A Fresh Way to Wear Tall Boots



I think I have finally cracked the code, ya’ll. I figured out how to successfully wear tall boots day-to-day, without feeling way over-dressed.

I’ve tried over-the-knee boots with a short little shift dress and, while it was cute, it wasn’t exactly practical – with having to pick up kids, chase after kids and yeh, BE A MOM. I was pregnant, nonetheless! I know I flashed at least a few people that day – live and learn, live and learn.

I decided to go the opposite direction this time – slouchy, comfortable and decidedly more casual.

Spoiler alert:  I FREEKIN’ ROCKED IT OUT.









outfit details

dress: Anthro. Northward Swing Dress – I really didn’t think much of this dress on the hanger, but then I tried it on and…AAAH! Ya’ll. It’s now my favorite causal, day-to-day dress. It’s comfortable and looks amazing with boots and cozy sweaters. I really recommend it. (I am wearing a size Small)

poncho: Isabel Oversized Poncho – cozy, amazing color for Fall/Winter…and I can see myself wearing it all Fall and Winter. Amazing sweater.

boots: Sole Society Calypso Tall Boot c/o – the first thing I noticed about these is that they weren’t super tall, did not have a heel, but look SO SEXY. I like that. A lot. They work perfectly with a bit longer of a dress, too, which I prefer – having to carry the baby and run around after the two other kids. I LOVE THEM. (I went up a half size to a 10, to leave room for socks and such…and I’m 5’10, so for anyone shorter they’ll probably be more of an over-the-knee boot). >> These are selling out fast, so if you can’t find your size…their Andie boot is very similar. If you like a heel, I’d go with the Claudia.

bag: Sole Society Bridgette Handbag c/o – great bag…and it has enough room for diapers, wipes, baby snacks, my wallet, keys and phone. I put it through the mom test. Also, I’ve gotten a few compliments on it with people asking me, “where did you get THAT bag?!”. I assume that’s a good thing. haha.

earrings: Sole Society Front to Back Pearl Earring c/o – I love a non-bulky earring, so YES. These are winners.

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Have you figured out a tall boot formula? SPILL, lady.
>> follow me on Instagram (@camilledipaola) for more daily outfits, candid motherhood moments and a bit of our home
All photos taken by the super cool and talented Ariana Clare.
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Wife, mama of 3, true believer in the importance of finding meaningful ways to stay sane(-ish) throughout motherhood, such as style blogging, making absurd videos on Instagram & hiding in the guest room. It's not always easy, but when it's hard...there's always Netflix. *peace sign*

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  1. Can anyone speak to the quality of Sole Society shoes? I have my eye on a few pairs of boots, but while the price point is great it worries me that they’ll only last a year.

    • Yes! In general, I find Sole Society boots to be of really good quality, especially considering the price point. The fabrics (or leathers) are decent, it’s the other pieces of the boot (the actual sole, the heel, etc.) that doesn’t last as long as my Weitzmans, etc. They will absolutely last more than a year (and I’m pretty hard on all of mine), but they prob wouldn’t last a lifetime. I use Sole Society to try out trends before totally committing to them (OTK boots are a good example), or to just add a fun shoe into my daily rotation. Does this help?

  2. Cam – I love the poncho! It has been added to my wish list at Anthro -how do you think it will look on short girls (5-2ish…)?

    Also, I’m in Charleston for work the next two days – any recommendations on places to go and eat after 5 for a mom without her kid or husband???? 🙂

    • Hi Becky! I think it will just look even more cozy and cool, in my opinion. It was even a bit short in the front (where it wraps or knots in the middle). It could have been a bit longer on me. I would love to send you ideas for Charleston, too! What’s your e-mail? You can find me on IG and message me there, too! @camilledipaola Cheers, Becky.

  3. For some reason I just don’t like tall boots, but living in Maine if I need to dress up in the winter they are a necessity. I prefer them to be tall, right up to the Knee, but not over. Personally I think that is the most flattering. If you haven’t tried Wolky brand I HIGHLY recommend them. If you go through their Amsterdam website there are much more options than the US website. I have had one pair for over 10 years! You can walk miles in them. For a little dressier I prefer Cole Haan- also pretty comfortable.

  4. I love this whole outfit! Makes me yearn for the days I shopped at Anthro before the oversized trend took over. My hourglass figure (and post-baby enormous boobies) can’t hang with that. Will have to check out this dress. You are rocking that poncho!

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