Few pieces have the power to anchor an outfit quite like a great pair of boots. As we move into fall, they are the natural bridge between lighter summer dressing and the richer textures, heavier layers and more considered style of the new season. The right pair should be practical, of course, but should also bring personality, whether your taste leans polished, rugged or somewhere in between. From the Chelsea boot that works with almost everything to the cowboy silhouette enjoying a revival, these are five styles I love.
Few boots move between smart and casual quite as effortlessly as the R.M. Williams Comfort Craftsman . Their sleek profile brings polish without feeling overly formal, making it as suitable for tailoring as it is for straight leg denim. Choose classic black for evening or rich brown for greater everyday versatility. If you are investing in one refined boot, this is the benchmark.
The Blundstone 585 has become a quiet style hero helped along by fans such as Jacob Elordi. Rugged, comfortable and wonderfully unfussy, they offer a more relaxed take on the classic Chelsea boot. Its weathered finish looks particularly good with washed denim, knitwear and practical outerwear. This is the pair to reach for when you want function, comfort and credibility in equal measure.
Originally designed as a work boot the Red Wing Classic Moc has developed into an enduring menswear icon. Its distinctive moc toe, substantial leather and contrasting wedge sole give even the simplest outfit character. They require some patience while the leather softens but the reward is a boot that becomes increasingly personal with wear. Pair them with denim, cords or relaxed tailoring and let the scuffs become part of the story.
The Danner Mountain Light II proves that hiking boots need not be confined to the trail. A robust leather construction, metal eyelets and substantial sole bring rugged texture to everyday clothes. Wear them with relaxed trousers, a chunky knit and an oversized coat for a look that feels considered rather than overly outdoorsy. They’re built to look better once they have seen a little life.
Common Projects brings its trademark minimalism to the biker boot with this clean black leather pair . The washed leather softens the finish while a discreet side zip preserves its streamlined profile. Lightweight rubber lug soles provide traction without making the boot feel cumbersome. Wear them with black denim and a leather jacket for tonal edge or use them to toughen relaxed tailoring.
Darren Kennedy is a dynamic television presenter, entrepreneur, and style expert, known for his vibrant energy and dazzling Irish charm. Originally hailing from Dublin, Darren has made his mark across the UK, Ireland, and most recently in the US presenting shows for NBC, the BBC, ITV, and RTÉ. In 2023 he launched the podcast The Number with Darren Kennedy, which quickly climbed to the top of the Apple Podcasts charts. Darren Kennedy’s email is [email protected]
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