THE SECRETS TO DRESSING WELL IN YOUR 40S

The 40s are a consequential decade for a man. If you're lucky, your life is only half finished. The previous decades were prologue. You've earned a measure of gravitas, but these are the years when everything really starts to matter—your job, your family, your health. This is the age at which people will always remember you, as if frozen in amber.

So you'd better look your best.

How you dress in your 40s should reflect both your years of experience as well as the fact that you're not old. Yes, it's a curious place to be. Some men give up on style around this time; others continue dressing as if they haven't aged. Don't do either of those things.

Remember: There is power in being in your 40s. Your body may have changed in the past decade, but so too have your budget and your confidence. This is the era in which you buy nice clothes that make you look good. It should be the best you've ever dressed.

Here are the essentials clothing items—and advice—for looking stylish in your 40s.

The Basics

You don't need an expansive wardrobe. At this age, your wardrobe should comprise fewer, nicer things that you wear often.

Aaron Levine is an impossibly stylish 40-something menswear designer who lives in Ohio and packs very little when he travels for work, which is often. He brings black workwear trousers (Carhartt double-knees, perhaps), dark denim jeans, a flannel shirt, a couple blue button-downs, a navy crewneck sweater, and an unstructured suit he can break apart when necessary. Add a beanie, a big coat, and a great pair of boots (Levine espouses all three) and there isn't much you couldn't handle.

If you're looking to recapture your sense of style in your 40s—or find it for the first time—it's as easy as buying a handful of evergreen items. Here's the 101 version: Start with a navy-blue blazer, a couple dress shirts, a pair of jeans, a sturdy chino, a light sweater in cream or navy, and a pair of dress shoes, ideally derbies. If you work in an office environment, you're all set for the workweek and any social occasions.

If your personal style is more evolved, focus your attention on buying high-quality items. Experiment with colour, pattern, and fit, but remember that outlandish trends are best reserved for those who are yet to know better.

You will need at least one nice suit at this age. Invest in this item—it should hurt your bank account just a little. At the mid-price point, you'll find very good suits at Paul Smith, Todd Snyder, Polo Ralph Lauren, and Drake's. If you don't have a navy-blue suit, get one. If you do, start expanding: grey, brown, or something with a pattern like houndstooth or a chalk stripe.

And even if you have few occasions to wear one, buy a couple nice ties. Drake's makes some of the best, as does Hermès, but you'll also find a nice selection at Ralph Lauren.

How Your Clothes Should Fit

Fit is a matter of concern in your 40s, especially if you've spent more time with your kids or in the office than you have at the gym. A good guideline is to avoid the margins—you don't want anything that's too skinny or too voluminous. Labels that say "classic fit" are your friend. Baggy jeans or flares (like those Kendrick Lamar wore during the Super Bowl halftime show) are fun, but they're also a more advanced move. Approach with caution.

Aaron Levine is keen on a roomier fit when it comes to tailoring. His jackets are cut with a softer shoulder and a longer body, and the pants sit higher on the waist, billow gently outward over the knee, and pool just a little at the shoe (often a low-profile Belgian loafer). We're not talking late-'90s-NBA-draft kinda big, but it's tailoring with room to move. It's especially good for those of the wrong side of 40, because it's physically forgiving but aesthetically interesting. Cool and comfy, essentially. Traditionally, that kind of tailoring was only available in vintage from Giorgio Armani and Valentino, but brands such as Stòffa, Saman Amel, P. Johnson, and Cos do it brand-new.

The Trousers You'll Need

Got any trousers with stretch in them? Throw 'em away. You need real trousers that have some heft.

In terms of fit, aim for the middle: a classic fit with a mid-to-high rise. Remember, you're avoiding the margins. The Levi's 501 is the platonic ideal, but that's not the only brand in town. Wrangler offers classics like the Cowboy Cut for a veritable steal, and Lee has an array of affordable options as well as some premium ones—like the famous 101—for bigger spenders. You can also look at Buck Mason (which recently collaborated with Lee), Ralph Lauren's RRL, Todd Snyder, 3sixteen, and Rag & Bone if your budget is higher. And then there are the more esoteric Japanese denim makers like OrSlow, Samurai, Sugar Cane, and Pure Blue Japan. Choose the wash that suits you and avoid anything that's too distressed. And don't sleep on white jeans, which you can wear with anything. Just make sure those aren't too skinny, otherwise you risk looking like a rich guy who can't buy taste.

