Jesper — The Jumper Boot
For me, The Jumper Boot is a perfect transitional shoe for the autumn. It has the sleek appearance of an Oxford, but of course, with a higher ankle and more rugged sole. Worn with a suit, you can pull off the perfect Agnelli look.
Jack — The Hiking Boot in Brown Suede
Hiking boots have gained more and more traction over the past few years — and for good reason. It's a great way of making any outfit look a bit more sporty. Not in the football kind of way, but rather in the K2 climbing, weather-defying gorpcore kind of way. The brown suede version is way easier to take care of than people think, and in my opinion, it brings out a more under-the-radar look of the whole silhouette.
Chris — The Chukka Boot
A classic Chukka boot is my go-to autumn essential. It's a more dressed-down alternative to, for example, a jumper boot, but it works great with everything from suits to denim. The low-cut ankle makes it easy to put on and take off, while the sole creates good traction for the tougher weather.
Lovisa — The Chelsea Boot
The Chelsea boot is such a great addition to any man's wardrobe. The silhouette is sleek while distinct. Matched with a pair of wider jeans in a dark wash, they become an understated essential.