How to Wear: The Best Boots For Fall

Step out in style

After months of bare ankles and toes, fall’s chillier temperatures provide an opportunity to skip the pedicure (not that you’d want to) and cozy up in some beautifully crafted, soft leather boots. These boots are made for walking, and can easily take you from apple picking to happy hour.

Ankle Boots

Simple ankle booties are a wardrobe staple season after season and these Savin Hill Stretch Ankle Boots look great both with and without tights - so you can still show off that lingering summer tan while keeping your toes warm and covered if you want. 

For a simple yet pulled together outfit, pair these boots with jeans and a super soft chunky knit like this Seymours River Merino Wool Swacket (pictured above). Or, if the occasion calls for something dressier, you can pair them with a loose fit shirt dress (below).

Dressy Boots

If you think that heels are too uncomfortable and impractical for day time, meet the Swazey Warm Lined Waterproof Boot (available in brown and black). Worn with jeans, the heel amps up an otherwise casual outfit and they’re comfortable enough to wear all night at a concert or shopping downtown. Downpour or snowstorm expected? Doesn’t matter – they’re waterproof.

Didn’t see that fleece lining coming, did you? Leave it rolled down to show off the detail and create a softer look. Bonus: it’s made with 50% PET (recycled plastic bottles).

Going out later? Wear these boots with black tights and a little black dress to elevate your look from casual to sophisticated. The soft teddy fleece lining will keep your ankles warm on even the coldest nights.

High Boots

Lastly, there’s nothing quite like a great pair of knee-high boots to draw practically any outfit together, and the Savin All-Fit Tall Stretch Boots (in brown or black leather) are no exception. 

The handy side-zipper means that they fit snugly around your calf but these boots were designed to stretch when needed. The stretch panel allows you to layer up with pants and thick socks on brisk days – and your circulation will remain in tact.

If you’ve been searching for a tall boot to fit over winter layers or athletic calves, the Savin All-Fit Tall Stretch Boot is the lifesaver you’ve been looking for. Need to wear thick tights and warm socks with jeans or a dress (see below) on colder days? Easy.

Whether you’re looking for an ankle boot, a dressy boot, or a tall boot that allows you to layer up, we’ve got you covered for autumn. The real dilemma? Deciding which one to wear.

Interested in how to wear metallic boots? Read our style editor’s guide to the metallic trend.