Stuart Weitzman 5050 Boots Review: Are Stuart Weitzman’s Famed Boots Really Worth It?

lindsay silberman aspen

Prior to purchasing my first pair of Stuart Weitzman 5050 boots, I had so many questions. How do the boots fit? Do they last over time? Are they comfortable? And—most importantly—are Stuart Weitzman 5050 boots worth it?

Since it was a big investment for me at the time, I needed to know with 100% certainty that they checked all of the boxes.

I obsessively read every single Stuart Weitzman 5050 boot review on the Internet, but I still felt like the reviews I read didn’t cover everything. (I am crazy about doing my research when it comes to purchases.)

If you’re reading this, I’m guessing that you’re probably in my shoes (see what I did there?) and you likely have many of the same questions I had.

stuart weitzman 5050 boots review

So, here’s my exhaustive Stuart Weitzman 5050 review. If there’s anything I didn’t cover here, just drop your question in the comments! I’m usually very fast to respond.

Stuart Weitzman 5050 Boots Review

Are Stuart Weitzman Boots Comfortable?

stuart weitzman napa leather over-the-knee boots

This was one of the primary questions I had before I tried them on for the first time.

And I can confirm: Stuart Weitzman boots are INSANELY comfortable. Particularly the 5050 over-the-knee style. (It’s why every woman who owns a pair is obsessed with them!)

I remember when I first touched them, the napa leather was the softest thing I’d ever felt; the stretchy fabric that covered the calf guarantees you’ll never be the girl wearing terrible slouchy boots again. They’re comfortable, yet chic; sophisticated, yet casual.

stuart weitzman 50/50 over-the-knee boot

What I like most about them, comfort-wise, is that they have a slight heel—¾-inches—that gives you just the right amount of “lift,” without sacrificing comfort.

When I tell you they’re comfortable, I’m not exaggerating: I’ve worn them for 10-hour work days. I’ve worn them to events where I was on my feet all night. I’ve even worn them in the winter to run around New York City (where I live)—and I have never once felt uncomfortable in them.

stuart weitzman boots

Also: I have a bad lower back because of an accident I was in years ago, and most shoes end up giving me back pain… these do not. If I find them comfortable, that’s saying a lot!

I find the Stuart Weitzman Tieland Over-the-Knee boot to be surprisingly comfortable as well. It has a higher heel (2 ¾ inches) but you honestly wouldn’t even know you were wearing a heeled boot because of how nice they feel. I was shocked the first time I put them on.

Do Stuart Weitzman Boots Stretch Out?

When investing in a quality pair of boots, the last thing you want is for them to stretch out. After years of wearing the Stuart Weitzman 5050 boots, I can confirm that they don’t stretch. The leather softens a little bit but they maintain their shape. I’ve had mine for years and they still look brand new.

Stuart Weitzman 5050 Boot Sizing

If you’re set on buying the 5050 boots and wondering how they fit, I can confirm that the boots run true to size. I’m a size 7.5 and that size fit me perfectly.

I desperately wanted a taupe suede pair and the only one left was an 8.5 so I figured “whatever, I’ll just size up!” I bought them—and yes, they are way too big. Thank goodness for thick socks. (They no longer make the 5050 in taupe suede, which I’m wearing below, but the Lowland is pretty similar!)

Stuart Weitzman 5050 Boot Sizing

If you’re in between sizes:

  • Go with the larger of the two if you’re wide
  • Go with the smaller of the two if you’re narrow

Do they work for wide calves?

In terms of the calf situation: I personally have narrow calves and “normal” boots tend to droop on me. But because these have a stretchy back panel, they stay up perfectly.

They also work for women with wide calves as well! Many of the women I’ve spoken to who previously had a hard time finding boots to fit over their calves have found success with the 5050s.

stuart weitzman leather boots
Here’s a close-up of the stretchy back.

I’ve heard from DOZENS of readers and followers who have athletic calves that love them. And find the stretchy back panel to be a game-changer.

I honestly think the stretchy back is the biggest differentiator between Stuart Weitzman boots and every other over-the-knee boot on the market. I’ve tried countless Stuart Weitzman 5050 dupes. And none of them were able to replicate the back panel in the same way.

stylish woman in aspen
Wearing my Stuart Weitzman 50/50s in Aspen.

Are Stuart Weitzman Boots Worth It?

Having owned my 5050s for six years, I somehow love them even more now than the day I bought them. I’m so paranoid about them being discontinued that I even bought a “back up” pair for when mine eventually bite the dust!

Even after 6 years, I’m not exaggerating when I say that my original pair still looks brand new, despite the fact that I wear them embarrassingly often: with black skinny jeans, with tights, without tights, with skirts, with faux leather leggings, with dresses, in the rain, in the snow (as evidenced by the photo below).

OTK boot outfit ideas

In fact—and this should come as no surprise—I’m actually wearing them right now.

Every so often, an impeccably dressed woman will come up to me on the street or in the ladies room at a restaurant and say, “Nice boots!”

