You know that meme about being careful who you call ugly in school? Well that goes for clothes, too. Something you swore off years ago might one day be totally in, and you’ll be excluded from all the fun. Penny loafers, for example, were once the reserve of barrel-chested-Berties in claret cords. They'd burst at the seams under the strain of decadent toes and gouty ankles. But as it happens, penny loafers are now cool, so you should probably get some. The landed gentry vibe is gone, replaced by a series of variations on the theme, which have given the humble penny new lif
Chunky Black Penny Loafers
In line with the Frankenstein’s Monster styling at Prada and the leopard print grunge at Celine, black loafers with gargantuan soles are in. They work best in a Teddy Boyish lewk—think cropped drainpipe trousers and boxy tailoring—but you can also go all Chandler Bing and wear them with washed-out, tapered denim and simple white tee. Cardigan optional, but they’re in again, too.
Church's Penny Loafer, farfetch.com
GH Bass Weejuns Larson Penny Loafer, ghbass-eu.com
Multicolor Penny Loafers
This is a bit counter-intuitive because multicolor loafers—especially those with pure white patches—seem to say fancy, but we think that they’re best worn dressed right down. Aime Leon Dore’s very easy-going, sportswear-led styling is a good example of what we mean. Think of them more like trainers than dress shoes (but know you can wear them with a suit, too.)
Aime Leon Dore Ald Penny Loafers, aimeleondore.com
Prada Logo-Saddle Leather Penny Loafers, matches.com
Scruffy Suede Penny Loafers
OK, so these aren’t a million miles away from what you think of when you think of penny loafers, but style is in the wearing, not the thing. Grenson is about to release its new Peter loafer, which is cut in snuff suede and equipped with a double leather sole, which makes all the difference. Get them a bit battered and wear them with white socks, and maybe some good jersey joggers. Seriously.
Grenson Suede Penny loafers, mrporter.com
John Lobb Lopez Suede Penny Loafers, mrporter.com
This story originally appeared on Esquire.co.uk. Minor edits have been made by the Esquiremag.ph editors.
