After a blisteringly hot summer, I’m ready to start shaping up my wardrobe for the cooler seasons. And while most of our attention might be turned towards clothing, it’s also worth investing in some decent footwear.
Whether you’re looking for a pair of solid boots for the wet and windy months, or a stylish pair of trainers to welcome in spring, I’ve got you covered.
Timberland Concrete Heritage Six-Inch Boots
Timberland
Launched earlier this week, these new Timberland boots look incredibly stylish in their concrete gray colorway. The shade was selected from the brand’s own archive, drawing on a style first seen back in the 90s.
There’s a whole range of different styles available in this hue, but for me, the classic Heritage Six-Inch Boots are the top pick. It’s the classic Timberland silhouette you know and love, now in a shade which is much more wearable. $220 snags you the look.
Maison Margiela Aqua Replica Sneakers
Maison Margiela
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When spring finally comes around, you’re going to want a colorful pair of sneakers to match the occasion. And while there are lots of options out there, I’ve been obsessed with these Maison Margiela Replica Sneakers – especially in the Aqua color.
Crafted from nappa leather and suede, with 100% cotton inside and a rubber sole, these really do feel like an exceptionally crafted product. Yes, the $850 price tag is steep, but for quality and design like this, it’s worth splurging.
Crockett and Jones Islay Boots
Crockett and Jones
If you’re a fan of exquisite, luxurious footwear, you need to know about Crockett and Jones. The British shoemaker has an enviable collection of gorgeous designs, and has even been worn by Daniel Craig as James Bond in the film Skyfall.
Despite offering a raft of dressier styles, I’ve picked out the Islay boots. They’re slightly dressier than other boots out there, but still offer enough ruggedness for day-to-day rigor, and you’ve got the peace of mind knowing they’re made by expert craftsmen. $1,020 isn’t cheap, but I still think it’s worthwhile.
Converse Chuck Taylor All Star High Street Colorblock
Converse
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I’ve always been a fan of Chuck Taylors, with the classic canvas design existing as a mainstay in alternative culture for decades. Still, it’s always nice to see something different, and I was really taken with these Converse Chuck Taylor All Star High Street Colorblock sneakers.
There’s an air of the Nike Air Jordans about them, which is no bad thing whatsoever. They also look like they’ve got some added padding around the heel. Priced at just $70, they’re the most affordable pair on this list.
Dr Martens 1460 Cappers
Dr Martens
Is there a bootmaker on the planet more iconic than Dr Martens? I don’t think so, and it’s why I’ve personally worn the brand for decades. The style can be found just about anywhere you look, from rockstars to kindergarten teachers.
I’ve always wanted to add a pair of red Docs to my wardrobe, and the 1460 Cappers edition seems like the perfect choice. Cut with classic calf leather and featuring an air-cushioned sole, these sound like a must-have addition to your wardrobe. $340 feels like a good price for these boots.
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Sam Cross
Sam Cross is an award-winning journalist and the current Editor of Recombu. Over the past decade, his work has been featured in publications as diverse as Metro, Oracle Time and Last Word on Sports, but the bulk of his career was spent at T3. He’s a lover of all things analog, including mechanical watches, film photography and cassette players. He also has a master’s degree in Magazine Journalism from Cardiff University.
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Surf legend Kelly Slater has a fitness regime which will shock you By Karen Carillo Aug 16, 2026 5 pairs of shoes in my basket right now – from fall boots to spring sneakers By Sam Cross Aug 16, 2026 This fire-resistant Mendocino home is a work of art By Karen Carillo Aug 15, 2026 AdvertisementStay in Touch
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