Reader Question | Can This Boot-Obsessed Mama Wear Her Boots All Summer? (Without looking ridiculous)


Reader Question:

I am writing in with a little style quandary that was inspired by your recent Style Rules for Moms part 1 – “if your bag is big and dark and leather, rethink the bag”.

It got my wheels turning, and made me realize I may be breaking a similar carnal sin – Wearing too wintery of a boot once the ice cream trucks are in full swing and the Hydrangea's start a-blooming.   While I always pack away the non-negotiably winter boot (black, over-the-knee, etc) I have one pair I just can’t seem to let go of for a whole season.  I invested in a pair of Fryes a few years ago, (specifically, the Carmen Harness Tall, in Brown), and ever since,  I think I may be guilty of wearing these bad boys a little TOO often.  I seldom put them away, even in the summer, and have been known to pair them with little sundresses  (even though I suspect the “boots + sundress” look might be slightly too Lilith fair 1994 for me to pull off at nearly 35 years of age..) 

Anywho,  I LIVE for these boots.   I wear them with EVERYTHING.  In the attached pics, you will see them worn last April (when I was 8 months pregnant):  


You will see the Frye Boots on the BEACH, in the sand,  in MAY.   Gasp!  I KNOW. 


See? I think I have a boot problem.

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I have had my eye on ANOTHER version of the SAME boots, the Carmen Harness short, in a sand or buff color, in the hopes that maybe that would be a little more acceptable in the warmer months to come?   

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Is this terribly misguided?  Am I boot blinded?   Save me.  Can I wear this kind of boot with a summery dress?  I love the way the slouchy distressed boot adds balance to my 5’10, size ten footed, size 12-14 bod.  And while I love the look of the shoes you posted last week, I fear the look might not work on my frame.  I tried the Madewells Whistlestop sandal you featured, they don’t work for me.  Not enough heel maybe, and I felt like they made my legs look stubby.  I need a little more of a heel, or else I feel like I walk like Shrek.     

– Sarah



Sarah.  I have been giggling over your email for the last few days.  I LOVE it.  I LOVE your style quandary and your phrase "boot blinded".  I promise you will see that little gem again on this blog.  (But Shrek?  OMG – maybe if Shrek was a tall, gorgeous Mama with fab boots and a cute baby.  Theeennnn maaaaybe I could see the resemblance.)

But let's chat about your potential boot blindness:  You love your boots, you are comfortable in your boots (even in the warm summer weather, at the beach, etc), the boots are obviously fab….but can/should you wear them all summer?

Why not?

Here's the deal: Sarah, these boots, for now, seem to be your thing.  And if you are totally comfortable and happy…then heck yeah!  Rock 'em all summer.  This is the kind of style diversity I love – it keeps us from all looking like clones.

To make your boots more summery, you are definitely on the right track.  Personally, I think the boots + sundress look is a classic.  I don't know if it's the Colorado/cowgirl influence or Lilith Fair (yup – you and I are the same age)…but I like it.  A lot.   

A few days after I received your email, a Sundance catalog came in the mail (IknowIknow).  But GUESS WHAT THEY HAD?  Yup:  Boots.  With sundresses.  And shorts.  Yee haw.

(photo credit:

Anyone else surprised by how much they like these looks?  Cute, right?  And that maxi is too die for.

But Sarah, here's the thing:  Your existing boots, although a darker color than the ones pictured, aren't that far off.  I think the most important point here is the height.  In the summer, a shorter boot looks much better.  Observe:


(THE LESSON, Mamas:  A lighter boot will almost always be more versatile.  So choose carefully.)

Sarah, you could buy the same boot in the lighter color.  You could.  And I've done the buy-two-in-different-colors-because-the-perfection-is-not-to-be-matched game before.  So I get it.  HOWEVER.  Each and every time I've bought another, uh, <insert fav item that is being worn daily> the minute the new (similar) item arrives…I'm over both of them.  Totally. Over. Both.

It's like the magic has worn off.  So proceed with caution.

