20 Best Waterproof Chukka Boots (2022 Updated)

I was so excited to receive these, but was so disappointed upon trying these on for the first time. My advice is to order your regular size; the description says to size down, and I followed the sizing chart and ended up ordering a size 10.

Way too small; should’ve gone with my normal 11. Also the midfoot of these shoes is SO tight, like my foot was folding on itself just to wear these, and I don’t have wide feet either. Lastly, I ordered the Major colorway, and was so disappointed to find that the website does not show true-to-color photos.

I expected a dark green/gray/brown suede boot, but instead got a straight up chocolate suede boot. Ignoring all of the above, the boot seems very high quality and would be comfortable if it fit my foot, but Sorel has totally missed the mark here.

I purchased these boots in anticipation they would be waterproof. Unfortunately however, they are not and leak badly when worn on damp parkland grass. Sorel’s response was disappointing and, despite their claim that the boots are waterproof, I was advised they are not however suitable for use on “wet grass; only light rain”.

I’d have expected some acknowledgement that the description of these boots is misleading and the offer of replacement footwear or a refund. Disappointingly, Sorel have taken a different view and, unnecessarily, lost a previously loyal customer.

These are the coolest, comfiest boots I have ever worn. They look great, which is what attracted me in the first place, but I was very pleased to find they are also incredibly light and comfortable with soles that give you a real soft bounce as you walk.

Rain doesn’t seem to bother them at all, they look great with any colour of jeans, and as someone who is pickier about these things than I thought, these genuinely feel just perfect. Please, keep making them, because I’ll be back for more if these ever wear out.

Purchased at Greaves Sports, Glasgow, Scotland. I’ll be back!.

I ordered these boots online after spending a lot of time sifting through reviews trying to find the perfect pair for winter. I’ve been wearing these about a month and am just entering the thick of Chicago winter (it’s only January), and I’m not too happy with these.

Here’s to keeping it to the point. What’s Good: These are beautiful looking boots and they are definitely very waterproof. I’ve walked in the snow in these and they have kept my feet very dry. They’re easy to get on and off.

What’s Not Good: First thing is these boots run tight. I have narrow width size 6 feet and small calves and these boots are just TIGHT. I wouldn’t say they run small, because my toes have room and they fit the length of my foot just fine – but the width of my feet and calves feel like they are being squeezed.

It took a lot of breaking in to get them to ease up on the squeeze, but the process of that was simply uncomfortable, and they’re still tight. Second – these boots do not keep any warmth at all. Although they keep my feet dry, any time I’m outside in 25 degrees or less, my toes go numb.

And because they are tight, I can’t layer socks. My overall experience with these boots has just been discomfort. These are not winter boots – granted, the listing doesn’t necessarily claim that they are, but the reviews seemed promising for cold weather.

These would likely be best for any other time of the year where it’s not really cold, but just wet out.

These boots are the most attractive duck boots I have ever seen. They are super cute on, exactly as pictured and I REALLY wanted to keep them. BUT – they absolutely have zero sport, there is no structure to the sole.

I placed a small rock on my tile floor and stepped on it and could feel the rock through the shank of the boot. It is just rubber, with no embedded support structure. If I were in my 20’s I would have kept them because they are so attractive.

In my 50’s I value the condition of my feet too much to put them through walking any distance in unsupportive boots. Seriously, these are no more supportive than rubber rain boots that are meant to be pulled over your shoes.

Also, the zipper is barely adequate for putting the boot on, if it were an inch longer it would be useful. As it is, you have to really work to get the boots on. Having had many duck boots from the brands you think of when you think of duck boots, I have to agree that the rubber on these boots marks so much more easily than other brands – making these purely a fashion boot, and light use at that.

I bought these at full price a while ago (cognac color) and I am literally getting ready to go and buy multiples of them in every color, just on the off chance they stop making these in the future. (Especially since they are on sale right now).

They are THE MOST comfortable shoes I’ve ever had, period. And I primarily used Birkenstocks in the past. These boots have amazing arch support (I have high arches and I’m very picky about this). The sole is a great thickness, you don’t feel ANYTHING when stepping on stuff.

