Brown puffer jacket, black hoodie & charcoal jeans
€895*For cool days, about 5–12°C · Weekend · 5 pieces from €115*
What to wear with penny loafers
Penny loafer outfits with trousers, denim and skirts, preppy or relaxed. 126 complete looks, each with why it works.
By Ivan Kachur · Updated October 2026
With black · 62 looks
Black jacket, brown tee & blue trousers
€590*For mild days, about 12–20°C · Outdoors · 4 pieces from €35*
Blue jacket, jumper & black trousers
€635*For cool days, about 5–12°C · Smart casual · 4 pieces from €120*
White shirt, black corduroy trousers & orange penny loafers
€544*For mild days, about 12–20°C · Smart casual · 4 pieces from €119*
Brown puffer jacket, brown jumper & black cargo trousers
€863*For cold days, about −5 to 5°C · Everyday · 5 pieces from €105*
Black gilet, cream top & khaki jeans
€575*For cool days, about 5–12°C · Weekend · 5 pieces from €50*
With brown · 63 looks
With cream · 52 looks
With grey · 38 looks
All looks
126 looks
Brown jumper, charcoal trousers & orange penny loafers
€395*For cool days, about 5–12°C · Work · 4 pieces from €92*
Would you wear it?
Green jacket, fleece & trousers
€850*For cool days, about 5–12°C · Everyday · 5 pieces from €108*
Would you wear it?
White polo, navy trousers & purple penny loafers
€780*For mild days, about 12–20°C · Work · 3 pieces from €190*
Would you wear it?
Striped jumper, black cargo trousers & grey penny loafers
€605*For cool days, about 5–12°C · Work · 3 pieces from €140*
Would you wear it?
Beige sweatshirt, beige joggers & black clogs
€973*For cool days, about 5–12°C · Active · 4 pieces from €159*
Brown jacket, blue jumper & brown trousers
€735*For cool days, about 5–12°C · Smart casual · 4 pieces from €140*
Cream jumper, camel trousers & brown penny loafers
€960*For cool days, about 5–12°C · Work · 4 pieces from €215*
Black puffer jacket, grey jumper & jeans
€910*For cool days, about 5–12°C · Outdoors · 5 pieces from €115*
Red sweatshirt, blue joggers & grey clogs
€999*For cool days, about 5–12°C · Active · 4 pieces from €185*
Brown puffer jacket, black jumper & black cargo trousers
€810*For cold days, about −5 to 5°C · Smart casual · 4 pieces from €105*
Blue sweatshirt, grey joggers & brown clogs
€643*For cool days, about 5–12°C · Active · 3 pieces from €159*
Black quarter zip, black trousers & penny loafers
€540*For cool days, about 5–12°C · Smart casual · 3 pieces from €135*
Brown jumper, beige shorts & black penny loafers
€422*For warm days, about 20–30°C · Smart casual · 3 pieces from €92*