Dressing Sharp and Casual for the Man in His 50s

Fashion models are, as a general rule, young men.

Even catalogs that cater to middle-aged and older men tend to use models that are substantially younger than their target market. It's not unusual to see twenty-somethings grinning at you from the pages of Brooks Brothers or London Fog catalogs, even though the vast majority of those companies' sales go to men in their forties and up.

That can be misleading. Looks aren't strictly limited by age, but the reality is that your style should change at least a little bit as you age. Most men in their fifties are not flattered by the clothing they wore in their twenties.

Business suits are, of course, almost always safe, and a good look so long as they're well-made and well-fitted, but they're also not much use outside of formal business settings. A lot of men don't even need them for work — and some men in their 50s don't work at all, if they've been fortunate enough to retire reasonably early in life.

That creates a big need for clothes that look sharp but are also casual enough to wear in relaxed, social settings. Fortunately, there are a lot of options out there — and with “silver foxes” like George Clooney and Richard Gere splashed all over the contemporary tabloids, there's no better time to be a good-looking middle-aged man than today.

The Advantages of Age: Personalize Your Look Over Time

Younger men have the advantage of a blank slate. They're just starting to come into their own, and many have full control over their wardrobes for the first time. That leads to some experimental young men looks (some good and some bad), but it also requires a lot of expense and some inevitable false starts.

Older men, on the other hand, enjoy a solid starting baseline: they've got a good twenty or thirty years of accumulated clothes to work with.

Not all of those will necessarily lend themselves to a sharp look. If you were a sloppy dresser for much of your life, and decided to sharpen your image up for the first time in your fifties, you've got some shopping ahead of you.

But most men can get at least some service out of even a modest wardrobe. Anything that fits well can be put back into use with a little effort. Look through your closet for good staple pieces that can form the backbone of a varied wardrobe:

• Dress slacks: Got some old gray slacks you wore once in a while for work, or even the pants of a suit whose jacket has long since died? Get those back into rotation as your new alternative to jeans and sweatpants. Turns out they're just a comfortable once you've had them tailored, and they make you look a million times classier.
• Khakis and chinos: Same principle but a little more relaxed. Pair them with jackets or sweater so that you don't have that office drone khakis-and-button-down look going on, but for the most part these are still a great jeans alternative.
• Sports jackets and blazers: The ability to wear a jacket any time you want, in almost any circumstance, is one of the perks of middle age. Get them adjusted for a good fit and look better than everyone else in the room.
• Dress shirts: Hopefully years of work clothes has left you with a decent collection of collared shirts. Keep a few plain white ones for their versatility, and add some color and patterns to the rest of the collection as needed. Nothing too soft or frumpy — a little crispness goes a long way in your shirt collars.
• Leather shoes: When in doubt, put leather on your feet. Nothing says “old man with nothing left to lose” like big, puffy sneakers. You don't want to be that guy. Get shoes with leather uppers and avoid the big, clunky, orthopedic soles as much as possible (use inserts if your feet need cushioning).

If you're lucky, you'll already own a lot of these. Some may not have seen use in years, depending on your style and your personal needs.

Don't be shy about expanding the closet when you need to, but don't waste the opportunities you already have, either. Get some of the old clothes back into rotation, with a trip to the tailor for adjustments if you need them. Odds are you've already got the backbone of a sharp style at your fingertips.

Items Every Man in His 50s Should Own

There's no one right look for your fifties. But a certain level of refinement goes well with gray hairs — and there are a few classic items worth having in your wardrobe no matter what your personal style leans toward.