Usually, she’s wearing them too.

Stuart Weitzman Over-the-Knee Boot

If you’re looking for other shoe recommendations, check out my guide to the best comfortable (but cute) winter boots.

How to Put On Over-the-Knee Boots

So, I’m going to let you in on a little secret. There’s actually a *trick* to putting on the Stuart Weitzman 5050s that I learned from a sales associate the day I bought my first pair.

OTK boot outfit ideas
  1. Place the boot on the floor standing upright.
  2. Stick your arm half-way down the boot.
  3. Pinch a piece of the stretchy back shaft with your fingertips.
  4. With your other hand, roll the top half down over the lower half of the boot. (Don’t freak out about doing this—they won’t stretch out. I’ve been doing it for 6 years!)
  5. Then slip your foot in, and roll the top half back up.
stuart weitzman leather 5050 boots

You can also store the boots rolled down half-way so that they’re not flopping over. Another hack re: how to store your Stuart Weitzman 5050s: when they’re rolled down half-way, stick an empty paper towel roll inside. They’ll stand upright perfectly and won’t get wrinkled.

How to Care for Your Boots

Below is what Stuart Weitzman advises, so when it doubt, I defer to them! I will say that I foolishly spent YEARS wearing my leather boots without having sprayed them with a stain repellant as the brand advises. They still look amazing—but it’s better to be safe than sorry!


  • Spray with stain repellant prior to use.
  • When soiled, wipe with a clean, damp cloth and apply neutral or colored polish or leather lotion.
  • Buff lightly with a soft cloth when dry.
  • Do not apply polish to oil tanned leathers.


Hopefully this addressed all of your questions! As always, drop me a line in the comments if there’s something I haven’t answered. And if you end up buying them because of this review, tag me in your photo (@LindsaySilb) so I can see how gorgeous you look!

Can You Return Stuart Weitzman Boots?

I know that ordering online can sometimes be hit or miss (especially with shoes since sizing can be tricky) so it’s always good to know the return policy ahead of time. Stuart Weitzman accepts returns 14 days upon receipt unless it’s noted that orders are final sale.

They also offer complimentary shipping and returns as long as the product reaches their distribution center within 14 days.

Purchases made from the Stuart Weitzman outlet, as well as any customized orders are typically final sale and are not eligible for returns or exchanges.

You can find out more about exchanges on the Stuart Weitzman website.

Here’s an essay I wrote for Town & Country about the boots back in 2017!

My longing for Stuart Weitzman’s impossibly perfect over-the-knee boot began in 2012, when I started to notice that every woman in New York—or at least all the chic ones—were wearing them.

Ordinarily I’d shy away from something so ubiquitous (which is why I never bothered with the Goyard St. Louis tote or Gucci’s shearling lined loafers) but for some reason, no matter how hard I tried, I just couldn’t get the boot off my mind.

At the time, splurging on a $655 pair of shoes (plus $58 in sales tax because…New York) seemed like an irresponsible decision for someone who could barely afford to pay her rent, so I suffered through the winter without them, and instead bought myself a similar (read: cheaper) alternative in an attempt to satiate my need.

That decision, it turned out, only made things worse. My $250 bootleg boots were ill-fitting and uncomfortable. The calf area was so baggy that with each step, they would inch their way down my leg, eventually settling mid-shin like a pair of ‘80s slouch socks. I wore them a total of two times before tucking them away in the back of my closet to collect dust.

By the fall of 2014, I told myself that if I still needed to have the boots, I could go try them on before winter—you know, just to see what they felt like.

I walked into the Stuart Weitzman store in Manhattan’s Columbus Circle on a chilly November night, marched right up to the sales associate, and announced that I was interested in trying on the “5050” in a size 7.5. She shook her head.

“So sorry! We’re actually sold out of that size! Did you try the Soho store?”

It hadn’t occurred to me that the boot might not even be available—which, of course, only made me want them more.

The following week I made my way to Soho, and as luck would have it, they had my size. When the salesperson emerged from the stock room carrying an obnoxiously large purple box, I felt like I was having an out-of-body experience. (Ok fine, it wasn’t that dramatic, but still, I had to have those damn boots.)

She removed the lid, unfurled the tissue paper. From the moment I had them on, I knew there was no turning back. I looked in the mirror and suddenly felt like a cooler, more confident version of myself.

I began fantasizing about all the outfits I could wear them with (Skirts! Dresses! Jeans!) and the occasions I could wear them to (Work! Parties! Even funerals!) In less than three minutes, I had signed the credit card receipt and was prancing down Mercer Street in my new 5050s.

A few years ago, the boot celebrated its 25th anniversary—a pretty remarkable feat when you consider the rising popularity of fast fashion, and the speed at which trends tend to come and go. To celebrate the occasion, the brand released a new campaign starring perennial cool girl Kate Moss, a woman who (like the boots) remains as relevant today as she was 25 years ago.

