Reader Question: What Types of Footwear Can You Wear with Leggings and Skinny Jeans?


Reader Question:

I have recently fallen in love with skinny jeans and leggings.  Heels really aren’t my thing and normally, I would wear UGG boots or ballet flats, but some outfits just don’t call for the winter boots but I am too cold to wear ballet flats.  Are there any other comfortable, warm choices you would recommend to go with skinny jeans?  Is it ever ok to wear a street shoe, like my slip-on sketchers with socks, with skinny jeans.


I love that you are embracing skinny jeans and leggings!!  But footwear for these styles can be tricky.  Let me first try to address which footwear I think looks best with leggings and skinny jeans, and then take on the more specific part of your question about leggings + sketcher sneaks.

Best (Easiest) Footwear Choices With Skinny Jeans & Leggings

1.  Boots

We’re talking any shape of boot, with any heel height: flat boots, high heeled boots, ankle boots, knee-high, or over-the-knee boots.  They all work.  In fact, boots of any shape and style work: winter boots, western boots, motorcycle boots, sleek boots, moccasin booties, rain boots, combat boots, rocker booties with chains, etc.  You get the picture.  Whatever you’re boot fetish, I’m willing to bet it will look amazing with skinny jeans or leggings.  Be wary of traditional Uggs (I’ll talk more about this below).  For a bit of inspiration, check out our November 2009 Street Style Mom, or the pics below (all from

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Lastly, I’m loving the outfit put together (pic below)  by K_Isa_Bella on  The socks and lace-up boots look just so cool.  You could certainly use this idea of layering socks and boots with other boot styles.


2. High Heels

Pumps and complicated strappy sandals are my favorite types of high heels with skinny jeans and leggings.  It’s just a wildly sexy look.  Probably not the best look for a playdate, but for date night?  Perfection.  A few pics for inspiration from

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3.  Ballet Flats Without Socks

1-twh_normalThe easiest way to wear ballet flats with skinny jeans and leggings is without socks, and to make sure your leggings/skinny jeans aren’t too long.  For leggings, jeggings, or really tight skinnies, you’ll want these to hit right above the ankle or above (cropped can be cute too).  To beautifully illustrate this point, check out the pic at left.  Erika from has put together several leggings outfits that I love (click the link to see all of them).  The outfit we’re showing is a perfect example of leggings and ballet flats, and I love her scarf embellishment.  It’s casual, comfy and ever-so-slightly glamorous.    Another pic for inspiration can be found on our post featuring Size 12 Skinny Jeans from Fashion for the Economically Challenged.

4. Flip Flops and other Strappy Flat Sandals

Self-explanatory, right?

5.  Clogs

Clogs are all the rage this Spring, and I’m especially loving them with leggings.  They are a nice, crunchy counter-point to sexy, sexy leggings.  Who knew?  And yes – they would also pair great with skinny jeans. (NOTE:  I’m talking about traditional ’70’s inspired high heel wood Clogs, not Danskos.)

However, high-heel haters take heart:  Clogs come in a wide range of heel sizes, and even clogs with a smaller heel work – you just want the traditional 70’s styling.

Proceed With Caution

1.  Traditional Uggs

Be careful when wearing traditional Uggs over skinny jeans.  The boot (despite looking so puffy) is a pretty tight fit around the calf.  If your skinny jeans have any bulk or extra fabric, your legs  will look like a stuffed sausages in your Uggs.  Leggings are a safer choice for traditional Uggs.

2. Wedge Heels

Unless your high heels are all kinds of strappy fabulous (and you want to show them off with ankle length skinnies), the best way to wear skinny jeans with heels is to simply pull the bottom cuff of the jean down below where the heel and shoe footbed meet.  This trick makes your legs look miles long.  The actual heel of most stilettos curve, and this curve will hold the skinny jeans down.  Wedges don’t usually have this kind of curve in the heel, so skinnies have to be the perfect ankle length.  (Leggings are easier because you can always discretely fold them to the length required).

3.  Ballet Flats With Socks

Knee socks with ballet flatsFor skinny jeans, this is easy:  throw a pair of trouser socks with your ballet flats.  Adds a bit of warmth, looks cute.  But with leggings?  Yikes.  You definitely can’t layer leggings over socks, but layering socks over leggings can be a bit tricky.

I actually don’t have a great solution myself (and wasn’t able to find a pic of anyone else), but I haven’t given up hope.  My next attempt, inspired by a post Fashion Me Fabulous did on pairing knee-socks with shoes (see pic at left), will involve messing around with thigh-high socks and ballet flats.  I think it might be cute to layer the thigh-highs over leggings and then add in the ballet flats.  We’ll see.

4. Oxfords

With skinny jeans, I love this look.  And with skinny jeans I can easily wear the oxfords with socks – a plus for warmth and comfort.

With leggings?  Not…so…much.  Shopbop is showing this pairing (pic below).  What do you think?  Does it work?


5.  Sneakers

Sneakers are fairly easy to wear with skinny jeans.  But because skinnies leave so much shoe showing,  they must be cute, stylish sneakers.  Check out the post I did on Rookie Moms for some of my favorite cute sneaks (and read through the comments for more ideas).  Or for an inexpensive option, go with a classic pair of Converse – you can’t go wrong.

Sneakers and leggings however, is a different story.  At first blush, my response to your “can I wear my sketchers and socks with leggings) is a resounding no.  But….I hate saying no.  I like to believe that anything is possible – you just need to get creative.  So I did a bit of research and found a couple of cool examples of leggings + sneakers:

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The pics are annoyingly small, but I’ve linked back to their original sites, so if you click, you’ll see the original (larger) pic.

First pic is of Maite P. on  The vibe is a funky-athletic one, but the overall look is pretty cool.  I love the striped socks and simple sneaks.  To recreate you’d want to keep the colors fairly monochromatic like she does – with the socks, there’s just a whole lot goin’ on.

The second pic is of Karolin L. on  I think she’s only 13, which makes me feel really damn old.  In any case, I love the pairing of the over-sized sweater and ironic tube socks with sneakers.  Although, for a 13 year old, the tube socks probably aren’t ironic.  In any case, we can certainly use her fresh outlook for our own inspiration.

A few other ideas for sneakers + leggings

  • Converse High Tops – they are a bit boot-like, so would pair easily with leggings.
  • Sneaker-like shoes like Sanuks, Toms, etc.
  • Try a sneaker-ballet flat hybrid and experiment with layering knee-socks or thigh-high socks over leggings.

What do the rest of you think?  Do you have another fabulous footwear option for leggings or skinny jeans?




  1. great question. i tried my cropped black leggings wit black old school cowboy boots…did nothing but make my legs looks short and stumpy. i think it was b/c the boots were an odd length. since i’m not super skinny the only thing that really looks good is flats (but that equals cold feet/legs) or knee high boots (equals not good for playdats).
    i know you said either black leggings or dark grey are good. should a size 8/10 stay with cropped or could i go with full length leggings?

  2. Cindy – I would definitely try full-length leggings. Obviously, heels will make you look taller, but aren’t playdate friendly.
    You mentioned that your tall boots aren’t playdate friendly…but are they flat or heelded? I wear tall flat boots daily (including playdates). Finding a tall flat pair that is fairly sleek would work, or you could try the new western short boot. Regular cowboy boots can be tough – they often hit at the widest point of the calf. Experiment with different boot heights.
    Lastly, I really like Minnetonka’s short fringed boot. For a long leg line, try it in black.

  3. Esther – I love that idea!!! Big slouchy socks – who knew they could look so cool? Hmmm….am thinking legwarmers might actually do something fun, also…

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