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How to Style Knee High Boots This Autumn (5 Outfits)

Knee high boots are back and better than ever. Five easy, foolproof ways to wear them this season, with dresses, denim, knits and everything between.

Brown suede knee high boots worn with a pale coat on stone steps
Quick answers
What do you wear with knee high boots?
A midi dress or skirt with a small gap of leg looks best, and they also work under straight or skinny jeans. Keep hems above the knee or tucked in so the boot stays the feature.
Are knee high boots in style this autumn?
Yes, tan and brown knee high boots are a key autumn shoe. A block heel version is the most wearable and goes with dresses, denim and knits alike.

Every few years a shoe quietly takes over autumn. This season it’s the knee high boot, sleeker than the chunky styles of recent years and far more versatile than it gets credit for. The secret is proportion. Get the balance right and knee highs flatter almost everything.

Here are five outfits that always work.

1. Knee highs and a midi dress

The pairing everyone reaches for, and for good reason. Leave a sliver of leg between the hem of a midi and the top of the boot; that little gap is what keeps the look leggy rather than heavy. A soft knit dress in rust or forest green is the easiest place to start.

2. Knee highs and slim denim, tucked in

Tuck a slim jean straight into the shaft for a clean riding boot line. Then balance that streamlined bottom half with volume up top. An oversized knit or a boxy blazer keeps the proportions modern rather than dated.

3. Knee highs and a mini with opaque tights

The season’s boldest option, and done right, the chicest. Match the tights to the boots in the same dark tone so you create one long line. It’s slimming, warm, and reads far more polished than bare legs in October.

The trick with knee highs is tone. Keep the boot and whatever sits above it in the same colour family and your legs look longer instantly.

4. Knee highs and wide leg trousers

Yes, really. Choose a trouser with enough drape to skim over the boot and you get a column of colour that’s quietly powerful. It works best in a matching tone; chocolate boots under chocolate trousers is a look that costs nothing extra and photographs beautifully.

5. Knee highs and an oversized knit as a dress

On the coziest days, let a long chunky knit do the work of a dress. Add opaque tights and tall boots and you’ve got an outfit that takes ninety seconds to assemble and looks like you tried far harder.

A quick word on fit. The most flattering knee high hits just below the knee, with a shaft that skims the widest part of your calf rather than squeezing it. If you’re between sizes, size up in the calf. A boot that gapes slightly always beats one that pinches.

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