What to Wear with Knee High Boots: Winter Outfits

Wear knee high boots with a midi skirt long enough to cover the top of the boot, or a shorter dress with opaque tights. Tuck skinny and straight jeans in; wear wide-leg trousers over them. Add a pencil skirt and blazer for work, a jumper dress at the weekend, and a slip dress with sheer tights for evening.

In short:

• Skirts and dresses: the hem covers the top of the boot or sits clearly above it.
• Jeans and trousers: skinny and straight legs tuck in; wide-leg cuts go over.
• Work: a pencil skirt, opaque tights, a shirt and a blazer.
• Weekend: a jumper dress or tucked-in jeans under a long coat.
• Evening: a slip dress, sheer tights and the block heel for height.
• Tights: match them to the boot, not to the dress.

A knee high boot decides where the hem sits, what the tights do and how the coat falls, from the school run to the dark walk home. Every outfit below is styled with Black Tulip's Maple Knee Boot, in Black or Chocolate full-grain leather, cut to sit just below the knee on a block heel.

What dresses and skirts go with knee high boots?

Most of them, once the hem and the boot agree. A hem works in two places: over the top of the boot, so skirt and leather read as one line, or clearly above it, with tights in the boot's shade in between. A hem that stops just short of the boot top cuts the leg in two.

A midi is the place to start: choose one long enough to fall over the top of the boot. A burgundy pleated midi, a cream knit tucked in at the front and the Maple Knee Boot in Chocolate: if you learn one knee high boot outfit, learn this one.

Shorter hems take the other route. With a shirt dress or an A-line skirt that ends above the knee, wear opaque tights in the boot's shade, and the leg reads as one colour to the floor. The shorter the hem, the more of the outfit the boot carries, which is exactly what December wants.

Styling note: try a new skirt on with the boots, standing and sitting, before the tags come off.

How do you wear knee high boots with jeans and trousers?

The cut of the leg decides. Skinny and straight-leg jeans go inside the boot; wide-leg trousers and bootcut jeans go over it.

Tucked in, the boot becomes the lower half of the outfit. Pull the denim smooth before you zip, and balance the long line of leather with length on top: a knit to the hip, a coat to the knee. Indigo jeans and a cream jumper suit the Chocolate; black jeans and a grey knit suit the Maple Knee Boot in Black.

Under wide-leg trousers and bootcut jeans, the boot works out of sight. Only the toe and the block heel show, and the heel lifts the hem so the trousers fall straight. Sit down and there is no cold gap at the ankle, which in a British January is not nothing.

Can you wear knee high boots to work?

Yes, and through the winter they can stand in for court shoes. A grey flannel pencil skirt, a white shirt and a navy blazer, with black opaque tights and the Maple Knee Boot in Black below, look as sharp as anything in the building.

Keep the palette quiet: grey, charcoal and navy tailoring with the Black; camel, cream and oatmeal with the Chocolate. The block heel gives real height, and a pencil skirt looks better for it. On trouser days, wear wide-leg tailoring over the boot; nobody in the meeting needs to know.

What do you wear with knee high boots at the weekend?

At the weekend, let the boot do the dressing up so everything else can relax. Two outfits cover most Saturdays.

The first is a jumper dress, opaque tights and a long coat. The Maple Knee Boot in Chocolate with an oatmeal jumper dress, deep chocolate tights and a camel coat is one colour story from collar to toe, and asks for no decisions before the first coffee.

The second is jeans tucked in, a chunky knit and a coat to the knee: the boot adds height and a clean line, so the outfit looks chosen rather than thrown on. On the coldest days, swap the jeans for black leggings and a knit that reaches mid-thigh.

How do you dress up knee high boots for the evening?

Let the boot take the place of evening heels, and keep everything above it light. A short black slip dress, sheer black tights and a black blazer with the Maple Knee Boot in Black run dark from shoulder to toe, with shine above the knee and leather below it.

Satin and silk look lighter against leather, and the block heel gives real height for the evening. For colour, a burgundy or deep green velvet dress goes with the Chocolate. Keep the hem long enough to cover the top of the boot, or short enough to show a clear stretch of sheer tights.

What tights go with knee high boots?

Match the tights to the boot, not to the dress. Black opaque tights with the Maple in Black make one unbroken line from hem to floor; with the Chocolate, choose a deep chocolate shade close to the leather. Matched to the dress instead, the tights draw a line across the leg at the top of the boot.

Then choose the weight by the hour. Opaque tights of 60 denier or more read as solid colour by day and sit closest to the leather. Sheer tights, around 20 denier, are for evening. Ribbed or fine-patterned tights work with a plain dress, as long as only one thing in the outfit carries a pattern.

Which pair, and which size?

Each outfit above names the colour that suits it best: Black with black, grey and navy; Chocolate with denim, cream, camel and burgundy. If you are weighing one against the other, our guide to choosing between Black and Chocolate boots takes it one wardrobe colour at a time.

For which colours to wear with the Maple in Black, see our guide to black knee high boots outfits by colour.

The Maple Knee Boot has a full-grain, LWG-certified leather upper, cut to sit just below the knee. Its block heel is 56 mm at UK 3 to 5 and 58 mm at UK 6 to 8, and it fastens with a short inside zip. See the Maple in Black or the Maple in Chocolate.

It comes in whole sizes only, UK 3 to 8. Measure your foot once, then check it against the Maple size chart in millimetres, which also lists the heel height and back height for every size.

For what to look for in any knee boot before you buy, starting with the leather, read our knee boot buyer's guide.

Knee high boot outfits: questions answered

Do you tuck jeans into knee high boots?

Tuck skinny and straight-leg jeans into knee high boots, and wear wide-leg and bootcut jeans over them. Tucked in, the whole boot shows, so dark denim pulled smooth looks sharpest. Worn over, only the toe and heel show. Black Tulip's Maple Knee Boot, cut to sit just below the knee on a block heel, works both ways.

What coat goes with knee high boots?

A long coat that reaches the knee or beyond. It meets the top of the boot or covers it, so coat and boot frame the outfit as one line. A short jacket works too, with jeans tucked in or a skirt above the knee, where the boot carries the lower half on its own.

Can you wear knee high boots with bare legs?

Yes, on milder autumn days, with a dress or skirt that ends above the knee, so a clear stretch of leg shows above the boot. A midi covers the top of the boot either way. From November, most UK days call for opaque tights in the boot's shade.

One pair covers every occasion above. See both colours side by side in the Maple Knee Boots collection.