Reaching your 50s or 60s older, is a significant life milestone. It’s a time to celebrate the wealth of experiences and stories you’ve accumulated, and your wardrobe often reflects your refined taste. Now, the opportunity arises to maximise your sartorial knowledge and investment pieces.

Ensuring that your clothing fits impeccably stands out among the essential aspects of dressing in your 50s and 60s. A thorough evaluation of your current wardrobe is necessary to ensure that everything fits comfortably on your frame; the goal extends beyond mere aesthetics; it’s about feeling at ease in your attire. When it comes to jeans, it’s advisable to leave behind the era of rips and excessive distressing. In your latter 50s and 60s and beyond, consider investing in sleek, selvedge denim in a solid, classic colour. Opt for a slim or straight fit, sidestepping the ultra-skinny styles that may no longer suit your evolving style. Just not skinny. Please.

While baggy skater jeans may be trendy, they might feel too trend-driven for the mature gentleman. Likewise, there are better choices than shapeless bootcut jeans, which sag in all the wrong places to maintain a polished appearance. Instead, gravitate toward jeans that mimic the fit of a well-tailored pair of trousers. Look for simple washes and solid colours to project a dignified aura. Brands like Levi’s 501, APC New Standard, and Anglo-Italian offer excellent selections designed to harmonise with more tailored garments on top, cultivating a sophisticated and age-appropriate look


In your late 50s and late 60s, your style remains open to evolution while preserving a timeless and confident presence. Your clothing choices should harmonise with your age and underscore the wisdom and experience you’ve acquired. Your wardrobe should mirror your character, and achieving the right fit in clothing represents the initial step in that direction. As for the era of skinny jeans, it’s undeniable that times have changed; these styles may no longer align with your evolving fashion sensibilities, but the realm of “normcore” or “geek denim” beckons as a refreshing alternative. 

Similarly, the list of fashion faux pas for older men is extensive, featuring items like bum bags, oversized Nineties suits, novelty ties and most of all, skinny jeans, arguably sartorial crimes by any standard. 53 is the age when men often reach a crossroads in their style journey, struggling to determine how to dress appropriately, and 42 percent of older men take pride in their questionable fashion sense, often playfully dismissing negative comments. Really guys?

And if you’re going to work and you dress like a 25-year man, you may express concerns about younger, more stylish colleagues at work, with 30 per cent believing that a wardrobe overhaul could advance their careers. Our perspective is that men should be quick to revamp their style and, in turn, reinvent themselves with a fresh wardrobe. Like your jeans.

A final note: Regardless of age, dressing is fundamentally influenced by your lifestyle and daily requirements. The pursuit of personal style transcends societal expectations, reminding us that age is but a number.