Reader Q | Lace Up Booties – How To Style For Tomboys?

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Reader Q:

Hi Shana! I can't explain to you how much I love your blog – it's always a high point in my day when I see you've put up a new post! I was hoping you could help me with a style problem…  I just got these Clarks Rosepoint booties:


I think they're super cute, but they're not really my usual style and I'm not sure how to wear them. Normally my style leans towards kind of casual boho tomboy (that's probably not a thing, I know) and these booties are pretty ladylike. Also I almost always wear more rugged, chunky shoes – moto boots, chucks… because I'm comfortable in them and I feel like they help balance out my, uh, ample…?… thighs and hips. I don't want to look like my curves are tapering down to tiny pointy toes. Right? I'm pretty sure you could make anything look cool, can you help me? thanks so much, and thanks for everything you do for all of us mamas!  

— Rachel



Rachel, I love this question.  I have very similar booties and I struggle with the same thing.  I find them to be…too precious sometimes. You know?  Yes.  You do.

Ok – so here's a few (thigh-friendly) ways to TOMBOY UP a sweet little laced bootie. 



Cut It Off

Whether shorts (hey – I did this pairing already), skinnies, or bootcut, the raw hem rocks.  Since it's winter, grab an old pair of bootcut denim and hack the legs off just above your booties. 



To get the proportion right, I love the cropped pant with a slight heel (BAM – your booties), and a longer top.  Let patterned socks peek out (I'm wearing Mike's).



sweater:  old Gap…similar on sale at Gap (I'd size up)

shirt: Elizabeth and James on eBay….similar on sale at Gap 

jeans:  old Indidenim…seriously loving these

boots: Clarks Heath Wren

socks: Express for Men

lipstick: Tarte Matte Liptint in Lively


Straight Leg Denim?  Cuff 'Em

Roll some straight legs so the hem rests just at the top of the laces.  Play around with a wider cuff (3-4") if your denim is long enough, or just keep it easy with a basic roll.  (Camo scarves and lipstick optional.)



sweater:  Zara

jeans:  AG Stevie

boots: Clarks Heath Wren

scarf: J.Crew, sold out. I love this fabric – here's another.

lipstick: YSL Rouge Pur in Le Orange.  Really.  It's just called orange.


Conceal The Problem Area With Flares    

And by problem area I mean the boot itself.  This is one of my favorite styling tricks for ugly-but-comfy shoes, so why not use it on these?  For days when you are just not feeling the ladylike boot, throw on some flares.



Add a rugged hat for good measure.



sweater:  ancient Splendid cardigan…current one

shirt: old Vince henley…similar

jeans:  JBrand Lovestory (size 25 and 27 on sale here)

boots: Clarks Heath Wren

hat: Anthro, sold out.  Similar.

lipstick: YSL Rouge Pur in Le Orange.  Really.  It's just called orange.



Rachel, thanks for writing in!  Hope this helps…





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. It is so weird because I have the opposite feelings – I just feel ridiculous when I’ve tried on converse high tops, doc martens, desert boots, moto boots. They just feel so clunky/chunky and I feel like a big phony most of all. I like them on other people (not a lot, but enough). But I am feeling so left out on this trend of manly ankle boots. And knee-high boots seems SO over now. What’s a girly girl to do with this trend? Wear heeled or wedged versions? (not practical for a pregnant mom of a toddler!) Spend the rest of the season in oxfords? Help!

  2. Love this post. Thank you! I have some of these similar booties in grey and also needed thigh-friendly, not too girlie looks. THANK YOU yet again! Woot!

  3. I had to laugh – I describe my style as glamorous boho tomboy, so I think if there’s at least two of us describing ourselves similarly, it might be a “thing” 🙂 Cute ideas for the boots!

  4. Thank you! I just bought a pair of leopard print kitten heel boots for no good reason and I think some of these tips will work!?

  5. Emily- I feel the same way.
    Have you tried the Rag and Bone Harrow, Kinsey or Newbury? They are expensive, but if you google them you can then see the style and look for imitation. (I know DV makes some that look similar.)
    For me, at least on, they are the ankle boot trend, but feel less clunky. And mine are super comfy- granted my kiddos are in elementary school now, so I am not chasing little ones around.

  6. shana, thank you so much!! this is awesome!!!!! I love, love all these ideas and as soon as I can ditch my kids…. nap time? I’m raiding the attic for some old boot cut jeans to cut off. you look gorgeous and this was a HUGE help. thankyouthankyouthankyou!

  7. Awesome way to kill two birds with one stone! Now those of us who happen to be pear-shaped tomboys can wear booties! I never thought I could, so thanks for the tips.

  8. You are like the macgyver of clothes. You serious make anything work. You do it so well that I immediately want to dress just like you in all of your pictures. xoxo

  9. I have those exact booties, and I find I can wear them with anything. I often wear them with bootcuts, long straight leg jeans, dresses and skirts (with tights). Since these boots have a wedge, they can be dressier than the Heath Wren boot. The only thing I have a hard time pairing them with is skinny jeans. I think the narrow opening of the boot paired with a narrow ankle just makes my middle look big. Also, shorts. I wouldn’t wear these with shorts. The Heath Wrens are much more masculine and casual – those would look better with shorts.

  10. Confession – I am NOT a girly girl, but I love the girly girl look with low-top Chucks. Maybe less objectionable than the high-top? And oh so toddler-wrangling-while-pregnant friendly says the voice of experience!
    As Beth suggested, I went a little less manly on the bootie and, frankly, cheap because I wasn’t too sure about them. Target did a knockoff of the Hudson Horrigan bootie that I love. The heel is low enough for baby-wearing and kid-chasing and the slip-on style is so darn easy that I keep reaching for them. And I get a compliment literally every time I wear them. Not bad for $30!

  11. Shanna, I have a pair of Miss Mooz boots that are very similar. Thanks for the fresh new ideas.
    I’m so glad to see you looking sassy and healthy.

  12. #1. Love love love your blog 🙂 I’m a nanny and resort to many of your posts to help me style while playing with a 3 yrs old and a 18 month old (and an newborn makes three come this summer)!
    #2. This is a great post! I just purchased these Kork-ease wedges
    And have been trying to figure out how to style them. I’m a nanny and I am oh so tired of wearing Vans, Converse, Merrells, etc. and I’m not a fan of the Moto/Ankle boot style. I was worried about the heel but since it’s a wedge it’s very supportive and I can still pull them off tromping about the playground.
    I struggle with not feeling “put together” enough and sometimes a new pair of shoes are just the trick 🙂

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