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Wholefit is an independent outfit recommendation site. It isn't affiliated with or endorsed by the brands it shows, and you buy each piece on the site of the store that sells it. No store or brand pays us a commission yet; when one does, it won't decide what we recommend. * Prices include VAT, plus each store's delivery charges. Each piece is sold by the store named on its page.

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Discover Search

New looks, once a week

A few complete outfits picked from what's new. No account needed, unsubscribe any time.

Email address

Outfit ideas Brands Christmas party outfits What to wear with white trainers Women's date night outfits Men's work outfits Autumn outfits Winter outfits Streetwear outfits Minimalist outfits Women's workout outfits Men's smart casual outfits Outfits under £100 Outfits under £200

Wholefit is an independent outfit recommendation site. It isn't affiliated with or endorsed by the brands it shows, and you buy each piece on the site of the store that sells it. No store or brand pays us a commission yet; when one does, it won't decide what we recommend. * Prices include VAT, plus each store's delivery charges. Each piece is sold by the store named on its page.

About Privacy Policy Your Privacy Choices Terms of Use Affiliate Disclosure Brands & Copyright Accessibility Contact

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What to Wear with Boots: 1,400+ Outfit Ideas · Wholefit

Outfits / What to wear with boots

What to wear with boots

Boot outfits for autumn and winter, with jeans, trousers, skirts and dresses. 1,421 complete looks, each with why it works.

By Ivan Kachur · Updated October 2026

Get looks picked for you · 1-minute quiz

With black · 758 looks

White tee, jeans & black desert boots
£197*
For mild days, about 12–20°C · Everyday · 4 pieces from £40*
Barn jacket, tee & jeans
£195*
For mild days, about 12–20°C · Everyday · 4 pieces from £15*
Brown tee, jeans & Chelsea boots
£192*
For mild days, about 12–20°C · Weekend · 3 pieces from £50*
Black shirt, navy trousers & beige desert boots
£197*
For mild days, about 12–20°C · Smart casual · 3 pieces from £32*
Navy jumper, khaki corduroy trousers & black desert boots
£197*
For cool days, about 5–12°C · Smart casual · 3 pieces from £32*
Cream cardigan, beige jumper & black trousers
£330*
For cool days, about 5–12°C · Everyday · 4 pieces from £65*

With cream · 580 looks

Beige fleece, jeans & Chelsea boots
£197*
For cool days, about 5–12°C · Outdoors · 3 pieces from £55*
Khaki linen shirt, black corduroy trousers & brown desert boots
£285*
For warm days, about 20–30°C · Smart casual · 3 pieces from £40*
Black jacket, green jumper & beige trousers
£775*
For cool days, about 5–12°C · Everyday · 4 pieces from £110*
Tee, trousers & black desert boots
£199*
For mild days, about 12–20°C · Everyday · 3 pieces from £40*
Cream jumper, navy trousers & brown boots
£785*
For cool days, about 5–12°C · Work · 3 pieces from £255*
Black polo, khaki corduroy trousers & tan desert boots
£153*
For mild days, about 12–20°C · Smart casual · 3 pieces from £28*

With green · 415 looks

Maxi dress, brown Blundstones & olive bag
£274*
For mild days, about 12–20°C · Date night · 3 pieces from £45*
Jumper, olive corduroy trousers & boots
£330*
For cool days, about 5–12°C · Smart casual · 3 pieces from £105*
Tee, navy trousers & olive Blundstones
£304*
For mild days, about 12–20°C · Everyday · 3 pieces from £40*
Green tee, jeans & grey Blundstones
£315*
For mild days, about 12–20°C · Weekend · 3 pieces from £36*
Black jumper, olive corduroy trousers & boots
£335*
For cool days, about 5–12°C · Smart casual · 3 pieces from £105*
Jumper, trousers & black boots
£164*
For mild days, about 12–20°C · Everyday · 3 pieces from £25*

With brown · 753 looks

Jumper, trousers & brown boots
£189*
For cool days, about 5–12°C · Smart casual · 3 pieces from £30*
Navy jumper, blue trousers & brown boots
£610*
For cool days, about 5–12°C · Smart casual · 3 pieces from £160*
Corduroy jacket, jumper & trousers
£163*
For cool days, about 5–12°C · Everyday · 4 pieces from £25*
Jacket, jumper & jeans
£706*
For cold days, about −5 to 5°C · Outdoors · 4 pieces from £147*
Jacket, cream top & navy trousers
£719*
For cool days, about 5–12°C · Everyday · 4 pieces from £169*
Navy polo, taupe trousers & brown boots
£835*
For mild days, about 12–20°C · Smart casual · 4 pieces from £135*

All looks

Filters

Budget for the whole look

Style

Colour

Season

One checkoutEvery piece from the same store

1,421 looks

Colorful Standard · £30

Dickies · £65

Clarks Originals · £105

Blue tee, black trousers & boots

£200* · Pieces from £30*

For mild days, about 12–20°C · Everyday · 3 pieces from £30*

Would you wear it?

