Olivia | Women's Orthopedic Waterproof Side-Zip Leather Ankle Boots

Name: Olivia | Women's Orthopedic Waterproof Side-Zip Leather Ankle Boots
Brand: US
Price: 74.99 USD
Availability: InStock

$109.99 $74.99 Save 32%

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2 items10% off
3 items15% off
4+ items20% off

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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

Women's Orthopedic Waterproof Side-Zip Leather Ankle Boots are your go-to choice for all-day comfort and all-weather confidence. Featuring a cushioned orthopedic footbed, side zipper with adjustable strap closure, and a durable waterproof build, these boots are perfect for women who need reliable support from morning to evening.

Why You'll Love It

Arch Support and Cushioning: Advanced orthopedic footbed helps improve alignment and reduces pressure during long hours on your feet.
Waterproof Build: Keeps your feet dry and protected in rain, puddles, and unpredictable weather.
Anti-Slip Sole: Durable rubber outsole provides secure traction on wet and uneven surfaces.

Perfect For

Pair them with jeans and a cozy sweater for weekend errands, wear them to the office with tailored trousers, style them with a midi skirt for casual outings, or reach for them on rainy city walks where comfort and protection both matter.

Care Instructions

Wipe clean with a soft, damp cloth.
Allow to air-dry fully before storing.
Apply a leather conditioner periodically to maintain suppleness.
Store away from direct sunlight and heat sources.

Frequently Asked Questions

How do these boots fasten?
They feature a side zipper for easy on and off, plus an adjustable strap closure at the ankle for a secure, customizable fit.

Are these boots suitable for wide feet?
The adjustable strap and roomy toe box make these boots a comfortable option for women with wider feet.

What occasions are these boots best suited for?
They are designed for everyday wear, including commuting, errands, casual outings, and light outdoor use in wet or uneven conditions.

Women's Shoe Size Chart

UK	US	Foot Length	Foot Width
UK 2.5	US 4	21.5-22.0 cm / 8.5-8.7 in	8.5 cm / 3.3 in
UK 3	US 4.5	22.0-22.5 cm / 8.7-8.9 in	8.5 cm / 3.3 in
UK 3.5	US 5	22.0-22.5 cm / 8.7-8.9 in	8.5 cm / 3.3 in
UK 4	US 5.5	22.5-23.0 cm / 8.9-9.1 in	8.5-9 cm / 3.3-3.5 in
UK 4.5	US 6	22.5-23.0 cm / 8.9-9.1 in	8.5-9 cm / 3.3-3.5 in
UK 5	US 6.5	23.0-23.5 cm / 9.1-9.3 in	9 cm / 3.5 in
UK 5.5	US 7	23.0-23.5 cm / 9.1-9.3 in	9 cm / 3.5 in
UK 6	US 7.5	23.5-24.0 cm / 9.3-9.5 in	9-9.5 cm / 3.5-3.7 in
UK 6.5	US 8	24.0-24.5 cm / 9.5-9.7 in	9.5 cm / 3.7 in
UK 7	US 8.5	24.5-25.0 cm / 9.7-9.9 in	9.5-10 cm / 3.7-3.9 in
UK 7.5	US 9	25.0-25.5 cm / 9.9-10.1 in	10 cm / 3.9 in
UK 8	US 9.5	25.5-26.0 cm / 10.1-10.3 in	10-10.5 cm / 3.9-4.1 in
UK 8.5	US 10	25.5-26.0 cm / 10.1-10.3 in	10-10.5 cm / 3.9-4.1 in
UK 9	US 10.5	26.0-26.5 cm / 10.3-10.5 in	10.5 cm / 4.1 in
UK 9.5	US 11	26.0-26.5 cm / 10.3-10.5 in	10.5 cm / 4.1 in
UK 10	US 11.5	26.5-27.0 cm / 10.5-10.6 in	10.5 cm / 4.1 in
UK 10.5	US 12	27.0-27.5 cm / 10.6-10.8 in	10.5 cm / 4.1 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

Size guide

Measurements & fit

Find your size in seconds: open the Size Assistant next to the size options on any product page, or use the charts below. All body measurements are in inches.

How to measure

Bust / chest: around the fullest part, keeping the tape level under your arms.
Waist: around your natural waistline, the narrowest part of your torso.
Hips: around the fullest part of your hips, feet together.
Foot length: stand on a sheet of paper, mark heel and longest toe, measure the distance.

Women's clothing

Size	US	Bust	Waist	Hips
XS	0–2	31–32.5	24–25.5	34–35.5
S	4–6	33–34.5	26–27.5	36–37.5
M	8–10	35–36.5	28–29.5	38–39.5
L	12–14	37.5–39.5	30.5–32.5	40.5–42.5
XL	16	40.5–42.5	33.5–35.5	43.5–45.5
XXL / 2XL	18	43.5–45.5	36.5–38.5	46.5–48.5
XXXL / 3XL	20	46.5–48.5	39.5–41.5	49.5–51.5

Men's clothing

Size	Chest	Waist	Neck
XS	32–34	26–28	13.5–14
S	35–37	29–31	14–14.5
M	38–40	32–34	15–15.5
L	41–43	35–37	16–16.5
XL	44–46	38–40	17–17.5
XXL / 2XL	47–49	41–43	18–18.5
XXXL / 3XL	50–52	44–46	19–19.5

Women's shoes

US	EU	Foot length (in)	Foot length (cm)
4	34–35	8.3	21.2
5	35–36	8.7	22.0
6	36–37	9.0	22.9
7	37–38	9.3	23.7
8	38–39	9.7	24.6
9	39–40	10.0	25.4
10	40–41	10.3	26.2
11	41–42	10.7	27.1
12	42–43	11.0	27.9

Men's shoes

US	EU	Foot length (in)	Foot length (cm)
6	39	9.5	24.1
7	40	9.8	25.0
8	41	10.2	25.8
9	42	10.5	26.7
10	43	10.8	27.5
11	44	11.2	28.4
12	45	11.5	29.2
13	46	11.8	30.0
14	47	12.2	30.9

Fit tips

Coats & jackets: if you're between sizes or plan to layer a heavy knit underneath, choose the larger size.
Knitwear: for a relaxed fit, size up; for a close fit, take your usual size.
Dresses & trousers: choose the size that fits your waist and hips.
Shoes: between sizes or with wide feet, go half a size up.

Still unsure? Email contact@winthroprow.com with your height, weight, usual size and the item you love — we reply with a personal recommendation within a few hours.

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

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

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

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

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

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

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

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

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

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

The Public Garden trench

Shop the look

Cobblestone leather

Shop the look

A weekend by the harbor

Shop the look

Evenings in the library

Shop the look

The café quarter-zip

Shop the look

Navy on the promenade

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.

Olivia | Women's Orthopedic Waterproof Side-Zip Leather Ankle Boots

Frequently Asked Questions

Women's Shoe Size Chart

Measurements & fit

How to measure

Women's clothing

Men's clothing

Women's shoes

Men's shoes

Fit tips

You may also like

Worn, loved, reviewed

Softest cardigan I own

Warm without the bulk

Beautifully packed

The perfect fall trench

Quality you can feel

His and hers, both perfect

Comfortable from day one

So many compliments

Fits like it was made for me

Survived a Boston downpour

Complete the look

Frequently asked questions

Recently viewed

Find your size in seconds