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Essential Wardrobe Downsizing Tips for Men Over 50

Curate a timeless wardrobe with versatile pieces that reflect your style


a collage showing various articles of clothing and shoes for men
(From left) Stock your closet with hardworking essentials, including: J. Crew’s 770 Chino Pant in Weathered Chino, Brooks Brothers’ Cotton Pique Half-Zip Sweater in Burgundy, Grayers Flex Everyday Knit Shirt – Faded Gray, On Cloudzone in Mulberry Black, Gap’s Modern Straight Khakis in Pilot Grey and the L.L. Bean Field Trip Shirt Jac in Olive Gray.
AARP (J. Crew, Brooks Brothers, Grayers, On, Gap, L.L. Bean)

There are many reasons for downsizing your wardrobe to just the essentials. By a certain age, a guy has usually done a fair share of experimenting with trendy fashions of youth (think jackets with linebacker shoulders, shirts in day-glo colors or eye-grating band T-shirts) or they’ve been talked to into an unnecessary and often unwearable apparel purchase by an overeager salesperson.

But most likely, at this point in life, you have a good sense of your own style and how you like to present yourself to the world. And the “world” —  at least the people you usually encounter — generally have an expectation of how you’ll look when you turn up to meet them. That sense of familiarity seemingly adds a sense of calming reassurance to our interpersonal relationships, even as the world seems crazier than ever.

Along with a well-defined wardrobe comes a couple of big “but’s.” With age comes more authenticity and its privileges, but it’s still important to make an effort to look sharp, whether you’re still working, traveling the world or just meeting up with friends and family members. That means your closet’s essentials must be well-fitting and timeless. In a well-edited closet, every piece is a prime player, so restock regularly whenever something looks too worn or shabby.

With all that in mind, there’s still room for expressing your personality by adapting the wearable suggestions outlined below to your needs. An unexpected style swerve, like a chili-red topper or a pair of bolder-than-usual blue “khakis,” can show that the older guy’s still got it.

a collage showing three different jackets
(From left) Alex Mill’s Garment Dyed Work Jacket in Recycled Denim in Red Pepper; Taylor Stitch’s The Ojai Jacket in Organic Navy Foundation Twill; L.L. Bean Field Trip Shirt Jac in Olive Gray
AARP (Alex Mill, Taylor Stitch, L.L. Bean)

Working prerogatives

There are many good reasons for keeping a casual jacket in your regular rotation. Besides pulling a look together, a lightweight top piece can camouflage a few extra pounds and provide a functional alternative for guys who might be used to wearing a suit jacket or blazer with handily accessible pockets. Unsurprisingly, dependable and functional workwear styles provide an updated springboard for a versatile alternative that’s about as dressed up as you’ll need in any situation.

One iteration is Taylor Stitch’s The Ojai Jacket ($198, taylorstitch.com), modeled on French utility outerwear in a year-round-weight Navy organic cotton twill that’s easy to dress up or down. Similarly styled, Alex Mill’s Garment Dyed Work Jacket in Recycled Denim ($225, alexmill.com) adds a hearty pop of color in Red Pepper or a reassuring neutral like Beeswax. Ruggedly handsome, the L.L. Bean Field Trip Shirt Jac in Olive Gray or Sand Dune ($85, llbean.com) in washable slubbed cotton elevates your look when layered over a button-up or tee.

a collage showing three different chambray shirts
(From left) Jockey Outdoor by Luke Bryan Long Sleeve Woven Button-Up Shirt in Chambray; Grayers Flex Everyday Knit Shirt - Washed Navy, Banana Republic’s Standard-Fit Chambray Shirt in Cerulean Blue
AARP (Kohl’s, Grayers, Banana Republic)

Trusty blues

Continuing in functionality and versatility, workwear inspires a classic but always apropos underlayer in a seasonless button-down in cotton chambray. And is there any gent who doesn’t look great in a blue shirt? The Jockey Outdoors by Luke Bryan Long Sleeve Woven Button-Up Shirt ($48, kohls.com) features snappy dual chest pockets and a relaxed fit as well as a moisture-lock collar to keep things cool all day long. Banana Republic’s Standard-Fit Chambray Shirt ($70, bananarepublic.com) is crafted from a washed cotton for an already-loved feel and comes in an unexpected cerulean hue.