For chinos, thicker is better. The trousers Steve McQueen wore in The Great Escape? They were made of a hefty cotton. So should yours be. Wide-legged chinos have become popular—thanks, in part, to J. Crew's giant-fit chinos—but you can leave those to the younger and more adventurous dressers. Still, your chinos shouldn't be tight. You should have some room to move, just like McQueen.

A Coat That Hides All Sins

London-based celebrity stylist Catherine Hayward—the woman Benedict Cumberbatch goes to when he needs to dress well—insists there are a few crucial items that any man in his 40s should have in his wardrobe. The first is a great coat that finishes at or below the knee, which Hayward says is good for hiding any and all "sins" (read: old band tees, wrinkled shirts, etc.). But it needs to be weighty and textured "so it has some heft to it," she adds.

A classic overcoat in thick wool is great, and something with a subtle check or herringbone would be the smart choice, because it can be dressed formally or casually. If you want real texture, look for something in wool bouclé, brushed alpaca (like this bonkers Dries Van Noten number), or shearling—but be careful, you want to avoid looking like a World War II aviator.

I recommend a double-breasted coat to ensure it indeed hides those sartorial sins—or a burgeoning dad bod, if that's the case—plus, double-breasted coats look especially good as the top layer to a tailoring look. If double-breasted feels too grand, try something with a raglan sleeve and collar you can pop. That'll look great with a suit, too, but have a slightly more low-key, bookish feel. Drake's is a good place to shop for this kind of coat.

Fundamentally, a great overcoat will give you "gravitas," according to Hayward.

When it gets warmer, swap that overcoat for a lightweight trench coat or sturdy overshirt. The lesser-known Teba jacket is a great blazer/overshirt hybrid that can be either smart or casual, depending on the occasion.

The Most Flattering Thing a Man Can Wear

Hayward's second pick is the perfect turtleneck sweater, which she suggests looks good on nearly everyone because it frames the face and can even obscure a neck and jawline that may not be as taut as they once were. The turtleneck is, as Esquire's Tom Junod once wrote (though not for this magazine), "the most flattering thing a man can wear."

The beauty of a great turtleneck—or roll-neck, as it's also called—is that it is casual and easy wearing but clearly a "choice," as fashion people like to say. That means you didn't just grab the nearest crewneck, but instead really thought about what you wanted to wear. And that's one of the golden rules of dressing well as a (slightly) older guy: making active style choices.

For warmer temperatures, knitted polos, such as those by Zegna and Sunspel, are great substitutes for turtlenecks and dress shirts. And lightweight knits in a varying blend of cotton, cashmere, linen, and merino wool can help breathe new life into a staid wardrobe that has become dependent on oxford button-downs and tees.

Comfort Is Good, Cosiness Less So

Speaking of choices, rather than buying New Balance sneakers or a Patagonia vest, you might opt for a similar alternative that does the same job but demonstrates your taste and brand awareness. Maybe those New Balances become Keen hiking sneakers and that techy vest is swapped out for a classic Rocky Mountain Featherbed vest or a down cardigan from Snow Peak. You want clothes that offer ease and comfort but don't necessarily scream that cosiness is their foremost function.

Comfort can also be found by a visit to a tailor, and they aren't just there to sort out your suits. Another of Hayward's top tips is to find a tailor to tweak pretty much everything you own to make it fit better. That way "everything looks good on you," she says. The shortening of a shirt sleeve, the nipping in of a blazer, even the cuffing of a pair of jeans that are just too damn long—it all counts, and it certainly costs less than buying a whole new wardrobe.

Keep Up Appearances

Finally, you should always keep up appearances. There isn't much we can do about those crow's-feet, nor the hairless voids that persist at our crowns, but we can be clean and smell good. For fellas leaving their youth behind, Hayward is gently insistent on regular manicures, pedicures, and haircuts and suggests a well-kept beard wouldn't be a bad idea. You should also consider your scent. It's common among teenage boys to collect colognes and spray them liberally. By your 40s, you should have a signature scent, which you might rotate based on the season or the occasion. "Those little key moments are sometimes worth investing in," she says.

2025-03-12T10:05:36Z