During the cooler months, I have one accessory that has become an absolute staple in my life. My riding boots. I actually own a black pair and a brown pair. I wear them both often, but it’s the brown pair that truly has my heart. I wear them several times a week with skinny jeans, Pixie pants, tights and a dress … you name it. I also wear them a lot in my Stitch Fix photos. You’ve probably seen them a few times yourself.
I actually wear those boots so often that I get a ton of questions about what brand the boots are and where they came from. (They are Enzo Angiolini boots that I purchased a few years ago. I can’t find the exact pair online anymore but I found similar pair listed on Amazon.) You aren’t the only one who has noticed my boots. My Stitch Fix stylist, Layla even sent a pair of jeans in a recent fix and told me they “will be perfect at the ankle to fit under your tall boots or short booties for a change up.” I read her note and figured this was Layla’s polite way of encouraging me to experiment with a new style in footwear.
I’ve actually been ogling the footwear of other Stitch Fix bloggers and women that I encounter on a daily basis. So many of them wear casual booties instead of riding boots and they look amazing in the shorter leathered footwear. When the New Year rolled in, I made a style resolution to step out of my comfort zone and give the bootie trend a try. The timing worked out perfectly with my recent partnership with Amazon Fashion to spread the word about the stylish segment of everyone’s favorite online superstore. I used my Amazon credit to purchase some new booties in the hopes that I would find at least one pair that I could add to my closet. Thanks to Amazon Prime, I was able to get free shipping on many of these boots and used the free returns to try them on risk-free.
If you love riding boots as much as I do and have been nervous to test the water and take a risk on a pair of booties, you are in luck! I tried on nine different pair of casual booties, took lots of photos and wrote a review of each one. This post contains affiliate links for your shopping convenience. Any purchases that you make using one of our links helps support the blog so we can continue to share posts like this with you. :)
Ash Women’s Ivana Boot
I wear my brown riding boots the most, so I was definitely looking for a new pair of brown booties. Brown is a great neutral that gives an outfit a casual-relaxed look and this camel pair of Ash Women’s Ivana Boots looked great. The best part is that these boots were a bargain. With a list price of $250, I bought these boots for less than $80 and saved 69%! Plus, they were Prime eligible.
The Ash Ivana Boots were a little reminiscent of cowboy boots (which don’t really fit my personal style) but once I tried them on, I decided they looked pretty great. The boots were comfortable and a good first step for me to overcome my fear of wearing booties. The fit was true to size. I think these shoes will be great for a date night with Rob, but are probably not comfortable enough to wear for a full day on my feet in the classroom. My one criticism is that the soles were very smooth and will need to be roughed up the first time I wear them out so I don’t slip and fall.
Aerosoles Women’s Acrobatic Boot
The next pair of boots that I tried on were a pair of Acrobatic Boots from Aerosoles. They were basic and black and had a cute little fringe on the zipper. They also seemed as good as any pair to try on. I liked the low heel and the simplicity of the shoe. The shoes cost $59.95, but came with a shipping fee of $7.99.
I noticed that several of the reviews talked about how these boots were comfortable, but were very difficult to put on. I had the exact same experience when I tried my pair on. I actually had to use a shoe horn to get my feet inside the shoes. Once the boots were on, they were indeed quite comfortable. They were easier to put on while I was wearing a pair of tights, but even that was more effort than I would have expected. These boots were flattering and comfortable, but squeezing my feet into them was more of a battle than I will have patience for on a daily basis. This pair of boots was destined to be returned.
Steve Madden Women’s Jaydun Boot
Priced at $150, the Steve Madden Jayden Boot was the most expensive pair of shoes that I tried on. I have owned several pairs of Steve Madden shoes over the year that I absolutely loved, so it was worth the investment to try them on. It also helped that they came with free shipping through Amazon Prime.
I loved the side zipper detail and the low heels made the Jayden boots comfortable enough for light weekend wear. They were very stylish and I almost talked myself into keeping them, but I preferred the color of the Ash Women’s Ivanka Boot and I couldn’t justify keeping two brown pair of boots.
Toms Womens Desert Wedge Suede Boots
I think I’m in the minority with my opinion of Toms, but I have never really been fond of the classic Tom’s shoe design. They seem to make feet long, narrow and strangely pointy. So imagine my surprise when I discovered that this casual black wedge boot was from Toms! The black Desert Wedge Suede Boots were priced at $83 (a 7% discount from their $89 list price). The boots were not Prime Eligible, but they did come with free shipping.
I tried the boots on and pretty much fell in love. They looked great and the streamlined design didn’t make my feet feel too bulky. The only issue was that the size I ordered felt a little too tight across the top of my foot. It’s a problem that happens to me from time to time. The rest of the fit was quite comfortable but I knew that I wouldn’t last long if I wore those Toms while I ran errands. So I exchanged the pair for a half-size up. The new pair was much more comfortable across the top of my foot and didn’t feel too spacious around my toes. This pair of Toms Desert Wedge Suede Boots was a definite keeper!
