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Clothing can be rather boring during the summer because you have to keep things simple and cool. But once November rolls around, the temps are cold enough you can pull out gear that has much more personality. Here’s a list of our favorite fall pieces and the accessories that go with them.

Rhodes Dean Boot ($220)

Every cool-weather setup should start a pair of leather boots. There are lots to choose from, but we often return to  because they’re so damn comfortable thanks to a calf leather build and shock-absorbing foam insole. Yes, they’re pricey, but the boots should last you at least 20 years if keep them clean and rub mink oil, leather conditioner, or leather salve on the outers. If your soles wear out, they can be easily replaced at any local boot shop.

Proof Field Jacket ($250)

When we don’t want to look like we just stepped off a ski hill, but still need something warm and weather resistant on blustery November mornings, this our . The design is based on the iconic M65 field jacket issued to American troops, but Proof has borrowed smart modern materials for their updated version. We particularly love the outer fabric, which maintains that matte green finish but comes coated with DWR and has four-way stretch for unrestricted movement. Inside, the jacket is packed with 80 grams of cozy synthetic insulation.

Sponsor Content: Citizen

Citizen Promaster Tough Watch ($396)

The  features a Super Titanium coating on a stainless steel case and bracelet becoming five times harder than stainless steel, Super LumiNova hands and marker, and the ability to function in extreme temperatures. It's powered by Eco-Drive.

Flint and Tinder White Oak Jeans ($100)

 require a break-in period. But that’s why we like them. They’re built from a stiff, thick, nearly indestructible denim that was manufactured it the storied White Oak factory and it takes a couple weeks before they start to soften up and conform to your body. Once you’ve put in the work, the White Oaks become uniquely yours and start to take on the patina of your world, just like a good leather jacket.

Goodr Running Sunglasses ($25)

No kit is fully accessorized without a good pair of glasses. We dig  because they have a classic Wayfarer style, come in a simple black finish, and compliment everything from a wool suit to a tracksuit. That, and they cost a fraction of what you’re used to paying but still come with polarized lenses, strong polycarbonate frames, and will stay on your face if you’re riding a bike or running at lunch.  

Arcade YOSAR Hudson Belt ($32)

Thanks to the woven design and leather trim,  is suitable for slacks or jeans. But the Hudson truly stands apart because it has built-in stretch (you’ll never go back once you’ve worn a stretchy belt) and because 10 percent of every purchase goes to support the Yosemite Search and Rescue (YOSAR) team that’s responsible for saving hundreds of lives every year in one of America’s most famous National Parks.