Ryan | Men&
Ryan | Men&
Ryan | Men&
Ryan | Men&
Ryan | Men&
Ryan | Men&
Ryan | Men&
Ryan | Men&
Ryan | Men&
Ryan | Men&
Winthrop Row · Boston

Ryan | Men's Ergonomic Orthopedic Side-Zip Leather Ankle Boots

$110.00 $62.95 Save 43%
/

Free U.S. shipping · 90-day returns · Taxes calculated at checkout

Color: Black

Color
Size
  • In stock, ready to ship
  • Visa
  • Mastercard
  • American Express
  • Apple Pay
  • Google Pay

Secure, encrypted checkout · Visa, Mastercard, Amex, Apple Pay, Google Pay

Free delivery in 4–8 business days Ships from our North American warehouse in 1–3 business days · delivery 3–5 business days
Buy more, save more
  • 2 items10% off
  • 3 items15% off
  • 4+ items20% off
Applied automatically in your cart — on top of sale prices.
  • 90-day returnsPlenty of time to decide
  • Free U.S. shippingOn every order
  • Designed in BostonShips from North America
  • Fast, human helpEmail replies within hours

Men's Ergonomic Orthopedic Side-Zip Leather Ankle Boots are your go-to choice for all-day comfort without sacrificing style. Featuring hand-stitched faux leather uppers, a supportive ergonomic footbed, and a convenient side zipper, these boots are built for men who spend long hours on their feet.

Why You'll Love It

  • Orthopedic Support: The contoured ergonomic footbed distributes weight evenly across the foot, reducing pressure on knees, hips, and lower back.
  • Easy On, Easy Off: The side zipper lets you slip in and out quickly while the structured upper keeps your foot firmly in place all day.
  • Non-Slip Outsole: The durable rubber outsole with hand-stitched detailing delivers steady grip on a variety of surfaces.

Perfect For

Wear them to the office with chinos for a polished look, pair with jeans for weekend errands, or keep them on for long walks around the city. They transition effortlessly from a casual dinner to a full workday on your feet.

Care Instructions

  • Wipe clean with a soft, damp cloth.
  • Avoid prolonged exposure to water or direct sunlight.
  • Allow to air-dry fully before storing.
  • Use a leather conditioner occasionally to maintain suppleness.

Frequently Asked Questions

How do I put these boots on and take them off?
These boots feature a side zipper for quick and easy entry and removal, so no lacing is required.

What occasions are these boots suitable for?
They are designed for everyday wear and work equally well in casual, business casual, and smart-casual settings.

Men's Shoe Size Chart


UK Szie US  Szie Foot Length Foot Width
UK 2 US 4 20.5 cm / 8.1 in 8 cm / 3.1 in
UK 2.5 US 4.5 21.0 cm / 8.3 in 8.5 cm / 3.3 in
UK 3 US 5 21.5 cm / 8.5 in 8.5 cm / 3.3 in
UK 3.5 US 5.5 22.0 cm / 8.7 in 8.5 cm / 3.3 in
UK 4 US 6 22.5 cm / 8.9 in 8.5 cm / 3.3 in
UK 4.5 US 6.5 23.0 cm / 9.1 in 9 cm / 3.5 in
UK 5 US 7 23.5 cm / 9.3 in 9 cm / 3.5 in
UK 5.5 US 7.5 24.0 cm / 9.5 in 9.5 cm / 3.7 in
UK 6 US 8 24.5 cm / 9.7 in 9.5 cm / 3.7 in
UK 6.5 US 8.5 25.0 cm / 9.9 in 10 cm / 3.9 in
UK 7 US 9 25.5 cm / 10.0 in 10 cm / 3.9 in
UK 7.5 US 9.5 26.0 cm / 10.2 in 10.5 cm / 4.1 in
UK 8 US 10 26.5 cm / 10.4 in 10.5 cm / 4.1 in
UK 8.5 US 10.5 27.0 cm / 10.6 in 11 cm / 4.3 in
UK 9 US 11 27.5 cm / 10.8 in 11 cm / 4.3 in
UK 9.5 US 11.5 28.0 cm / 11.0 in 11 cm / 4.3 in
UK 10 US 12 28.5 cm / 11.2 in 11 cm / 4.3 in

Not sure which size to choose? Tap Find my size above — answer a few quick questions and get your size in seconds.

