Rockport
Men's Classic Penny Loafer
Cognac 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
Energy Return
Flexible
Smooth Ride
Stability
Genuine LeatherShoe 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
United StatesMaterial looks and feels cheap. Size is way off. Sizing is small and narrower than any of my other dress shoes of similar size.
United StatesSizing
Good looking high quality shoes, but model I ordered ran small and product was sold out in larger size. Disappointing.
United StatesExcellent Experience
Rockport shoes are great - but fitting shoes is hit or miss. My experience with Rockport was great however. Delivery was quick - I had to return for a new size - super easy. I will order again.
United StatesThe consistent, high-quality of this product is appreciated.
I had owned a pair of these shoes for many years (8 to 10 years) and liked them a lot. I kept wooden shoe trees in them when not wearing them and polished them about 2-3 times per year. Recently our 6-month-old labrador found one of these shoes and chewed it up. I found the same shoes on-line at Rockport, ordered them in the size indicated inside my old shoes, received them, and they are an excellent match in all ways. Great shoes. I did not punish the dog: my fault for leaving the shoes where he could reach them.
United StatesShoes
Had them many times before. Well pleased.
United StatesVery nice. Well finished and exactly as advertised.
United Statesjimfromtennessee
So far, I have only tried on one shoe of two pair. It was a bit snug but I think They will work over time. The tan pair were a bit lighter than I expected but this too, will resolve itself.
United StatesClassic Penny Loafers
Shoes slipped on like they were made for me. They fitted correctly and comfortably. Of course, they look great!
United StatesLiked
United StatesGreat looking shoe