Roamers · £32

Black tee, black trousers & beige desert boots

£182* · Pieces from £32*

For mild days, about 12–20°C · Everyday · 3 pieces from £32*

Would you wear it?

Blundstone · £124

Barbour · £24

Tee, jeans & olive Blundstones

£238* · Pieces from £25*

For mild days, about 12–20°C · Everyday · 4 pieces from £25*

Would you wear it?

Brown tee, navy trousers & beige desert boots

£180* · Pieces from £40*

For mild days, about 12–20°C · Everyday · 3 pieces from £40*

Would you wear it?

Barbour · £57

Hoodie, jeans & Chelsea boots

£188* · Pieces from £29*

For mild days, about 12–20°C · Outdoors · 4 pieces from £29*

Olive tee, navy trousers & brown desert boots

£180* · Pieces from £40*

For mild days, about 12–20°C · Everyday · 3 pieces from £40*

Pittari · £160

Carhartt WIP · £85

Timberland · £190

Navy jumper, blue trousers & beige Timberland boots

£435* · Pieces from £85*

For cool days, about 5–12°C · Smart casual · 3 pieces from £85*

Green jumper, black pleated trousers & black boots

£755* · Pieces from £220*

For cool days, about 5–12°C · Smart casual · 3 pieces from £220*

Sporty & Rich · £130

Sporty & Rich · £270

Clarks Originals · £110

White polo, brown trousers & black boots

£510* · Pieces from £110*

For mild days, about 12–20°C · Smart casual · 3 pieces from £110*

Carhartt WIP · £185

Norse Projects · £195

Polar Skate Co. · £125

Kleman · £199

Black Carhartt jacket, purple jumper & black trousers

£704* · Pieces from £125*

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

Norse Projects · £195

Frizmworks · £130

Clarks Originals · £165

Black jacket, purple jumper & cream corduroy trousers

£740* · Pieces from £130*

For cool days, about 5–12°C · Smart casual · 4 pieces from £130*

Community Clothing · £87

Community Clothing · £142

Blundstone · £119

Green top, jeans & grey Blundstones

£348* · Pieces from £87*

For mild days, about 12–20°C · Outdoors · 3 pieces from £87*

Carhartt WIP · £130

G.H. Bass · £250

Sweatshirt, jeans & black boots

£645* · Pieces from £130*

For mild days, about 12–20°C · Outdoors · 3 pieces from £130*

Navy polo, green pleated trousers & camel boots

£725* · Pieces from £190*

For mild days, about 12–20°C · Smart casual · 3 pieces from £190*

Sporty & Rich · £320

Sporty & Rich · £270

Blundstone · £138

Camel hoodie, baggy jeans & black Blundstones

£728* · Pieces from £138*

For cool days, about 5–12°C · Weekend · 3 pieces from £138*

Duke + Dexter · £250

Orange tee, black trousers & black boots

£395* · Pieces from £55*

For mild days, about 12–20°C · Everyday · 3 pieces from £55*

More outfit ideas

Women's outfits with boots
Men's outfits with boots
What to wear with white trainers
What to wear with black jeans
What to wear with jeans
What to wear with brown boots
What to wear with black boots
What to wear with loafers
What to wear with black trousers
What to wear with a blazer
What to wear with a cardigan
What to wear with a hoodie

What goes with boots

On top: Knitwear or t-shirts & tops
Bottoms: Trousers or jeans
Layers: Jackets
Colours that work: Black, brown, cream and green

How to wear boots

Counted from 40 of these looks.

What goes with boots

On top: Knitwear or t-shirts & tops
Bottoms: Trousers or jeans
Layers: Jackets

Colours that work

Black, brown, cream and green come up most often across these looks, so they make an easy base to build on.

What a complete look costs

Most whole outfits here cost between £197 and £704; the typical one is £315. Swap any piece to change the total.

Brands in these looks

Most pieces come from Folk, Clarks Originals, Blundstone, howies and Roamers. Each look checks out on the stores' own sites, one store at a time.