• Blazer jackets: Crisp, sturdy, plain, and elegant to a tee. Go ahead and buy at least one really nice navy blazer. When you need a dapper, conservative look, it'll make you look like a million bucks. And if you wait for a good sale or keep an eye on thrift markets, it should only cost you a couple hundred at the worst.
• Sports jackets: For the less conservative, more casual look, but still keeping the flattering shape of a tapered jacket. Be bold with your patterns and textures. Plaids, stripes, windowpane checks; whatever you want. You're telling people that you're old enough and confident enough to make your own style choices when you move away from the monochromes.
• Fitted sweaters: Cardigan or pullover style both work fine, but stay away from anything too oversized or soft-collared. You want a close fit and a fairly sleek profile to keep you away from the “grandpa sweater” stereotype.
• Gray slacks: Preferably multiple pairs, preferably multiple shades of gray, and always in real wool. You should be wearing nice slacks as often as you wear jeans, or more so. You're not limited to gray, of course — but it's a good starting place, and at least one pair is a definite must-have.
• Wool overcoats: You're wearing lots of blazers and sports jackets, right? If you are, you'll need a decent coat to go over them. Something simple, wool, and about thigh-length should do just fine. Look for sales or second-hand options if your budget is tight. Thrift stores often have a lot of these, because not many men think to buy one.
• Dapper hats: The details make the man, and you've been around long enough to buy yourself some nice, personalized details. Go ahead and be one of those men who don't leave the house without a hat on. If your hats are nice (and you own a few of them), it'll impress the heck out of people.
• Dress wristwatches: See previous statement on details. Own watches; wear watches. There's no excuse not to.

Obviously, this list isn't a comprehensive wardrobe. You'll look awfully silly if those are the only things you own.

Rely on your existing wardrobe staples (dress shirts, belts, shoes, etc.) to tie together your style pieces. But try to own all or most of these must-haves, and use them regularly. It'll go a long way toward making you a sharp-dressed man in his fifties, rather than just a man in his fifties.

Dressing for Specific Occasions

Not all “sharp” clothes serve the same purpose.

Some look intensely stylish for a night out on the town, but would seem too fashion-forward or extravagant for a conventional workday. Others will stand you in good stead at an office party or a weekend golf outing, but would look frumpy and bland at a nightclub.

Choosing the right attire for different occasions is a nuanced art that goes beyond simply following dress codes. Tailoring your outfit to the specific event reflects not only your understanding of social norms but also your respect for the occasion and those attending.

Whether it's a formal business meeting, a casual gathering with friends, or a black-tie affair, your clothing communicates volumes about your intentions and personality. By acknowledging and adapting to the expectations of each setting, you not only enhance your own comfort but also showcase a thoughtful and considerate approach to social interactions.

Mastering the skill of dressing for specific occasions ensures you're always appropriately attired and makes a lasting impression on those around you.

Choose your battles wisely — and don't be afraid to add to the wardrobe as needed.

Fashion For Men Over 50 – Dressing for Work: Business Attire

Not all men need a business suit for work. These days, the majority doesn’t, although the percentage of middle-aged men who need one is higher than the percentage of younger men. As you rise in the ranks, a higher dress standard is only natural.

So assuming you do need a business suit from time to time, what should it look like?

• Dark color is a must — navy blue or charcoal gray are the best. Very fine pinstripes are acceptable in most situations, but they do make the look a little bolder. It's worth owning at least one plain-colored suit for somber occasions (or for when you need to appear humble, like in a courtroom).
• You can go single-breasted or double for the jacket. Double-breasted is a little more formal-looking and a little less versatile, but it has a refined air that suits older men very well.
• The accompanying shirts should be plain white, or white with a very light pattern. Err toward plain white if your suit has pinstripes.
• Neckties and pocket squares are where you personalize the outfit. It's worth spending a little more to get the ones you want. Stay away from matched sets — that's a rental tux look, and not a good one. The tie and the square can complement, but they shouldn't be made from the exact same cloth.
• A slim black belt and a pair of black oxfords are your traditional accompaniments here. For a slightly more relaxed look, black loafers, brogues, or dress boots can stand in for the oxfords.

Some workplaces will be more relaxed than others, so you'll have to get a feel for how far from this “gold standard” look you can go. But when in doubt, follow this outline to look like you belong in the halls of power.

Fashion For Men Over 50 – Dressing for Work: Business Casual

Now that we've covered the highest standard, let's look at what most men end up wearing to work these days: the broad, nebulous category known as “business casual.”

This can mean a lot of things. Some workplaces have a specific set of guidelines printed up; others just say “business casual” and let people figure it out for themselves.

At the dressiest end of the spectrum it can mean crisp slacks, blazers, and neckties. Down at the other end it might mean outfits as casual as dark jeans and turtlenecks.

