The Most Comfortable Chelsea Boots (and All the Fall Feels)


There are few things that make me happier than the chill that Autumn brings. I flit around like a little Fall fairy, swathing myself in layers, sipping my hot mug of…err…warm-ish coffee (still have kids), playing all the ‘Fall Feels’ playlists, throwing open all of the windows around the house with reckless abandon. Yep. I open the windows when the autumn chill arrives.

It may seem like a weird thing to do, but I grew up with my parents doing this, and it honestly was one of the best things. I remember my dad walking around, singing, throwing open the windows. It was almost an invitation to the beauty of the golden Fall — to come inside and make itself known to us so that we could really appreciate it and live in it. We even slept some nights with the windows open. Now that I’m older, I appreciate my parent’s affinity for the outdoors, and their efforts when we were growing up to get all six of us outside to either hike, camp or just eat meals in the backyard. It’s something I’ve tried to carry over into our home and family life. Matt looks at me with that questioning stare every year now like, “you really gonna open that window?”…and I stare back at him as if to say, “HELLZ YES, I AM”. Up goes the window.

Some of my best moments with our kids have been when we’re outside together. We don’t always make it to the mountains or get much farther than our front door, but it never seems to make a difference. It’s just being outdoors that does the trick…or even just cracking open the windows! It never fails to make a bad day turn into a good one, no matter how thick of a funk we find ourselves in.

The Perfect Boots for Outdoor Fun

I actually chose the particular boots I am wearing, for this very purpose. When Born contacted us, I immediately landed on their Chelsea style boot. It looked comfortable and functional — something I could actually wear while adventuring around outside with the fam. Also, since this is always important to me when choosing footwear…I wanted it to look good. I have a hard time sacrificing what looks nice with functionality. I don’t have to give up anything with these boots, though!

blue suede chelsea booties

cozy sweater and jeans

navy blue born booties

ivory turtleneck sweater

fall style family

cool mom style for fall and winter

white sweater styled with denim

christmas card idea family

Outfit Details

boots: Born Casco Suede Boot (Indaco Suede) – I wear a 9.5 in most shoes but in boots…I always go up a half-size. I like having a bit more room for cozier socks, and I just find that boots fit better in a half size up. That said, I am wearing a 10 in these booties and they fit perfectly on my feet. I have a bit of room for chunkier socks when the weather gets colder. Also available in a cool grey and cognac brown.

sweater: Topshop Chunky Roll Sweater (wearing 6, which fits like a 2-4) – this is more of a boxy crop style, which I like a lot with either jeans or skirt that hit higher on the waist (like the jeans I am wearing). I like having a go-to ivory sweater in the Fall/Winter, and this one is a cozy little option.

jeans: Levi’s 501 High Waist Skinny Jean (wearing 27×28, TTS) – the 501 fit just so happens to be my favorite one to wear. I just ordered a couple more in a few different styles and washes, actually (I have a problem). They just fit me so well, and I haven’t had the problem with them being too short, even on my 5’10 frame. This particular pair has a button-fly, too, which makes me feel cooler…and more vintage-y. ha.

Shop My Favorite Born Boots

A huge thank you to Born Shoes for sponsoring this post! Your shoes are comfortable, functional and good looking. Also, thank you readers, for supporting us and the brands we work with. We appreciate it more than you know.


Find me over on IG, for more #totallycasualmotherhood moments (@camilledipaola).

Photos by Christina Hussey Photography.

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