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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 Penny Loafers: 600+ Outfit Ideas · Wholefit

Outfits / What to wear with penny loafers

What to wear with penny loafers

Penny loafer outfits with trousers, denim and skirts, preppy or relaxed. 627 complete looks, each with why it works.

By Ivan Kachur · Updated October 2026

Get looks picked for you · 1-minute quiz

With black · 342 looks

Black puffer jacket, green jumper & black trousers
£695*
For cold days, about −5 to 5°C · Smart casual · 4 pieces from £75*
Brown jumper, olive corduroy trousers & black penny loafers
£477*
For cool days, about 5–12°C · Everyday · 4 pieces from £128*
Black polo, olive trousers & black penny loafers
£375*
For mild days, about 12–20°C · Smart casual · 3 pieces from £45*
Green fleece, brown sweatshirt & trousers
£605*
For cool days, about 5–12°C · Outdoors · 4 pieces from £95*
Brown coat, green polo & cream trousers
£591*
For cold days, about −5 to 5°C · Work · 4 pieces from £41*
Green tee, beige corduroy trousers & black penny loafers
£420*
For mild days, about 12–20°C · Everyday · 4 pieces from £45*

With brown · 253 looks

Brown jumper, navy trousers & penny loafers
£758*
For cool days, about 5–12°C · Work · 3 pieces from £249*
Navy sweatshirt, jeans & penny loafers
£849*
For cool days, about 5–12°C · Everyday · 4 pieces from £205*
Jacket, jumper & navy trousers
£715*
For cool days, about 5–12°C · Smart casual · 4 pieces from £125*
Brown cardigan, jumper & black trousers
£760*
For cool days, about 5–12°C · Smart casual · 4 pieces from £131*
Jacket, maxi dress & orange penny loafers
£164*
For mild days, about 12–20°C · Smart casual · 3 pieces from £30*
Cream jacket, cream jumper & brown trousers
£585*
For cool days, about 5–12°C · Smart casual · 4 pieces from £110*

With green · 146 looks

Jacket, green jumper & black trousers
£730*
For cool days, about 5–12°C · Smart casual · 4 pieces from £120*
Olive jacket, charcoal sweatshirt & black trousers
£630*
For mild days, about 12–20°C · Everyday · 4 pieces from £95*
Olive puffer jacket, brown sweatshirt & beige trousers
£725*
For cold days, about −5 to 5°C · Outdoors · 5 pieces from £95*
Green jumper, navy trousers & penny loafers
£768*
For cool days, about 5–12°C · Work · 3 pieces from £249*
Olive jacket, jumper & trousers
£680*
For cool days, about 5–12°C · Smart casual · 4 pieces from £110*
Olive coat, navy jumper & trousers
£587*
For cold days, about −5 to 5°C · Work · 4 pieces from £72*

With cream · 198 looks

Cream jumper, trousers & penny loafers
£525*
For cool days, about 5–12°C · Work · 3 pieces from £120*
Navy rugby shirt, tan trousers & burgundy penny loafers
£297*
For mild days, about 12–20°C · Work · 3 pieces from £55*
Beige coat, jumper & trousers
£592*
For cold days, about −5 to 5°C · Work · 4 pieces from £90*
Camel cardigan, taupe knit polo & brown trousers
£940*
For cool days, about 5–12°C · Smart casual · 4 pieces from £180*
Jacket, brown shirt & cream trousers
£943*
For cool days, about 5–12°C · Smart casual · 4 pieces from £149*
Cream jumper, charcoal trousers & burgundy penny loafers
£385*
For cool days, about 5–12°C · Everyday · 4 pieces from £70*

All looks

Filters

Budget for the whole look

Style

Colour

Season

One checkoutEvery piece from the same store

627 looks

Albaray · £25

Albaray · £25

Albaray · £40

Rothy's · £99

Trench coat, roll neck & beige trousers

£189* · Pieces from £25*

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

Would you wear it?

Universal Works · £160

Corduroy jacket, jumper & trousers

£293* · Pieces from £25*

For cool days, about 5–12°C · Everyday · 4 pieces from £25*

Would you wear it?

