Winter Shoe Essentials For Moms – A List of Must-Have Shoes


PA110014 "if a woman…never takes off her high-heeled shoes, how will she ever know how far she could walk or how fast she could run?"  

                            –Germaine Greer

While Germaine Greer was speaking figuratively, us moms can certainly take a literal translation of this quote.  High heels make it tough to be an engaged, involved mom.  I can't climb the jungle gym in my heels, I can't kick a satisfying amount of leaves in my heels, and baby-wearing?  Not for any length of time in heels.

Prior to having kids, I only wore heels, and consequently, was able to get by without
hemming my jeans or revealing my true height.  But once the little man was born, most of my heels were set aside so I could find out, like Germaine Greer said, "how fast could she run".  (NOTE:  Just fast enough to keep my toddler from throwing himself into the street, but not fast enough to prevent him from launching off the back of the couch.)

The shoe thing has been one of the biggest fashion challenges I've faced since becoming a mom.  It's amazing how so many of my "go-to" outfits now look a bit off when paired with flat shoes.  Trying to figure out the whole stylish mum thing was an exercise in frustration….but was also the impetus to start this blog. 

At some point in the last two years, I finally bit the bullet and hemmed several pairs of jeans to be worn with flat shoes.  Based on feedback from some of our previous shoe posts, I know many of you are also struggling with this same cute-yet-flat shoe dilemma.  Can one actually be stylish (and warm) in flat shoes? 

Yes.  Absolutely.  Based on current trends, and the fact that winter has arrived, here are a list of mom-friendly shoes that I think every mom should have in her closet. 

(NOTE for working moms — this list is does not include any of the fabulous heels you can still wear to work.  My definition of mom-friendly shoes are shoes you can wear when the little ones are actually with you.)

1.  Boots to Wear in the Snow

Unless you live in the South, the need for this one is obvious. But the good news is that this year's crop of winter boots are the coolest I've seen.  Well, the coolest I've seen since my hot pink moon boots at age eight.  Check out M's post on Hot Cold Weather Boots For Moms  – the name pretty much says it all.

2.  Flat Tall Boots

Every mom needs a pair of flat, tall boots.  These aren't snow boots, you want something a little bit dressier.  These are the boots you wear when you and the little one are running errands, going to the museum, the zoo, or strolling downtown.  These boots can be worn over tights, leggings, or skinny jeans. These boots can be slipped under cuffed boyfriend (or straight leg) jeans.  In the spring (or early fall), these boots are great with skirts or summer dresses.  You want something comfortable, yet something fabulous.  One great pair of flat boots can make an outfit.  If you are worried about pulling off the skinny jean look, a substantial or slouchy pair is the way to go.  UPDATE:  Here's our list of Fav Tall, Flat Boots.

3.  Sturdy Wedge Heels

These are obviously not your playground shoes.  However, a pair of cute wedge heels are perfect for family outings or other times when you have HELP.  If the whole fam is attending a kid's birthday party, a BBQ, going out to lunch, or for any other occasion when you want to feel a bit more festive but still need to be able to keep up with the kiddo, a sturdy wedge heel is your best bet.  You won't be able to baby-wear for extended periods of time, but that's what your partner is for, right?  My current favorite wedge heels are in boot form (perfect for winter) but there are tons of other options.  UPDATE:  Here's our favorite Sturdy, But Cute Winter Wedges for Moms

4. Cute Sneaks

Cute sneaks are a mom's best friend.  Cute sneaks can go virtually anywhere, with the added benefit of being perfectly suited to playground stops, games in the park, and leaf kicking.  The only weakness of the cute sneak is snow.  In that situation, see #1 above.  I've covered my favorite cute sneak options in the guest post I did for Rookie Moms (also be sure to check out the comments for more ideas).

5.  Cute, Comfy Flats

A cute, comfy flat is a necessity for those times when your outfit calls for something a bit more feminine than a cute sneak, but you want something just as comfortable.  In the winter, cute flats look amazing with thick tights, leggings, or even little socks paired with jeans (especially boyfriend jeans).  For specific ideas, M has been hard at work rounding up the cutest pairs of comfy flats.  Her post can now be found here!

6. Amazing Going-Out Shoes

All moms need one pair of super hot shoes for parties, date-night, etc.  This should be the shoe equivalent of a black lace bra:  pure sex.  Ideally, it should also go with a wide range of outfits. UPDATE: Here are my current favorites.

7. Flip-flops

Flip-flops in winter?  Yes – have you seen the floor of the pool locker-room?  Also, winter brings winter storms and stranded travelers, so make sure you throw a pair into your carry-on.  I've been in many a skeevy hotel room, thankful for my flip-flops.  My hands-down favorite pair for both comfort and style are the Ginger flip-flops by Reef.  Go with a solid color – brown, black or white. 