If you are willing to branch out, just a teeny bit, I'm thinking that a boot reminiscent of Isabel Marant or Rachel Comey booties would work:  

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Isabel Marant suede ankle booties, $580 | Rachel Comey Huron boots, $420

I don't know how closely you follow trends, but the two above booties are hot.  And have caused a whole rash of knock-offs.  Steve Madden makes a pretty good one.  So does DV.  But I'm kinda partial to these:  

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Marta Crossover Boots, $168

Still boots.  With a heel.  But the shape, while pleasantly chunky, is a bit more modern, and the zippers are pretty rad.  These would pair easily with shorts/sundresses/etc.  

OR…if you want to get REALLY WILD AND CRAZY…remember M's shabootie discussion?  I'm really loving these:

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Chunky Heel Shootie Sandals – OMG!  That's the name!  Really!  $160

The heel might be too high to be practical, but wow.  Sundance.  Who knew?

Sarah, if I were you, here's what I'd do:  

  1. Try your existing boots with some sundresses and shorts – they just might work.
  2. Try on a few alternate boot styles (in a lighter color) and a few seriously cool shabooties.  See how you feel pairing the new styles with your existing go-to outfits.  They might just change the look altogether (in a good way), giving you more wardrobe diversity.  


Once you've played around a bit, then make your decision.  But really, there's no wrong answer.  You have some fab boots, and you are looking at other fab boots.  Trust your gut.

(And WOW. Can anyone use 'wardrobe diversity' and 'boot blindness' in the same sentence?) 



ps.  Wondering why this isn't Part 3 of our Summer Style Rules series?  Yeah…it's not ready.  In the last article, I'm attempting to clear up crop-pant confusion and Mamas:  It is NOT easy.  It is starting to feel like rocket science (which makes me laugh – forget missile warning systems – cropped pants are TRICKY.  There's so many!  With subtle differences!  How to break it all down?? Ooooh…my head….)  So I'm going to go home and raid my mother's closet – the woman could outfit a baseball team with all of her cropped pants.  



  1. It’s fun to see Sundance stuff here. I actually own a lot of Sundance pieces that I adore! Sometimes their clothes veer off into crazy-cowgirl territory but often they nail the effortless boho thing, which works well for mid-30’s Momming. The boot pics you pulled sum it up. (PS love the original poster’s quandary as I always hate putting away my boots in the spring!)

  2. Great post! I love the fact that you are able to give suggestions to let Sarah stay within her comfort zone yet mix things up a bit. For isn’t that what our mom style is all about?
    And, I have never had even the least bit of an inkling to wear something from Sundance. However, I too received their catalog in the spring and have been loving that maxi dress!
    Question- with the shorter boots, is there a general rule of thumb of how high? You know how you are trying to figure out the crop pant dilemma? Well, for me, the shorter boot presents the same challenge…I don’t want them to hit at an awkward place on my calves…Thoughts?
    Thanks again for the great post- you rock! And, Sarah, you look FABULOUS!!!! Keep rocking the boots- you are beautiful chicky!

  3. Hooray! – I’m SO looking forward to your post regarding the cropped pants. I’ve got a lot of them but am completely ignorant as to which ones are stylish and which ones are close relatives of the mom jeans.

  4. Ha! I wore my Frye Cindy Slouch boots (in the light natural color) with a black sundress and denim jacket on a 70-degree day this week and was starting to wonder the same thing. Thank you for the tips!

  5. Great post – I had exactly this dilemma too. I LOVE my Frye boots, but then seemingly overnight no one was wearing boots anymore. Mine are mid-color, but tall. Guess I’ll put them away and look forward to fall.
    So happy to hear you’re coming back to cropped pants! I’m still completely at sea trying to figure them out. In fact, I was just trying on a pair of jeans yesterday that had shrunk oddly in the dryer — too short, and also tight on top but wide at the bottom. I thought, what if I roll them? Do ankle pants have to be narrow on the bottom? I have no idea, but maybe you do!

