Loafers are the most versatile flat shoe of the season, and they look just as good with a midi skirt as with jeans. These outfits run from a glossy penny loafer with a printed dress to suede loafers with a plain tee and menswear loafers with cargo trousers. Leopard, burgundy and shearling-lined styles add some variety.
Loafer Outfits for Fall, Preppy to Polished

Pick Your Loafer
Loafers come in more variations than ever, from buckled and glossy to soft suede and shearling-lined. Start with the one that suits the way you dress most days. Gianvito Rossi's leopard-print Georgie loafers, Acne Studios' dark brown leather loafers, Saint Laurent's brown eel Le Loafers and The Row's tan shearling-lined Lucca loafers cover a lot of ground.
Loafers and a Midi Skirt
A smooth loafer with a midi skirt is polished without trying too hard. Khaite's burgundy Colt loafers and Valentino's gold lace-trimmed Lurex midi skirt meet Allude's brown wool and cashmere sweater, and Stella McCartney's black Appaloosa Tiny bag keeps the look compact.
Glossy Loafers, Printed Dress
A shiny black loafer grounds a busy print. Burberry's black Opal penny loafers work with Gabriela Hearst's printed silk-satin Adolphine maxi, and Dries Van Noten's Fair Isle cardigan and Savette's dark brown suede Slim Symmetry bag add warmth.
Suede Loafers, Plain Tee
Suede loafers make the plainest outfit look considered. Aeyde's chocolate Aldous penny loafers pair with On's navy All-Day Rib tee and Agolde's light-wash 90's jeans, and Brandon Maxwell's black Ryder leather jacket adds a sharp layer.
Menswear Loafers With Cargos
A heavier loafer suits utility trousers. Gucci's black Horsebit Rhody loafers and Balenciaga's black cargo trousers set the tone, while Missoni's striped crochet-knit shirt and Toteme's dark gray herringbone blazer mix textures.
Our honest take
A good loafer is one of the hardest-working shoes you can own. If you take one thing away, let it be that the finish should match the outfit: glossy leather for dresses and tailoring, suede for jeans and knits, and a heavier sole for utility pieces. Brown and burgundy are easier to wear than you might think, and they soften an all-black look. We would skip very chunky platform loafers if you mostly wear skirts, since they can look heavy with a bare leg. A slim, low-profile pair is the one you will reach for most.


























