The Best Boots for Upgrading Your Fall Wardrobe

These will be the most comfortable boots in your closet.


As the days get shorter, it’s time to bring out your fall wardrobe. Putting your sandals away for cooler weather doesn’t mean saying so long to comfortable footwear, however.

Boots can be comfortable as well as functional. The best boots keep your feet warm and dry, but they also cushion your feet and make walking a joy.

We’ve found some boots that are easy on your feet.

Easy Slip-ons

Why We Picked It What if boots were as easy to put on as a pair of slippers? Check out these Bitflex boots from Astorflex—they slip on. You got that right. The style is classic, the leather smooth and supple, and the leather sole is a testament to the hand-made Northern Italian construction of these boots.

Hiking Boots

Why We Picked It These Timberland hiking boots are rugged and durable, designed to hold up to tough terrain or hard work. The 100% leather uppers are waterproof and the seams are sealed to keep out wet and cold. The hardware is also rustproof. The rubber soles and padded collar keep your feet comfortable from your ankles on down.

Classic Lace-ups

Why We Picked It The Captain is an ankle-boot sporting a classic cap-toe style with speed-hook eyelets. The footbed is made of cork and has an EVA comfort strip that will form to your feet over time – so the more you wear them, the better they feel. The uppers are all leather, including a full glove leather lining, and the rubber outsoles are studded for better grip on all surfaces. The company suggests ordering these boots one-half size smaller than your sneaker size.