Most pieces follow standard U.S. sizing. You'll find all measurements in our size guide. For personal help, email contact@winthroprow.com — we reply within a few hours.

Every Winthrop Row piece is selected in Boston for its fabric, fit and finish. The exact composition is listed in the description and on the care label.

  • Knitwear: hand wash cold or dry clean, dry flat, fold instead of hanging.
  • Coats & tailoring: dry clean, hang on a wide hanger, brush after wearing.
  • Leather & suede: brush regularly, protect before wet weather, dry naturally.
  • Shirts & dresses: wash cool, iron on low heat.

Free U.S. shipping on every order. Processing takes 1–3 business days, delivery 3–5 business days from our North American warehouse. You'll receive a tracking link by email.

90-day returns. Email us and we send a printable return label. Return shipping is paid by the customer — free if an item arrives damaged, defective or incorrect.

Shipping details · Returns & exchanges

  • 90-day returnsTake your time to decide
  • Free U.S. shippingShips in 1–3 business days
  • Designed in BostonShips from North America
  • Real people, fast repliescontact@winthroprow.com
Customer reviews

Worn, loved, reviewed

Oct 3, 2026

Softest cardigan I own

I was worried it would be itchy, but it is soft from the first wear. The cable pattern looks even better in person and the fit is exactly as the size assistant suggested.

E Emily R. · Portland, MECable-knit cardigan · Size M
Sep 28, 2026

Warm without the bulk

Wore it all week on my commute. Sharp enough for the office, warm enough for the wind off the harbor. Shoulders fit perfectly.

J James T. · Hartford, CTWool overcoat · Size L
Beautifully packed
Oct 6, 2026

Beautifully packed

Arrived in five business days, wrapped like a gift. You can tell they care about the details. Ordering again for the holidays.

S Sophia L. · Brooklyn, NYOrder of 3 items
The perfect fall trench
Sep 30, 2026

The perfect fall trench

Classic cut, nice weight and the color is exactly like the photos. I get stopped on the street and asked where it is from.

O Olivia M. · Chicago, ILTrench coat · Size S
Quality you can feel
Oct 1, 2026

Quality you can feel

Thick, even knit and clean seams. Washed it by hand as recommended and it kept its shape.

H Hannah K. · Burlington, VTWool knit sweater · Size M
His and hers, both perfect
Sep 25, 2026

His and hers, both perfect

We ordered a sweater each and used the bundle discount. Both sizes were spot on and delivery was quicker than expected.

M Megan & Ryan D. · Providence, RI2 knit sweaters
Comfortable from day one
Sep 22, 2026

Comfortable from day one

Soft leather that did not need breaking in. They run slightly roomy — I took a half size down and they are perfect.

D Daniel P. · Philadelphia, PALeather loafers · US 10
So many compliments
Oct 4, 2026

So many compliments

Wore it to a fall wedding. The fabric drapes beautifully and the color is rich in person. Fit true to size.

A Ava S. · Charleston, SCSatin midi dress · Size S
Fits like it was made for me
Sep 19, 2026

Fits like it was made for me

Supple leather, good hardware, and it already looks better with wear. Customer care answered my sizing question within an hour.

M Michael B. · Denver, COLeather jacket · Size M
Survived a Boston downpour
Oct 7, 2026

Survived a Boston downpour

Got caught in the rain on day two and they still look great. Comfortable for a full day of walking.