I fall often and the high ankle help stabilize me. I never avoid puddles now, even fairly deep ones. The zipper makes it to where I don’t have to tie my laces every time. They’re super cute no matter what I am wearing.

The traction is amazing! They aren’t hot and stuffy like some boots can get, but they keep me warm and dry in winter. They’re literally the perfect boot. I really hope the sale isn’t due to them discontinuing them.

I have looked for years to discover a great feeling, good looking wider boot that was in an affordable price range. I discovered Nunn Bush at the local shoe store, but there was very little selection in my size.

Then my wife discovered your website! You definitely have a new customer. I love being stylish and comfortable again!.

I normally wear 13D or medium width in shoes but due to a foot injury on one foot I am moving up to 13 Wide (13 EE) for just a little bit more room for my injured foot. I ordered pairs of these Ozark boots in both tan and black.

When these arrived I really like the looks and the leather upper is actually quite soft for a dressy style boot. But the wide boots, even on my non-injured foot, were not wide at all, feeling even a bit tighter than other boots I have owned in 13D size.

After trying to wear them around a bit in the house on carpet I decided to return them after about 2 minutes in them as they were definitely too tight across the forefoot. It is something about this particular model as both the black pair and the tan pair fit almost exactly the same, too narrow.

I bought another similar boot of only a slightly different build style and model name and the wide in that fits wonderfully, far looser than these Ozark models.

I snagged a pair just before a two-week trip to Spain in December. Looking cool in a cosmopolitan city that’s also getting rained on is a tall order, but these kept my feet dry, were comfortable for big walking days on cobblestone and pavement, and had plenty of room for comfort on the plane.

Now that I’m back, they look great at work and having a beer afterward. Aesthetically, they split the difference between chukka boots and high-top sneakers, look awesome with dark jeans, and should be comfortable for year-round wear in Colorado as long as it’s not far below freezing.

These shoes gives me a feeling of security knowing my feet are protected from daily cruising. From feeling at ease with secure foot traction regardless of surface to stability on every step knowing I’m never going to roll an ankle these are amazing.

The inside of the shoe welcomes my wide feet, guiding them into a secure tighter fit I find reinforcing rather than restrictive or uncomfortable. With my abnormally high arch the padded tongue securely covers my entire bridge like a pillow.

I don’t have lace marks on the sides of my foot where the tongue slips or moves during the day. The laces are a perfect length as well and have yet to untie themselves through all sorts of daily events.

I ordered the Fog and what I thought were Tan boots showed up. They were marked as Fog on the box but i presumed them to be mislabeled. I kept them and ordered another Fog pair. The second pair were in a box marked as Fog but only slightly darker.

They were more taupe than gray and side by side they were almost indistinguishable. So, one should infer the pictures of the gray boots are not accurate.

I bought Timberland’s Kinsley Boot in black a while ago and loved how comfy and practical they were, that when I saw these, I knew I had to have them! I love the color and fur around the ankle. These truly are waterproof, that’s why I love them.

I am careful not to get these dirty, but had a couple of small spots of dirt on the top already and just wiped it off. Came off super easy. Not sure what I’ll do if the fur gets dirty, so if you don’t want to worry about where you’re stepping, I’d suggest going with the darker colors.

I do have wide feet, so I ordered half a size up. The length was a tad long, but they were still snug width wise, so I kept them. They loosened up after a few wears, so I may have been able to get away with just getting my size.

All in all, definitely recommend!.

A good place would be when I purchased these bad boys during my time working at Cabela’s 4 years ago. Once I placed these glorious looking fiends on a display rack, I knew I had to have them. And boy am I glad I do.

These have been my year-round daily boot, for literally all weathers in Colorado, and I wear them literally every day. The leather has worn in so amazingly, that I forget I’m wearing them sometimes. I have worn the soles down to being almost flat, now, and have swapped out insoles for some Meindl ones, but man, insoles only do so much.

