The Best Barefoot Chelsea Boots That Don’t Squish Your Toes!

I love the Chelsea boot look, but I’m tired of cute shoes that are uncomfortable. That’s why I wear barefoot Chelsea boots instead! They don’t squish my toes or aggravate my back, like most stylish shoes do. Want the Chelsea boot look without hurting your feet? You’re in the right place.

Find here my all-time favorite wide toe box Chelsea boots, including barefoot, cushioned, and budget options.

Why I Wear Barefoot Chelsea Boots

Most fashion footwear, like the Chelsea boots on me above right, have a pointy narrow shape that can really hurt! By contrast, barefoot Chelsea boots have a natural foot shape with space for the toes to lay flat. Unlike shoes that claim to be good for wide feet but still come to a point at the end, barefoot boots actually give you the space you need where you need it.

And barefoot Chelsea boots also don’t have a heel, which can be a real back saver. Same style essence, but so much more comfortable!

So I wear barefoot Chelsea boots because:

1. They have a wide anatomical toe box that doesn’t squish my toes
2. They are flat (zero drop) and don’t push my weight forward
3. They style the same as regular Chelsea boots!
4. And you can choose more cushioned options or add insoles if you don’t want a thin sole!

I also make use of a few easy fit hacks to ensure I get a perfect fit, since Chelsea boots don’t have laces. Now let’s talk about my personal favorite barefoot Chelsea boots that have space for your toes to wiggle AND are stylish and trendy.

The Best Barefoot Chelsea Boots

I love a Chelsea boot moment. The understated design is both easy to style and easy to wear (love me a pull-on shoe). And they will basically never go out of style, so you can be sure to get lots of use out of them! Here are my all time top picks for the best barefoot Chelsea boots.

Lila by Anya

Leather Upper | Leather Lining | Sizes EU 34-45

When it comes to Chelsea boot styling, the Lila is my go-to. I wanted something that looked more like a classic Chelsea boot than other barefoot options, so I went out and designed one! The leather paneling over the elastic makes for a more sophisticated look, so these dress up really well too. I reach for them and the Rosa boot (similar but with side zipper) all fall and winter when I really want to look good!

Lila Chelsea boots have a quality leather upper, leather lining, and leather insole – all chrome free and vegetable tanned without the use of harsh chemicals. It takes significantly longer and is more expensive to tan leather in this way, but it’s safer for skin and is softer/more breathable than chrome tanned leather.

The outsole has a rubber bottom for a bit of grip, but they are not intended for rugged use. And it is a bit thicker and stiffer sole than some barefoot Chelsea boots, so if you want a real flexible feel you’ll probably like the others here better!

Me at the leather production facility in Gaziantep, Turkey during the tanning process!

Sizing & Fit:

• True to size, but slightly short for some. I wear my usual size still.
• Medium wide – suitable for average and wide feet, but not best for extra wide feet.
• High volume above the arch, so I added tongue pads to mine to get a secure fit (just be aware that tongue pads are semi permanent and don’t come off easily).

Mukishoes Chelsea

Leather | Wool Lining | Sizes EU 36-45

Use code ANYAMUKI for 10% off directly from Mukishoes in the EU

I love that the Mukishoes Chelsea is a lower cut than most other wide toe box options, which gives you different styling options – easier to wear with jeans than taller Chelsea boots! They are also very light, flexible, and come with a real wool lining – not too thick, but nice for cold days.

They can get a little wrinkly/frumpy because they are so soft and unstructured, but it doesn’t stop me from styling them with lots of outfits. I reach for them often when I want a quick and easy look that’s still stylish. Mukishoes Chelsea is unisex.

Sizing & Fit:

• Slightly small – I have a pair in both my regular size and a size up and wear the bigger size with socks.
• Medium wide – best for average and some wide feet. The outsole is very soft and can flatten out a bit under wider feet as they break in, but don’t feel super wide when brand new.
• Medium volume – the ankle opening is slim and lower cut, so some people say the front edge cuts into their ankle a bit. But it helps keep the shoe from being floppy even on different instep heights.

Xero Ridgeway

Leather | Mesh Lining | Sizes US W5 – M15

The Xero Ridgeway is a new style for fall 2024, and they’ve been very popular with both men and women. They have that rugged Chelsea boot look that’s so trendy right now, and an actual rugged outsole to go with it! So they look cool and are practical for hiking, light work, and a bit of weather.

The outsole on the thicker side with tread, but still flexible. The leather upper is thick and stiff when new, but break in.

I personally found them too stiff in the back heel area for my liking, but I am sensitive there and go for softer over more durable most of the time. The Lems Chelsea (in the Cushioned section of this article) is a better option in this style for me.

Sizing & Fit:

• True to size for most people, but ran small for Justin (he wears a 13 but needed 14 in Ridgeway Chelsea)
• Medium to wide width – Men’s models are wider than women’s
• Medium to high volume with removable insole

Vivobarefoot Gobi Chelsea

Leather Upper | Leather or Fleece Lining | Sizes EU 35-43

Use code VIVO20ANYA for 20% off.

