Rockport
Men's Classic Penny Loafer
Black Leather Dress Loafers
Discount at Checkout
Details:
Offer valid at rockport.com for 20-40% off select styles. Not valid on past purchases or towards the purchase of gift cards. Valid through 4:59 a.m. EDT on March 24, 2026. Additional exclusions may apply.
Some shoes earn their place through decades of quiet dependability. The Classic Penny Loafer delivers exactly that, with Rockport's truTECH® cushioning built into the heel for lightweight shock absorption that lasts from morning meetings through evening plans. Rich leather shapes a traditional penny loafer silhouette, finished with clean stitching along the moc toe and a polished, rounded profile that pairs as easily with a suit as it does with chinos. A contoured footbed conforms over time for a fit that only improves with wear, while the durable outsole and low stacked heel provide steady footing all day long. This is the dress shoe that doesn't feel like one.
Benefits
Shoe Size Chart and Conversion
Shoe Size Chart and Conversion
Shoe/Width Sizing
To ensure the right fit, please refer to the size chart, width offerings, and sizing tips below.
| Rockport Men’s | M (medium), W (wide), XW (extra wide), XXW (extra-extra wide), N (narrow) |
|---|---|
| Rockport Women’s | M (medium), W (wide), XW (extra wide), N (narrow) |
| Dunham | D (medium), 2E (wide), 4E (extra wide), 6E (extra-extra wide), B (narrow) |
| Men's Footwear | ||||
|---|---|---|---|---|
| US/CA | Europe | UK | JP | MM |
| 5 | 37.5 | 4.5 | 23 | 230 |
| 5.5 | 38 | 5 | 23.5 | 235 |
| 6 | 38.5 | 5.5 | 24 | 240 |
| 6.5 | 39 | 6 | 24.5 | 245 |
| 7 | 40 | 6.5 | 25 | 250 |
| 7.5 | 40.5 | 7 | 25.5 | 255 |
| 8 | 41 | 7.5 | 26 | 260 |
| 8.5 | 42 | 8 | 26.5 | 265 |
| 9 | 42.5 | 8.5 | 27 | 270 |
| 9.5 | 43 | 9 | 27.5 | 275 |
| 10 | 44 | 9.5 | 28 | 280 |
| 10.5 | 44.5 | 10 | 28.5 | 285 |
| 11 | 45 | 10.5 | 29 | 290 |
| 11.5 | 46 | 11 | 29.5 | 295 |
| 12 | 46.5 | 11.5 | 30 | 300 |
| 12.5 | 47 | 12 | 30.5 | 305 |
| 13 | 47.5 | 12.5 | 31 | 310 |
| 14 | 49 | 13.5 | 32 | 320 |
| 15 | 50 | 14.5 | 33 | 330 |
| 16 | 51.5 | 15.5 | 34 | 340 |
| 17 | 53 | 16.5 | 35 | 350 |
| 18 | 54 | 17.5 | 36 | 360 |
| 19 | 55 | 18.5 | 37 | 370 |
| 20 | 56 | 19.5 | 38 | 380 |
| Women's Footwear | ||||
| US/CA | Europe | UK | JP | MM |
| 5 | 35 | 2.5 | 22 | 220 |
| 5.5 | 35.5 | 3 | 22.5 | 225 |
| 6 | 36 | 3.5 | 23 | 230 |
| 6.5 | 37 | 4 | 23.5 | 235 |
| 7 | 37.5 | 4.5 | 24 | 240 |
| 7.5 | 38 | 5 | 24.5 | 245 |
| 8 | 39 | 5.5 | 25 | 250 |
| 8.5 | 39.5 | 6 | 25.5 | 255 |
| 9 | 40 | 6.5 | 26 | 260 |
| 9.5 | 41 | 7 | 26.5 | 265 |
| 10 | 41.5 | 7.5 | 27 | 270 |
| 10.5 | 42 | 8 | 27.5 | 275 |
| 11 | 42.5 | 8.5 | 28 | 280 |
| 11.5 | 43 | 9.0 | 28.5 | 285 |
| 12 | 44 | 9.5 | 29 | 290 |
| 13 | 45 | 10.5 | 30 | 300 |
| 14 | 46 | 11.5 | 31 | 310 |
Sizing Tips
- Your heel should fit snug with no slipping. The midfoot of the shoe under your arch and over the top of your foot should be snug but not tight. You should have enough room in the toe box to wiggle your toes. Our shoes are made to fit directly out of the box. They do not need to be broken in.
- People are more than twice as likely to buy a shoe that is too small than too big. Clues that your shoes are too small or narrow include - foot cramping or "falling asleep" or the formation of blisters and calluses between or on your toes.
- Feet typically get bigger with age. We encourage you to have your feet measured every year. Women's feet often become a half-size (or more) larger after pregnancy.
- Your left and right feet may differ in length or width as much as a full size. Be sure to measure and try shoes on both feet, and always buy shoes to fit your larger foot.
- While the incremental enlargement/reductions between the sizes and widths are industry standards – not every manufacturer starts with the same measurement for their model size.
- Rockport uses the Brannock Device measurement along with several taped forefoot volume measurements as a starting point for both men’s and women’s shoes.
- Reviews
- Questions
My new Penny Loafers
Great fitting shoes
Very good and comfortable shoes
Wore this for 10 years
Title explains all. Good stuff.
Awesome shoes!
I’m wearing these penny loafers as my work shoe. They are made for men but I like them very much and I’m female! Quality in every detail!
Very nice
And very comfortable
My second pair.
Very comfortable shoe. Wear every day. Very durable.
Comfortable Penny Loafer
I’ve had a similar shoe in the past and ordered these from Rockport. Nice looking and comfortable.
Great shoes
Great as always
Black Penny loafer
order arrived as advertised. fit was just fine.
Rocking with Rockport
I have been buying Rockport shoes since Adam was a Boy Scout. Well, maybe that is a stretch, but I had numerous pairs of Rockport shoes over many decades. Nothing says satisfaction like a long-term, repeat customer.
A Comfy Shoe That Looks Great
I've spent tons of money on other shoes that advertised they were "the most comfortable shoe on Earth" only to find out they weren't really that comfortable. I owned Rockport shoes years ago and just recently bout some penny loafers that were a touch tight to get into but after walking around, they felt fine.
Gorgeous shoes
Gorgeous shoes. But even the wide width was too narrow for me so I had to return them.