I wear these hiking, Jeeping, running errands, going outside in general, these are what I want on my feet. I have worn these at several jobs, ranging from my mechanic work, to the tarmac as ground crew for an airline, and they are still solid, no tears, rips, anything! (there is some stuffing from the belly of the airplanes when I was stuck on my knees, but it does matter to me, they still look great!) They are such amazing boots, that I base any other boot I try on them.

And none have compared yet. You still debating whether to get them or not? Do you like/want to buy multiple pairs of the same boot, or have one that will last through the ages, and all the crazy in between? You won’t regret these, I guarantee.

I have been wearing these boots for a couple decades and this is my 3rd pair. I end up wearing out the soles after wearing them every day. I love the fact that they are waterproof so that I can wear them during winter here in ND.

They go with my jeans or Dockers. To me they are the perfect everyday boot!.

Being on my feet most of the days for the past 30+ years of my career, I need a greatly comfortable pair of shoes. especially with my lower discs deteriorated. Also need the shock resistance working on 120-480 volt equipment.

Also need the slip resistance on slippery and/or oily surfaces. These have been my ‘go-to’ for a couple decades now. These are more comfortable to me than any pair of ‘tennis show’ I’ve worn There is a negative to the comfort.

the shoes are actually designed as a ‘trail style’ shoe. That means the soles are softer than a typical work shoe/boot. It’s worth my comfort to have to buy a new pair a little sooner than I would another work boot.

I wear the low and high tops.

I purchased these boots for work. It?s my go to boots for work for several years. My last pair lasted me 2 years before buying a new pair. I?m in Security work so not sure how long the?ll hold up for construction type of work.

I?m a long time fan of timberland.

The boots arrived within a few days after placing the order. I was worried they would not arrive in time for Christmas but they did. My husband loved them and was so happy. He has been looking for these boots in a size 13 for years.

I’ve had these for a few months now and they are my go-to boot more than any other. I even match my clothes to the boots so I can wear them more often. Sturdily made, these feel like they pass the universal test of a man’s footwear: be able to run and stomp out a fire (if your shoes can’t do either, put them back).

I can wear these all day no problem and walk all over the city with no pain. Plus I think they look great!.

I bought two pair (black & brown) a month ago from the Clarks Outlet store. The black was in stock and the brown they shipped to me. Very, very comfortable boot. The round toe adds to the comfort your feet feel snug but not cramped.

I will buy again.

Excellent construction, soft leather uppers, perfect size and fit, comfortable and supportive for long days on feet…and they look good. I will buy again when or if these wear out. They look better the more I wear them.

I am really happy with the quality. I have been wearing them in the streets and in the forest on hikes. I was a little skepticle of the leather actually being water proof but they really are water proof ( unless you are walking through deep puddles for an hour).

The only thing about them that I do not like is how narrow they are. My toes can’t spread out and it feels good to take them off after wearing them for a couple of hours. However the soles are a comfortable support.

I received these a little after lunch time and repackaged them and dropped them off at UPS before 3 pm. The soles looked like hard plastic and were so slick they slid on carpet and hard floors. There’s no inside padding and felt like walking on plastic surrounded be cheap material glued to cardboard.

I’ll never purchase anything from Tom’s again.

Purchased these on sale online. They look great, I have gotten several compliments on them. They are also very comfortable for being waterproof and looking like a boot. Highly recommend.

Purchase boots for my 17 year old son. Boots look big and fits 1/2 size bigger than regular 10. 5. Overall looks very handsome for young person or older gentlemen to wear during cold weather for dresser purposes.

Side note my husband wants a pair himself due to quality and fashion. Great for wide feet.

These were a gift for my boyfriend and he loves them. I read the reviews which said these run slightly big. He’s normally a size 10. 5, I purchased a 10 and they fit him perfectly. He doesn’t like anything too tight on his ankles and he says they are comfortable.

He also has flat feet but can wear them all day without any complaints.

I bought these for my husband for Christmas. He absolutely loves them. Timberlands always make great stylish boots that can be worn casually with jeans or dressed up. Chukka boots are always a plus to any wardrobe!.

Great Shoe, they are great everyday shoes. The are casual and at the same time rugged looking to wear doing yard work or just looking casual with jeans or slacks. When they get wet they dry real fast.

