Buy Now, Pay Later
As low as
$12.13
/ mo
Learn more
- – 6-month term
- – No impact on credit to apply
- – Instant approval decision
- – Secure and straightforward checkout
Ready to go? Add this product to your cart and select a plan during checkout.
Payment plans are offered through our trusted finance partners Klarna, Affirm, Afterpay, Zip, Apple Pay, and Google Pay. No-credit-needed leasing options through Acima may also be available at checkout.
Learn more about financing & leasing here.
Selected Option
Free shipping on this product
30-day returns
Learn more
FREE 30-day refund/replacement
To qualify for a full refund, items must be returned in their original, unused condition. If an item is returned in a used, damaged, or materially different state, you may be granted a partial refund.
To initiate a return, please visit our Returns Center.
View our full returns policy here.
Availability:
17 left in stock
Arrives
Tuesday, Oct 13
Size: 7
Color: Black 001
Description
Step into fierce style with the Guess Olanna combat boot featuring a convinient side zip closure, gold hardware eyelets,and signature G buckle strap. Chunky lug platform sole delivers rugged edge and lasting comfort. Bold, rebellious, and effortlessly chic.
Department : womens
Date First Available : April 9, 2026
Manufacturer : Guess
Manufacturer’s warranty can be requested from customer service. Click here to make a request to customer service.:
Best Sellers Rank: #614,185 in Clothing, Shoes & Jewelry (See Top 100 in Clothing, Shoes & Jewelry) #1,946 in Women's Ankle Boots & Booties
#1,946 in Women's Ankle Boots & Booties:
Customer Reviews: 4.6 4.6 out of 5 stars (14)
Color: Black 001
Toe Style: Closed Toe, Round Toe
Boot Form Type: Combat
Heel Type: Block Heel
Seasons: Fall
Style Name: Olanna
Boot Shaft Height: Ankle
Shoe Height Map: Ankle-High
Shaft Circumference: 10.63 inches
Outer Material: Polyurethane (PU)
Sole Material: Rubber
Brand: GUESS
Model Name: Olanna
Style Number: gwOLANNA
UPC: 199593616849
Manufacturer: Guess
Item Type Name: Combat Boot
Closure Type: Zip
Water Resistance Level: Not Water Resistant
Frequently asked questions
If you place your order now, the estimated arrival date for this product is:
Tuesday, Oct 13
Yes, absolutely! You may return this product for a full refund within 30 days of receiving it.
To initiate a return, please visit our Returns Center.
View our full returns policy here.
To initiate a return, please visit our Returns Center.
View our full returns policy here.
- Klarna Financing
- Affirm Pay in 4
- Affirm Financing
- Afterpay Financing
- Zip Pay in 4
- Financing through Apple Pay
- Financing through Google Pay
Learn more about financing & leasing here.
Similar Products
$27/mo*
Ariat Men's Groundbreaker Wide Square Toe Work Boots
$32/mo*
ARIAT Rambler® Patriot
$189.95
$27/mo*
Ariat Men's Groundbreaker Wide Square Toe Work Boots
$27/mo*
Ariat Men's Groundbreaker Wide Square Toe Work Boots
$26/mo*
Ariat Men's Groundbreaker Wide Square Toe Work Boots
$27/mo*
Ariat Men's Groundbreaker Wide Square Toe Work Boots
Top Amazon Reviews
Size: 11
Color: Black 001
This is a pair of boots from GUESS. I ordered a size 11 in black. Truthfully, I had no expectations that they would fit or even be really attractive. Footwear has never excited me. As long as I had a need for shoes and they were functional, that is all I cared about. This pair of boots has changed my mind or at least for this pair of boots. Right out of the box, the silvertone buckle, zipper and heel trim caught my eye as they are a stunning contrast to the black. Of course that silver tone matches the grommets for the shoe laces. Those accents seemed to pull it all together. The materials are all manmade, but they do have the look of natural leather and rubber on the soles. Somehow, when I took these out of the box, they seemed really heavy, but when I put them on my feet, they didn't feel at all like they were too heavy for my damaged feet and ankles. Over the last few years since broke them, I have not been able to bend my feet enough to fit it into any boot at all. This Guess boot has a full length zipper and shoelaces that can be loosened as well as the belt across the ankle that can be loosened. So I opened them all and prepared to struggle trying them on. I was so shocked when my feet went right in the boot. Both of them!! These boots went up over my ankles and ended above my ankles. That meant they would not hurt the ankles when closed, but in fact they protected my ankle. Even when they were swollen, they fit. The inside sole was padded especially in the heel. I did feel the balls of my feet needed a bit more padding. I tightened everything up and walked around in my home, expecting them to hurt my feet shortly. They did not. I tread also surprised me. I thought it would be too thick for me to safely walk in, but it worked! Also the pronounced tread makes it safer for me to walk. The listing says these are for fall, but for me I needed winter boots. With that in mind, I tried them on again with heavy winter socks. It was harder but I got my feet into them. These boots fit my feet so I know they will be true to size for other women. Guess seemed to know just what I needed in these boots. I don't think I could change a thing. I love the fit and the style and the freedom they will give me to walk more. I expect to pay more for boots so this is right in the range for high quality boots. They are worth more to me, though.
