Whimsical Walk
The ouroboros penny loafers
4.8 / 5 (124 reviews)Product Details
The Ouroboros is a classic black penny loafer carrying the ancient serpent motif, the snake eating its own tail, a symbol of eternity. A quiet statement on a proper handmade shoe, welted, leather soled, made to order.
The symbol and the shoe
The ouroboros is a very old symbol, appearing in Egyptian, Greek and Norse traditions. It stands for renewal and the endless cycle. On a black penny loafer, it reads as a subtle detail rather than a costume, for men who like their shoes to say something without shouting. See the rest of our loafers.
How it is built
Goodyear welted and hand stitched, so the leather sole is stitched on and can be resoled for years. Smooth black calf upper carrying the ouroboros motif, classic penny saddle, stacked leather heel, hand finishing throughout. Made to order, so placement and treatment of the motif can be tuned to your preference.
Fit and sizing
True to size on our round last. Snug from new, relaxes slightly with wear; between sizes, size down half. Measure against our men's size guide.
Who these are for
Men who appreciate a shoe with a story. The black base is versatile enough for work and evenings; the ouroboros makes them yours rather than everyone's. Pair with dark tailoring or plain denim and let the detail speak.
Care
Brush after wear, use a black or neutral cream polish sparingly around the motif, and store with shoe trees. Rest a day between wears; the calf deepens with age and the motif stays sharp.
FAQ
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.
Is the ouroboros hand painted or embossed?
It is hand finished onto the leather, so each pair carries small natural variations. Because every pair is made to order, the placement and treatment can be tuned to your preference before we cut.
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