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Le Travel Style

by Courtney Delfino • a San Diego based travel + lifestyle blog inspiring you to travel in style

Product Reviews · Last Updated: June 5, 2025

My Honest Stuart Weitzman 5050 Boot Review + How to Style

My love for the Stuart Weitzman 5050 boots started in 2011 when I was working at Nordstrom and continually sold them to my customers. I waited for the opportunity to purchase them at 40% off (perks of employee discounts) and finally splurged after months of fawning over them. Since then, I have worn them every week (when weather appropriate) and they are easily my favorite purchase of ALL TIME! I wrote this candid review of the Stuart Weitzman 5050 Boot. Which may I add NEVER goes out of style. I cover the pros and cons so you can feel at ease about this pricey purchase.

While all opinions and recommendations are always my own, my content on this blog post may contain affiliate links for products I use and love. This means I get a small commission if you make a purchase after clicking one of these links, at no additional cost to you. As always, I am so thankful for your support and will continue to offer free resources!

Comfort + Durability + Sizing

girl sitting on a curb with fall foliage at stuyvesant street in New York
girl posing in front of the chicago theatre in jewel toned dress

From the gardens of Versailles to walking around New York City, these over-the-knee boots have been my ride-or-die boots on most of my fall/winter travels. I spent the entire day walking around Paris in them and did not have one complaint. They are my most comfortable pair of boots!

Not only that but during the colder months, they keep my feet nice and warm (I pair them with tall socks). The best part about the boots is that the back part is stretchy which makes them great for any size calves! As far as the sizing goes, if you’re between sizes normally choose the smaller size. They do stretch quite a bit after a couple of wears due to the soft leather. But I recommend getting your true size.

How to Style

Below you’ll see a couple of ways to style the Stuart Weitzman women’s boots. I tend to wear them most with leggings and skirts but they look incredible with:

  • mini-skirts
  • mini dresses
  • leggings
  • skinny jeans
  • skinny pants
  • dresses with tights
girl in front of fall foliage holding a leaf
girl in front of wrigley building in Chicago

How to Care for the 5050 Boots

I have replaced the soles once since I purchased them in 2013. They have survived so many trips and harsh winters. But I do take them to my local shoe cobbler roughly once every two years to shine up the leather and make them feel brand new. If you want your designer items to last you need to give them proper TLC.

girl in front of honeycomb in chicago

Where to Buy the Stuart Weitzman 5050 Boot + Pricing

You can purchase the Stuart Weitzman boots at all the designer retailers: Nordstrom, Bloomingdales, ShopBop, etc. I found that Stuart Weitzman always has the most sizes in stock since these boots tend to sell out quite often. You can sometimes catch these on sale for Black Friday. I would like to note that I’ve had mine for the past 10 years, wore it multiple times a year, and it still looks incredible. This boot holds its value for years to come so it’s most definitely worth the investment.

Click the pictures below to shop

I hope this Stuart Weitzman 5050 boot review was helpful to you! And it gave you the push to finally purchase these babies. If you have additional questions, leave them below and I’ll get back to you. Don’t forget to check out more of my product reviews.

Stylishly yours,

Courtney

In: Product Reviews · Tagged: fashion, stuart weitzman, styling

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Comments

  1. Aishah says

    December 1, 2022 at 7:27 am

    I am very in between sizes. I can be anywhere from a 6-7. I usually am a 6.5 in boots because I like a tighter fit as they stretch over time. I received in the mail and they are tight, I am worried if I size up they’ll be too loose.

  2. Courtney Delfino says

    December 1, 2022 at 3:30 pm

    After a few wears, they will stretch out! I would keep the size you have. Just wear light socks with them!

  3. Nina says

    October 20, 2023 at 6:28 pm

    Hi! Thank you for this review! Seems to be exactly what I was looking for. I have two questions though, how is the arch on them and which 5050 do you have? I didn’t see which. Thanks again! Great photos!

  4. Courtney Delfino says

    October 26, 2023 at 8:39 pm

    The arch is good I have a high arch myself and if you click the link on my page it links to my exact boot

  5. Veronica says

    November 25, 2023 at 11:09 pm

    Hello! Came across your review because I need to get my 50/50 soles replaced! After so many years, the rubber part of the sole cracked. How did you get your soles replaced? And did you replace the whole rubber part? Stuart Weitzman is trying to tell me to get a new pair but the rest of the boot is still in great condition. Thanks so much.

  6. Courtney Delfino says

    November 27, 2023 at 10:42 am

    I would take it to your local shoe repair place. I always check yelp for the best reviewed ones and I’m sure they’d be able to help you!

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I'm Courtney. A 30 something San Diego travel + lifestyle blogger sharing travel resources, city guides, packing tips, hotel reviews, skincare advice, and style guides. All to inspire you to wander the world in style!

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