Winslow | Men's Black Leather Penny Loafers
Buy More, Pay Less
- 2 items10% off
- 3 items15% off
- 4+ items25% off
*Extra discount is applied on top of existing sale prices.
The Winslow from Kessoro is proof that the classics got it right the first time. These black leather penny loafers carry the timeless strap detail and sleek round-toe silhouette that have anchored smart wardrobes for generations, polished to a clean, understated finish that works as hard at the office as it does at a wedding.
Smooth leather uppers pair with a flexible, durable sole for a structured feel that stays comfortable through full days on your feet. The slip-on design makes them effortless to wear, while the true-to-size fit settles in quickly without a long break-in. Care is simple: wipe clean with a soft damp cloth and store them dry, and the finish keeps its composure for years.
Wear them with tailored trousers for formal occasions, chinos for the office, or dark denim when smart casual is the call. As fall fills with dinners, events, and holiday gatherings, the Winslow is the one pair of dress shoes that answers every invitation. Quiet, versatile, and permanently in style: that is the penny loafer promise, kept. They travel beautifully too, holding their shape in a suitcase and stepping off the plane ready for the dinner reservation. If your rotation still leans on one tired pair of dress shoes, the Winslow is the straightforward upgrade that earns its keep at every wedding, interview, and client dinner on the calendar.
- Smooth black leather upper
- Timeless penny strap detail
- Sleek round-toe silhouette
- Flexible, durable sole
- Slip-on fit for formal and smart casual
Size guide
Kessoro garments are cut to US sizing. The charts below are body measurements — measure yourself, then pick the size your measurements fall into. They are not the flat measurements of the garment itself.
How to measure
- Chest / bust — around the fullest part, keeping the tape level under your arms.
- Waist — around your natural waist, the narrowest point, usually just above the navel.
- Hips — around the fullest part, roughly 8 inches below the waist.
- Inseam — from the crotch seam to the bottom of the ankle.
Keep the tape snug but not tight, and measure over light clothing or bare skin.
Women's sizing
| Size | US | Bust (in) | Waist (in) | Hip (in) |
|---|---|---|---|---|
| XS | 0–2 | 31–32 | 24–25 | 34–35 |
| S | 4–6 | 33–34 | 26–27 | 36–37 |
| M | 8–10 | 35–36 | 28–29 | 38–39 |
| L | 12–14 | 37–39 | 30–32 | 40–42 |
| XL | 16–18 | 40–42 | 33–35 | 43–45 |
| 2XL | 20–22 | 43–45 | 36–38 | 46–48 |
Men's sizing
| Size | Chest (in) | Waist (in) | Neck (in) |
|---|---|---|---|
| S | 35–37 | 29–31 | 14–14½ |
| M | 38–40 | 32–34 | 15–15½ |
| L | 41–43 | 35–37 | 16–16½ |
| XL | 44–46 | 38–40 | 17–17½ |
| 2XL | 47–49 | 41–43 | 18–18½ |
| 3XL | 50–52 | 44–46 | 18½–19 |
Footwear
Shoe sizes are listed in US sizing on the product page. If you are normally a half size, we recommend taking the next size up — most of our footwear runs slightly narrow through the toe box.
If you're between sizes
Size up. This is the single most common piece of advice we give. It applies especially to:
- Knitwear, sweaters and cardigans, which are cut closer than you might expect.
- Anything described as slim-fit or tailored.
- Outerwear you plan to layer over a shirt or sweater.
If you prefer a relaxed or oversized look, size up regardless of where your measurements land.
Still not sure?
Email customersupport@kessoro.co with the product name and your measurements and we'll tell you which size to order. We'd much rather answer a question than process a return.
And if the fit isn't right when it arrives, you have 30 days to return it — unworn, unwashed, with tags attached. Full details on our returns page.
Shipping & returns
Free shipping on every US order, with tracking. Orders are processed in 1 to 3 business days and arrive 5 to 12 business days after dispatch.
Return or exchange within 30 days of delivery, unworn and with tags attached. No restocking fees. Email customersupport@kessoro.co to start a return.
Size Guide
Kessoro garments are cut to US sizing. The charts below are body measurements — measure yourself, then pick the size your measurements fall into. They are not the flat measurements of the garment itself.
