Whimsical Walk
The ouroboros penny loafers
4.8 / 5 (124 reviews)Product Details
The Ouroboros is a penny loafer with a story on it. The ouroboros, the ancient symbol of a serpent eating its own tail, sits as the detail that turns a classic black slip-on into a quiet talking point. Underneath the symbolism it is a proper shoe: a welted penny loafer in smooth black calf, made to order. For the man who likes his footwear classic in shape but personal in the details.
The ouroboros, and what it means
The ouroboros is one of the oldest symbols there is, a serpent or dragon curled to swallow its own tail, representing eternity, renewal and the cycle of things. As a detail on a shoe it reads as considered rather than loud, the kind of motif that most people simply find handsome and a few recognise and appreciate. It sits on a classic penny loafer base, so the symbolism never overwhelms the shoe. See the rest of our loafers.
A classic penny loafer underneath
The base is a traditional penny loafer, the saddle strap across the vamp with its signature slot, in smooth black calf that takes a high polish. Black keeps it versatile enough to wear with tailoring or dark denim, so the ouroboros detail is the only thing that marks it out as unusual. Made to order, with custom detailing available on request.
How it is built
Welted construction, so the leather sole is stitched on and can be resoled for years rather than glued and discarded. Black calf upper with the ouroboros motif, the classic penny saddle, and hand finishing throughout. Each pair is made after you order, so the width is set for your foot before the leather is cut.
Fit and sizing
True to size on our round last. Penny loafers fit snug from new and relax slightly with wear, so if you are between sizes, size down half. Want the classic penny without the motif? We make a plain black penny loafer too.
How to wear ouroboros penny loafers
Wear them like any good black penny loafer and let the detail be the surprise. Grey and charcoal trousers, navy and black tailoring, dark denim for the evening. Because the shape is classic and the colour is black, these work in the same places a plain penny loafer does, the ouroboros is simply the part people notice on a second look. Keep the outfit simple and let the shoes reward attention.
Care
Brush after wear and use black cream polish worked in with a soft brush, taking care around the ouroboros detailing so polish does not clog it. Rest a day between wears and use shoe trees to hold the shape. Black calf deepens and improves with regular polishing over the years.
Questions we get about these shoes
What does the ouroboros symbol mean?
The ouroboros is an ancient symbol of a serpent or dragon eating its own tail, representing eternity, renewal and the endless cycle. On these loafers it is a decorative motif with that meaning behind it, for those who appreciate a shoe with a story.
Are these formal enough for work?
The base is a classic black penny loafer, which is smart and versatile, so they suit most business-casual and smart settings. The ouroboros detail is subtle enough not to read as costume, though very conservative offices may prefer our plain black penny.
Can these be resoled?
Yes, by any competent cobbler. Welted construction means the sole is replaceable, so these are loafers you keep rather than replace.
Size & Fit
Select your usual formal shoe size. If your foot is wider, choose “Wide”. If your foot is slimmer, choose “Narrow”.
Belt Size
If you choose a matching belt, select your waist size in inches. For a custom belt size, select “Custom Size” and add details in Customization Notes.
Leather Care
Use soft cloth, avoid direct water exposure, and store shoes with shoe trees for better shape retention.
Shipping & Returns
Shipping Policy
Timeline: Made-to-Order Items
Since the item you are interested in is Made-to-Order, it is crafted specifically for you after your purchase. This means the production and delivery process differs from standard in-stock items.
Please note the following timeline:
1. Production Time:
- Your item will require an estimated (Ten to 14 days ) to be expertly crafted and completed.
- This period begins the business day after your order is successfully placed.
2. Shipping & Delivery:
- Once production is complete, your item will be immediately prepared for shipment.
- The final delivery time is determined by the shipping method you select at checkout.
- We will send you a shipping confirmation email with tracking information as soon as your order leaves our facility.
Total Estimated Wait Time: 10 to 14 Days
Return & Refund Policy
Eligibility Period: 15-Day Guarantee
We stand by the quality of our products. If you are not completely satisfied with your purchase, you may initiate a return or exchange within fifteen (15) calendar days from the date you received your order.
- For Returns: A full refund, minus any original shipping charges, will be issued to your original payment method.
- For Exchanges: We will be happy to exchange the item for a different size, color, or a product of equal or lesser value, subject to stock availability.
2. Condition of Product: Must Be Unworn and New
To qualify for a return or exchange, the item must meet the following strict conditions:
- Unworn/Unused: The product must show absolutely no signs of wear, use, damage, or alteration. This includes (but is not limited to) no stains, scuffs, tears, stretching, or odors (such as perfume, smoke, or pet scents).
- New/Original Condition: The item must be returned in the exact condition it was received.
- Original Packaging: All original packaging, boxes, protective films, tags, labels, and documentation must be included and intact.
⚠️ Note on Damaged or Used Items: We reserve the right to refuse a return or exchange if the product does not comply with the above conditions. Items sent back in a used, worn, or damaged state will be returned to the customer, and a refund will not be issued.
3. How to Initiate a Return or Exchange
- Contact Us: Please email our customer service team at [WHIMSICALWALKOFFICIAL@GMAIL.COM] within the 15-day period.
- Provide Information: Include your Order Number, the name of the item(s) you wish to return/exchange, and the reason for the return/exchange.
- Receive Authorization: Our team will review your request and provide you with a Return Merchandise Authorization (RMA) number and detailed shipping instructions. Please do not send items back without an RMA number.
