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


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…