Mom Street Style: Jenna Struggles With Ankle Boots

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Mamas!  I had the pleasure of working with this hot Mama a couple of months ago:


Jenna had emailed me because she bought a pair of ankle boots but they…just…weren't…working.  She sent pics, saying:

I bought these coach priscilla booties at a great sale at bloomingdales but every time I try them on with skinny jeans, leggings or tights they look weird.  My friend said it's b/c my ankle looks skinny and that makes my feet look big 🙁  Should I return them? Please help!  


Hunh.  Up close, they are cute boots.  And Coach typically is right on-trend.  But…Jenna's right.  Something is off.  Here was my response:

Jenna, I'm thinking…these may not be your boots.  The pic with the rolled black jeans –  it looks great.  But the others….something is off.  I think part of the issue may be the shiny-ness of the boot and the tassel.  Us….ahem…petite gals gotta be careful with booties…and in this case, it just might be too much?


A few things to try:

1.  The outfit with the striped sweater:  Try rolling the jeans.  Try both the small cuff (like you did with your black jeans) and a large cuff (turned up only once or twice).  

2.  Booties with tights should look good.  Period.  If you are struggling with booties and tights, that's not a good sign. Try black tights to lengthen your leg line…and try taping your skirt up an inch or two (duct tape works really well, LOL).  Something is off on the proportion….we need to fix it.  You have such rockin' legs that a couple extra inches showing will only be a good thing. 

Needless to say, Jenna returned the boots.  Happily, she found a new pair….at DSW!  For $35.
So much better, right?  But WHY?  Let's look closer.


The best I can tell….the second pair of booties have the following going for them:

1.  They have more shape.  The top has a nice, sexy curve over the foot and the heel is narrower, giving these boots more shape overall.  Coach's boots go straight down to the top of the foot, and the heel is clunky.  This makes the boot look awkward, despite the cool tassel.

2.  They aren't so shiny.  Unless it's date night, I find high-shine booties tough to wear when you are short.

3.  They are wider at the top, but shorter overall.  The lower profile is better for Mamas with muscular calves, and the fact that the opening is wider allows Jenna to tuck in her jeans with minimal bunching.  

In hindsight, the tassel didn't matter a bit. (Jenna, your new ankle boots would also look adorable with rolled skinnies.)

It seems like ankle boots should be easier than this, right??  I don't get it…but finding a pair that fits well with your body type, your style, and your existing wardrobe is really hard.  Despite all of my best efforts, my mom still hasn't found a pair, and it took me over a year to really get into this trend.   Any other Mamas still struggling with the ankle boot thing?



ps.  Jenna, thanks for the pics and for being such a great sport!!!  (Her awesome bird shirt was a total Anthropologie sale rack score, BTW.)


About Author

Shana founded The Mom Edit in 2008. She lives with the love of her life (his name's Mike) and their two crazy boys in downtown Philadelphia. She loves a good styling challenge (her engineering side shows eventually), appreciates kindness, and usually picks scotch over wine, sneakers over stilettos, and denim-underwear, always.

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  1. I’m still struggling with the pair of ankle boots I bought too! I don’t know why, but I just can’t seem to get it right?!? Shall I too send pics? Help!

  2. I’m still not feeling the ankle boot love. I just don’t know they feel, awkward or something. But I want to, I really do!
    I love the tunic she’s wearing in the last pic, can she send a link?

  3. As a petite, curvy/muscular and boobs kind of girl, I have not figured out a way to make this work for me. I’d really like a pair of wedge suede lace ups but I haven’t found a pair yet that look good, are reasonably priced and are something I would wear.
    I’ve also noticed a lot of the skinnier, slimmer shoe profiles coming back in “high” fashion. Which I kind I like (a skinny, point shoe is just so slimming and ladylike). Anyways, this makes me hesitate on the booties longevitivty. I remember being in middle school and my mom wearing booties and thinking it just looks like you couldn’t afford a whole damn boot. I hated them. Anyways. I haven’t overcome all those issues yet but in theory, I’d like to.

  4. Hot Mama is RIGHT! I wish I had those slim legs…and with such a wee one on your hip no less. Jealous!
    Ankle boot issues galore here. I ordered and returned the DV Javas…muy uncomfortable for me. Next. But I scored some sexy black date night booties on super sale (what to wear with them past the black tights/dress combo not so sure, but….) and I’m struggling with bopping-around booties. I snagged a pair of cheapies (under $30) from Aerosoles (where I was busy ordering those red Tapestry pumps that have been calling to me for months cough*enabler*cough) because they were comfy and cheap, which seemed as good a way as any to figure out if I can make this doggone style work. But I’m struggling. Keep these posts coming PUH-LEASE!!!

