Harry Styles walked eight miles in loafers. Is he ruining his feet? There’s only one way to find out
For his trek across New York City, the singer wore a pair of Prada slip-ons. I tried to do the same in my penny loafers – and soon found out why experts advise against it

TL;DR
- Harry Styles walked eight miles in New York City wearing Prada loafers.
- Experts advise against walking long distances in loafers due to their narrow forefoot, which can compress toes.
- Wearing insubstantial shoes like loafers or flip-flops on hard pavements can cause foot problems, with a rise in plantar fasciitis cases noted during a hot summer.
- Fashion trends show a decline in trainers and a rise in loafers, particularly slim-soled styles popular in the 1970s.
- The writer experienced toe compression and heel slippage while attempting to walk eight miles in penny loafers.
- Experts suggest that poorly made or overly cushioned trainers are a more common and significant problem than wearing loafers for daily commutes.
- A well-made dress shoe with orthotic inserts is recommended as a compromise for walk-to-work footwear.
- Foot strength and a foot shape complementary to the shoe are important for comfort and injury prevention when wearing less supportive footwear.
- The writer abandoned their loafer experiment due to discomfort.
- Paparazzi photos later showed Styles wearing trainers, suggesting he might have reconsidered his footwear choice.