Fall/Winter
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Best Women’s Lug Sole Chelsea Boots

A couple of weeks ago, I set out to find flat boots to wear with casual winter outfits for the rest of the season, and I fell down the rabbit hole ordering allllll the lug sole Chelsea boots! Today I’m reviewing the six pairs I ordered.

And yes, I realize that picture only includes five pairs; that’s because the sixth pair is not really available. Plus, it isn’t a lug sole either…

Although as I was editing these pictures, I realized that one of the other pairs isn’t technically a lug sole, and one pair isn’t a Chelsea boot, but anyway! They all serve about the same purpose, and most still have good inventory available.

I tried lug sole Chelsea boots several times over the last few years, and I never thought they suited my style. They felt a little too rugged, plus I found the higher shaft challenging to pair with skinny jeans… which is all I wore for many years.

But now that I’m wearing so many straight ankle jeans, I realized that Chelsea boots are the PERFECT boot to pair with them for casual looks!

Straight leg jeans slip easily over the boot shaft for a sleek and chic look, or you can cuff your jeans and wear chunky socks. That seems to look best with more relaxed straight leg styles, but I prefer a slimmer silhouette, so I just keep my jeans untucked and let them fall right over top of the boots.

Okay, without further ado, let’s get started!

Best Women’s Lug Sole Chelsea Boots for Winter 2023

For size reference, I am typically a size 8 in boots. Occasionally, I need the 8 1/2, and very rarely I size down to 7 1/2. I have the size 8 in all six pairs of boots reviewed in this post, and I found them all true to size.

Tory Burch Chelsea Boot

at Nordstrom (also in brown) // at toryburch.com

I’ll start with the pair that isn’t really available… this is the one I found at the mall, and the pair that got this ball rolling.

I went to my local Nordstrom in search of a flat boot to wear with casual outfits, but I didn’t have a particular style in mind. These gorgeous Tory Burch Chelsea Boots were on sale, and when I slipped them on, I felt like they were made for my feet.

They aren’t comfortable in a soft and squishy kind of way, but you can just tell they’re very well constructed, and the leather is the kind that will soften up and mold to my feet very quickly.

sweater (S) // jeans (29) // boots (8)

I also appreciate that 7 1/2″ shaft – it’s nice and high so my jeans don’t get hung up on the tab in the back the way they do with some of the lower shaft styles. They have a 1 3/4″ heel, so not exactly flat, but very walkable. These boots run true to size, and they’re probably better suited to narrower feet.

Unfortunately, there are only a few sizes left at Nordstrom and Tory Burch, but I didn’t want to write this post without including them.


FREDA SALVADOR Brooke Rain Resistant Boot

at fredasalvador.com // limited sizes on sale at Zappos

This brand is a new one to me. As I mentioned in my last Try-On Haul, I saw these boots on another influencer I follow the day after I’d found the Tory Burch Chelsea Boots at the mall. The second I saw these on on my Instagram feed, I knew this was the style I was searching for.

The lug sole and almond-shaped toe look slightly more casual and less masculine than the snipped toe and stacked heel, and I hadn’t yet worn my Tory Burch boots, so I impulsively ordered these from the Freda Salvador website.

Here’s what Freda Salvador has to say about them:

BROOKE is our first rain-or-shine Chelsea boot featuring waterproof black calf leather and a lightweight foam rubber lug sole. The comfortable round toe, lug sole and studded welt combines everyday style and pound-the-pavement function.

These boots are made in Spain of 100% Italian waterproof leather in black calf, and they’re also 100% Spanish leather lined. In other words, they are gorgeous, high quality boots.

sweater (S) // jeans (29) // boots (8)

The first thing I noticed when I pulled these boots out of the box was how lightweight they are. It’s quite remarkable for a chunky boot, and Zappos confirms that they’re only 11 oz. each. But the leather seemed a bit “paperish” to me… does that even make sense? I can’t think of a better way to describe it. It just wasn’t as luxe as I was expecting for the price tag.

When I put my feet inside, they felt roomy, but not in such a way that I could size down. They also crease in a funny way when I move around, so I think they’d be better suited to a woman with wider feet or a higher instep.

