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 to wear Chelsea boots without hurting your feet? You’re in the right place.
Find here my all-time favorite wide toe box Chelsea boots, including barefoot, cushioned, extra wide, and budget options.
Why I Wear Barefoot Chelsea Boots
My feet are important to me, and I am done stuffing them into shoes that don’t respect their natural shape. I wear barefoot Chelsea boots because:
- They have a wide anatomical toe box that doesn’t squish my toes
- They are flat (zero drop) and don’t push my weight forward
- They style the same as regular Chelsea boots!
- And you can choose more cushioned options or add insoles if you don’t want a thin sole!
Most fashion footwear, like the Chelsea boots on me above right and below right, have a pointy narrow shape and heel that can really hurt! 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 and the flexibility where you need it.
The Best Barefoot Chelsea Boots
These are my all time top picks for the best barefoot Chelsea boots!
But first – Pro tip: Chelsea boots don’t have laces, which means they can be more slide-y and floppy than other shoes. I frequently make use of a few easy fit hacks to ensure I get a perfect fit. Ok NOW let’s talk about my personal favorite barefoot Chelsea boots that have space for your toes to wiggle AND are stylish and trendy.
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 (because it’s entirely leather) 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).
Lang.S Luna
Leather | Leather Lining | Sizes EU 36-42*
*Sizes up to EU 44 are available directly from Lang S in the EU
Use code ANYALANG for 10% off directly from Lang S
These were an unexpected favorite from Lang.S (formerly Tikki), which has recently started making adult shoes. They have that ample toe box room both in width and in height – that means no toe pinching from any direction. They are lined with a soft chrome-free natural leather, and are so soft and lightweight. I also like the sole, which has a traditional welt and feels more classic.
Sizing & Fit:
- All around roomy, but I still wear my normal size
- Wide to extra wide fit
- High volume – I need an extra insole and thick socks
Xero Shoes
Leather | Mesh Lining | Sizes US W5 – M15
Xero has two barefoot Chelsea boots – the rugged Ridgeway, which comes in men’s and women’s sizing and the Tari II. The Ridgeway has been very popular as an all-purpose functional Chelsea, that also looks trendy. I personally found them too stiff in the back heel area for my liking, but I am quite sensitive there. The Lems Chelsea (also featured here) is a better option in this chunky style for me.
The other Xero Chelsea boot is the women’s Tari II – which I co-designed with them! I wanted to see a Chelsea with a touch more sophistication, and that something extra that makes you excited to put them.
Sizing & Fit:
- True to size for most people, but the Ridgeway 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
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 both in my regular size and a size up – both fit but the smaller size is a bit short.
- 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.
Lems Chelsea
Leather | Waterproof Options | Sizes US W6 – M15
If you’re outside the US, shop Lems EU here.
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.
Groundies
Leather | Velvet or no lining | Two Width Options | Sizes EU 36-43
Groundies has a few different Chelsea models, and all are well made and stylish. My favorite is the Camden, above left, which comes in Barefoot and Barefoot+ (extra wide). They are light, so flexible, and have a taller shaft for an edgier, slim-fit look. The Sienna, above right, has a trendy chunky look, and I like them but they’re not quite as flexible or as forgiving in the toe box.
The Camden has a slip-resistant outsole, which is handy in the fall and winter, and 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.
The Barefoot+ width is extra wide friendly and high volume – they’re one of the best wide options if you have trouble fitting into most barefoot shoes.
Sizing & Fit:
- True to size
- Medium width in Barefoot) and extra wide in Barefoot+
- Medium volume in Barefoot, medium-high volume in Barefoot +
Zaqq Equity
Leather | Leather lining | Sizes EU 36-46*
*Sizes up to EU 50 are available directly from Zaqq in the EU.
For me a sleek, glossy all-black Chelsea boot is a fall/winter wardrobe essential. They do double as an everyday shoe and a dress shoe, because they’re understated and match every outfit – the cold weather version of the Little Black Flat. The Zaqq Equity is my top pick in this category.
Sizing & Fit:
- True to size
- Medium width – fit my slightly wider feet, but wouldn’t work for extra wide feet.
- Higher volume – I add an extra insole and a tongue pad for an optimal fit
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!
Freet Durham
Leather | Textile lining | Sizes EU 37-48
Use code AnyaFreet for 10% off
Another rugged Chelsea boot option that fits extra wide feet – the Durham is new for 2025. It is a solid boot, with a little thinner sole than the Lems and Xero boots featured here. They can function for everyday wear, light hiking, and a light work boot because the leather is thick and the outsole has some tread.
Sizing & Fit:
- Mostly true to size, but if you have extra wide feet I’d suggest going up one size
- Wide to extra wide fit
- High volume – they come with a removable insole, and even with it in they are quite spacious on me.
Feelgrounds Chelsea
Vegan Leather | Velvety Lining | Sizes EU 35-49
Use code ANYA5 for 5% off your first order.
Feelgrounds Chelsea boots have that chunky style that is a bit more urban but still sleek. The functional outsole is nice for winter weather, and they have an all around good fit. Truthfully, I don’t often like to wear faux leather, but I still reach for these when I want a sleek look but a bit more outsole.
Sizing & Fit:
- Runs small for me – I sized up one
- Wide fit – not quite extra wide, but wider than your standard barefoot shoe
- Medium volume – I am able to wear mine comfortable with a pair of socks and don’t need to add an extra insole.
Best Budget Chelsea Boot
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.
