One of the joys of old age is that you no longer look like you're trying too hard if you wear a suit for fun, or are the only man in a crowd wearing a blazer. You're an old guy.
You get to do things like that. Casual suits are one of the underused joys of American menswear. Have a few — in striped seersucker, plaid wool, pastel linen, or anything else that strikes your fancy. When you're not in the mood for a suit, go for slacks and a sports jacket instead.
The key thing to avoid is anything that smacks of laziness rather than studied casualness. Your outfits should look like they took a little thought and work. It's surprising how many great pieces of clothing some men never bother to wear. Hats, gloves, scarves, cufflinks — these are the refinements that an elder gentleman can use in his everyday wardrobe. A few beloved hats are something every man should own by the time he's If you don't have them yet, work on finding them. Colored leather gloves anything from a sedate burgundy to a stylish yellow are a three-season piece that almost nobody thinks to wear anymore, setting you firmly apart without being anything but the soul of dignity.
Smaller accents like French-cuff shirts with casual cufflinks, colored pocket squares, and neck scarves all complete the image of a man with both the time and the skill to out-dress everyone, even on his day off. The only touches worth avoiding are ones that evoke a specific past era, whether they've come back into style or not — younger men are wearing cravats again, for example, but an elder gentleman wearing one is going to look like an oil painting from the 19th century. Stick to timeless styles.
Wear the unusual, the interesting, and occasionally the downright startling when you're on your own time. Got a favorite old tweed jacket? Mid-forties and up is also the age at which it finally becomes acceptable to wear novelty ties for fun. Don't make a habit of it, but don't shy away from the occasional startling necktie either. It'll put a smile on people's faces when they're looking at you, and that's always a good thing. Just a sharp-looking pair of shoes can be enough to draw the eye in an otherwise-relaxed outfit like slacks and a knit fishing sweater.
Whatever it takes to remind people that you're there and, if necessary, that you're older and wiser than them. Even what you carry in your pockets can come in handy here; young people these days are always impressed when someone in their 60s pulls out a smart phone and opens its web browser. These can be casually patterned or made from traditionally casual materials like linen and seersucker.
Have a few in the closet, either as part of three-piece suits or on their own.
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The more colors, patterns, and textures you have in the wardrobe, the more mix-and-match looks you can create. Nothing baggy or shapeless. A few pairs of dress boots wouldn't hurt either. More than one in varying colors is no bad thing. Business is a whole different world for older men. If you're coming in to a new job it's going to be important to prove that you can keep up with younger workers; if you're in charge of your own employees it's vital to demonstrate gravitas and wisdom.
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Happily, business suits never look better than they do paired with gray hairs. You have access to the widest range of business styles, and no one will dare challenge your right to wear the sharpest of them. Single-breasted, two-button suits in plain navy or charcoal are for young strivers. An older man has the dignity and the weight of experience to carry a double-breasted suit, or a three-piece, and he doesn't need to shy away from elegant pinstripes either. You don't want to violate good business dress here, of course. If you're wearing a suit for serious and formal business it should be dark, sober, and restrained.
But a dark navy, charcoal, or black with pinstripes more than qualifies, and the added elegance of a full waist covering either a waistcoat or the fold of a double-breasted jacket is hard to argue with. If suits are a regular business necessity, invest in a variety of business-appropriate styles. Mix it up for maximum effect. Subtle differences are the key to any older man's wardrobe. You don't need your suits or blazers to be remarkably different than a younger man's — but they should be better.
High-quality cloth and tailored fits are the best way to achieve that subtle superiority. Two navy blazers in the same cut and color can look markedly different if one is made from a thick, rich wool and cut to the wearer's measurements and the other is a thinner, cheaper cloth with only a few adjustments. Having clothes that are just a little bit better than everyone else's is worth a bit of an investment in your later life. And it gives the younger men something to strive for, which they can always use.
All that said, an older man doesn't need flash in his business dress. Restrained elegance is the key. Good fabrics, fine suits, and all the details right — and then stop there. Flashy watches, designer labels, and aggressively tight silhouettes are for younger men.
Your clothing should look fine, dignified, and comfortable. That puts you above the fray of any subtle one-upsmanship. In suits and jackets, this can be achieved with softer shoulders and a less distinct taper at the waist. In more casual outfits, sticking to darker, softer colors and avoiding stark blacks and whites achieves a similar effect. Seriously, this is your time to shine. Do not be shy about living the good life in your choice of suits.
For an elegant touch, wear ivory or cream rather than pure bleached white. You've been collecting them for twenty-plus years now; you should have plenty. Leather soles are an added touch of elegance and very comfortable to walk in, once you get used to the feel. Dark navy or charcoal are good colors, and camelhair or khaki make a good choice for a second coat.
Embrace the new opportunities to try different styles as you age. Don't be afraid to completely change your style as you move from one decade to another. The Young Man: A full head of ungrayed hair and a body that stays in shape with unfair ease goes a long way in fashion. Casual Dress for the Young Man Young men can usually wear just about any style as long as they're willing to really own it.
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