4. Shipping Costs and Processing
- Return Shipping: The customer is responsible for all shipping costs associated with sending the item back to our facility for both returns and exchanges, unless the item received was defective or incorrect.
- Processing Time: Once we receive your return, please allow 3-5 business days for inspection and processing. Once approved, refunds may take an additional 5-10 business days to reflect in your bank or credit card account, depending on your financial institution.
NON REFUNDABLE PRODUCTS
-
Shoe Shape Verification: Customers are responsible for reviewing and confirming the product design, including the toe shape (such as round, squared, or chiselled), prior to finalizing their purchase. Because our product images accurately reflect the advertised design, refunds or exchanges cannot be issued if the requested shape was not verified or if a different style was preferred after delivery.
-
Sizing Accuracy: Customers must provide accurate measurements or select the correct size during the ordering process. We cannot offer refunds or free replacements for orders placed with incorrect sizing information provided by the customer.
Men's Shoe Size Guide
| US | UK | EU | CM | IN |
|---|---|---|---|---|
| 4 | 3.5 | 37 | 22.9 | 9 |
| 4.5 | 3.5 | 37-38 | 23.3 | 9 1/4 |
| 5 | 4 | 38 | 23.8 | 9 3/8 |
| 5.5 | 5 | 38-39 | 24.1 | 9 1/2 |
| 6 | 5.5 | 38-40 | 25.4 | 9 7/8 |
| 6.5 | 6 | 40 | 25.8 | 9 7/8 |
| 7 | 7 | 41-42 | 26 | 10 |
| 7.5 | 7.5 | 41 | 26.7 | 10 1/8 |
| 8.5 | 7.5 | 42 | 26.3 | 10 3/4 |
| 9 | 8.5 | 43-44 | 27.7 | 10 7/8 |
| 10 | 9 | 44 | 27.9 | 11 |
| 10.5 | 9.5 | 44-45 | 28.6 | 11 1/4 |
| 11 | 10 | 45 | 29.2 | 11 1/2 |
| 11.5 | 10.5 | 45-46 | 29.8 | 11 5/8 |
| 12 | 11 | 46 | 30.8 | 11 3/4 |
| 13 | 12 | 48 | 30.5 | 12 |
| 15 | 13 | 50 | 31.7 | 12 1/2 |
How to do exact measurement
Shipping & Returns
Shipping Policy
Timeline: Made-to-Order Items
Since the item you are interested in is Made-to-Order, it is crafted specifically for you after your purchase. This means the production and delivery process differs from standard in-stock items.
Please note the following timeline:
1. Production Time:
- Your item will require an estimated (Ten to 14 days ) to be expertly crafted and completed.
- This period begins the business day after your order is successfully placed.
2. Shipping & Delivery:
- Once production is complete, your item will be immediately prepared for shipment.
- The final delivery time is determined by the shipping method you select at checkout.
- We will send you a shipping confirmation email with tracking information as soon as your order leaves our facility.
Total Estimated Wait Time: 10 to 14 Days
Return & Refund Policy
Eligibility Period: 15-Day Guarantee
We stand by the quality of our products. If you are not completely satisfied with your purchase, you may initiate a return or exchange within fifteen (15) calendar days from the date you received your order.
- For Returns: A full refund, minus any original shipping charges, will be issued to your original payment method.
- For Exchanges: We will be happy to exchange the item for a different size, color, or a product of equal or lesser value, subject to stock availability.
2. Condition of Product: Must Be Unworn and New
To qualify for a return or exchange, the item must meet the following strict conditions:
- Unworn/Unused: The product must show absolutely no signs of wear, use, damage, or alteration. This includes (but is not limited to) no stains, scuffs, tears, stretching, or odors (such as perfume, smoke, or pet scents).
- New/Original Condition: The item must be returned in the exact condition it was received.
- Original Packaging: All original packaging, boxes, protective films, tags, labels, and documentation must be included and intact.
⚠️ Note on Damaged or Used Items: We reserve the right to refuse a return or exchange if the product does not comply with the above conditions. Items sent back in a used, worn, or damaged state will be returned to the customer, and a refund will not be issued.
3. How to Initiate a Return or Exchange
- Contact Us: Please email our customer service team at [WHIMSICALWALKOFFICIAL@GMAIL.COM] within the 15-day period.
- Provide Information: Include your Order Number, the name of the item(s) you wish to return/exchange, and the reason for the return/exchange.
- Receive Authorization: Our team will review your request and provide you with a Return Merchandise Authorization (RMA) number and detailed shipping instructions. Please do not send items back without an RMA number.
4. Shipping Costs and Processing
- Return Shipping: The customer is responsible for all shipping costs associated with sending the item back to our facility for both returns and exchanges, unless the item received was defective or incorrect.
- Processing Time: Once we receive your return, please allow 3-5 business days for inspection and processing. Once approved, refunds may take an additional 5-10 business days to reflect in your bank or credit card account, depending on your financial institution.
NON REFUNDABLE PRODUCTS
-
Shoe Shape Verification: Customers are responsible for reviewing and confirming the product design, including the toe shape (such as round, squared, or chiselled), prior to finalizing their purchase. Because our product images accurately reflect the advertised design, refunds or exchanges cannot be issued if the requested shape was not verified or if a different style was preferred after delivery.
-
Sizing Accuracy: Customers must provide accurate measurements or select the correct size during the ordering process. We cannot offer refunds or free replacements for orders placed with incorrect sizing information provided by the customer.
Customer Experiences