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Olive Night Dress
$269Smart casual · 3 pieces · 3 stores
What to wear with penny loafers
Penny loafer outfits with trousers, denim and skirts, preppy or relaxed. 59 complete looks from in-stock pieces, each one shoppable in a click per store.
59 looks
Black Jacket & Green Knit
$730Smart casual · 4 pieces · 3 stores
Olive Night Dress
$297Smart casual · 3 pieces · 3 stores
Light Brown Jacket & Red Knit
$661Smart casual · 4 pieces · 4 stores
Ivy Green Jacket & Green Polo
$751Smart casual · 4 pieces · 4 stores
Orange Jacket & White Knit
$640Smart casual · 4 pieces · 3 stores
Victory Blue Dress
$294Smart casual · 3 pieces · 3 stores
Pink Shirt & Black (mps) Pants
$453Smart casual · 3 pieces · 3 stores
Black Dress
$618Work · 3 pieces · 2 stores
Printed Knit & Gray Pants
$562Smart casual · 4 pieces · 4 stores
Deep Ocean Polo & Charcoal Pants
$591Smart casual · 4 pieces · 4 stores
Bone Overall
$246Smart casual · 3 pieces · 3 stores
How to wear penny loafers
Counted from the 48 looks above, all built from pieces in stock today.
What goes with penny loafers
- On top
- Knitwear or shirts
- Bottoms
- Pants or trousers
- Layers
- Jackets
Colors 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 $414 and $730; the typical one is $558. 23 include a piece on sale. Swap any piece to change the total.
Brands in these looks
Most pieces come from Rothy's, Thursday Boots, Outerknown, Taylor Stitch and Noah. Each look checks out on the brands' own sites, one store at a time.