  5. Can’t wait for sandal weather so I can deny this trend ever exists. I’d love to rock ankle boots but just can’t figure out how (especially with chicken legs).

  6. I tried on a couple pairs of booties and felt like they just did not work with my pear body shape.. unless they were a little bit taller. In which case, I felt like they’re not that much different/cooler than my tall boots 🙁 I was disappointed.

  7. Thanks ladies! The DSW pair are :,300102&isBrand=y&categoryName=women.
    Found them on the clearance rack. They are actually really comfortable for an inexpensive shoe.
    The black tunic is actually TWO tunics layered- A James Perse long ribbed tank underneath that I wore through both pregnancies and still wear it. It’s on sale on today actually- almost got it in white) Plus I added a tunic from H&M on top that was $10.

  8. What a difference! The second pair is so flattering and have a versatile feel to them! It took me reading your blogs and seeing how you styled ankle boots for me to get over my aversion. I was sooo skeptical that I could pull off this look for the longest time! (truth be told:I’m still trying to figure it out..will I be brave enough to wear them with shorts? Eeeeek! Then again, will I be brave enough to wear shorts, period. ha!)

  9. Yes! I got the DV Javas today and it’s gonna take me a little bit to figure them out. Time to scroll through the archives and take styling points from Shana. Even though we have, you know, completely and totally different shapes. Should be fun!

  10. I have been struggling with the short booties lately too! I just don’t think its flattering on my pear shaped body. I think longer bum covering jackets are probably the essential item to this look for me and I am kicking myself for not buying a longer parka this winter. Anyway I have these and I really like them with skinny jeans. They would look good with bare legs and shorts but I just can’t go there. I’m honestly feeling old and ready to give up on the whole cropped, skinny, coloured, look at me jeans. Somebody please hand me some boot cut jeans!
    P.S. I bought the Ag jeans from your last post, hoping they will help out a lost cause right now…

  11. Love the new boots, Jenna!
    I struggle with all of it – if I’m going to work, I’m good, but anywhere else and I’m at a loss. I am a short-waisted, long legged, curvy mom of a 13 mo. old boy (for reference, I sometimes shop in the petite section for tops and dresses but buy long length pants). I can rock heels and a dress like nobody’s business, but my “Saturday” clothes are a complete 180. I bought a pair of ankle boots from Target (the Kinley?) but took them back because, I don’t know, they just were off. I feel like when I try to go casual, I just look frumpy. So I bust out the workout clothes (again) and the hat and I leave the house. I would love to have casual options that included skinny jeans, ankle boots, button down shirts, and tshirts (hands down, the most difficult thing for me to find and wear – anything tight and my pooch is on full display and anything loose and I look pregnant).

  12. I have abandoned my attempt to find an ankle boot to wear with my rolled jeans, but I love them paired with the red pumps you gave me for Christmas. xxoo

  13. This was really helpful. Maybe it’s not me, maybe it’s the booties I bought. Being short and muscular makes it difficult. I live in Texas, so I’m just hanging on now for sandal weather, which should arrive in 3 weeks or so. But if they are still around next year, I promise to try again.

  14. I bought your DV Java booties and can’t get them to work, either. 🙁 So sad because I love the boots in and of themselves, just not with me/my clothes?

  15. I have been having a little trouble too. I bought Miz Mooz booties sale and it has taken me a while to figure out how to wear them.
    I always seem to have to roll my pants because I just can’t seem to get jeans skinny enough to go inside without bunching(though they look okay with leggings). I finally bought some Levi’s 535s and they are at least thin enough, but I have to roll them anyway because they are so long on my short legs. Is it okay that the roll shows through the slit? Or should I just roll them up high so it looks deliberate?
    Also, because of the slit in the side, my socks are pretty much always showing. I just try to choose a colorful pair to make it interesting, but I have no idea what I am doing!

  16. Yep, I have trouble with my black ankle boots too. I’m 5’3″ with a long torso so maybe they are just wrong for my body type. I do wear them with boot cut and flare jeans, but that’s it. They look too big with skinnies (like in the first set of pictures above), and with skirts it looks like I should be carrying a broom stick and conjuring up potions. Not the look I’m going for these days. My feeling is that I don’t have to wear every trend, you know? I didn’t touch the gladiator sandal trend with a ten foot pole and that was fine.

  17. I was also wondering about that! I just got a pair of ankle boots and was all excited to wear them. I thought I could pull them off because I’m 5’7″. HOWEVER, after wearing them with skinny jeans, they just looked odd, I think because my body is pear shaped? My ankles are really thin, so it looks disproportionate? What do you think?

  18. Try an ankle boot that slants down from ankle to toe (am I saying that correctly?) instead of cutting off the ankle straight across. It will help elongate the leg.

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