...
show more
Reviewed in the United States on August 13, 2026 by Spirit
Size: 8.5
Color: Black 001
Very cute very stylish. Great price for such a cute boot! Adequate laces for my chunky ankles and room to tie them still. Which is a problem if you've ever had chunky ankles and bought nice boots and discovered that you could not tie them or lace them through the top loop, that's not a problem with these boots. Super cute details there's the guess logo right across the front with a fancy fastening belt I'll hold your laces down for you. Very sturdy eyelets and sturdy boot construction. Silver detail around the back of the ankle that says the Guess brand name. Chunky heel with lots of tread for lots of grip. Toe box is a little narrow but I'm sure that will rectify itself with a few wears. Laces are sturdy tie very easily and make it easy to adjust the boot but they stay tied. Overall a very stylish look and very cute. There is a side zipper so that you can take your boots on and off without having to lace them every time. If you've ever walked into your home with wet winter boots on or out of the rain you'll know it's very nice to have the zipper for easy off. The box came a little cut up and destroyed but I always chalk that up to the postal service because I swear they throw my packages, well, everyone's packages. Given how stylish these are and the fact that they are not a shiny leather material the grip on the sole the ease of lacing and the ability to take them on and off without fighting with them I would give these a 9 out of 10 and I would highly recommend them.
...
show more
Reviewed in the United States on August 4, 2026 by Stormie Holmes
Size: 8
Color: Black 001
I love a combat boot for fall. They are comfortable and sturdy. I saw these new ones by Guess and had to give them a try. I normally wear a size 8 and ordered the 8. It fits perfectly. The boot is made entirely of manmade material, but it really looks like real leather. But what makes this boot extra special, is all the accoutrements. First there is a silver metal embellished strap and buckle with the signature G emblazoned on the front of the strap. Next up is the silver metal heel guard. It covers the back of the boot and has Guess inscribed. Last but not least is the silver metal pull with Guess on the zipper. It’s going to look great this fall! What’s even more exciting is the comfort. I’m not a heels girl. I need something I’m not going to fall off of! This 1+” heel is the perfect height for me. There’s a nice lug sole as well to help with traction in the snow and slush. The one minor thing I would tweak are the laces. They come fully laced up and very tight. I had to loosen them and it was a bit of a pain. They are real and you will need to tie them. I felt like the laces could have been made just for show, but I guess that allows for a truly custom fit. I’d highly recommend these boots for fall!
...
show more
Reviewed in the United States on August 8, 2026 by Rover Girl
Size: 9
Color: Black 001
These GUESS Olanna boots are really cute in person. The gold on them and the little G‑buckle strap give them a stylish look without being too flashy, and the chunky lug sole adds that nice combat‑boot vibe while still feeling comfortable to walk in. The side zipper is a big plus which makes them easy to get on and off without messing with the laces every time. The material feels sturdy. The heel is just the right height to give a little height without feeling unstable. They fit true to size for me, though the toe part is a bit narrow, so thicker socks might make them snug. Overall, they’re a cute pair of boots that work with jeans, leggings, or even a dress. Great for fall and winter, and they look more expensive than they are.
