- You’ll shine up like a pretty Penny in these killer Sam Edelman® boots!
- Back-zip closure with snap tap at shaft.
- Leather upper with asymmetrical collar.
- Man-made lining.
- Lightly cushioned man-made footbed.
- Stacked heel.
- Man-made sole.
- Product measurements were taken using size 8.5, width M. Please note that measurements may vary by size.
- Weight of footwear is based on a single item, not a pair.
- Heel Height: 1 in
- Weight: 1 lb 5 oz
- Circumference: 15 in
- Shaft: 15 1⁄2 in
- Platform Height: 1⁄4 in
Hot Sale 🤩 Sam Edelman Penny Leather Riding Boot | 🥾 Boots 👏
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4, 4.5, 5, 5.5, 6, 6.5, 7, 7.5, 8.5
25 reviews for Hot Sale 🤩 Sam Edelman Penny Leather Riding Boot | 🥾 Boots 👏
Rated 4.29 out of 5
Rated 4.88 out of 5
Rated 4.08 out of 5
Rated 2.00 out of 5
Rated 3.00 out of 5
These boots are very good quality. The leather is soft and the design details are great. I usually wear an 8 or 8 1/2, I got the 8 1/2 and they were too big, so if you are on the fence about two different sizes, I would suggest going smaller. I loved the boots but only gave a four out of five stars rating because they were too wide at the top for my leg and I prefer the height of boots be closer to the knee. Excellent quality boot overall!
My boots just arrived today, and I am impressed with the quality of the leather which is very soft. They have a similar appearance to the Frye boots except at a lower cost. I usually wear 6 1/2 or 7 so I ordered the smaller size and they fit well around the foot and ankle except for the calf circumference which is a bit wide. Although, I do have very thin calves, so I plan on wearing chunky boot socks underneath. I am 5’3″ and the top does not come all the way up to my knees, so they don’t make my legs appear shorter like other riding boots I have tried on. After much trial and error, I have finally found the perfect riding boot for me.
I’ve been on the search for a riding boot for a while now. These boots are awesome! Very soft, well made and even has arch support inside. I am petite (5ft, 115lbs and a runner with muscular calves. These fit great! They hit right below my knee and feel broken in. I love the zipper in back and minimal hardware. It’s enough to give the boot personality without being tacky. I recently bought Tory Burch boots but in no way shape or form are they made for short people or anyone with a calf. I had to return them and very disappointed. I also tried the Frye Melissa button backs and they were the runner up but a tad too tall and fit more snug all around. These SE’s have room to wear with skinnys and I love the diagonal shaft. The inside feels like soft suede.
I am very pleased with these boots. I wear a size 10 and have very athletic calves (border on wide calf size in some brands). This pair of boots fit well with jeans tucked in. I also really like the asymmetrical height (higher on the outside). Just the right amount of hardware.
I just received these from Zappos and was so thrilled with the style, I immediately put them on! They are classic. The leather is soft and the inside lining is quality. Most importantly, the sole is substantial. Not in a bad way, I am just coming from an old pair of boots that would make my socks wet the second I stepped in any snow. I also had a few odd things I was looking for in new boots: they stand up and stay up on my calves and you don’t have to constantly pull them up. Secondly, I also wanted to be able to cross my legs without having any embellishments make it uncomfortable. The minimal zipper and clasp are out of the way!
I’ve been wearing these boots just about every other day since I got them. Having worn these boots for the past 2-3 weeks I don’t think I would repurchase this boot if I had to do it again because for the price, I would have just invested another 100$ for a more high quality boot because I can’t imagine this boot lasting as long as I want it to.
The leather is thin and the inside is lined with a stretchy fabric making it have virtually zero break-in time. However, I already see my boots slouching a bit and getting stretched out a lot faster than I would want. The aesthetics are cute and is what made me attracted to them (classic cut without being generic/boring.) but if you look too closely, it a little on the cheap end thanks to the leather being so thin. It’s like shopping at a department store, you get what you pay for. I like these boots but I don’t think I “love” them.
They are a decent boot, but the type of thing you’ll find at discount stores like Marshall’s or TJMAXX. In fact, after I returned these, I found the same brand there. They aren’t bad boots, but I wasn’t in love with them at all. I thought the pictures looked much nicer than what showed up at my doorstep. I guess I’m really picky about leather. They almost felt plasticy to me. I guess I’m going to have to buckle down and spend more money on something like a pair of Frye’s to get the quality I want.
Love these. Comfortable straight out of the box. Fit true to size. Whiskey color is great, and leather is flexible and soft. Good foot support. Bought instead of Frye because of the zipper and lower price. Very satisfied.
I love these boots. They were comfortable right out of the box; stand up nicely (I hate slouchy boots) and the grey color is fantastic. Also, I almost did not buy these because of all the reviews that said the calf is so wide; I am not sure what folks are talking about. I consider my calves thin to average, and these fit perfectly around the calfs!