  6. Nice. I can’t wait for the cropped pant post! I just tried to make a boyfriend jean look with some old boot cuts but I’m not sure about the width of the roll. I feel like I’m wearing rolled up boot cuts, not fooling anyone. I tried googling the boyfriend jean and scouring clothing store websites but found a ton of different cuff widths and different overall lengths. Now I’m confused. What works and what doesn’t. Wow, part 3 is exactly what I need! Cannot wait.

  7. Love this post and all the looks, and i have never heard of Sundance, totally my style!
    I am sitting on the edge of my seat waiting for your cropped pants thesis!

  8. This post is seriously hysterical! The original email from Sarah cracked me up & I echo Shana’s sentiments – gorgeous Mama! Gorgeous baby!
    Gorgeous BOOTS – I used to do the same thing when I lived in colder climes (Chicago), esp if I was in need of a pedicure.
    Maybe it’s kind of a regional thing? The boots can totally go farther into spring/summer when you live in places like Denver, Chicago, San Fran, New England or at Lilith Fair where there is something of a cowboy vibe.
    Or maybe I am just an old fart & need to start breaking more style rules. 🙂

  9. Thanks for posting my question! I was afraid you might suggest my family conduct a Boot intervention (Boot-er-vention?), so I’m super psyched to see there’s still hope for this look. I’m digging the dress/boot pairings you found in Sundance, and thinking my Fryes might work – They actually have a pretty good slouch to them, and aren’t nearly as tall as you might expect.
    You talked me off the ledge about getting the same boot in a different color. I’m def not willing to risk killing the magic of my original Fryes by introducing a twin. But I should mention, the ones I was considering are not ONLY a lighter color, they are shorter too. So while they’re pretty similar, they are a LEEETLE different (like a cousin, or a brotha from anotha motha, if you will.)
    I must admit I’m pretty smitten with the Marta Crossover boot you suggested – the chunky stacked heel and stitching around the toe is reminiscent of my old standbys, but the zipper and ankle height adds some serious freshness to the look. I just wish Sundance had some shots of these boots styled for summer! It’s always helpful to see how the shoe actually looks on the leg, as opposed to a standalone pic of just the shoe itself.
    Thanks again for enabling me and my boot habit. And be warned, guys – Comfy boots like these are a total gateway shoe. Once you try em, you just might find yourself reaching for them every day. I, for one, decided it was time to get help.

  10. I wasn’t ready to put ALL of my boots away, so when we had a low-70’s day last week, I have to admit I played the tall boots + short shorts game. I think it worked…

  11. Along with the crop pants tutorial, can you also include one on the tucking of tops? I keep trying it -I LOVE the James Perse tops. However, I have no idea if I look cool and hip a la you gals at ANMJ or if I look completely ridiculous!
    Thanks for helping all of us with our rocket science questions regarding wardrobe essentials!

  12. Nordy’s has another great Isabel Marant knockoff–the Report “Marks” bootie–that I’m strooooongly leaning toward buying, like, yesterday. But seeing as how I am eternally babywearing, and will be for a long time (LO was just born on 4/20/12!), I wonder if you’d consider these 3″ stacked heels babywearing-friendly? I’m trying to remain at least slightly practical here… Yay? Nay?

  13. Oh, and for the record, I am strongly pro-mid height boot with shorts. My 3.5 year old looked at my most recent pairing of harness boots/shorts and said, “Wow mama, you look reeeeeeeally cool!” (Gotta love the toddler fashion police.) I’ve also been known to rock the short Minnetonkas with shorts/skirts as well.

  14. Last summer I wore my black docs with faded black cutoffs all. summer. long. I had a rotating cast of bf’ing friendly shirts, threw a scarf on, and called it a day. I felt like an awesome bad*ss all summer long, like a Laura Croft version of myself. So when I saw this post I thought, “H*ll yeah you can wear your boots through the summer!”
    Awesome ideas for lightening things up though, I’ve been coveting a pair of the short Minnetonka booties for a while and I think you’ve convinced me that I NEED them! (my husband will send his thanks, I’m sure!)

  15. I’m a year around boots kind of girl too haha. I think I have boots syndrome soo I can one day wear boots to the beach at a whim as well =) glad im not the only one who is like this

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