8. Slippers

C'mon girls – we wear these things all of the time.  Let's get some cute ones.  And this season, there are many, many cute ones.  M has been talking non-stop about the amazing slippers she's found.  And after her post next week, you will be too. 

9. Trendy Shoes to Change Things Up

If you hate fashion, or just want to stick to the basics, you can skip this last shoe recommendation.  However, for those of us who consider fashion a passion, this category is nothing but fun.  There are a number of trendy shoes that are, in fact, mom-friendly.  They may not be your daily go-to shoe, but for those days you are feeling inspired, or want to shake things up a bit, these shoes help you do it.  But because these types of shoes are trendy, you don't need to spend a fortune.  If you find yourself considering a trendy new shoe style, you can always do a "test run" by finding a cheap version at Payless or Target.  Then, if you find yourself wearing it over and over, trade up for a more expensive (and better made) version.   

One last thing to consider:  if your shoe wardrobe consists of nothing BUT these types of shoes, you are looking at a dysfunctional shoe wardrobe.  It might be time to spend some $$ on more practical shoes. 

My favorite trendy shoes for moms include: 

Uggs — I know there is lots of Ugg hate out there, but I am a firm Ugg-lover.  So much so that I will be posting (at some point this winter) a post on how to wear Uggs.  There is a way to make this style work.

Flat Ankle Booties — I especially like these with a slight rocker vibe.  See my previous post.

Flat or Low Heeled Over-The-Knee Boots — My favorite picks are in our Mom Street Style post for October.

Oxfords – You know the shoes your Dad wore to work?  The slightly glossy leather dress shoe that ties?  That's the one.  They are making these for girls in patent leathers, and other fun colors.  I think I love them…they are very androgynous looking, so I would suggest pairing them with a feminine shirt.  Let me think about styling tips and get back to you.  My current favorite pair is actually a bootie, the Jeffrey Campbell Berry Oxford Bootie, $158 at Urban Outfitters.

Doc Marten Style Boots – These are basically combat looking boots.  I hate wearing actual Doc Martens because they require too much time to break in, but there are a ton of similar style boots.  I'm loving black ones paired wit
h leggings and an oversize cozy sweater. 

Moccasins – I love mocs.  If you do too, just go right to the source:  Minnetonka.  I've been coveting my friend Jayme's, and will try to do a little write-up on this style later this winter.

A whole week talking about shoes?  Bliss.




  1. Love this list of shoes and can’t wait for more details! As a Mom of three, I have to add in a pair that is my absolute essential, everyday stand-by, super comfy and cute Mom shoe:
    These mary janes go with skinny or boot-leg jeans, skirts or slacks. I get tons on compliments on mine and I’m sure that someone else will delight in this find.

  2. Is it bad that I have everything on this list? Sheepish grin…
    However, I feel like I should make a special plug for 2 things in the “trendy” category–oxfords and moccasins. I bought a pair of soft grey suede oxfords at the very end of last winter–I decided they were so hideously ugly they were cute. And they ARE. I wear them mot of the time with rolled-up boyfriend jeans, striped socks, and a cashmere sweater–such a fun little update to my normal wardrobe.
    And I bought my Minnetonka moccasins about 6 weeks ago–and have worn them at least part of every day since then (they are on my feet right now–they helped me rock out at a Grace Potter & the Nocturnals concert!). They are like soft, squishy little clouds for your feet. I pick up the mail in them, throw them on with a maxi dress and a scarf, toss them on with jeans and a fleece. Unbelievable. They have definitely become my “pregnancy shoes”–and they’re still so cute!
    I too have had a hard time giving up my heels, and I certainly still wear my cute pumps to work most days. But shoes like moccasins make the sacrifice worth it–both stylish and MUCH better for my feet!

  3. Molly – thanks for the shoe reco! One of my friends has this shoe, and she was running late for something, but was out walking with the kiddo when she remembered…anyway, she ended up running, with the kid in her arms, over a MILE in these shoes. She said they were as comfy as running shoes! Can you confirm? Are they that good?
    Tegan and Tage – I heart your encouraging comments! Thank you!
    Amy – You might be, quite possibly, the most stylish pregnant chick ever. I am totally going to copy your oxford shoe look (are yours comfortable? I’m having trouble finding a man-style pair that is totally comfortable…I’m very picky in the comfort dept) and I really, REALLY must have “soft squishy clouds” for my feet. Really. Mocs will be mine.
    And think about sending in a photo of your bad self in your oxford shoe outfit. You’d be a great mom of the month!

  4. Christian — To add our blog, look on the far right hand side. There should be a couple of choices: you can subscribe by email by entering in your email, or directly below the email form, there should be a big orange button next to the words, “Subscribe in a Reader”. That’s the RSS feed. If you click the button, you should be prompted to select which RSS feed reader you are using (Google, Yahoo, etc)
    Hope that helps!

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