In the grand scheme of life, as long as you’ve got shoes on your feet, you’re good. I mean, lots of people don’t. Style doesn’t actually matter.

But since I’m a first-world girl with first-world problems, I have been known to get a wee bit fixated on finding the perfect fill-in-the-blank for the style I want.

Usually, it’s house stuff. Like a rug with a certain pattern + colors for the kitchen or a bedspread for the girls’ room.

And there’s always the budget consideration.

I want exactly what I want for a really low price.

And in this case (back to the shoe reference), what I want is a pair of simple, genuine leather cognac ankle boots. Preferably with no higher than a 1″ heel.

Like, the ultimate hipster boot, basically.

Which, I’m not even sure I can pull off with my not-exactly-hipster style and my short legs to long torso ratio (I do much better with a heel of at least 2″).

But back to the hunt for this so-called perfect ankle boot. I’ve put a lot of nursing-the-baby-while-browsing-my-phone internet miles into finding said boot, and I figured that it would just be selfish (not mention the loss of a great justification for all of that time wasted spent) not to share my findings with you.

So, without further ado, I give you a round-up of 8 of my favorite boots that I stumbled upon in my research.

Disclaimer: I mentioned the budget consideration for my very particularly quests for the illusive ____________. And I’ll get back to that. But this particular list is not really that budget friendly. Because, apparently, real leather ankle boots are expensive. Period. Especially while they’re in season. So, if you were expecting amazing finds for $30 or something, I’m afraid I’m going to disappoint. ankle boot

1/ 2 / 3 / 4 / 5 / 6 / 7 / 8

I’d certainly wear any of these boots (assuming they were, at least, marginally comfy), but my faves BY far are:

#3–the BP Trolley boot (which is shown in a maroon color because I couldn’t find a picture of the actual cognac that it comes in…but it’s gorgeous!)


#8 , which is the Kork-Ease Velma boot, and it comes in a rich brown leather like I want, but, for some reason, I’m really digging the grayish hue with the contrasting wooden heel.

So…did I actually pull the trigger on any of these?


But I did buy a pair of cognac leather ankle boots.

Wanna see?


Are they what I was looking for?


And no.

On the one hand, they’re real leather. And the color on the box says “cognac” (although in real life, it’s more of an–intentionally–scuffy true brown).

But it’s not the super-simple silhouette I wanted (I wasn’t interested in buckles or elastic goring), and the heel is 2 1/2″ rather than the ideal 1″ I was looking for.

So, why did I buy them? (I bet you can guess).

They were cheap. The style is Steve Madden Spunkk, and it’s only available on ebay (that I’ve found). And a lot of the ones I found were still close to $100, but then I found one pair in my size with an (easily fixable) “defect” for waaaaaay less…and I went for it.

Am I happy with them?


And no.

It’s complicated. 🙂

Have you found the perfect cognac leather ankle boot? (Because I’m so sure this is what everybody else is on the hunt for). If so, share!


  1. Hi Abbie!
    Great list! I especially like numbers, 1, 2, and, 8. One of my absolute favorite pairs of ankle boots I actually bought last season are the CAT brand in the style “Spencer” (Yep, Caterpillar makes ladies shoes too!) Like I said, I bought them last year and LOVE them! Very, very comfortable and they still look almost new this year. 🙂 Here’s a link in case you’re interested.

  2. I have been searching for the perfect pair of ankle boots for a while also. I LOVEEEE the ones you ended up choosing! I have a hard time finding a pair because I am so I have only ever bought myself one pair of shoes that cost over $20 and that was a really fantastic pair of leather high heeled boots that kill my feet and were definitely an impulse buy. sooo, boots under $20? yeah pretty much dream on. I’ve been watching ThredUp for a pair with no luck so I’ll probably end up going with a cheapo pair from target, cute but not gonna last forever.

    1. What size are you? I’m not 100% sure I’m going to keep these, and they’re brand new. Not quite as cheap as $20, but really good quality.

  3. Last year I bought Chinese Laundry leather ankle boots at DSW that are super comfy with less than 1″ heel. My only wish is they were more fitted on my tiny ankles but I do love them. I’m on the hunt for nude booties this year!

  4. I have the Steve Madden Gilte in Taupe, but they also come in cognac and are super comfy with a small heel. I got mine new on eBay for a great deal.:). I also have a short leg-to-torso ratio, but I decided I don’t care.:)

  5. I have been on the exact same hunt! It’s harder than you would think, isn’t it?!?! I initially bought the Lucky Brand (2) that you have pictured. I just couldn’t get them to be comfy. . . I’m size 7 1/4 I guess! 7 slightly tight. . .. 7 1/2 is sloppy. Anyway, I just ended up with the Clarks Gelata Freeza which are not as clean as the Lucky Brand but are so ridiculously comfortable, I think I could wear them as slippers. 🙂

  6. I went through a similar hunt for grey/taupe/tan booties about six weeks ago. It took close to a month, but I finally found a pair of Dolce Vita ones on Amazon for less than $30. They kinda hurt the fourth toe on my left foot, but they *look* fabulous, so of course I wear them nearly every day.

  7. My husband does not understand my struggle in the quest to find THE perfect cognac/dark camel colored ankle boot! I’m so glad to find like minded crazy ladies. It has to have a heel, but not too much of one. Simple, but not like an old man would wear. Not a rounded toe, but not a point. I’m also cheap. That doesn’t help.

  8. had the same issue with locating the shoe I wanted that was not the cognac that I wanted. so, I went for it and in the shoe dept located a wonderful cognac shoe dye and used it following the directions. superb results and got some great compliments on them. later I used the same dye on a purse not necessarily going for a matchy matchy situation. that dye really made for a happy couple of seasons and later gave a nice boost and revitalization. well worth the 3.98

I love hearing from you guys!