What to wear with knee-high boots

Knee-high boot outfits with skirts, dresses, jeans and leggings, for autumn and winter. 13 complete looks, each with why it works.

By Ivan Kachur · Updated October 2026

Get looks picked for you · 1-minute quiz

13 looks

Grey jumper, brown trousers & brown knee-high boots

€3,750*

For cool days, about 5–12°C · Smart casual · 4 pieces from €520*

Would you wear it?

Jumper, black skirt & brown knee-high boots

€2,395*

For cool days, about 5–12°C · Smart casual · 4 pieces from €395*

Would you wear it?

Jumper, brown trousers & brown knee-high boots

€2,530*

For cool days, about 5–12°C · Smart casual · 4 pieces from €340*

Would you wear it?

Pink dress, cream knee-high boots & brown bag

€2,420*

For mild days, about 12–20°C · Smart casual · 3 pieces from €685*

Would you wear it?

Cream jumper dress, brown knee-high boots & blue bag

€2,130*

For mild days, about 12–20°C · Smart casual · 3 pieces from €395*

Jacket, navy dress & cream knee-high boots

€1,490*

For mild days, about 12–20°C · Smart casual · 3 pieces from €90*

Grey cardigan, blue dress & brown knee-high boots

€1,470*

For cool days, about 5–12°C · Smart casual · 3 pieces from €120*

Green jacket, cream jumper & navy corduroy trousers

€1,630*

For cool days, about 5–12°C · Smart casual · 4 pieces from €125*

Striped dress, cream knee-high boots & brown bag

€1,790*

For mild days, about 12–20°C · Smart casual · 3 pieces from €285*

Brown bomber jacket, pink shirt & brown skirt

€3,602*

For mild days, about 12–20°C · Smart casual · 4 pieces from €412*

Orange overshirt, dress & cream knee-high boots

€1,575*

For mild days, about 12–20°C · Smart casual · 3 pieces from €185*

Orange overshirt, brown jumper dress & cream knee-high boots

€1,610*

For mild days, about 12–20°C · Smart casual · 3 pieces from €220*

What to wear with knee-high boots

Grey jumper, brown trousers & brown knee-high boots

Jumper, black skirt & brown knee-high boots

Jumper, brown trousers & brown knee-high boots

Pink dress, cream knee-high boots & brown bag

Cream jumper dress, brown knee-high boots & blue bag

Jacket, navy dress & cream knee-high boots

Grey cardigan, blue dress & brown knee-high boots

Green jacket, cream jumper & navy corduroy trousers

Striped dress, cream knee-high boots & brown bag

Brown bomber jacket, pink shirt & brown skirt

Orange overshirt, dress & cream knee-high boots

Orange overshirt, brown jumper dress & cream knee-high boots

What to wear with knee-high boots

Grey jumper, brown trousers & brown knee-high boots

Jumper, black skirt & brown knee-high boots

Jumper, brown trousers & brown knee-high boots

Pink dress, cream knee-high boots & brown bag

Cream jumper dress, brown knee-high boots & blue bag

Jacket, navy dress & cream knee-high boots

Grey cardigan, blue dress & brown knee-high boots

Green jacket, cream jumper & navy corduroy trousers

Striped dress, cream knee-high boots & brown bag

Brown bomber jacket, pink shirt & brown skirt

Orange overshirt, dress & cream knee-high boots

Orange overshirt, brown jumper dress & cream knee-high boots

What goes with knee-high boots

How to wear knee-high boots

What goes with knee-high boots

Colours that work

What a complete look costs

Brands in these looks