U.S. Polo Assn. · £65

U.S. Polo Assn. · £25

Rothy's · £99

U.S. Polo Assn. · £7

White jumper, trousers & pink penny loafers

£196* · Pieces from £25*

For cool days, about 5–12°C · Everyday · 4 pieces from £25*

Would you wear it?

Universal Works · £160

Universal Works · £35

Jumper, trousers & black penny loafers

£299* · Pieces from £49*

For cool days, about 5–12°C · Work · 4 pieces from £49*

Would you wear it?

The Couture Club · £45

The Couture Club · £75

Duke + Dexter · £100

Red polo, grey trousers & black penny loafers

£220* · Pieces from £45*

For mild days, about 12–20°C · Everyday · 3 pieces from £45*

Rise & Fall · £80

Rise & Fall · £105

Rothy's · £180

Blue knit polo, black trousers & black penny loafers

£365* · Pieces from £80*

For cool days, about 5–12°C · Work · 3 pieces from £80*

Finisterre · £175

Finisterre · £125

Finisterre · £110

Duke + Dexter · £220

Brown jacket, jumper & olive trousers

£630* · Pieces from £110*

For cool days, about 5–12°C · Work · 4 pieces from £110*

Sporty & Rich · £255

Sporty & Rich · £270

G.H. Bass · £165

Frizmworks · £65

Navy knit polo, taupe trousers & burgundy penny loafers

£755* · Pieces from £165*

For cool days, about 5–12°C · Everyday · 4 pieces from £165*

Turnbull & Asser · £130

Turnbull & Asser · £455

Duke + Dexter · £320

Grey jumper, burgundy corduroy trousers & black penny loafers

£905* · Pieces from £130*

For cool days, about 5–12°C · Work · 3 pieces from £130*

Selected Femme · £65

Selected Femme · £115

Duke + Dexter · £220

Green cardigan, brown jumper & navy trousers

£595* · Pieces from £65*

For cool days, about 5–12°C · Work · 4 pieces from £65*

Sporty & Rich · £160

Sporty & Rich · £270

Rothy's · £180

Navy jumper, brown trousers & penny loafers

£610* · Pieces from £160*

For cool days, about 5–12°C · Work · 3 pieces from £160*

Frizmworks · £190

G.H. Bass · £185

Butter Goods · £110

Purple cardigan, cream jumper & trousers

£730* · Pieces from £120*

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

Wax London · £165

Wax London · £41

Wax London · £105

Duke + Dexter · £220

Jacket, green polo & cream trousers

£531* · Pieces from £41*

For cold days, about −5 to 5°C · Work · 4 pieces from £41*

Stan Ray · £120

Norse Projects · £70

Polar Skate Co. · £125

Rothy's · £180

Black puffer jacket, green tee & trousers

£495* · Pieces from £70*

For cool days, about 5–12°C · Everyday · 4 pieces from £70*

Duke + Dexter · £250

Blue cardigan, black hoodie & jeans

£855* · Pieces from £175*

For cool days, about 5–12°C · Everyday · 4 pieces from £175*

Rothy's · £180

Navy jumper, green trousers & navy penny loafers

£945* · Pieces from £180*

For cool days, about 5–12°C · Work · 3 pieces from £180*

Rise & Fall · £95

Rise & Fall · £105

Duke + Dexter · £250

Khaki linen shirt, green trousers & brown penny loafers

£450* · Pieces from £95*

For warm days, about 20–30°C · Work · 3 pieces from £95*

More outfit ideas

Women's outfits with penny loafers
Men's outfits with penny loafers
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 penny loafers

On top: Knitwear or polos
Bottoms: Trousers or trousers
Layers: Jackets or coats
Colours that work: Black, brown, green and cream

How to wear penny loafers

Counted from 41 of these looks.

What goes with penny loafers

On top: Knitwear or polos
Bottoms: Trousers or trousers
Layers: Jackets or coats

Colours that work

Black, brown, green and cream 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 £420 and £730; the typical one is £595. Swap any piece to change the total.

Brands in these looks

Most pieces come from Rothy's, Duke + Dexter, G.H. Bass, Wax London and Universal Works. Each look checks out on the stores' own sites, one store at a time.