How you can still wear cargo pants in your 50s – and the best styles to try now

Jennifer Aniston has been wearing and taking off cargo pants since the 1990s, and so have I. This, plus the fact that we’re both in our 50s and don’t want to join TikTok, is probably all we have in common. But, anyway, if there’s a fashion myth I’d like to bust, it’s the one that says “if you wore something the first time…”. Honestly, if I paid attention to such an outdated commandment, my wardrobe would be half empty. No turtlenecks. No biker jacket. No combinations. No Chelsea boots. These items are loved from generation to generation as they are timeless classics. Portable and versatile, they have no age limit and last for decades.

Rather than excluding clothes because of an archaic decree, I prefer to see this as an ageless style challenge and finding new ways to wear old favorites. In the 1990s, I paired my skintight Topshop cargo pants (Aniston wore a more expensive Maharishi) with a skintight t-shirt. Today, what were once called combat pants are modernized with a gorgeous floral print pussy bow jacket and blouse. Workwear meets workwear in a stylish juxtaposition. For a more polished silhouette, swap the double-breasted blazer for a more fitted style, like the Hobbs Alva jacket on the right, which sits above or below the waistband of the trousers. With a loose bottom half, it’s a good idea to keep the top half smarter and more fitted.

Another winning combination is the Chanel-style tweed jacket with combats and simple low-heeled ankle boots. Military-inspired pants also look lovely with a collared cardigan or sweater and smart flats. Late model Stella Tennant looked super chic in baggy fatigues, a plain black silk blouse, single-breasted overcoat and silver metallic high heels. The form-fitting silk blouse and sturdy pants are another beautiful juxtaposition; avoid shirts with chest pockets as it looks like a pocket too far. My other advice is to avoid chunky boots, utility jackets, and any item that moves an outfit into Private Benjamin territory. Comedic army officer is not the look we are going for.

There are several different shaped cargo pants available; I voluntarily opted for a flexible version. Stan Ray’s utility pants are the ones I’m wearing in the picture. Reasonably priced and durable, this is the pair I recommend if you like your pants on the utilitarian side.

As with straight-leg jeans, the slimmer cargo pant is a universal style that suits most body types. And I like comfortable fights. There’s a reason all those leather cargo pants are now on sale…

Four of the Best Stylish Cargo Pants

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