They’re very comfortable to walk in, though, and I love the studded detail around the lug sole. I also appreciate the higher 6 1/2″ shaft – it’s not as high as the Tory Burch, but it’s higher than the La Canadienne Connor, which is this boot’s stiffest competition. (No pun intended… neither boot is stiff, haha!)

I really wanted to love these boots; I love the idea of supporting a smaller family-owned brand, and I love the styling details, but they just aren’t a great fit for my feet.


La Canadienne Connor Waterproof Leather Chelsea Boots

at Nordstrom // at Saks (Gift Card Offer) // at Neiman’s // at Bloomies (Power Points)

I came across these boots when I googled the Freda Salvador pair. They look so similar, I had to study these pictures to be sure I was showing the right ones, and they’re also about the same price.

At that point, I was more curious than anything, since I had the Tory Burch pair and was thrilled with their sale price. But I’ve always been curious to try the La Canadienne brand; I associate with Aquatalia in my mind, and you know how much I love my Aquatalia boots. And since I was searching for this exact look, I decided to at least order them to see what I think.

Here’s what La Canadienne has to say about them:

A classic Chelsea boot with a sturdy lug sole… Round toe character with spacious toe bed. Our City Dry™ technology features waterproof Italian leather and a breathable microfiber lining that keeps you comfortable whether indoors or outside. Cushioned memory foam insole. City Dry™ guarantee excludes elastic.

sweater (S) // jeans (29) // boots (8)

These boots are handmade in Canada, and they have a slightly lower (5 1/2″) shaft and no stud detail. The lug sole isn’t quite as chunky as the Freda Salvador Brooke, and the toe might be every-so-slightly more rounded and less almond-shaped, but the difference in the look of the leather and the feel of the inside of the boot was what I really noticed.

I love the microfiber lining; it’s so comfortable and warm against the foot, and sometimes I don’t bother wearing socks with my boots, so the way they feel inside is important to me. They also a memory-foam insole, and they almost hug my foot, if that makes sense. I don’t feel like my feet are swimming in them the way I feel in the Freda Salvador Brooke. Every time I put these on, I don’t want to take them off.

I said in last week’s Try-On Haul that the leather looks almost look plasticky, but now that I’ve had several pairs of boots sitting side-by-side, and considering the fact that they’re completely waterproof, I don’t feel that these look cheap in any way. In fact, they’re definitely “growing on me”.

If it weren’t for the hefty price tag, these would be a strong contender. And (spoiler alert) I’ve already worn the Tory Burch pair, so I really can’t justify both. But if these go on sale before the end of the season, all bets are off!


Frye Melissa Double Sole Chelsea

 at thefryecompany.com // at Zappos // at Nordstrom

You know how it is when you start looking for something in particular. Every website you go to offers similar styles to consider, so I found myself ordering a few more pairs of Chelsea boots…. for research purposes, of course!

I’ve always loved Frye boots; the quality and craftsmanship is outstanding, and the classic but slightly edgy style appeals to me.

Here’s what Frye has to say about these:

A new take on the classic Chelsea boot. Built on a double outsole, this rugged pattern features a mini lugged outsole for traction and snug goring for ease of entry and all day comfort.

I like how these Frye boots are sort of a cross between the Tory Burch pair and the La Canadienne/Freda Salvador pairs. They have a lower profile sole, with just enough of a lugged outsole to offer some traction, but they have more of a rounded toe like the boots with the chunkier rubber lug soles.

sweater (S) // jeans (29) // boots (8)

These boots are made of a gorgeous shiny leather that’s a bit stiff, but it’s definitely that iconic Frye quality, and I’m sure it will soften up with wear. They’re also lined with leather, and they’re handcrafted in Mexico. They seem like an excellent value for the price point.

My biggest issue with these boots is they are very hard to get off and on. After I tried them on a few times with various outfits, they started to loosen up, and I expect they’d be okay for me in time, but I wanted to mention it for those who might be considering them.