The Vivobarefoot Gobi Chelsea is a new silhouette, unique from the other barefoot Chelsea boots. They come in an unlined and fleece lined version, and have more of an urban vibe to them. For me they felt kind of stiff when brand new and rubbed, but got softer with wear.

They come with a removable cork insole for a bit of extra fit adjustability, but tend to fit medium volume best.

Sizing & Fit:

• True to size – fits longer than the first two boots listed here, but I don’t size up!
• Medium wide – best for average and some wide feet, but not extra wide.
• Medium volume

Angles Nyx

Leather | Leather or Wool lined | Sizes EU 37-45

If the Vivobarefoot Chelsea isn’t a good fit for you or doesn’t go big enough for you, I recommend the Angles Nyx next. It has a similar sleek shape and extra sheen that looks dressy, and they are a little bit wider and higher volume if you need some more space. They are also designed to be unisex.

While I love a super soft, flexible shoe (like Mukishoes Chelsea) I also like my stylish boots to have a bit of structure so they stay classy. A sophisticated but straight forward black Chelsea is one of my closet work horses and these fit the bill perfectly.

Sizing & Fit:

• True to size
• Medium to wide width – will work for wider than average feet!
• Medium to high volume

The Best Extra Wide Chelsea Boots

For when even barefoot boots aren’t wide enough! These are the widest of the wide barefoot Chelsea boots.

Groundies Camden

Leather | Velvet lining | Two Width Options | Sizes EU 36-43

The Camden Chelsea in Barefoot+ fit has an extra wide toe box with room for toes to splay for days. This boot also comes in their regular Barefoot width, which is best for average width feet. So if you want the extra wide option make sure you choose Barefoot+!

They are really nice quality, have a slip-resistant outsole, plus a thin velvety lining for a little bit of extra warmth. They feel great on foot! I love them in both widths myself since I don’t have an extra wide foot.

Groundies also has the Camden Mid available in Barefoot+ which features a shorter height and handy side zipper.

Be Lenka Entice

Leather | Fleece lined | Sizes EU 36-43

The Be Lenka Entice is a little more rugged of a Chelsea boot style with a durable outsole. They have an extra wide, fan-shaped fit for those of you who really need all the toe space while still styling like other Chelsea boots.

They are heavier than the Groundies Camden and other barefoot Chelsea boots – some people love that extra durability and traction though. They certainly are good quality!

Be Lenka also has the Mojo chelsea boot that we really like. It’s not quite as wide as as Entice, but is still plenty wide for me and features a comfortable knit ankle opening.

Sizing & Fit:

• Runs small – I size up one
• Extra wide
• Medium volume – they do not have a removable insole, and people with high volume feet often find them tight over the top of the foot. They can loosen with wear though!

The Best Chelsea Boots with Cushion

Lems Chelsea

Leather | Waterproof Options | Sizes US W6 – M15

Hands down my favorite wide toe box Chelsea boot with cushion is the Lems Chelsea. They are really lightweight, have a very spacious toe box shape that can fit most foot shapes and widths, and they are soft and cushioned. Justin and I both have had great luck with ours – the quality, fit, and feel are all on point.

Also from Lems is the Chelsea Tuff. The brown color has a fluffy collar and lining that is surprisingly warm. The sole is quite thick (makes me feel so tall!) but flexes at the toe. Really well-made waterproof shoes with a grippy practical outsole. The black color has no fluff, but is still insulated.

Best Budget

For when you want the comfort of a wide toe box barefoot Chelsea boot, but can’t swing the price.

Saguaro Urban

Faux Leather | 4mm Outsole | Sizes EU 36-42

Use code ANYASREVIEWS for 15% off

These faux leather Chelsea boots from Saguaro have a classy look and a nice little perforation detail around the edge. They’re really comfortable straight away, without any hard edges or rough bits. I don’t expect the faux leather to be as durable as real leather, but it does make the price more affordable.

We found them true to size, with an extra wide toe box. They’re best for a medium volume foot, but higher volume can remove the insole for a little extra space (this is how Samantha is most comfortable!).

Whitin Chelsea

Faux Leather | Sock Opening | Sizes US Women’s 5.5-10.5

At $40, this is about as cheap as it gets for wide toe box barefoot Chelsea boots! They have a decently wide toe box and a soft sock opening. Not as high quality as the others listed here and made of a pleather type of material (as expected at this price). But they are pretty comfy and have a little bit of extra cushion.

The sock opening is more casual, but still you can style them the same way you would other Chelsea boots. Whitin shoes tend to have a little bit of toe spring, which I don’t love. But it’s not excessive and I am not feeling it too strongly in these.

More Barefoot Chelsea Boots

If you’re looking for even barefoot Chelsea boots options, you can find a full alphabetical list below in different price ranges and locations around the world. I also have a full list of barefoot boots available for tons of other options in different boot styles.

---

---

---

---

---

---

---

---

---

---

---

---

---

Vegan Options

---

---

---

---

---

Check out my 10 All Time Favorite Barefoot Boots for more of my top fall boot picks!