...
show more
Reviewed in the United States on August 15, 2026 by Kookabura
Size: 7
Color: Black 001
These boots are made of a thick and stiff fabric. They feel well made and durable. I typically wear a size 6.5 wide. I ordered a size 7 in these boots to accommodate for the lack of width. The upsized boots fit me. My feet don't slide around during usage. If you are in between sizes or have wider feet, I would suggest sizing up a little. Due to the stiff nature of the fabric of these boots, they will take a long time to break in. They are snug around the widest part of my foot at the base of the toes/ball of the foot area. It's not comfortable, but not wholly unexpected since these boots are not wide with. What I did find surprising was how much the heels hurt. The heels have an additional plate of stiff fabric. It almost feels like this area curves back into the top of the heel. I love that these boots have both a zipper and laces for closure. This definitely makes them more accommodating for people with different sized ankles. I always struggle to find boots that I can wear over my ankles. With the dual closures, I can widen the boots enough to close over my ankles. The design of the boots is nice. The outer fabric has a good quality appearance. The buckles and heel add a bit of bling and add more visual appeal. The boots have a nice deep tread on the rubber soles. These should be quite slip resistant.
...
show more
Reviewed in the United States on August 16, 2026 by Kristine
Size: 7
Color: Black 001
I love a combat boot, and the gold hardware on these Guess boots caught my eye right away! They look both edgy and polished at the same time. You can easily dress them up or down. The shoes are made of durable materials with a nice rubbery sole, instead of the slippery kind. At the same time, the sole doesn't have those deep/ wide grooves like some combat boots and chunky platforms that let small pebbles get stuck! The material of the outer sole looks decent, without that shine that cheaper faux leathers have. They were not the most comfortable. I am normally a 6.5, but usually size up in boots so I can wear thicker socks in winter. I tried a 7, and they felt a little narrow in the toe box. I was wearing pretty thick socks, though. Additionally, after a few hours of wear, I could feel some pressure in the upper heel. I would definitely recommend wearing these for some shorter sprints to break them in a bit before wearing them to an all-day event. They are quite easy to wear. Since there is a zipper, there's no need to lace up every time. Given the brand, they are a pretty decent value--not the most expensive option, but not the cheapest. And the quality falls in that spot as well.
...
show more
Reviewed in the United States on August 4, 2026 by David
Size: 8
Color: Black 001
Being a well known brand, I have always been impressed with GUESS. These combat style boot is just another perfect example. The soles have some aggressive tread that provides excellent slip resistance and shock resistance. I was able step on a couple exposed wires on the job site and I did not feel any sensation. It’s extreme to test it that way but GUESS was telling the truth; the overall appearance still has plenty of styling to it where you can wear them in public. The leather like material which is man made it’s been imitated so well that you can’t really tell the difference from afar or up close. I just don’t know if they used faux or another material. Fitment is good too as well, my wide feet fits like a glove which is just awesome! In the end, the boots are fantastic for both on the job and in fashion. 🥾
...
show more
Reviewed in the United States on August 12, 2026 by Xandry
Size: 8
Color: Black 001
Oooh! These black combat boots with chrome gold accents by GUESS are so tuff! I ordered a size 8 and they are absolutely true to size 🙌 These boots have a chunky heel and great grippy bottoms (not smooth or slick), but actually a great tread that is ideal for walking on slicker surfaces like the grocery store, malls, and even when it’s rainy outside. The lace ups on these boots don’t need “work” when taking the shoes off or even putting them on. The laces adjust to desired tightness and feel secure so they don’t lift up or feel loose when walking. The insoles are comfortable to wear all day and don’t cause foot pain or soreness. For beauty, style and comfort my overall rating is 5 stars! I love them!!
...
show more
Reviewed in the United States on August 16, 2026 by BDEF