If you’re familiar with our regular style advice, you’ll be aware that, although we’re appreciative of trends that come and go, above all we love a great sartorial staple. Chelsea boots are a case in point. Often referred to as a classic, they’re sometimes overlooked in favour of more rugged styles, or of-the-moment trends, such as hiking boots. I have had the pleasure of being surrounded by several dozen pairs of Chelsea boots this week and I’ve been struck by how remarkably versatile the style is. Despite each pair having their own design nuances, when paired with slim cut denim or a tailored suit the style is truly timeless. On a more cautionary note, though, pay close attention to the shape of the toes (not too pointed) and the height of the heels – too high and you’re in Tom Cruise territory. Which is not a good place to be.
1. R.M Williams ‘Comfort Craftsman’ Chelsea boots
This Australian boot maker is well known for crafting no nonsense, robust Chelsea boots. The style really comes into its own at this time of year and these suede examples are classic R.M Williams. The twin pull-tabs at the top of the boots have become synonymous with the brand. They’re ideal for off-duty weekend pursuits, whether it’s dog walking or for Sunday lunch at your local pub. Pull these on with mid-blue jeans, a cream cable knit sweater and a navy quilted jacket.
£350, shop now
2. Church’s Houston Chelsea boots
British footwear maker Church’s show off its dedication to craftsmanship and timeless style with these sharp looking black Chelsea boots. The smart leather upper and sole will lend itself to be being worn with more tailored trousers as part of a suit or separates. Navy or charcoal wool pleated trousers will show off this fine pair of boots, as long as you make sure they’re tapered and the hem sits just above the ankle for a more contemporary shape.
£390, shop now
3. Crockett & Jones ‘Chelsea XI’ boots
While Northampton-based shoe maker Crockett & Jones are maybe more recognised for their fine craftsmanship across their formal footwear offering, this boot demonstrates how well they can pull off something a little more relaxed, but no less smart. We love the Scotch grain leather upper, along with the meaty tread rubber sole. They look robust, well made and will work with a multitude of outfits, making them a canny investment for now and many future wears. This pair naturally lends its profile to a paired down outfit of dark denim, rollneck and a corduroy trucker jacket, but would look sharp worn with a more contemporary suit, too.
£450, shop now
4. Blundstone waxed suede boots
There has been a strong focus across menswear on the great outdoors this season. This trend includes high-performance footwear, and Blundstone’s classic round-toed boots are a fine example of this. They are also having a bit of a moment, if the well-shod feet of Londoners are to go by (and they are). Above all, they’re perfect to wear on wet weather days and a great weekend boot to pull on with slim cut navy chinos or corduroys trousers. The rubber soles give good traction on rain soaked pavements, giving you a solid footing without fear of any embarrassing slip-ups. Wear these with a waxed jacket and slim cut jeans for blustery weekend walks.
£125, shop now
5. O’Keeffe ‘Bristol’ Chelsea boots
These suede Chelsea boots with their graduated soft patina are a real winner when looking for a something refined, well made and with the appearance of being well loved. I can testify that a number of actors I’ve been working with recently have all been drawn to these boots, mainly for their lived in look, but also for the flattering shape of the last. The burnished suede also makes them an attractive choice to be worn with blue or black denim, and they look fantastic paired with this season’s autumnal shade of corduroy trousers.
€480, shop now