My neighbors are wondering if I am opening a shoe store with all the Zappos boxes that have come and gone in the past week! I initially got these Penny boots in my size, 7½M. Much too my dismay these were impossible to zip over my 16″ athletic calves. I literally broke a sweat trying to zip them and was not successful. I thought I might need the wide calf, but those were way too wide. So my final order and last resort was to simply size up to an 8M in the regular width boot and pray that the extra half inch in the calf would help. Success! I am so glad because these boots are beautiful: the leather is buttery, the stacked heal has a cool suede finish, the snap detail and burnished brown on the heel and toe are really nice, stylish touches! I got them in Whiskey and now that I know my size I am very tempted to get them in more colors! If you have a 16″ calf and a larger shoe size you will probably be fine. If you are my size go up half a size to an 8M, but know that even with that you can wear these over leggings, but not likely over jeans. I may try it once they stretch out more but for now I know they zip up over leggings just fine. These are true to size, so the 8 is a touch roomy but nothing thicker socks cannot help.
I really wanted to love these. They are super cute and exactly what I was looking for style-wise. Unfortunately they just didn’t feel right. The back zip ends about mid heel and it is so annoying. You can definitely feel it and it’s all I could think about when I had them on.
They also ran a little small. I am a pretty true 8.5 and they were a bit too snug so I returned them for a 9, which fit better but didn’t alleviate the annoyance of the zipper. Also was really disappointed in Zappos for the first time because when I revived the 9, they were just in an unmarked cardboard box, too small for the boots so they were folded over. The 8.5 that I originally received didn’t have that problem. They were in a real Sam Edelman box that was the correct size so that the boots didn’t have to be folded over.
These boots have the potential to be perfect, but they missed the mark. The first issue is the deal breaker for me – the whiskey color looks absolutely NOTHING like the photo! The photo shows a beautiful, rich, almost distressed leather in a deep whiskey shade. In person, the boots are a flimsy, cheap-looking light brown. No “whiskey” color at all – just light brown. At first I thought I’d received a dud pair – but I exchanged for another pair and they’re exactly the same. Cheap leather that resembles pleather. My second issue was the width – I ordered a size “wide” (regular calf, wide foot) and it’s narrower than some of my regular shoes. So I’d say the shoe runs extremely narrow. Zappos really needs to change the photo for this product in “whiskey” because it’s false advertising at this point. Zappos has great customer service so I know I can return the boots, but it’s a waste of time and resources and money to go back and forth with shipments because the item pictured is not the item received. Disappointed – the search for boots continues.
Horrible! When I opened the package the smell of “chemical” was so strong I had to take the boots and the box into another room where I could contain the stench. What was that? Do I really want to know? After a few hours with the box open closed up in a guest bedroom with the window open and I went back, you could begin to smell the “good leather” smell a quality boot/shoe is supposed to have but that other smell has me extremely wary. Well. I am an exact 8.5 Wide. The reviews said size down so I went for an 8 Wide. It was very much too small. And not too short, either, the boot was NARROW. I don’t think sizing up two sizes would allow it to be wide enough. This is a narrow foot boot. Now, I’m athletic and have muscular calves. As for the shaft, yes, it was wide and there was plenty of room for an athletic/full calf. Overall, however, I would say this boot is a complete failure. Something I might expect in the wally world price range. Some people praised the look of the leather and it was okay, in my humble opinion, while yes, you can tell it is real leather it had more of a “pleather” or “PU leather” than what it was. This was my first Sam Edelman purchase and if this is representative of their work I’ll not be shopping their products again. Except for the fact they do accommodate a full calf well I would say this boot is a complete failure and for goodness sakes, that chemical SMELL. What is going on there? That was bizarre, and not in a good way!
Love these boots. The whiskey color is what I’ve been looking for and the leather is soft. I also like the fact the leather was not pebbled. I originally purchased this Penny boot in my regular size 7.5 in the regular width. When I tried them on, they felt really narrow and tight in the footbed. I thought they would stretch out after a few wears. I didn’t last through a few wears. The first time I wore them was to a holiday photoshoot which lasted no more than 20 mins. My feet were in PAIN! The footbed was so narrow it squeezed my toes together to where I couldn’t move them at all and they fell numb. I couldn’t wait to get home and pull them off! I gave them a second chance though. I put them on one morning and was ready to go run errands. I didn’t make it out of the house before I had to take them off because my toes fell numb again. That’s when I decided to return them.
After shopping around for a new pair and didn’t find anything, I got an idea of trying this boot in a WIDE; not wide calf but wide footbed. Again, Zappos didn’t disappoint with their shipping time. I ordered it in the afternoon and it arrived the NEXT day. They always AMAZE me with their shipping time. I was nervous trying them on but to my surprise they felt perfect. SO much more comfortable than the regular size. The calf circumference was the same, just the footbed felt normal and not extra narrow.
Sorry for the long review but it did take me awhile to find these and think maybe others have had the same issue with the narrow footbed so hoping this review will help. Definitely order your regular size but select WIDE WIDTH. Can’t wait to wear these boots this winter.