C Caroline W. · Boston, MAChelsea boots · US 8
Styled in New England

Complete the look

Shop Fall / Winter
Fireside knits Shop the look
Fireside knits
The Public Garden trench Shop the look
The Public Garden trench
Cobblestone leather Shop the look
Cobblestone leather
A weekend by the harbor Shop the look
A weekend by the harbor
Evenings in the library Shop the look
Evenings in the library
The café quarter-zip Shop the look
The café quarter-zip
Navy on the promenade Shop the look
Navy on the promenade
Farmhouse layers Shop the look
Farmhouse layers
Help & answers

Frequently asked questions

Everything you need to know about ordering, delivery, returns, sizing and care. Can't find your answer? We're one email away.

Still have a question?Email contact@winthroprow.com — a real person replies within a few hours.
Which payment methods do you accept?

We accept Visa, Mastercard, American Express, Apple Pay and Google Pay. Every payment is processed through an encrypted, PCI-compliant checkout — we never see or store your full card details.

When will my card be charged?

Your payment is taken when you place your order. If an item can't be shipped for any reason, we refund it right away to your original payment method.

Can I change or cancel my order?

Yes, as long as it hasn't shipped yet. Email contact@winthroprow.com with your order number as soon as possible — orders usually leave our warehouse within 1–3 business days.

Do the multi-item savings combine with sale prices?

Yes. Our bundle savings — 10% off 2 items, 15% off 3 items and 20% off 4 or more — are applied automatically in your cart, on top of our Fall/Winter 2026 prices of up to 40% off.

How much does shipping cost?

Shipping is free on every order to a U.S. address — no minimum order value.

How long will my delivery take?

Orders are processed within 1–3 business days and delivered within 3–5 business days after shipping. Most orders arrive within 4–8 business days of purchase.

Where do you ship from?

All orders ship from our North American warehouse. As soon as your parcel is on its way, you receive an email with a tracking link.

Do you ship outside the United States?

At the moment we ship to addresses within the United States only.

What is your return policy?

You have 90 days from delivery to return unworn items with their original tags for a full refund to your original payment method.

How do I start a return?

Email contact@winthroprow.com with your order number and the item(s) you want to return. We reply within a few hours with a printable return label and simple instructions.

Who pays for return shipping?

Return shipping is paid by the customer. If an item arrives damaged, defective or isn't what you ordered, your return is free — we send you a prepaid label.

Can I exchange an item for another size?

Yes. The fastest way is to return the item and place a new order for the size you need, so it's reserved for you right away. Not sure which size? Email us for personal sizing help.

When will I receive my refund?

As soon as your return has arrived and been checked, we issue your refund to the original payment method and confirm it by email. Depending on your bank, it can take a few business days to appear on your statement.

How do I find my size?

Use the Size Assistant next to the size options on every product page. Enter your height and weight, answer two quick questions about your build and preferred fit, and get a recommendation from XS to XXXL in seconds. Shoes have their own assistant.

Do your clothes run true to size?

Most pieces follow standard U.S. sizing. Our size guide lists bust, waist, hip and chest measurements for every size.

What if I'm between two sizes?

For coats, jackets and knitwear you'd like to layer, choose the larger size. For dresses and trousers, choose the size that fits your waist and hips. For shoes, go half a size up.

Can someone help me choose a size personally?

Of course. Email contact@winthroprow.com with your height, weight, usual size and the item you're considering — a real person replies within a few hours.

How should I care for wool and cashmere knits?

Hand wash cold or dry clean, lay flat to dry and fold instead of hanging so the knit keeps its shape. Always follow the care label on your garment.

How do I care for leather and suede?

Brush suede regularly, condition smooth leather a few times per season and use a protective spray before wearing in wet weather. Let wet pieces dry naturally, away from direct heat.

What if my item arrives damaged or defective?

Email us a photo and your order number. We'll arrange a free return with a prepaid label and send a replacement or a full refund — whichever you prefer.

Recently viewed