to look for in your clothing purchases at this age. With that in mind, here's a few looks that should keep your friends and offspring good and jealous:

The Casual, Double-Breasted Jacket

A combination of phrases you won't see often before you turn sixty: "casual" and "double-breasted."

Most men think of the double-breasted jacket as stodgier and more formal than its single-breasted cousin. They're partway right — but only partway.

An older gentleman has the inherent dignity it takes to wear a double-breasted jacket well. Buck the business-dress standard by getting it in a color or pattern that wouldn't work in a boardroom: forest green, chocolate brown; heather gray. Throw in some pinstripes if you feel like it. Jazz it up until no one can mistake it for anything but casual, purely-for-pleasure wear.

This works with both matched suits and blazers. Double-breasted blazers, you say disbelievingly? Yes. They exist, and they don't have to be restricted to navy blue with brass buttons. Try one on in a rich, dark color, or even a plaid.

You'll be the only one in the room wearing anything like it, and that's a good thing.

The Southern Gentleman

Borrow a bit of timeless elegance from America's tradition-soaked South for the hotter months: white trousers, striped seersucker jackets and suits, straw hats, and of course the red-soled white buck shoe.

There are hundreds of variations on the basic idea. Pick the one you like. It's the most respectable solution to heat and humidity: light-colored, lightweight cotton and linen. You'll still have your jacket on when everyone else is rolling up their shirtsleeves, and you'll feel just fine.

This look requires some investment in quality — you can't get away with anything but a 100% cotton shirt, for example, and it needs to be a light, breathable weave, too, preferably made from long-staple cottons like the Egyptian, Sea Island, or Pima varieties.

Play around with colorful accents in your light-colored ensemble to complete the look. A bright red pocket square puffing insouciantly up from a white or white-and-blue-stripe blazer grabs the attention — politely, of course. This is a Southern style.

Soft Tweed

The hallmark of Oxford professors and British country gentlemen for generations, tweed is fuzzy, wooly stuff. It often blends different colors of threads, making a subtle pattern in addition to the visible texture of the cloth.

Own a couple pieces in tweed. Jackets, trousers, matched suits, overcoats — it's a gentleman's three-season leisure fabric.

Older gentlemen look particularly good in relatively high-fronted jackets with plenty of pockets, usually flap pockets. Any sort of gray or earth tone works well. Check and plaid patterns are relatively common. There's really no limit to the styles you can find, so browse until you find one that you like.

Pair a tweedy outfit with relaxed leather shoes like brogues or monkstraps, or with a pair of dress boots for a subtle equestrian flavor. A tweed jacket can take a dress shirt and tie or a soft rollneck shirt — your call. You can even slip an unmatched vest underneath for a very country esquire feel.

3 Wardrobe Pieces Every Man Older than 60 Should Own

The Perfect Overcoat

A full or three-quarter length wool overcoat is the senior gentleman's best friend. It's well worth having one custom-made to get the perfect fit in the shoulders — with a straight coat, everything else follows from that, though some men like a bit of taper at the waist or flare at the hem.

You shouldn't restrict yourself to just one. A plain, dark gray or navy blue overcoat is a good starting place, but men in their sixties (and up) can get a lot of mileage out of a camelhair or olive overcoat as well.

The key is to get good, sober coats in rich wool. Stay away from baggy trenchcoats with lots of buckles and flaps, and from plastic-like synthetics. If you want a casual style, a duffel coat or a shorter coat like a blouson works well.

His Own Tuxedo

By his sixties, a man can reasonably expect to be attending at least a few black tie events here and there. There will be weddings, charity or corporate events, award ceremonies, and perhaps even the occasional New Year's Eve ball or the like.

At some point it becomes more cost-effective to have a proper tuxedo made to measure (or completely bespoke) rather than renting each time. You also end up with a much higher quality of garment, and an unmatched fit, which helps you shine in comparison to guests still stuck in rentals.

Stick to the basics here and have a classic black tie dinner suit made: tuxedo jacket with either peak or shawl lapels, plain-front trousers with the proper braiding, white formal shirt, and all the necessary accents (black bow tie, shirt studs and cufflinks, dress pumps or highly-polished black oxfords, and so on).

If you find yourself going on cruises or otherwise ending up at white tie, rather than black tie, events, invest in the necessary shirt, tie, and tailcoat, but those are much less common than black tie events.

It's one of those investments that only gets used a handful of times — but that earns its worth after just one or two uses.

A Few Good Waistcoats

Waistcoats are another of those looks that seems made for the dignity of an older man. Of course, one of their initial functions was covering the paunch of men who'd let themselves slip a bit, but you don't have to be expanding at the waistline to benefit from the nappy look.

The easiest way to acquire good waistcoats is to have three-piece suits made for yourself. In casual colors and patterns, that gets you not only a few "social" suits, it also gives you vests that can be worn with unmatched jackets or trousers for a more contrasting look.

It takes a bit of practice to get the hang of swapping vests — it's possible to make some unsightly combinations if you get too many patterns and colors going on — but once you get it down you'll have access to a look that most men never touch.

It is also possible to buy waistcoats that are not part of a suit, and in many cases these are flashier, with elaborate "wallpapering" patterns or high-sheen facings. Don't shy away from these if you like them, just wear them judiciously, and only with sober, rich jackets and trousers that can balance them out.

Looks for the Man Over 60 to Absolutely Avoid

You're old enough now that you don't need anyone telling you what you can and can't wear — but we're going to anyway, just for one or two of the most egregious looks that should never, ever appear on a man older than sixty. If you're thinking that you're the exception to one of these rules, you probably aren't. Or maybe you're just an unrecognized fashion genius. You decide.

Logo T-shirts. If you're washing the car or something, fine. Otherwise, no logo T-shirts. No band names, no corporate brands, nothing. Leave the T-shirts to younger men in general, and if you have to wear one, keep it close-fitted, dark, and one solid color. One possible exception? If you have a super-rare, super awesome vintage shirt from at least thirty years ago — something from a The Who concert or whatever — and you want to make younger men jealous. Age has its perks.
Novelty neckties. At this age your ties should be elegant, silk, and expensive. If it has Mickey Mouse or Star Wars on it, you're doing something wrong.
Hawaiian and camouflage prints. Like the neckties, you're past the age where novelty prints really work for you. Will you still see old retired guys on the beach in tacky Hawaiian shirts? Absolutely. Should you be those guys? Probably not.

You'll also want to steer clear of all the usual badly-dressed suspects, especially athletic gear (including sneakers) and absolutely anything with an elasticized waist. Wear them at the gym and nowhere else.

A final concern that older men do sometimes run into: what about clothing necessitated by a medical condition? That is to say, if your hands aren't working too well anymore and you can't do up buttons, can you switch to velcro pants, and so on?

The simple answer is "yes." You do what you gotta do, right? Age and ill health hit us all differently, and at different times. We make the best of it. If you need chunky orthopedic shoes, or a cane, or an extra-long jacket to drape over a curved spine, you get those things and you wear them, and you don't take any crap from anyone about them either.

It may be worth building a relationship with a tailor. Work with them to keep any medically necessitated alterations discreet — there are some tailors doing fantastic work for people with partial paralysis, motor problems, and similar conditions, and a lot of their stuff is hard to tell from "normal" menswear until you get right up close and notice that there's no buttons or zippers. If you could benefit from that sort of tailoring, and you can find someone who specializes in it, it's a great way to stay looking sharp.

But if you can't, stock your wardrobe well anyway, and wear your nice clothes with whatever small nods to necessity you have to. That's life. You still look good. Don't sweat it.

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Source: https://www.realmenrealstyle.com/man-over-60/