Ankle Boots Galore


I pretty much left you hanging after posting about the Great Ankle Boot Search of 2012. Sorry ’bout that.

Turns out – I DID find the perfect boots. When in New York last month, I just happened to stroll by Isabel Marant’s boutique in Soho. (Meaning I googled her store, mapped out the best walking directions from the hotel, and carved out a portion of one evening to make it over there. All before I even left California, ahem.) I walked into the boutique, requested my size in the Jenny boot, and was told they were sold out. This didn’t surprise me because the boot was impossible to find in that particular color and size (see previous post), so I accepted defeat. The associate sauntered into the back to grab a black pair for me to try on for size, and when she returned she was holding the taupe suede ones. She had found one last pair of the boots. “IT’S A SIGN! IT’S A SIIIIIIIGN!,” I yelled. (In my head, at least.)

And that was that. I bought ’em, and I love ’em. Yes, they were well above the price I wanted to spend, but I pooled together my holiday cash and pulled the trigger. And let’s just talk about ROI for a second. I’ve worn these boots almost every day since. With skinny jeans, rolled up boyfriend jeans, J. Crew Minnie pants, long accordion pleat skirts, you name it. And I love them. I LOVE THEM, WORLD!

Anyway, Jenny boots by Isabel Marant. Best boots ever.

Above are all the boots I tried in an attempt to find the perfect ones.

From the top middle, clockwise:

Sam Edelman Petty

DV Juju Boot ON SALE

Madewell Biker Boot

Hudson Rosse Boot

J Crew Aggie Boot ON SALE

Jeffrey Campbell Youngers Boot

Madewell Barnwood Boot

If you have any questions about any of those boots, let me know. I’d be happy to give you my opinion, and a few are on sale right now.

  1. lynn

    January 22, 2013 at 9:32 am

    My question is, how should booties of this (pull-onish) style fit? I’ve been ordering pairs to try but it seems like they’re either too small or there is major heel slippage. Is the heel slippage typical with pull-on booties? Or do yours fit pretty snugly? Thanks!

    • whoorl

      January 22, 2013 at 10:35 am

      Hey Lynn, it’s definitely normal to have a little heel slippage with the ankle boots. The fit should be similar to a cowboy boot – snug around the top and sides with a little slippage in the heel. As the boots become worn-in, the heel will stop slipping.

  2. Tanya

    January 22, 2013 at 2:23 pm

    Do they make your feet hot. I live in Tucson and have that problem with boots here. It would be nice to find a pair that didn’t make your feet totally hot.

    • whoorl

      January 22, 2013 at 2:41 pm

      I would say they feel the same as most suede boots do. (I don’t notice my feet feeling hot.)

  3. Jenni

    January 22, 2013 at 3:15 pm

    I love the IM Jenny’s but they’re a little of my price range. I would love to hear your thoughts on the JC Youngers boot and the Madewell Barnwood bootie. Thank you!

    • whoorl

      January 22, 2013 at 4:52 pm

      LOVED the Madewell Barnwoods! They are a greenish grey – really pretty color, and I do believe they come in black too. The best part is that the top of the boot is narrow enough to wear with skinnies or skirts, yet wider leg pants can fit over without it looking bulgy. The reason I didn’t keep them was that I was really looking for a slouchy boot.

      As for the Youngers, they are fun too. My beef was that the shaft was a little tall for my legs. (I’ve got big calves, so they hit in a funny place on me.) However, if I had skinny legs, I would have kept them for sure. Hope this helps!

  4. Jen

    January 22, 2013 at 9:01 pm

    They (ankle boots) just aren’t cute. Bottom line. They don’t flatter. They are not going to last. They are – in a nutshell – extremely gooby. Don’t do it!

  5. laziza

    January 23, 2013 at 10:29 am

    I do like those boots – mucho like – but just gave away a pair of ankle boots because I just. Couldn’t. Figure Out. How to. STYLE them. Would you mind posting a couple of pictures of the outfits you wore with them? I’d love to get some ideas. Thanks!

    • whoorl

      January 24, 2013 at 2:49 pm

      I’ll try to put something together for you!

  6. Mary

    January 24, 2013 at 12:34 pm

    It’s like most skinny pants/jeans either bunch up around the top of the boot, or the boot itself has a way too big opening which looks terrible, or if the boots aren’t the right shape, they make your feet look big when wearing with skinnies. It’s definitely not that easy. I see people wearing them with their pants all jacked up around the ankles and it can look really really bad. I’m just way picky with this whole style I guess.

  7. Tina

    January 27, 2013 at 2:47 pm

    I’m really crushing on the Youngers but don’t see a post where you gave them a test drive. Did they run small? And I just read your comment about where they hit and you “big calves”, which made me chuckle because I am certain that is NOT true. MY calves are a bit wide and I am short with very short legs. Would these hit me in a funny spot or maybe the style is best for long, thin leggy gals? I love the look of them and like another reader said, it would be a bit of a different style for me so I’d love to see how you style them. I’ve had the page up ready to buy them but they frighten me! LOL

    • whoorl

      February 1, 2013 at 2:43 pm

      Hi Tina! I would say pass on the Youngers if you are on the shorter side….they are just that strange in-between height…

  8. bridget

    February 3, 2013 at 10:32 am

    i want the free people ones in the worsssst wayyyyy.