Reader Question: Footwear For When It’s Too Hot For Boots, But Too Cold To Go Without Socks


Reader Question:

I am a mama of twin 5 year old boys.  I have recently found your site and love it!  I work from home so I easily fall into the trap of wearing the same old unfashionable clothes and have also been known to go a day or two (or three!) without showering.  Your blog has really helped me take on a renewed focus on being more fashionable and just feeling better about myself.
One area that I continue to struggle with is shoes.  I live in Michigan and find that there is a period of time between winter and spring where I don't know what shoes to wear.  It is not cold enough to wear boots, but not warm enough for sandals or flats with no socks.  I struggle to find fashionable shoes that I can wear with some type of sock, and have them be comfortable.  I need to chase around my boys so comfort is a must.  But I also don't want to look like an old lady in orthopedic shoes.  Can you please help by giving me some suggestions?  





Sarah, thanks for writing in!  Growing up in MI myself, I know exactly what you are talking about.  And this transitional weather often drives me crazy, too.   But I've been thinking about your request…and now that the weather in Philly is chilly again I've found myself struggling with the same thing.

Here's what I've been happy wearing…


I don't typically wear these shoes to the park, but for general errands and outings with the kiddos, I find the heel comfortable enough for baby-wearing.

Note my Smartwool socks peeking out.  Navy denim + navy-ish wool socks = close enough.


 (wearing: Levis skinnies, J.Crew Factory sweater, Madewell plaid shirt, Clarks booties, Bella leopard-print baby carrier. Makr backpack, Salt sunnies)

Cute Sneaks

I'm slowly figuring out the whole cute sneaks + skinny jeans thing.  Personally, I like this look a whole lot better if the skinnies aren't legging-tight.  But that might just be me.  And since I'm not the tallest person around, I roll 'em. 

My converse are high-tops, but this look would work even if a bit of white sock showed.

(Also?  This is a different day….but Raines likes to wear the same thing over & over & over….)


 (wearing: J.Crew sweatshirt, Stylemint tee, Urban Outfitters faux-fur cowl, Paige denim leggings in tumble wash, Converse hightops, Makr backpack, Salt sunnies)

Cute, Patterned Socks (wear with almost any shoe)

Ok – I've talked about loafers and socks before in our Shop Your Closet series.  If you recall, I wore leopard-print socks with loafers and cropped denim.  The same idea could work with other shoes.  The key, I think, is to show off your patterned sock by rolling your denim just above the ankle bone (or by wearing cropped denim).  The look is quirky, to be sure, but it's cute and intentional.

Even TOMS work…although I had more luck with my solid TOMS than my patterned ones. 


 (wearing:  Levis denim leggings, Gap sweater, Happy Socks striped socks, TOMS, Rayban sunnies)


Also….oxfords!  I don't own a pair of oxfords, although I'm drooling over these (Cole Haan Alisa Oxford, $178 at Nordstroms):

Screen Shot 2012-03-28 at 11.22.01 AM

Or maybe even these (b.p. oxford flat, $60 at Nordstroms):

Screen Shot 2012-03-28 at 11.23.09 AM

In any case, oxfords would look adorable with a patterned sock and a boyfriend jean (or skinny, of course).


Soft Booties (Mocs)

You guys have seen the below pic before, here, but Moc booties are a great Spring transition boot.  They are soft, comfortable, and will look cute with socks now (only a teeny tiny bit will peek out) or with bare legs later.  One of the few pairs of shoes I own that are just as comfortable with and without socks.  

Screen Shot 2012-03-28 at 11.41.35 AM


Wear Flares With Caution

Lastly, you can wear flare denim over practically any 'ol comfort shoe (and sock)!  Even…sigh…orthopedic ones.  My mother does this.  (Who is, at this moment, having a heart-attack that I called her shoes orthopedic.  Let's just stick with 'comfort shoes' shall we?  Besides, they do look cute from under her flares…like I'd let my own mother venture out in public looking orthopedic.  Never, Mom, never.  I swear.)

But!!  A Warning!!!  A Flare Warning!!  When wearing flares, consider first how much actual mama-running is needed.  After several face-plant incidents (by, um, me), I stopped wearing my flares to the playground (or – even worse – the soccer field).  R is just so fast now that I need to be able to run – like, really, really run – in order to keep up with him.  And I found myself tripping over the wide flare (even when wearing flats!).  

So…twin 5 year old boys you say?  I'd stick with loafers, TOMS or cute sneaks.

Sarah, best of luck and I hope this helps!!



  1. These are great! I love the booties – both the first look and the last one with the mocs. Where did you get them? And, it is so helpful to see how to wear the jeans – between skinnies, looser skinnies, rolled, or unrolled.
    Thanks for the post!!! Oh -and I am in LOVE with the back pack!!!

  2. Back in my pre-baby days I would do the not-so-tight skinnies with sneaks. Usually my low-top Converse or a sleek-not-sporty sneaker. Now I can’t get away with wearing skinny jeans, but it’s still one of my favorite looks. And I’ve done the TOMS/striped sock too.

  3. I saw you mention mocassins and I had a question. I bought some Minnetonkas and the due bled on everything – socks, my legs. How do you deal with that? I reluctantly returned them but still really want a pair!

  4. I love the striped sock look, and the booties. I have a pair of inexpensive ankle books with a great chunky heel that I love for spring, especially with bootleg jeans. Living in New England, spring is usually so wet & muddy that having a bit of a heel makes navigating easier – plus it makes me feel a little dressier. As the weather warms, I switch to flats or loafers without socks.

  5. I’m with Rebecca. Can you please give an update of how the Makr backpack has worked out as a diaper bag? I’ve had my finger on the submit order button since you posted these pics the other day. Thanks!

  6. Thanks for the comments, girls!
    Beth – the booties are from Clark’s, of all places. I LOVE them – so comfortable!
    Jess – The tye-dyed denim is Paige’s Verdugo (sp?) legging jean in Tumble wash. They are at Nordstrom’s. Styling these is actually really similar to M’s write-up on her leopard-print denim. I’ve actually been wearing them the same ways….
    Miranda – Mine too! I didn’t actually notice this problem in Denver…since it never rains, but OMG out in Philly it’s a whole different ballgame. I try to save them for cooler and dry days. I know Lane found a pair in a soft gray that probably would be better…but UGH. It is annoying.
    Ok – the Makr backpack: I can easily fit my wallet, sunglasses, a million lipsticks, etc as well as 2 diapers, a large package of wipes, a Sigg bottle, snacks and a change of clothes for Pax. If necessary, I can throw in a change of clothes for Raines. And we often take it to the library – I’ve thrown as many as 12 kid’s books in that thing. However, the more stuff I add, the harder it is to root around in there. Cleaning has actually not been a problem – I’ve spilled coffee on it a million times and just spot-cleaned it right out. HOWEVER: The tab closures are annoying. As the bag ages the leather gets softer and I can now open and close the flap pretty easily, but at first it was me, balancing on one leg, trying to hold up the bag with the other knee while holding babies and trying to force stiff leather through a small opening. Not fun.

  7. Great post 🙂 I am loving my Bass Ely oxfords for spring. They can be worn with or without socks very comfortably – I roll up my skinnies to show a little ankle. — Lauren

  8. I love this site! I just discovered it while searching for cute pregnancy clothes (I’m 12 weeks tomorrow), and it’s such an awesome resource. Also, I just bought those Clarks booties – I can’t wait to get them! Perfect for not-too-pregnant winter/spring here in NYC (once it warms up!!!)

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