The Secrets to Dressing Well in Your 40s

The forties is 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 forties 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 forties. Your body may have changed in the past decade, but so too has 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 forties.

The Basics

You don’t need an expansive wardrobe. At this age, your closet should be comprised of fewer, nicer things that you wear often.

Aaron Levine is an impossibly stylish forty-something menswear designer who lives in Ohio and packs very little when he travels for work, which is often. He brings black workwear pants (Carhartt double-knees, perhaps), dark denim jeans, a flannel shirt, a couple blue button-downs, a navy crew neck 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.

Christopher Fenimore

Aaron Levine is an impossibly stylish man in his forties.

If you’re looking to recapture your sense of style in your forties—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 of 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 work week and any social occasions.

KEEP READING: The 15 Items Every Guy Should Have in His Closet

If your personal style is more evolved, focus your attention on buying high-quality items. Experiment with color, 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, Drake’s, or J.Mueser. If you don’t have a navy blue suit, get one. If you do, start expanding: gray, brown, or something with a pattern like houndstooth or a chalk stripe.

MORE: The Three Types of Suits Every Man Should Own

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

MORE: The Indispensable Guide to Buying—and Wearing!—a Tie

Todd Snyder Italian Cotton Madison Jacket

Buck Mason Seafarer Cotton Rib Crew

L.L. Bean Wrinkle-Free Double L Chinos

G.H. Bass Monogram Derby Shoes

Uniqlo Selvedge Straight Jeans

J.Crew Broken-In Oxford Shirt

How Your Clothes Should Fit

Fit is a matter of concern in your forties, 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 half-time 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 forty 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.

KEEP READING: The Most Common Mistakes Guys Make When Suiting Up

The Pants You’ll Need

Got any pants with stretch in them—jeans, chinos, dress slacks? 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. Levi’s 501 is the platonic ideal, but it’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.

MORE: How to Find the Perfect Pair of Jeans

For chinos, thicker is better. The pants 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. Take a look at the new Docker’s Eighty-Six collection, The Real McCoy’s, and (surprise, surprise) Buck Mason and Todd Snyder.

KEEP READING: How Your Pants Should Fit Now

3sixteen Classic Tapered Jeans

RRL Straight Fit Once-Washed Selvedge Jean

Dockers Eighty-Six Alpha Chinos

Buck Mason Paperback Twill Full Saddle Chino

The Real McCoy’s Joe McCoy Chinos

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 forties 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 boucle, 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.

Madewell Raglan-Sleeve Coat

Todd Snyder Italian Wool Officer Coat

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 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 or Sunspel, are great substitutes for turtlenecks or dress shirts. And lightweight knits in a varying blend of cotton, cashmere, linen, and merino wool can help to breathe new life into a staid wardrobe that has become dependent on oxford button-downs and tees.

Quince Cotton Turtleneck Sweater

Extra‑Fine Merino Roll Neck

Todd Snyder Cashmere Turtleneck

Comfort Is Good, Coziness 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 tech-y 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 coziness is their foremost function.

MORE: The Comfortable, Cool, Affordable Sneakers Every Man Should Wear

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 READING: The Three Essential Style Details Every Man Should Know

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 forties, 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.