How to measure
- Chest / bust — around the fullest part, keeping the tape level under your arms.
- Waist — around your natural waist, the narrowest point, usually just above the navel.
- Hips — around the fullest part, roughly 8 inches below the waist.
- Inseam — from the crotch seam to the bottom of the ankle.
Keep the tape snug but not tight, and measure over light clothing or bare skin.
Women's sizing
| Size | US | Bust (in) | Waist (in) | Hip (in) |
|---|---|---|---|---|
| XS | 0–2 | 31–32 | 24–25 | 34–35 |
| S | 4–6 | 33–34 | 26–27 | 36–37 |
| M | 8–10 | 35–36 | 28–29 | 38–39 |
| L | 12–14 | 37–39 | 30–32 | 40–42 |
| XL | 16–18 | 40–42 | 33–35 | 43–45 |
| 2XL | 20–22 | 43–45 | 36–38 | 46–48 |
Men's sizing
| Size | Chest (in) | Waist (in) | Neck (in) |
|---|---|---|---|
| S | 35–37 | 29–31 | 14–14½ |
| M | 38–40 | 32–34 | 15–15½ |
| L | 41–43 | 35–37 | 16–16½ |
| XL | 44–46 | 38–40 | 17–17½ |
| 2XL | 47–49 | 41–43 | 18–18½ |
| 3XL | 50–52 | 44–46 | 18½–19 |
Footwear
Shoe sizes are listed in US sizing on the product page. If you are normally a half size, we recommend taking the next size up — most of our footwear runs slightly narrow through the toe box.
If you're between sizes
Size up. This is the single most common piece of advice we give. It applies especially to:
- Knitwear, sweaters and cardigans, which are cut closer than you might expect.
- Anything described as slim-fit or tailored.
- Outerwear you plan to layer over a shirt or sweater.
If you prefer a relaxed or oversized look, size up regardless of where your measurements land.
Still not sure?
Email customersupport@kessoro.co with the product name and your measurements and we'll tell you which size to order. We'd much rather answer a question than process a return.
And if the fit isn't right when it arrives, you have 30 days to return it — unworn, unwashed, with tags attached. Full details on our returns page.
Complete the look
Mix and match: 2 pieces 10% off, 3 pieces 15% off, 4+ pieces 25% off. Applied automatically at checkout.
Our 30-day promise.
Inspected by hand.
Every piece is checked before it leaves us.
Always your choice.
Return or exchange within 30 days. No restocking fees, no questions asked.
Real people, on hand.
For sizing, exchanges, or anything else, our team is at customersupport@kessoro.co.
Loved by 1,200+ customers.
Real, verified reviews from people who wear Kessoro.
I screamed when I opened this - the packaging was gorgeous and the piece inside was even better. Exactly what I ordered, true to size, and the quality is incredible. Already planning my next purchase.
Finally found a brand that gets elevated basics right. Everything feels premium without that ridiculous markup. The fabric on this is so soft and the fit is genuinely flattering. Will be back for more.
Bought this for a work trip and got so many compliments. Clean, well-fitted, and the material holds up all day without wrinkling. Kessoro is my new go-to for business casual.
The color is even better in person than the photos, which never happens. Fits beautifully, shipped faster than expected, and the returns process was super easy when I needed to swap a size. Love this brand.
I'm very picky about quality and Kessoro delivered. The stitching is clean, the fabric is substantial, and it washes perfectly. I've bought from a lot of online brands and this is one of the few that actually matched the photos.
Ordered two pieces and both arrived beautifully packaged and exactly as described. The sizing is spot on — I'm usually between sizes and went with the recommendation in the size guide, which was perfect.
Needed something sharp for a dinner out and this delivered. Looked expensive, wore comfortably all evening, and held its shape. Already told three friends about Kessoro. Solid brand.
As someone who struggles to find things that fit well off the rack, I was shocked at how perfectly this fit. True to size, great length, and the material doesn't cling. I've already ordered two more colors.
Super impressed with the quality for the price. I've paid twice as much for less at other stores. The fabric feels premium, shipping was fast, and customer service responded to my question within hours. 10/10.
I bought this as a gift for my daughter and she absolutely loves it. The quality is evident from the moment you open the box. Classic, elegant, and beautifully made. Kessoro has a new loyal customer.
