Rainy commutes and damp weekends are rites of passage in autumn. You can’t beat it, so you’re going to have to make the best of it. Having the essentials that can take you from your puddle-jumping commute, into the office and then off for a weekend in the country can be a high bar to pass. The place to start is your footwear. You need a boot rugged enough to handle the rough weather, stylish enough to fit in at the office, and comfortable enough to rock all weekend. The rest of our must-haves will easily take you from a fall Friday at the office to a weekend in the woods — from a solid pair of socks to the requisite thermos filled with a something a bit stronger than your morning coffee.

The Boots

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The boots that will take you from city to countryside are the 6″ APEX Wedge from 5.11 Tactical. The boot is rough and tumble ready, while still fitting in perfectly in the city — it’ll go toe-to-toe with most kicks on your office floor no problem. Lightweight for its size, you won’t have to worry about lugging these around on your feet, plus the D30 support footbed offers revolutionary shock absorption and lasting heel and arch support — forget about your dogs barking all weekend. You can put the worry of puddles and a little bit of rainwater out of mind too, thanks to the Vibram Newflex outsole that will let you keep your grip and help keep you off the water. The boots are ready to clock some serious miles over all kinds of territory.

The Essentials

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Goldwin: Coach Jacket Shirt $330
Raleigh Denim Workshop: Graham Selvage Raw $325
5.11 Tactical: Dart Pack 25L $100
Stanley: 20 oz Classic Legendary Bottle $30
CWC: British Military G10 Learn More
5.11 Tactical: EDC PL 2AAA Flashlight $25
American Trench: Merino Activity Socks with Silver $20

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