All Jonathan Abel shoes are made according to European sizing and standard E width, unless otherwise stated. Our shoes tend to run larger, so we recommend taking 1 size smaller than your usual.

EUR 39 40 41 42 43 44 45
US/Canada 6 7 8 9 9.5 10 11
UK 5.5 6.5 7.5 8 8.5 9 10.5
Length of Foot (CM) 23.7 24.5 25.4 26.2 26.7 27 27.9



All measurements are approximate and are meant for reference only. All measurements in centimetres (cm).

EUR 39 40 41 42 43 44 45
E Width 9.37 9.68 10 10.32 10.48 10.64 10.95
EE Width 9.84 10.16 10.48 10.8 10.95 11.11 11.43
EEE Width 10.32 10.64 10.95 11.27 11.43 11.59 11.9
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Step into refined elegance with our Chicago Walnut Goodyear Welted Loafers, meticulously crafted in Portugal. The warm walnut hue adds sophistication to your ensemble, making these Goodyear welted Loafers a versatile choice for various occasions. Whether you're heading to the office or enjoying a casual outing, Chicago ensures you do so with style. Immerse yourself in the comfort of full-grain Italian leather, complemented by soft cushion leather inserts that adapt to your foot over time.


Our new GYFlex collection features the same level of craftsmanship in all our footwear, with one main exception - we've made comfortable, more comfortable. Each pair is made with a rubber sole, and stitched without a metal shank in the middle to allow for maximum bend when you walk. That means a shorter break-in period, shoes that conform more easily to your style of walking, and increased overall comfort. 


The Chicago is a close cousin of our beloved loafer style Maine, only in a round toe style. This style was designed with feedback from customers who wanted a penny loafer with a round toe box like our Connor tassel loafers, and the Chicago is a response to that feedback. 

Built on our R385 round toe last, featuring black rubber soles. 

Only the finest leathers from Tanneries d'Annonay. Goodyear welted construction. Handmade with care in Portugal. 

This style runs large. Pick one size smaller than your usual when ordering. View our size guide here.


Construction: Goodyear Welted
Sole: Black Rubber
Last: R385 Round Toe

Shoe Care

Smooth Leather:
Elevate the care of your smooth leather shoes with our curated selection of premium shoe care essentials. Begin by indulging in our Jonathan Abel Leather Cleaner, expertly formulated to gently remove dirt and grime without drying out the leather. Next, nourish and protect your shoes with Jonathan Abel Leather Cream Polish, available in a spectrum of colors to match your footwear perfectly.

For an added layer of protection and shine, finish with Jonathan Abel Shoe Wax Polish, enriched with natural waxes for a long-lasting, glossy finish.

If Jonathan Abel products are not available, you can use a mild leather cleaner, followed by a high-quality leather cream polish and wax polish from reputable brands.

By following these tailored care instructions and utilizing our premium shoe care products or suitable alternatives, you can ensure that your Jonathan Abel shoes receive the attention they deserve, allowing you to enjoy them for years to come.

Shipping & Returns

At Jonathan Abel, we offer international shipping to ensure you can enjoy our premium-quality footwear, regardless of your location. Our service includes worldwide shipping to selected countries, with a dedicated team ensuring your shoes are dispatched promptly and arrive safely through our reliable shipping carriers. We provide various shipping options, with fees and timelines varying by location and selected shipping method, viewable at checkout. It's important to note that international orders might incur additional customs duties and taxes, for which the buyer is responsible.

Our return policy is designed to guarantee your satisfaction. Eligible items for return should be in their original packaging and unworn condition, with some exceptions like personalized or final sale items. You can initiate a return within [number] days of receipt by contacting our customer service for authorization and shipping instructions. We process refunds or exchanges once the returned item is received, with refunds credited to the original payment method. Our commitment is to provide you with a seamless shopping experience, ensuring high levels of service and customer satisfaction.

The Style

The Style


Loafers are a timeless men's footwear staple, distinguished by their slip-on style that merges convenience with comfort. These shoes typically feature a low heel and a flat sole. Their laceless design ensures a smooth, uncluttered appearance, although some models are accentuated with decorative tassells or metal embellishments.

Versatile in nature, loafers can complement a spectrum of outfits from casual to semi-formal, pairing well with jeans, chinos, or dress trousers. They are particularly favoured for their ease of wear, slipping on and off effortlessly. Recently, they've gained traction in formal settings too, with refined versions crafted from premium leather and designed with a more polished silhouette, making them suitable even for pairing with suits or formal wear, thereby elevating any ensemble with a sophisticated flair.

The Sole

The Sole

Black Rubber

Our black rubber soles are engineered for maximum slip resistance, providing enhanced traction on hazardous surfaces. Their composition offers an advantage, as they are resistant to both oil and water. 

Integrating this sole into your footwear enhances safety by significantly reducing the risk of slips and falls, ensuring stability across various challenging conditions, including wet, muddy, or slippery terrains.

The Last

The Last

R385 Round Toe

Our signature style, distinguished by its generously spacious round toe box, is the perfect starting point for those new to our brand. We highly recommend trying this design first to experience the model of our craftsmanship and comfort.

Refined elegance with our Chicago Walnut Goodyear Welted loafers

Customer Reviews

Based on 1 review
Conrad L.
Jonathan Abel Chicago

Good quality product