Been wearing this first part for over a year and I really like them, much better than tennis shoes for everyday use. Just bought a second pair but can’t seem to wear out the first pair. Just need to sit back and wait till they go on sale then buy two pair, you will be happy.

I have purchased 4 pairs of these boots over the last few years. Overall, I love these boots! I do have 2 complaints. 1) The boot laces become frayed in a very short period of time. The rubbing on the hook eyelets creates a cut in the outer layer.

I always have to aquire a more quality set of laces. 2) The hook eyelets have a tendency to bend over time. Maybe this is the cause for the fraying of the laces.

Bought these to wear on my boat fishing during cold months here. Yesterday was my third trip with them. Love everything except soles already coming off the shoe. Pitiful. Where is the quality? So disappointed.

Will be contacting cabelas Monday to send them back and get my money back. Design flaw now that I have looked closely. That’s why another pair will probably do the same. The shoe is waterproof but if the soles can not handle being in water then they are pretty much useless to me.

I have been swayed to Nunn Bush products for their fit and comfort right out of the box. I am a Chukka boot fan. My Park Falls and Quest boots were worth repurchasing, though their lifespans are limited.

This boot is ultralight, comfortable and has a distinctly different outsole. It took mink oiling well and has survived a few hikes. All signs point to YEAH!.

LOVE these shoes! They are stylish and my husband says they are the most comfortable shoes he has ever worn. My husband works in a setting which requires he be on his feet most of the day. These shoes have been an absolute game changer for him! He says his feet no longer are sore/hurt after his long days at work.

Would definitely recommend!.

This boot is EXACTLY what I was looking for in a waterproof everyday boot. What I like about them the most is how light weight they are. They have a very comfortable sole and the size I ordered was my true size.

I was a little nervous that the suede material would stain in wet environments but there has been no sign of that happening. They can be dressed up or down which is another sweet thing about these boots.

I would recommend these to anyone looking for an every day light weight winter boot.

Highly disappointed. Love the look! Very poor fit. I usually wear an 8. 5 or 9. Ordered a 9. Could not get foot into the shoe. Returned for a 9. 5 and could barely get foot into the shoe. V V disappointed.

So returned for a refund. A waste of my time twice to return and then I have to pay $5 to get my refund on top of that. Can Sperry make this right????.

These shoes survived a my daily life at home and trip to Ireland that included city walks and hiking. They run a little wide, which was perfect for me and the waterproof feature made it easy to walk around rainy Dublin for a week.

They’re stylish, and go with just about anything. I’ll probably end up buying another pair for backup!.

When I ordered the Sperry Striper II Waterproof Chukka shoes on line I was a little concerned about choosing the right size and hoping I wouldn’t need to go through the exchange process. Thankfully the shoes fit perfectly and were comfortable right out of the box.

No break in period needed! Over the years I’ve been completely satisfied with the quality and durability of Sperry shoes, the Striper II Chukka’s are no exception. Quality built is an understatement.

I’ve owned many styles of Sperry shoes over the years and they have never disappointed me in terms of quality, style, fit or durability. The Striper II Chukka is a home run, buy them with confidence you will love them from the day they arrive.

This is my 4th hybrid from Ecco and it might last 7 years. I only wore it briefly since purchase, as there was no proper occasion yet that demands these shoes. Comfort is perfect with the given insole or with orthotics.

Look is obviously rich and unique. I would like to compare it with a combo of chocolate top with vanilla ice-cream in the bottom. The secret to getting the perfect fit in a hybrid, is to order one size lesser than other Ecco models.

Thanks to Ecco for always considering larger sizes when designing shoes. I am thinking about long holidays this pair.

First time trying Ecco shoes. After reading reviews, decided to give this pair a try. At first, I was impressed with the quality. Tried on, firstly felt good size. But after two full day use, my feet started to hurt, feeling being squashed.

