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Stuart Weitzman 5050 Boots Review: Are They 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 really 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.

EDITOR’S NOTE: The Stuart Weitzman 5050 boots are currently on MAJOR SALE here! I literally couldn’t believe my eyes when I saw the price, because they’re never discounted. (There’s also a slightly heeled version of the 5050 called the Stuart Weitzman Alina Over-the-Knee leather boot, but it seems to be sold out.)

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
GET THEM WHILE THEY’RE STILL AVAIL ON SALE!

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.

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 taupe Lowland is pretty similar!)

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 gamechanger.

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 dresses, in the rain, in the snow (as evidenced by the photo below).

stuart weitzman 5050 boot

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 (on sale)


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.

what to wear with over-the-knee boots
  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!

Leather

  • 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.

Suede

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!

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.

4 Comments

  • 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!

    Reply
    • 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!

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

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

    Reply
    • 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!

      Reply

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