Coconuts by Matisse Women’s Cody Boot
It’s no secret that I love soft feminine colors and I ordered this pair of suede Cody Boots from Coconuts in “natural” because I thought it would look great with a soft color palette. I was also excited to experiment with the fringe trend and this was a subtle way for me to incorporate fringe detail into my wardrobe. These boots came with free shipping thanks to Amazon Prime and the $73 price tag was a 24% discount from their list price of $95.
The Cody Boots fit just fine (although the bottom of the soles had no texture and they were very slippery to wear on the carpet in our condo.) This particular style just didn’t suit my personal taste. I think it’s because the style of the booties were so low. They had a low heel and the boots themselves didn’t extend very far up my ankle. Add in the slightly pointed toe and it felt like I was wearing some type of shoe made for an elf. I know a ton of women who could pull these off and look fabulous in them, but pair wasn’t for me.
Reneeze Zipper Stacked Chunky Heels Strappy Ankle Booties
I ordered the Reneeze Zipper Stacked Booties pair of boots because they seemed like a great, thrifty alternative to the Steve Madden Jayden Boots. They were nearly the same color, had a similar heel, and even a decorative zipper detail. I typically opt to purchase a more expensive (better quality) pair of shoes but these were on sale for $34.99, which made them a bargain compared to the Steve Madden shoes with a price tag that was $100 higher. Shipping was free too, although they were not Prime eligible.
Well, as it turns out, there’s a reason I usually opt to purchase the more expensive shoes. They just fit better. This pair had a great price tag but was strangely boxy. My foot fit just fine on the sole of the shoe, but the faux-leather wasn’t very supple. In fact, it was pretty rigid and the boots had a larger cavity inside than my foot (or anyone’s foot) needed. If the pair of Toms booties was too snug across the top of my foot, these shoes had the opposite problem. Yes, they were thrifty. No, they were not for me. They were also a minor hassle to return. I couldn’t instantly print a return label. Instead, I had to “request” a return through Amazon. The company honored my request within 24 hours but it was an extra step and I was nervous that I would be stuck with a pair of shoes that I didn’t wish to keep.
Sam Edelman Women’s Petty Ankle Boot
I have heard only good things about Sam Edelman shoes and I know how popular they are right now, so I ordered a black pair of the Sam Edelman Women’s Petty Ankle Boots. These boots were simple, classic and perfectly comfortable to try on. They also cost $140, but I saved on shipping thanks to Amazon Prime.
The only problem was that they felt a little too modern and edgy for my taste. There wasn’t a lot of room for an easy-feminine style with these shoes. The Petty Ankle Boots looked great, but were so not me. I blame the short height of the boot. For someone that’s just beginning to experiment with wearing short boots, these were too much of a risk. Maybe you should buy them and tag me on Instagram so I can live vicariously through your footwear experience.
Refresh Womens Tildon Almond Simple Flat Heel Ankle Booties
These Tildon Simple Flat Ankle Booties from Refresh were the biggest bargain in my shopping spree. They had a regular price of $50.99 and I got them for only $19.16. I didn’t think they would be my favorite shoes, but they were Prime eligible so there was no risk in ordering a pair to try on!
The Refresh Tildon booties fit fine and were easy to slide my foot into, thanks to the stretchy fabric around the top of the boot. I loved the color, but that was the only thing I truly loved. Maybe it was the silhouette or the lack of zippers, but these booties felt so plain and once again reminded me of shoes than an elf would wear. They just weren’t for me.
Dream Pairs Women’s Casual Outdoor Low Wedge Heel Booties
I’m not sure if it was an act of desperation, an intense desire to find a quality pair of booties for a bargain, or the fact that the brand of these shoes was called “Dream Pairs” and I was secretly hopeful that they would be the answer to my dream for a perfect pair of booties. Whatever the case, I ordered a gray pair of the Dream Pairs casual outdoor low wedge heel booties. The $29.99 price tag was also a dream come true because it was a 60% savings from their $75 list price -- and they were Prime eligible!
These shoes are definitely called Dream Pairs for a reason! They fit perfectly and were insanely comfortable. Wear them to school while I teach kindergarten kind of comfortable. These will also be perfect for when I dress in a softer color palette.
My Top Three Boot Picks
After trying on all of those boots, I decided to keep three pair and add them to my closet. Here are my three favorite pairs of boots. Click any image to read more on Amazon.
I now have a brown, gray and black pair of booties to add to my closet and nudge me out of my personal style comfort zone. I’m definitely keeping my riding boots around, but these will be fun to add to the mix! Did you have a favorite pair from the post? Would you have kept something different? I’d love to hear your thoughts in the comments!