If you have a higher instep or wider feet, you might try the Frye Veronica Chelsea Boot. It has a zipper on the inside, which would probably alleviate this issue. In fact, now that I’m looking at that boot… I’m very tempted to try it. Haha! #justwalkaway

Alrighty, movingrightalong…


Sam Edelman Laguna Waterproof Lug Sole Chelsea Boot

at Zappos // at Nordstrom // at Bloomingdale’s (Power Points)

This pair of Sam Edelman boots has been around for a while. I’ve always bypassed them because they look so chunky, and because I didn’t have this style of boot on my radar until very recently. But for the purposes of this post, I thought I should check them out.

Here’s what Sam Edelman has to say about them:

A heavily lugged sole with a utilitarian style update to a classic Chelsea boot.

Short, and sweet! I will say this, for waterproof leather, it looks incredibly soft and supple.

But these boots are also quite heavy, and they feel and look clunkier on the foot than the ones mentioned above. I definitely felt like my feet were swimming in them.

sweater (S) // jeans (29) // boots (8)

I’m also conflicted about the contrasting trim around the lug sole; I like the look, but it’s somewhat limiting. I prefer the all-black color palette of the rest of the boots in this post.

These are comfortable, well-made boots, though, and the price is much more palatable than the others I tried. They also come in a lot of color options, if you’re looking for something besides black.


Vince Remi Leather Pull Tab Ankle Booties

on sale at Bloomies (plus Power Points) // at Neimans

Finally, I came across these Vince boots in my travels, and since I’m a huge fan of Vince boots, and they were on sale, I thought I’d order them to compare.

They have a similar silhouette to the Tory Burch Chelsea Boots, but with a lug sole and inside zip closure rather than the goring… so they technically aren’t a Chelsea boot. I actually like that about them.

The interior is entirely leather lined, and the exterior leather is soft and supple. They’re everything I’ve come to expect with Vince boots as far as comfort and quality.

sweater (S) // jeans (29) // boots (8)

All that said, they look heavy and clunky to me. I think they run a bit large, and that might be the issue there. Unfortunately, I just noticed they’re almost sold out!

If I hadn’t worn the Tory pair already, and if these were available in the 7 1/2, they might be a strong contender.

In Conclusion

I’ve already worn the Tory Burch Chelsea Boots, and I really don’t need another pair of black boots in this category, but if I did, the La Canadienne Connor would be the ones I’d keep… Actually, I’d probably return them and watch for a sale. I’d at least take advantage of the Bloomies Power Points offer!

When I go to put outfits together, there are times when the Torys seem a bit much for the outfit or the destination. The Connor is a little more casual/rugged, which works well for my lifestyle and my wardrobe, but I have a lot of black boots, and I can always find something else that works.

But if you’ve been looking for a pair of lug sole Chelsea boots to round out your winter wardrobe, I hope this post is helpful!

Shop More Chelsea Boots:

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photos: Alison Cornell

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28 thoughts on “Best Women’s Lug Sole Chelsea Boots

  1. My favorite “clunky” Chelsea boots are Blundstones. I LOVE the brand because they are so comfy and they’re waterproof and last me years. I plan to wear mine in the spring on a girls’ road trip through Ireland. This time of year, I wear them most days. I love the look with my shorter-length, straight-leg jeans and a sweater or nice sweatshirt and they are perfect for Delaware winters. However, I really need a “dressier” pair of classic-style Chelsea boots (no lug sole) like my six-year-old Aquatalias, only with a higher shaft. The Tory Burch boots were PERFECT for what I was looking for because of the heel height, shaft height, and toebox shape and I ordered them from Nordstrom immediately when I saw them featured here last week. When they arrived, I pulled one on and was so excited, then removed the other from the box and it was 2 SIZES SMALLER!! By then my size was sold out. I looked everywhere online and couldn’t find them for any price in my size. I may call my local Nordys later and see if they can find a pair. A couple of years ago they did that for me. Happy Friday!

  2. I am looking for a Chelsea boot. Love the ones you wrote about. Can you recommend one that is more budget friendly. Thank you!

  3. Hi,
    Would the Tory Burch boots look good with a dressier style pant, such as black Vince crop leggings (which aren’t really a legging)?

  4. Thanks so much for the insight- I’m in the process of looking so this helps. By the way, I love the outfit- can you give details for the jeans and sweater?