Love the color. They are a bit lighter in person than what the website shows. A little narrow. Had to return for a larger size. I can wear them all day with no problems.
These don’t look anything like the picture. They are orange, with an ombré black toe. They smell good, like genuine leather, but not as cute as they look in the picture. Also, I ordered wide width, and I couldn’t even get my foot in the boot. Big disappointment.
They were not wide and fit just like any regular width boots I have tried in the stores. I also have a high arch and they did not feel like they had any arch support.
I searched forever on Zappos to find a reasonably priced, good looking, and comfortable boot and I found it in these! Everything is just as expected. The leather is buttery soft and exactly the whiskey color I was looking for. I was worried about the calf size since I did not get wide calf, but they fit perfectly over leggings and skinny jeans. Highly recommend!
I really like this boot. I wore with Jeans and they fit great! I’m 5’10” tall so I have long legs and I have muscular calves/legs so the boot was a perfect fit for me. First day wearing them, no pain or blisters. Very comfortable.
My only small complaint is the color does not exactly look like the picture. I was expecting a darker brown “whiskey” color as shown above. However the color was more of a “camel” or light tan. I can live with the color because it pairs well with jeans.
I really wanted to like these boots as they are the closest I have been able to find to what I want and they don’t cost and arm and a leg. They are decent quality leather, carefully constructed, and have a nice lining. The arch support is not very good, and the foot area feels a little flimsy, but I wasn’t really expecting these to be super supportive. Unfortunately, I am returning these as the very top of the shaft was just too wide for my muscular calves to the point where the top stuck out from my leg especially in the back. It was especially noticeable when I tried them on with tights. It might be ok with jeans, but my primary use for these is with dresses and skirts in the winter and I’ll be wearing tights.
To further add to my review, the boots I have are actually two different colors?? What a terrible buy for $150.
I was so scared to receive these in the mail because I have a bigger leg, so I was scared they wouldn’t fit. I also read the reviews and it said order a size up because they run small. NOT TRUE! I wear an 8 and I got a 8 1/2 wide and I would have preferred a 8, but I’m not sending them back because I have somewhere to go this weekend (hahaha), but I love them. Get true to your size and don’t be afraid to order if you have a larger calf. They fit!
For reference, I’m 5’2″ with large feet and an athletic calf circumference of 16 inches, which is supposed to be on the border between the regular (Penny) and wide-calf (Penny2) versions, so I tried both. Remember that this measurement is at the top of the boot, and the widest part of the calf is much lower. So, the height of your calf does make a difference. Well, the wide-calf ones were huge. And the regular-calf ones were initially so tight that zipping them up over bare legs was a challenge (the shoelace trick works well to avoid bruising your fingers). Sad, because I love the style, and the leather and quality seem excellent. However, after walking around the house for a few minutes, I noticed that the calves seemed looser—becoming very comfortable in fact. But, I wanted to wear them with my skinny jeans, not bare legs, so I tried again. Once again, they were so tight that using a shoelace was the only way to get them zipped (being very careful not to break the zipper, of course). I finally succeeded in getting them zipped all the way up, and again noticed that the calf began to loosen after a few minutes walking around. WOW! Perfect fit! Cuddly-snug without feeling tight. Yes, these are real leather. Soft leather that conforms to the body very nicely. After a couple of days wearing them over jeans, I no longer need the shoelace to get them zipped. I also read the reviews that said these run narrow, so I got the wide-width (9W) although I generally wear a medium width. They do run narrow. The wide-width felt snug across the instep, but not uncomfortably tight. My normal size is 8.5 or 9, so I got the 9W. Lengthwise, an 8.5 probably would have worked fine, even with heavy socks. By the time I figured that part out, I’d worn them for a day and so can’t return them. If my heel keeps slipping, I’ll add a heel pad or an extra pair of socks. The color is slightly lighter than the photo on my monitor, but is a medium shade, warm, light brown, not as pale as some reviewers have reported. For the nerds out there, the closest color match is R133 G65 B28. Whiskey is a reasonable color-name. They’re so comfortable that I’m considering getting another pair in black or grey. Finally, in the long-lasting hunt for great boots—success at last! They also look very well made and should last a long time.
Wow! These are really great, well made boots! I just put some candle wax on zipper because they were stiff and I am ready to go! My calf is 13 1/2 inches wide and I’m a true size 7. I love the non-slip, stacked heels. They are so soft and don’t need any breaking in…in fact I don’t think I’ve ever had a more comfortable boot! They will to be great for CA winters and travel!!!
Super fashionable and functional!!! I walked over 169,000 steps while honeymooning in London & Paris – most of those steps were taken while wearing these boots. My feet did not get sore. I did not get one blister. It is the first time I’ve made it through a vacation that included a lot of walking without suffering some awful foot related pain. I have bad ankles, bone spurs, weak arches, and over-pronate. I am absolutely amazed (and super grateful) for how well these boots did. They were also perfect for the fall weather!