What Women’s Shoes to Wear in Autumn: Boots, Loafers and Trainers

The shoes to wear in autumn are knee boots, kitten heel ankle boots, loafers and leather trainers in autumn colours. Knee boots go over straight jeans and under a midi. A kitten heel ankle boot lifts trousers and dresses. Loafers carry you from summer into autumn, and a chocolate leather trainer keeps denim relaxed.

Autumn is when the shoe does the most work. Hems drop, tights go on and coats get longer, and the pair at the bottom decides whether the whole outfit looks finished.

The four pairs, in short:

• Knee boots: with jeans tucked in, midi skirts and knit dresses.
• Kitten heel ankle boots: with tailored trousers by day and dresses for evening.
• Loafers: the closed flat for the weeks between sandals and boots.
• Leather trainers: in chocolate, with denim, camel and cream.

Each section below says what the shoe does in autumn and names the Black Tulip pair for it. The Maple, Iris and Clover come in Black and Chocolate; the Arbi is shown here in Chocolate. All four come in whole sizes only, UK 3 to 8: measure your foot once and check it against each style's size chart in millimetres.

How do you wear knee boots in autumn?

Start with knee boots: they go with most of what you wear from October on. Tuck straight or slim jeans inside, let a midi skirt meet the top of the boot or fall over it, or wear them with a knit dress and opaque tights. The shaft closes the gap between hem and shoe, so the outfit reads as one line.

The Maple Knee Boot in Black is full-grain leather, LWG-certified, cut to sit just below the knee, with a short inside zip and a block heel of 56 mm at UK 3 to 5 and 58 mm at UK 6 to 8. The block heel gives real height, and the boot goes from the school run to the dark walk home. The Maple in Chocolate is the softer match for denim, camel and cream.

For what to look for in a pair, read our buyer's guide to leather knee boots.

Under shorter skirts, match the tights to the boot, so the leg reads as one colour from hem to toe.

Are kitten heel ankle boots right for autumn?

Yes. A kitten heel is a short, slim heel, so it lifts an outfit without the height of a high heel, and an ankle boot keeps the ankle covered when a trouser hem lifts. Wear one with tailored trousers and a knit for work, with dark jeans at the weekend, or with a slip dress and sheer tights for evening.

The Iris Kitten Heel Ankle Boot in Black is suede, LWG-certified, with a pointed square toe, a zip and a slim kitten heel of 43 mm at UK 3 to 5 and 45 mm at UK 6 to 8. The heel lifts an outfit: tailored trousers, dark denim, the dress that usually waits for better shoes. The Iris also comes in Chocolate suede.

For what makes a heel a kitten heel, read our guide to kitten heel ankle boots.

For five outfits, from wide-leg trousers to a slip dress, read what to wear with kitten heel ankle boots.

Can you wear loafers in autumn?

Yes, and they are the pair that bridges the seasons. A loafer is a closed flat, so it takes over from sandals in September and carries on until the weather calls for boots. Wear it with cropped trousers and a fine sock, with straight jeans turned up once, or with a midi skirt and opaque tights.

Black Tulip's hand-woven leather loafer is the Clover Woven Loafer in Black, its upper worked strand by strand over a barefoot-toe last. The hand-woven leather takes approximately 8 hours a pair. Its heel is 8 mm, so the Clover is a flat, and the weave gives a plain outfit texture: a navy knit, grey trousers, dark denim. The Clover in Chocolate suits camel and cream.

For loafer styles and more ways to wear them, read our guide to women's loafers.

Can you wear trainers in autumn?

Yes, in leather and in an autumn colour. A white canvas trainer reads as summer once the coats come out. A chocolate leather trainer sits with camel, cream, olive and every wash of denim, and looks deliberate with tailoring.

The Arbi in Chocolate is a retro-shaped leather trainer with a panelled upper of leather and leather suede on a durable man-made sole. It is slim enough to read polished with tailoring and easy with denim: straight jeans and a trench, or grey trousers and a knit.

Chocolate trainers sit best with camel, cream, olive and denim.

For what to look for in leather, read our guide to women's leather trainers.

Chocolate or black: which colour suits autumn shoes?

Choose by the colour you wear most. Black suits a wardrobe built on black, grey and navy, and it is the surer choice for evenings and formal dress codes. Chocolate suits denim, cream, camel, olive and burgundy, and makes a softer stop at the ankle by day. If you already own black boots, make the next pair Chocolate: it opens up outfits a second black pair cannot.

For outfits in each colour, read chocolate brown boots or black: which to buy.

How do you wear autumn shoes with jeans?

Each pair takes a different hem. Tuck straight or slim jeans into knee boots. With ankle boots, let the hem cover the boot or sit clearly above it, never in between. Over loafers, turn straight jeans up once so a little ankle or sock shows. Leather trainers take any cut, with the hem just reaching the top of the shoe.

For the hem rule for every cut, read how to wear ankle boots with jeans.

Women's Autumn Shoes: Questions Answered

What boots should women wear in autumn?

Knee boots and ankle boots. Knee boots go over straight jeans and under midi skirts and dresses. Ankle boots with a kitten heel lift tailored trousers and dresses. Choose black for a wardrobe of black, grey and navy, and chocolate for denim, cream, camel and olive.

What shoes transition from summer to autumn?

Loafers and leather trainers. A loafer is a closed flat for the weeks between sandals and boots, worn with bare ankles in September and a fine sock or tights later. Black Tulip's Clover Woven Loafer is hand-woven leather, approximately 8 hours a pair, in Black or Chocolate.

Which autumn shoes also work in winter?

Knee boots and suede ankle boots carry on into winter with heavier coats, knits and opaque tights. Look after them as the weather turns: suede needs a brush-and-protect routine, and leather a neutral leather conditioner as needed. Air-dry both away from direct heat.

If you buy one pair this autumn, make it the one that covers the most outfits: the Maple Knee Boot in Black or in Chocolate.