Outfit ideas
What to Wear with Knee High Boots in the Fall (Outfit Ideas)
Short answer: In the fall, wear knee high boots with slim jeans, leggings or a midi skirt, then add a sweater and a light coat. Let the boots be the main event and keep the rest of the outfit simple.
Knee high boots are one of the easiest things to wear once the weather cools, but the outfit changes a lot depending on the boot. Here are seven full looks, each built around a pair we sell, with layers and accessories that go with them.
Camel Suede Boots with a Cream Sweater and Plaid Scarf
The Suede Knee High Boots for Wide Calves in tan/camel have a loose, slouchy shaft that folds and drapes instead of hugging the leg. Wear them with dark slim jeans or a fitted knit dress. Add a cream chunky sweater, a plaid scarf and a small brown crossbody. The pointed toe and thin stiletto heel keep the look polished, so it works for dinner or the office on a crisp day. Skip very wide-leg pants, which fight the slouch.
Suede Knee High Boots for Wide Calves 18 Inches · Apricot · $119
See the dressBrown Block Heel Boots with a Rust Midi Skirt
These Block Heel Knee High Boots for Wide Calves are smooth brown faux leather with a square toe, a side zipper and a block heel of about 2.5 inches. The shaft is straight and sleek, so a midi skirt in rust or olive looks clean above it. Add a fitted black turtleneck, a tan trench coat and a leather-look belt. The zipper makes them simple to get on, and the heel is low enough for a full day out.
Block Heel Knee High Boots for Wide Calves 18 Inches · Brown · $109
See the dressSlouchy Buckle Boots with Dark Jeans and a Flannel
For an easy weekend outfit, try the Knee High Boots with Low Block Heel and Buckle in brown or black. They have a slouchy faux-leather shaft, a round toe, wide buckle straps at the ankle and shaft, and a low chunky heel. Tuck in dark skinny jeans, then add an oversized flannel shirt, a denim jacket and a knit beanie. A canvas tote finishes it. The buckles are the detail, so keep your jewelry minimal.
Knee High Boots with Low Block Heel and Buckle · Black · $99
See the dressBlack Fold-Over Boots with a Sweater Dress and Long Coat
The Leather Knee High Boots for Wide Calves 18 Inches in black have a smooth leather-look finish, a fold-over shaft and a silver buckle strap at the top. The pointed toe sits on a hidden wedge heel. Wear them with a charcoal or camel sweater dress and a long wool coat. Sheer black tights are optional. Add a structured bag and simple silver earrings that echo the buckle. It is a good look for evenings when the temperature drops.
Leather Knee High Boots for Wide Calves 18 Inches · Black · $99
See the dressFlat Riding Boots with Skinny Jeans and a Quilted Vest
The Lace Up Flat Knee High Riding Boots for Walking are black leather-look with a truly flat sole, a round toe and crisscross lacing up a wide shaft. The wrinkled finish gives them a classic equestrian feel. Tuck in slim jeans, then add a cream cable-knit sweater, a quilted vest and a blanket scarf. It is a comfortable outfit for apple orchards, farmers markets and long walks. These are listed as unisex, so check the size chart.
Lace Up Flat Knee High Riding Boots for Walking · Brown · $139
See the dressPink Rain Boots with a Raincoat and Striped Sweater
Fall means rain, and the Waterproof Knee High Boots for Wide Calves are glossy pink molded rubber with a chunky non-slip sole. The straight tube reaches just below the knee, and a side buckle strap adjusts the fit at the top. Wear them with black leggings tucked in, a navy or olive raincoat and a striped sweater. Add a clear umbrella. The bright boots make a gray day look more cheerful without any extra effort.
Waterproof Knee High Boots for Wide Calves 18 Inches · Army Green · $99
See the dressBeige Suede-Look Boots with Corduroy and a Chore Jacket
The Suede Knee High Boots with Low Block Heel are beige faux suede with a slouchy shaft, a pointed almond toe and a low stacked heel. A side zip and a small strap at the top finish them off. Wear them with a chocolate brown corduroy skirt, a ribbed cream top and a tan chore jacket. Staying in warm neutrals makes the outfit look pulled together. Carry a brown leather bag and add a thin gold necklace.
Suede Knee High Boots with Low Block Heel · Black 6 cm Lace-Up · $89
See the dressChoose Colors and Layers That Suit Fall
Warm neutrals like cream, rust, olive, camel and chocolate brown look good with most knee high boots. Black boots work with almost everything, including gray and navy. For layers, start with a fitted base such as a turtleneck or ribbed top, then add one outer piece like a trench, blazer or wool coat. Because the boots cover your legs, you can wear a skirt or dress into October without feeling cold. Keep accessories simple: a scarf, a bag and one or two pieces of jewelry.
Check the Fit Before You Order
Knee high boots are all about shaft fit, so look at the size chart and compare it with your calf measurement before you order. Use the photos and the listing details to judge how slouchy or straight the shaft is. All sales are final, with no returns or exchanges for fit or change of mind. If an item arrives damaged, defective or wrong, we replace or refund it within 14 days of delivery. Shipping is free to the US and takes 7 to 14 business days, so order early for fall.
Want more options? Browse all knee high boots.
Questions, answered
Should I tuck jeans into knee high boots in the fall?
Yes, slim or skinny jeans tucked in give the cleanest line, especially with slouchy or wide-shaft boots. A fitted sweater or a longer jacket balances the look.
Can I wear knee high boots with a dress or skirt in the fall?
Yes. A midi skirt or a sweater dress works well, and the hem can sit just above or at the top of the boot. Add tights if the day is cold.
What colors of knee high boots go with the most fall outfits?
Black and brown go with nearly everything. Camel and beige suede-look boots are good with cream, olive, rust and denim, as long as you keep the rest of the outfit neutral.