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.




  1. Flares look refreshing after all that skinny. And high waisted denim just seems right. My concern is for us hourglass types. I am hoping I can pull off a wide leg pant instead of the stiffer flare, because flats are my friends. Thanks for the great post!

  2. For which type of pant are flats ideal? A bit slow on the style-curve, I’ve always thought flats looked better with flares or bootcut than with skinnies, because it seems like with skinnies my feet look huge (better with boots or with sandals, or at most flats without socks). But I’m probably wrong on this one, so please enlighten me!

  3. Very helpful post! I like to dress up, but when I am out and about with the kids, I like to just throw on sneaks and jeans. This summer I was wearing skinny jeans cuffed with my sneaks, but I didnt know what to do for winter. Thanks so much!

  4. I never stopped wearing boot/flare jeans in winter. They just work better with substantial shoes for me in cold weather. (Rolled + socks + booties = shortest short legs this side of Shortsville). I wear mine with Danskos, flat boots, cowboy boots, TOMS desert wedges, or casual sneakers.

    • OMG YES I DID! EXACTLY this. Thankfully, mine were on super sale but GAH!! It’s like I wrecked the most fabulous pair of flares ever. I’ve worn them – now as meh-bootcuts – around with my vans and…it’s…fine. I guess. Their only saving grace at this point is the fact that the pockets are so cool, so I try to keep shirts tucked in. But I’ll let you know if I have any epiphanies. (You, too.)

  5. I know this entry is from TWO YEARS ago but I am finding it super timely! I love this look (and your hair!) and would love to see your thoughts on how this translates to the styles this fall.

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