Sizing & Fit:
- True to size
- Wide to extra wide toe box
- Medium volume, but can work for high volume feet with the insole removed.
More Barefoot Chelsea Boots
If you’re looking for even more barefoot Chelsea boots options, you can find a complete list below with brands from all around the world.
Softstar Primal Chelsea (US) – Unisex sizes 5U – 14U in regular or wide. These have the widest, most square foot shape of all the barefoot boots! They are low volume over the toes, which can be uncomfortable during the break-in time. Once you know you want to keep them, I suggest stuffing the toe box with socks or paper towels and letting that area stretch out.
Magical Shoes Lupino (EU) – Sizes EU 36-47. Get 10% off with code ANYA. These run small, I recommend sizing up one. Love how soft and flexible they are! You can find them in the US at Pedterra and use code ANYASREVIEWS for 10% off your first order. The Lupino also comes in a vegan option!
Wildling Bruklin – These have a wool lining and a wool/hemp upper paired with a water resistant membrane. The higher cup sole is also more weather friendly and they are just dang comfy!
Use code AWN_ANYA_S for a one-time free shipping offer. If you live outside the US/Canada, shop Wildling Shoes via this link.
Peerko Chelsea (EU) – Sizes EU 37-43. Use code ANYASREVIEWS10 for 10% off. Returns are not accepted outside the EU. I love Peerko’s fit and quality!
Annika Barefoot (EU) – Sizes EU 37-42. These have an extra wide toe box, and a nice fitted heel. Perfect for fan-shaped feet! They’re also available in all black and come with two insoles options of 5mm or 7mm.
Aintap FeelBarefoot (EU) – Sizes US Women’s 3.5 – Men’s 15. Read my Review here. You can use code ANYA50 for a discount! They come in all kinds of colors, which is fun.
Ahinsa (EU) – Sizes EU 37-46. Use code ANYASREVIEWS for 10% off
Bohempia Rola (EU) – Sizes EU 36-43. Regular and Wide width available. Use ANYASREVIEWS for 10% off. This is an excellent extra wide vegan barefoot Chelsea boot.
Angles Nyx (EU only) – Sizes EU 37-45. You can find a limited selection at Anya’s Shop
Conker Shoes (UK) – Sizes UK 1-13 with 3 different width options and different sole options.
Drifter Leather (EU) – Sizes EU 34-49 with custom fit available. See my reviews of the Drifter Leather here.
Gaucho Ninja Chelsea (UK) – Sizes EU 36-45. Read my Gaucho Ninja Review here. Use code ANYASREVIEWS for 10% off! Pricey, but beautifully made.
Koel Fila (EU) – Sizes 36-45. These come in a few colors you don’t often see in Chelsea boots. I like them for average width, average volume feet.
Also available at retailer Mugavik Barefoot with worldwide shipping. Code ANYASREVIEWS gets you 5% off from Mugavik.
PaperKrane Chelsea boot (AU) – Sizes EU 19-42. PK is a great brand for a pop of color! Use code ANYASREVIEWS for 10% off. Pedterra in the US also often has PaperKrane models and you can use code ANYASREVIEWS for 10% off
Shapen Barefoot (EU) – Sizes EU 36-43. Several See my Shapen review for more details about this brand. I found Shapen Chelsea boots to be difficult to get on and off, even though they have a generous toe box. You can use code ANYA5 for 5% off, but they do not accept returns outside the EU.
102 thoughts on “The Best Barefoot Chelsea Boots That Won’t Squish Your Toes!”
Hey Anja, Froddo Chelys is also a very comfortable barefoot Chelsea boot.
I can agree. Thise were the most comfortable on my feet. Pretty narrie and in between sizes. Be lenka was too wide and in between sizes, Kedo the same, so i got my first barefoot boots Froddo🤩
Do you have a review on Birkenstock model : Highwood Chelsea boots?
I have not tried those yet.
What do you think about the sole for the Lems Chelsea Tuff? Their website says that groundfeel and flex will be similar to the outlander and boulder summit. I like the look of the Tuff a lot more than the regular Chelseas, but not sure if this is going to be a good option for me. (But I am looking to get something with a bit more cushion.)
The sole on the Tuff is more like a traditional rugged outsole – quite sturdy and practical but still flexible. I wouldn’t say there is much ground feel in them. The regular Chelsea is lighter and more cushy, but both have a similar sole thickness so if you want more sole and cushioning I think both achieve that.
Hello Anya, what about the sizing of the chelsea Tuff? I use a lot my boulders, and use a 7 -women-. Thanks
The sizing on Chelsea Tuff is the same for me as other Lems Shoes. I find they all run a bit small and in Lems boots I size up to a women’s 8. In Lem’s sneakers, a 7.5. My Tuff boots are a women’s 8 and they fit me great.
Hey Anya! Do you know if any of these are water resistant?
Yeah, Lems has two waterproof options. Feelgrounds Chelsea boots are also water resistant.
Hi Anya:
Your site has helped guide me in the transition(s) to barefoot shoes (Correct Toes, Softstar Primal Sawyer’s and Run Amoc’s, Vibram Roadaround, Vibram Eco Wool and Wildling Ranidae rain boot.) The Sofstar Primal series (10U) are ideal for my wide feet, but their Primal Chelseas are not made in brown yet – although they’ve said they may manufacture them in black in the future. All the Men’s black Chelsea’s don’t look wide enough for my feet. I came across VIBAe Helsinki’s which look wide enough but are not true barefoot. Have you seen them? What do you think?
Hi Tim! We have some limited information about Vibae here.