Sole felt bit hard to walk on, comparing to other well know brand. My foot is not even wide foot. Somehow this shoe seems narrow and gives me foot ache. A bit disappointed with uncomfortable first two use.

overall i like the boots. i rarely order shoes without trying them on first, but these worked out nicely. some pros include: makes for a good casual/fashion boot. they are comfortable and stylish. the leather is softening up and breaking in nicely after a few wears, and so far they’ve been waterproof enough to keep my feet dry and warm when walking around my field and woods.

some cons include: the traction on slippery floors isn’t great, and the sizes run a little big (i’m usually a 9. 5 but had to get a 9 in these with a little room to spare still). the leather on the upper felt a little cheap and plastic-like, but it’s softened up after a few wears and has broken in nicely.

i dont believe these would hold up as a work boot or a heavy-hiker, but for casual, everyday wear they’re pretty nice. 4/5 stars, would recommend.

Bought these because BC has been getting hit hard with a lot of snow , colder temps and then a warm front hits and we get rain coupled with melting snow that turns to slush. These were perfect as my daily wearing go to boots during all of the aforementioned conditions – and they held up perfectly – kept my feet warm and comfortable plus they were styling all along the way! I wear a size 9 – and these boots fit just a tad larger than other size 9 boots/shoes I own – but when I wore my darn tough wool sock – they fit perfectly! And – I liked this brand so much after purchasing these, I ordered up another pair in a different style!.

I am very pleased with the finish, and style of the shoe. It is a quality product. The insole adds to the cushioning of the shoe which results in a comfortable walk. I am usually a size 10. I have a wide foot, and usually size 10 is fine since my actual size is 9.

5. However this boot has a wide fit. I corrected this extra size by inserting an insole under the footbed. Now it fits well. I have only worn the boots a half dozen times, and they are breaking in beautifully.

If the style suits you, I recommend the boot. It is a hybrid between a fashion boot and a work boot. I am very pleased with my purchase.

I ordered these for my 13 yr old son since he had hit a growth spurt and had no shoes to dress up in & he goes on and on about how comfortable & durable they are & he looks great in them in his sundays best or just cute & casual.

They hold up very well since he is a rough & tough 8th grader. They are very versatile. 2 thumbs up from this mom. Thank you Toms for making a great looking and comfortable shoe, not to mention you give back with each purchase.

We will continue to shop with you. And thank you Buckle for carrying this amazing shoe. My son has gotten tons of compliments.

Received this jacket as a gift. Waited a while to review it so I could write on using it as a jacket and vest. The Verdict: LOVE IT! So perfectfor ridingin a huge rangeof weather. And I lovethatif Igetwarm,I can remove the sleeves and keep my core warm.

A must in the ever-changing New England weather!.

I had two pairs of Larchmont ll Chukka boots. They look and feel nice. Waterproof but did not last long enough for me. I’m doing garden maintenance in Central London. Nothing heavy and hard like landscaping! Both pairs last about 6-7 months everyday use.

Leather is strong enough but the shoesole splits and my feet got wet. They will last longer if you used them only over the weekends.

I bought a pair in the lighter brown 3 years ago and I’m replacing after a lot of use. They’re really versatile and have been worn on the family farm (occasionally) and in the city and in wet outdoors weather (a lot); I’d say 7/10 for comfort and 9/10 for build quality.

Only replacing my current pair because the fabric inside the shoe has worn out but otherwise the sole and upper are still solid. Hopefully there’s no changes to the next pair I receive!.

Lovely looking boots, the tongue which make them waterproof feels odd but would probably soften after wearing them a while. Chose to return and got a full refund quickly. Great service Thanks!

I bought these for my husband for Christmas. He loved the look and the waterproof feature, and they fit in his usual size. However, after wearing them around the house, he found that one boot rubbed on the side of one foot and he was afraid he would get a blister.

He opted to stick with the more casual looking Ecco he already had in brown and knew to be very comfortable, so these got returned.

Great boots! they look great and are super comfortable, as they have very cushioned insole. They appear to be very well made with durable rubber inlaid sole, so hope they are long lasting. Can’t vouch on how waterproof or resistant yet either, which is why just 4 stars.

If the are as water resistant as they say then def 5 stars.

I got these for my husband for his birthday. He already wants to start turning over his shoe collection to 100% Blondo’s! Can’t recomend this brand enough. (and this shoe specifically is great, too!)