This article originally appeared in Town & Country.


  • Anne
    November 13, 2018 at 6:23 am

    Hi Linds, what about wearing them in slush and heavy snow? Would you dare? I live in Montreal, Canada and our winter is no flipping joke… thanks!

    • Lindsay Silberman
      November 15, 2018 at 11:11 pm

      I definitely wouldn’t recommend it. I dont think it will ruin them, but probably won’t keep your toes very warm!

  • Emily R
    December 22, 2019 at 6:11 pm

    Did you ever have a problem getting past the heel when sliding them on?

    • Lindsay Silberman
      December 27, 2019 at 9:00 pm

      no! never! but i think that’s because I always have them rolled down when i slide my foot in. thats the trick!

  • Kat
    September 26, 2020 at 5:49 am

    So you said the 9 was way to big & thank god for thick socks. Then you recommend to go half a size up for wide feet. So you think the half size up would be a good idea if I want to wear them in cold weather & want my toes to stay warm wearing thicker socks? In your normal sizing do you wear thin socks?

    • Lindsay Silberman
      September 30, 2020 at 2:55 pm

      I have very narrow feet so for me going up wasn’t ideal. If you have normal/wide feet and want to wear super thick socks, I’d say you’ll be fine with a 1/2 size up.

    • Molly
      November 8, 2022 at 9:11 pm

      Thank you for sharing such an awesome tips! I just scored a pair of these in suede. Do you think leather or suede feel more comfortable? Do your suede pairs last a long time and look brand new as well?
      Enjoy your blog a lot!

    • Sandra
      November 25, 2022 at 4:41 pm

      I have wide feet. My size nine 5050 seude boot fits beautifully. Should I order an 1/2 size larger in a leather 5050 stuart weitzman?

  • Christine Schultz
    December 24, 2020 at 12:42 pm

    Hi! Thank you for your article. So helpful. I ordered the 5050 lift! They are a new version of the classic. Everyone says to order a half size down. Do you still believe that your regular size is best?

    Waiting for Santa to arrive 🙂

    Thank You!

    • Lindsay Silberman
      January 13, 2021 at 8:58 pm

      Hi Christine! Assumed you already made your decision by now, but I would only go down a half size if you have very narrow feet!

  • Julie
    July 21, 2021 at 12:14 am

    Thanks for the review. I’m tossing up between the Tieland and 5050’s. Which do you wear more?

  • Gina
    August 28, 2021 at 2:34 am

    I saw on Gilt the 5050s are at a discount but it is listed as “Stuart Weitzman Reddy 5050 Leather”. Is it the same as the regular 5050 from the SW store? Thanks.

  • Jennifer
    October 28, 2021 at 2:13 am

    What are your thoughts about the 5050 City boot vs the original?

  • meta mehling
    December 10, 2021 at 4:41 am

    Thank you thank you thank you.
    I just got my first pair and could not get my foot in, and was just about to send back…. So grateful that I found you. I have them on now with your advice – and now I’m wondering …. same process to take them off? They are so comfy I could likely sleep in them.

    • Lindsay Silberman
      January 29, 2022 at 9:58 pm

      Yes same exact process! Roll them down while they are still on you, and then just leave them that way. Much easier to slide back on. It won’t ruin the leather (I’ve been doing it to mine for 8 years!)

  • Priscilla Bos
    May 3, 2022 at 1:41 pm

    Hi Lindsay!

    I was looking for some NYC spots for my trip in October and ended up at your page, thankfully! BUT how and most of al WHY did I end up in this blog?! I love Stuart Weitzman shoes, but I never wear flat boots, because of my height (167cm). But these boots look and sound so good! They go with everything. My question is now, how do you think about these flat boots with someone less tall. I don’t know how tall you are, but you look taller than me in your pictures. I absolutely LOVE the idea how you can wear these boots and you really had me at “running around in NYC”. Now I’m dying to have these boots just to wear them in NYC! Well, hope to hear you say these boots are awful when you’re not tall enough haha 😉

    • Lindsay Silberman
      May 3, 2022 at 9:30 pm

      You can totally rock them!! I believe they even have a version with a shorter shaft length that you might feel is more proportionate! so glaf you found your way to my page!

  • Elizabeth
    August 20, 2022 at 1:04 am

    Can’t decide….do I get the Leather or Suede???

  • Alsa
    November 20, 2022 at 6:19 pm

    Does it need water repellent? I live in the UK and it rains all the time. And do you find it slippery with the smooth sole?

  • Candace Ferreira
    November 24, 2022 at 2:47 am

    Okay the fact that you’ve been to snow polo (I work for Aspen valley polo club!!) totally sold me on these!!

  • Amy Cline
    December 3, 2022 at 2:09 am

    Just curious, is there a reason the 5050 boots are approximately $700 on some site and as low as $300 on Ruelala, Saks Off etc? It looks like the only difference is that the heel is 1.5 inches instead of 1 inch.
    Any thoughts on this?


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