Clothing styles for men in their 50s

Updated March 23, 2017

There’s no reason why a man in his fifties can’t look fashionable. While style gurus insist that middle-aged men can or can’t wear certain clothes, the true secret to age appropriate dressing is wearing what feels comfortable and suitably reflects the wearer’s personality. For example, a bookish 50-year-old in a small town is unlikely to feel happy wearing aviators.


Seek inspiration from other men in their fifties. Actors such as Andy Garcia, Tom Hanks, Bruce Willis, Billy Bob Thornton and Kevin Costner have all continued to dress fashionably, as have musicians such as Bryan Ferry, Sting, Bono and David Bowie. The pages of women’s magazines are filled with images of celebrities, some of which will inevitably be men in their fifties. Closer to home, keep an eye on what other men are wearing. Develop a critical eye for combinations that work and those that don’t.


Shop around to see what’s on offer. It’s difficult to get an impression of the sheer range of clothes out there by simply browsing online. Take a trip to the nearest large urban population centre and browse the shops. Don’t be restricted to shops and department stores designed to appeal to the middle aged – they inevitably favour the blandest of clothes. Be bold, try things on and see what looks good. Get a feel for how different cuts and styles look.


Dress according to the situation. Jeans, lumberjack shirt and desert boots are fine for slumming round the house. Those who attend a lot of formal events should consider getting a made-to-measure suit. Before placing an order, shop around to get an eye for current styles. On the beach, boardshorts and flip flops are the way forward for the active man who takes pride in his body. Avoid Crocs and Speedos at all costs.


The dullest outfit can transform with the right accessories. Try a pair of Ray Ban aviators with a jean-based outfit. The Rolex submariner watch will set off more formal attire for those that can afford one. Avoid baseball caps and bandannas. Beanies are an option on a cold day or when playing sports. Invest in a quality scarf and a pair of leather gloves for the winter.

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About the Author

Justin Schamotta began writing in 2003. His articles have appeared in "New Internationalist," "Bizarre," "Windsurf Magazine," "Cadogan Travel Guides" and "Juno." He was a deputy editor at Corporate Watch and co-editor of "BULB" magazine. Schamotta has a Bachelor of Science in psychology from Plymouth University and a postgraduate diploma in journalism from Cardiff University.