If you want a similar chambray effect but with the suppleness of a cotton knit, try Grayers Flex Everyday Knit Shirt in Washed Navy ($88, grayers.com), a button-up that feels like a comfy T-shirt.

a collage showing three different pairs of straight leg trousers
(From left) J. Crew’s 770 Chino Pant in Catskill Green; Lands’ End Knockabout Comfort Waist Classic Fit Chino Pant in Khaki; Gap’s Modern Straight Khakis in Pilot Grey
AARP (J. Crew, Lands’ End, Gap)

Bearing straight

In the past decade, men’s trousers have gone from chokingly super-skinny to almost comically wide-legged models. But for a lasting look that staunches the throes of trendiness, we’ve settled on the straight-fit as a clean-lined, versatile standby, with a bit of stretch for nonbinding ease. J. Crew’s 770 Straight-Fit Stretch Chino Pant ($98, jcrew.com) comes in a raft of colors, though we’re partial to the Catskill Green, an olive hue with a little extra oomph. For a pair of updated khakis, the Lands’ End Knockabout Comfort Waist Classic Fit Chino Pant in Forest Moss and Khaki  ($80, landsend.com) offers four different inseam lengths and a hidden elastic sideband at the waist to stretch up to two inches. And Gap’s Modern Straight Khakis ($60, gap.com) go beyond the usual tan shades with colors like Pilot Grey and Blue Ridge in a highly wearable stretch, twill-weave cotton.

a collage showing two different half zip pullover sweaters
(From left) Brooks Brothers’ Cotton Pique Half-Zip Sweater in Dark Green; L.L. Bean Essential Merino Sweater, Quarter-Zip in Red Chestnut Heather
AARP (Brooks Brothers, L.L. Bean)

Taking the zip line

If you haven’t figured it out yet, less is definitely more as a guy ages upward. Streamlined shapes and gently saturated hues do a man proud — and one indispensable example is a lightweight half-zip sweater with a stand-up mock collar. It’s another outer piece that brings an elevated finish to an outfit when layered over a tee or woven shirt.

Brooks Brothers’ Supima Cotton Pique Half-Zip Sweater in Dark Green or Camel ($128, brooksbrothers.com) features an ultra-fine yarn count for a seasonless weight and ribbed trim at the neck, cuffs and hem. In a range of muted shades like Cottage Blue and Evening Tide, the Peter Millar Crown Comfort Pullover ($155, petermillar.com) in a soft blend of cotton, modal and performance yarns has a roomy classic fit for sweatshirt-like ease. And more than living up to its name, the L.L. Bean Essential Merino Sweater, Quarter-Zip in Pine Green Heather ($110, llbean.com) is made from washable 100 percent premium wool in a year-round version with temperature-regulating properties and an extra-soft feel.

two different types of casual shoes
(From left) On Cloudzone in Mulberry Black; Johnston & Murphy’s Amherst 2.0 Embossed U-Throat in Tan Full Grain
AARP (On, Macy’s)

Grounded in comfort

By now, sneakers have become the de facto choice for most men, given the kicks’ combination of unfussy looks and, most persuasively, all-day comfort. For a pared-down wardrobe, you’ll want a style with versatile finesse that lends itself to dressing up or dressing down.

The Johnston & Murphy’s Amherst 2.0 Embossed U-Throat ($139, macys.com) in Tan Full Grain leather features a memory foam footbed and a lightweight cushioned sole. The On Cloudzone ($150, on.com) adapts the brand’s signature walking comfort in a minimalist design with a breathable woven upper, in both calm neutral shades like Pearl/Truffle or color-accent combos. Charles Tyrwhitt’s Knitted Sneakers in Navy ($89, charlestyrwhitt.com) lighten things up with a seamless knitted upper that brings flexibility and breathability.

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