Reader Q: How To Wear Flares With Flats


I received this awesome question from Leslie:

Hi Shana, I am a long time reader of your blog and I love how you are encouraging moms to be stylish in ways that work for our lifestyle. I am taking your Fall Edit to heart and looking for some interesting jeans and am particularly drawn to flares…I love my skinnies but am ready for a break! But I am having the hardest time figuring out what shoes to wear them! Everyone styles flares with heels, which I love, but this momma needs the practicality of flats for everyday life (parks, play dates, Target runs…). Any styling tips?

Thanks so much!


Leslie, I HEAR YA.  My biggest problem with flares is that they look so much better with heels.  Like, no contest, heels win hands-down.  But like you, I’m most often in flats.  So I took this styling challenge to heart to see if I could figure out a chic way to wear flats and flares.  After an embarrassing amount of tries over many weeks, I think I came up with something worth hemming for.

(And only one pair of flares were harmed in the process. RIP, Seafarer flares.  Thank goodness you were bought on sale for a mere fraction of your usual cost else I would’ve lost my mind.  #allinthenameofresearch)








I wanted to style flares with sneakers.  I figured if flares could look good with sneaks, they’ll look good with Tieks.  You know?  So I started by pulling up the old series How To Make Your Legs Look Longer While Wearing Flats.   First point?  High-waisted denim.





Second point?  There’s a world of difference between a stiff flare jean that flares out below the knee and a soft, voluminous flare (also called a wide-leg).  When wearing heels, I’m OK with either approach, but in flats?  Wide-legs win.


The process of hemming a flare takes away some…flare.  And in the case of a true flare (one that starts below the knee) you are basically hemming away the best part, leaving you with a rather boring-looking bootcut jean.  However, if you start with a wide-leg jean in a soft denim, even if you hem some of the flare away, you haven’t lost the overall intention of the jean.  Also, when hemming flares for flats, I think the jean should ever-so-slightly drag on the ground.  This approach works best with a softer fabric.  Soft fabric will drape nicely, even if a little long, stiffer fabric will just bunch.  (If you are tall enough to buy a pair of flare jeans and not have to hem, then I suspect you can pretty much ignore everything I just said.  Lucky girl.)

And a pretty top never hurts, either.








top: Piperlime Collection c/o (now sold out)…also love this machine-washable silky top by Velvet.  It would pair perfectly with Chucks and flares.

sweater: Nordstrom Collection (old)….but I love Autumn Cashmere’s oversized, black cowl-neck sweater at Bluefly

flares: Mother Denim (old), but my new favorite flares (shown here) would be perfect for hemming for flats – Level 99 High Rise Trousers at Anthro

shoes: Black Converse HighTop sneakers worn over Smartwool socks….but seriously wow, Converse is getting some seriously style.  Check out this pair of leather and studded Converse hightops.

bag: Kate Spade Lola Ave Plaid c/o

umbrella: MoMA Mini Sky Umbrella


Leslie, I hope this helps!!  Thanks for your kind words and great question.