How To Rock Skirts With a Toddler Underfoot


One of our readers asked about skirts.  Which is a good question.  With the exception of maxi dresses this past summer, I last wore a skirt on January 2nd, 2008…aka three days before R was born.  I am clearly not qualified to answer this question.

Emily, however, is.  Em (pictured below) is Raines' fabulous, much-loved nanny, and she comes over – each and every time – dressed like this.  Totally adorable.  Totally comfortable.  And usually pant-less (in a non-Lady GaGa way).


Em's wearing:  similar shirt, Target boots, similar skirt, and Hue tights.

Em, it turns out, is just more comfortable in skirts, and never considered abandoning them even in light of her current profession. After years of nannying in a skirt (for kiddos of all ages), here are her rules for rockin' the skirt with toddlers underfoot:

1.  Obvious:  Be very careful sitting and crouching 🙂

2.  Maxi skirts & maxi dresses are the easiest option.  They can easily be maneuvered so that you are completely covered, and the risk of the wind blowing it up is almost non-existent.

3. With shorter skirts, dark tights/leggings are a must.  (Especially for the park, library, etc, anywhere with crouching/bending…so I guess everywhere.  This way, if your skirt accidentally gets pulled up while a cute, blond two year old plays with it you are essentially covered…and only minimally embarrassed.)  Speaking from experience, Em???

4.  Short skirts can work…but watch the flowiness.  The shorter the skirt, the easier the wind flips it up…or the kiddos will want to hide in it.  "Look Em – it's a tent!"  Keep the short skirts a bit tighter (like a denim mini).  The easiest skirt it a little bit flowy and hits right above the knee.

5.  When all else fails (or the summer hits) I wear biking shorts under the skirt…but these are not to be shown!  No early 90's here!!  This way I can move around without thinking about what I am wearing.
It all comes down to the fact that I would rather show too much leg than wear pants and risk muffin-top, a crack showing or the inevitable hiking up of the pants all day long…ha!  Maybe I just need new pants?!



And here are a few outfits that Em picked out for us….

Look 1 – Short Skirt

Em says, "I think this short skirt would work because it doesn't have a lot of volume and a legging or thick tight would cover everything up."

Look 2 – Mid-Length Skirt

Em says: "I love this skirt because it is so multifunctional…casual with a loose shirt tucked in and either an oxford or ankle boot.  Or it could be a little dressier with a tighter top and heels.  Also, it's a perfect 'mom' length. :)"


Small Tucks Skirt
$206 -
Striped skirt »



Bronx 'Heather Bee' Oxford
$79 -
Oxfords »


Look 3 – Maxi Skirt

Em says: "I love the idea of a maxi skirt (could also use summer maxi dress) with a cropped/boxy shirt.
I'm not sure what shoes would work (I certainly wouldn't wear these boots often!) but I do like the idea of a lace-up boot."  (NOTE from S:  I second the lace-up boot choice for winter.  Once Spring hits, you could even do a ballet flat or TOMS.)

Em – LOVE all of these.  Thanks, girl!

Gah.  If Em ever leaves us, I'm screwed.  Not only will have to find another fabulous nanny (sob!) but I'd have to write into the job description, "must also have impeccable taste and show up in totally inspirational, yet functional outfits."  I'll be the crazy-lady over at ABC nanny services fo' sho.





  1. “It all comes down to the fact that I would rather show too much leg than wear pants and risk muffin-top, a crack showing or the inevitable hiking up of the pants all day long”
    I’m laughing, but it is completely true. Today I’m rocking a sweater dress, crazy warm Lush fleece tights (thank you) and boots in the snowy midwest.

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