  5. Love the post, would love the Tory Burch boots but can’t justify right now. I can testify about Frye boots, have a pair of Frye Veronica moto short boots than have a suede like finish; Billy western boot and tall riding boots and I just love that they are all leather lined and break in nicely to conform to your feet. I was lucky to find each pair with sale prices and each pair are several years old not but seem to transend style changes well. I don’t have any Chelsea boots but will still watch for the Tory Burch or Aqualia sales, love both looks on you!

    1. Love the post, would love the Tory Burch boots but can’t justify right now. I can testify about Frye boots, have a pair of Frye Veronica moto short boots than have a suede like finish; Billy western boot and tall riding boots and I just love that they are all leather lined and break in nicely to conform to your feet. I was lucky to find each pair with sale prices and each pair are several years old not but seem to transend style changes well. I don’t have any Chelsea boots but will still watch for the Tory Burch or Aqualia sales, love both looks on you!
      BTW, the soles of the Frye boots your’re wearing remind me of my Frye moto boots, the forefoot sole is kind of an extra layer making it look a little more rugged rather than too over the top, nice natural look!

  6. Very informative post!

    On a different topic, I purchased the Evereve Stella sweater, which I love but it’s “dry clean only” wondering if you have tried hand washing and if so what were the results? Or even in the machine with a gently cycle?

    Thank you for all that you do, look forward to each post!

  7. Chaco has some Chelsea boots that I love. I ended up getting them in two different colors. The first pair I bought felt so good on my feet I decided I needed another color.

  8. I have discovered Thursday Boot
    company and quite like their various styles. They are a great price point and run true to size.

  9. I’ve tried on Chelsea boots but find them too chunky. I have a narrow foot so they never feel right and if I size down they hurt my toes. This is one style I’m going to sit out.

  10. I live in Colorado, and tromp through plenty of snow! I’ve had a pair of ankle moto boots by Gentle Souls for years. They go with everything, and are super comfy. They aren’t specifically waterproof, but they keep my feet dry. I wore them to work often before I retired. I worked in a library, and spent hours on my feet.
    Anyway, here is the current version. They’re on sale too!
    https://www.kennethcole.com/collections/gentle-souls-women-boots-booties/products/best-slit-moto-2-gsf1090le-black

  11. This is a great post! I have been on the hunt for the perfect Chelsea boot. My kids wear doc martins and have for years since they came back in style, but those are too ‘young’ for me. I have tried probably 10 pairs. I think I have a similar foot to yours. Most are too big inside both arch and width wise. I always end up with lace up options. I found an amazing pair, it is Stuart Weitzman 5050 bootie. I found it at nordstrom rack for a great price, around $250 and it was not final sale. Not sure if they are around anywhere, but they are amazing. I like that the back has that stretchy fabric. It makes it not impossible to get on but feels good on the leg/calf/ankle and the foot area is perfect, sole is great enough lug sole but slim looking and great shape. And excellent quality. I’m off to London and planning on wearing them a lot there.

  12. Thank you for a great post. I won’t be purchasing any because I already have…ahem…enough pairs of this boot style, but I can attest that if you can find the right pair(s), you will get good use out of them.

  13. A very nice selection of Chelsea boots. I have a few pairs, in black and brown, but here’s my problem. My older pairs have a lower shaft which means the back tab gets caught on my straight legs jeans when I go from sitting to standing. Do I wear them only with my flared or wide leg jeans, cut off the tabs (which was suggested online) or just let it happen and try not to care? Thanks!

    1. I wonder if you have a shoe repair shop near?
      They would certainly be able to help. If the tab can be removed, they could do that. If it can only be cut, they could do it neatly, and stitch the edge.
      It makes sense to modify what you already have, so it works for you.

  14. I bought my Caslon lug sole Chelsea Boots in black during the Nordstrom Anniversary sale in ‘22. I’m glad I did because they were quite popular and I’ve gotten compliments and “where did you get those?” each time I wear them. They were very reasonable. Do you remember them from your Anniversary sale shopping? They look most like the Sam Edelman. Not sure if they’re even available.

  15. I bought a pair of water resistant lug sole Chelsea boots from Talbots, They have a great look and fit, too. They come in black or brown leather.

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