Handmade Leather Shoes · Direct From Our WorkshopMade-to-Order Shoes · 7–10 Working Days Before DispatchDoesn’t Fit? · Free Remake & Free Return ShippingFit Promise · Contact Us Within 14 Days of DeliveryMen's Wide Dress Shoes · US 6–15, Half Sizes & D–EEE WidthsHandmade Leather Shoes · Direct From Our WorkshopMade-to-Order Shoes · 7–10 Working Days Before DispatchDoesn’t Fit? · Free Remake & Free Return ShippingFit Promise · Contact Us Within 14 Days of DeliveryMen's Wide Dress Shoes · US 6–15, Half Sizes & D–EEE Widths
Brown oily pull-up leather · Penny strap with cut-out and perforated apron border · Rounded toe
Brown pull-up leather gives this penny loafer a warm, understated character, with subtle tonal variation across the upper. A classic cut-out penny strap crosses the vamp, while a raised apron seam and small perforations define the rounded forepart. The decorative border adds interest without turning the toe into a wingtip or cap-toe design. Brown sole edging and a layered heel keep the profile cohesive. This slip-on pairs familiar loafer details with the less uniform surface of oily pull-up leather, making it a natural option for relaxed tailoring and everyday leather-shoe outfits. Brown penny loafers for men in oily pull-up leather that lightens where it flexes.
Apron Toe LoafersBrown Leather LoafersCasual Leather ShoesLeather Sole LoafersPenny LoafersExplore more loafers →
Color
$249.00
Handmade · Free remake if it doesn't fit
Choose color, US size and width. We make this pair for your order in 7–10 working days, then ship worldwide in 5–7 days.
Rounded toe — this shape defines the shoe's toe profile and internal volume. Choose any listed size and width for this design; we make the pair to your selected configuration.
Best for
Chinos and denimRelaxed office dressingCasual tailoring
Fit Confidence
⊞
The penny strap is decorative and does not adjust the fit. The vamp therefore needs to suit your instep from the start. Avoid choosing a short size to reduce heel movement if it creates pressure across the foot. Consider your intended socks and use your measurements to assess the fit, particularly if you usually need more room through the instep.
Saves this product and your selected color, US size and width. This does not subscribe you to the newsletter.
↺Free remake if it doesn't fit
✦Handmade construction
◈Worldwide shipping, 5–7 days
⊡Secure checkout
Last & Fit
How these brown penny loafers fit
The toe is rounded, which gives the toes room. Pull-up leather is soft and shapes to the foot quickly, so the pair should feel close over the instep when new. Order your usual US dress shoe size, 6 to 15 including half sizes. A little heel lift when new is normal and settles as the sole starts to flex; a heel that comes right out of the shoe means the size or width is wrong. Try them with the socks you plan to wear, because sock thickness changes how the shoe holds, and remember your dress shoe size is often different from your sneaker size. We make men's brown penny loafers in every size from 6 to 15, including size 13, 14 and 15.
Because the leather eases with wear, do not size up. For a broad foot choose E, EE or EEE in your usual length. The four widths are D (standard), E (wide), EE (extra wide) and EEE. Going up a size to gain width only makes a slip-on loose at the heel, so choose your true length and the width that matches your foot.
✓ Rounded toe✓ Defined silhouetteInstep volumeCheck Fit Guide
Pull-up leather is packed with oils and waxes. When it bends or is pulled over the last, the oils move and the colour lightens in that spot, so a pair in pull-up leather has light and dark tones in it from the day it is made. It cannot be corrected with polish afterwards, so the leather has to be cut and lasted with the stretch running the right way. The round toe and the perforated apron border give the shoe an easy, traditional look, and the brown lining and brown leather sole keep everything in one warm colour family.
Brown pull-up leather · Cut-out penny strap · Perforated apron
The detail is all in one colour: a penny strap with the classic cut-out and a row of small perforations around the apron. Brown penny loafers for men do not come more relaxed than this, and the leather only looks better as it scuffs and softens. The pair is hand-welted with the welt stitching visible along the sole edge, so it can be resoled. If you are looking for casual penny loafers, brown leather loafers for jeans, or a pair of handmade loafers that will age well, this is the one.
Materials & Construction
Materials & Construction
Brown oily pull-up leather upper, brown interior lining and a hand-welted brown leather outsole. Every pair is made to order in 7 to 10 working days.
Upper
Brown oily pull-up leather
Cut-out penny strap, perforated apron border and brown leather grain.
Lining
Brown interior lining
Interior facing complements the leather upper.
Sole
Brown leather outsole
Leather outsole with a dark heel top lift.
Construction
Hand-welted
Hand-welted construction, with the stitched welt visible along the sole edge.
Insole
Branded dark footbed
Dark footbed with HANDSOLE branding.
Hardware
Penny strap with cut-out and perforated apron border
Worn in 14 countries
Made one pair at a time, worn worldwide
1,000+orders fulfilled
14countries shipped to
84cities reached
Before you order
Common questions
Use the size guide for US sizing, width and last guidance. If you are between sizes or unsure about width/last, compare your measurements with the product fit notes or contact Handsole before production. Break-in varies by the specific upper, lining, sole, construction and fit.
If the pair doesn’t fit, contact us within 14 days of delivery and we remake it free, with free return shipping.
Break-in varies by leather, lining, last and fit. A correctly sized pair should feel secure rather than painfully tight; the leather and insole will gradually conform with wear.
Construction details for this product are listed in the Materials & Construction section above. Where the build is resoleable, the upper can be retained while a worn sole is replaced when the pair remains serviceable.
Choose from the widths offered above. If you need unusual forefoot or instep room, have different left/right measurements, or repeatedly struggle with fit, review the Sizing & Fit guide or contact us before production so we can compare the available last/width options or a custom adjustment.
Remove loose dust with a soft brush or clean cloth. Follow the care instructions for the specific leather and finish; suede, patent, patina and two-tone uppers may need different products. Test any suitable cleaner, cream or conditioner on an inconspicuous area first, and use separate clean applicators on contrasting colours. Condition only when the leather and finish need it, rather than on a fixed schedule. Let damp shoes dry naturally away from direct heat. Contact Handsole before attempting recolouring or using a treatment whose compatibility is uncertain.
Click to enlarge