The best thing a man in his fifties can do for a dress-casual workplace environment is be varied. Don't wear the same combination every day. If your default has always been khakis and a button-down, throw a sports jacket or a necktie on some day to switch it up. If you're constantly on the dressy end of the spectrum with a blazer and slacks, try throwing some dark jeans on for Friday instead. And so on.

When in doubt, however, slacks or chinos, a dress shirt, and a sports jacket is always a safe bet. (Throw a necktie on if the dress code requires it, but in most places the jacket is dressy enough on its own.) Vary your look — but if you're coming back regularly to the slacks-and-jacket option, you're probably doing okay.

Fashion For Men Over 50 – Dressing for Yourself: Daytime Errands

Work wear is important, but it's also less of a personal statement. A man who looks like he's going to or coming from the office is understood to be dressing for his employer, not for himself.

That means the clothes you wear in your personal hours take on a special significance. They are, in a big way, an expression of the “real you.”

An older man also has some practical motivation to look a little sharp when he goes out in public: the more dressed-down and sloppy you look, the more younger people are going to think “depressed retiree.” Stay clear of work-out clothes and gym shoes, and sharpen up your look with some non-work dress clothes:

• Daytime suits: An underused option these days, but a good one for men of means — get some matched suits in light colors and patterns. These are clearly not work wear (too informal), but they're still a head and shoulders above nearly everyone else's street clothes. Perfect for the truly dapper fifty-something.
• Sports jackets and slacks: Wear them with an open collar rather than a necktie to look less like you're coming from the office, and throw a colorful pocket square into any jacket that needs livening up. You can do this with dark jeans, too, but it's a little bit of a younger man's look. If you've got nice slacks, use 'em.
• Fitted sweaters and turtlenecks: Not every outfit has to have a tapered jacket in it. A sleek, body-hugging sweater or turtleneck paired with slacks or dark jeans looks just fine. Make sure your belt and shoes look nice, though — that upgrades the look from “meh” to “sharp.”

Details count for a lot in your casual look. If you have a good fit and one or two sharp accents, almost anything can look dapper. If the clothes are slumped or you're wearing them with dinged-up old shoes and overcoats, suddenly you look a lot less like a man who's still living life to the fullest.

Fashion For Men Over 50 – Dressing for Yourself: Evenings Out

Daytime looks and evening looks aren't as clearly divided as they used to be, but you still want a noticeable difference. If you're going to the grocery store in the same outfit you wear to the theater, you're doing one of those two things wrong.

How dressy you look in the evening depends a lot on where you're going. Theater, opera, and symphony performances are traditionally more conservative (though there's a younger art crowd that's bucking those trends). Sit-down restaurants with linen tablecloths are similarly high-standard. Those are places where a suit and even a necktie would not be inappropriate.

Bars and nightclubs, on the other hand, or concert venues for rock, country, and other contemporary genres, are likely to see a suit as hopelessly conservative, especially with an accompanying necktie.

Broadly speaking, be thinking darker colors rather than light, suits and blazers rather than sports jackets, and open collars rather than neckties unless you're somewhere very formal.

As with your daytime outfit, some attention to detail is a big help here too. Don't just be the guy in gray slacks and a navy blazer — be the guy in gray slacks and a navy blazer with some sleek black dress boots and a fancy gold belt buckle that matches the blazer buttons.

Conclusion: The Fifty-Something Man in Brief

Your fifties is a great decade to dress sharp.

This is an age where men have experience, a sense of who they are, and — hopefully — a little more disposable income than younger men.

Make the most of it. You're old enough now that you don't need to feel limited by fixed “looks.” You're not a punk, a cowboy, a student, whatever — you're just you, as dapper as you want to be.

Navigating the style landscape in your fifties involves a blend of confidence, comfort, and timeless elegance. Embrace quality fabrics, refined tailoring, and a dash of personal flair to curate a wardrobe that exudes maturity without sacrificing individuality.

Pay attention to grooming, maintain a versatile selection of classic pieces, and let your style evolve with a touch of contemporary trends.

Ultimately, the fifty-something man defines his fashion narrative by embracing authenticity, celebrating the wisdom of experience, and projecting a self-assured image that commands respect and admiration. In the world of style, maturity is not a limitation but an opportunity for sophistication.

Here's a hard fact for you – every guy is going to experience shocking changes in his life. Click here to discover the top 5 things every man needs to accept as he gets older.

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