You know, it’s funny. The exact reason I got the idea for Curvy Girl Guide two years ago was because I wanted to try tall boots, but I’m plus size,  had no idea how they would actually look, I couldn’t find any real life pictures, and all the boots I tried on in stores didn’t zip past my ankle. I wanted to see a person who looked like me wearing them.

I found wide calf boots online, but they were really expensive and I’m really cheap, so spending money that could otherwise be delegated to Redbox fees and Indian Food, which happen to always fit, was not in the cards.

I was just a girl with 17.25 inch calves in jeans, standing in front of the internet, asking it to tell me if I was going to look like I had sausage legs or not. The dream was back burnered.

Then, my friend, Emily, introduced me to, which is essentially a Zappos outlet, you have to check back regularly, and sizing can be spotty, but I decided to take advantage of the affordability to dip my toes in the wide calf boot pool. Color me addicted.

I spent six months accumulating tall boots on sale, and thanks to Andy, his fetish with making-out outdoors, my camera, and the fields behind my parents house, I’m finally ready to report my findings.

Boots: The very first pair of tall boots I attempted were these Fitzwell Valencia wide calfs; I found them on the cheap at, and I am so glad I started with these, because not only did they fit perfectly, they totally boosted my fat leg self esteem. The only pants that work for me under tall boots are jeggings or leggings, and I have plenty of room in these Valencia boots. I wear them almost daily. They are entirely soft and gorgeous leather. Worth every penny.

Outfit: I came across this huge men’s sweater on clearance at Gap, and immediately decided it would be my new favorite thing, and it is. It’s warm, I can cuff the sleeves a mile, and it’s the perfect around the house/running errands sweater over a fitted cami and a pair of leggings. This outfit is my happy place.

Fitzwell Valencia Wide Calf Boot, Black size 10, Zappos $169
Men’s Wool Sweater, size XXL, Gap $20.99 In Store Clearance
Women’s Stretch Leggings, Black size L, Old Navy $10
Stretch Cami, White size XXL, Target $8

Boots: Alright, yes. I wish I was Princess Kate. I drool over Wellies. I over-use the phrase spotted dick. I have a secret Spice Girl identity. But don’t we all? So I ordered these rubber boots to get me through the wet Ohio fall and then into a slushy Ohio winter. In theory, these boots fit, but they were tight and cut into the fat part of my calf; not super attractive. If I was wearing these under jeans, it would be fine, but I wanted to Pippa Middleton these suckers over my jeggings, so after thinking about it, I decided to cut a slit down the middle between the laces. This ended up working perfectly.

Outfit: This is my run kids to school outfit. I bought this canvas coat last year from Target and toss it over whatever top I roll out of bed in, add in some Old Navy Rockstar Super Skinny jeans (don’t let the name fool you, these are stretchy jeggings that I can pull up high enough to feel held in, like spanx, this is what thirty year olds do), and the rubber boots, and boom. I’m basically in Forks waiting to break headboards with vampires.

Tretorn Staika Wide Calf, Black size 10, Zappos $90
Green Hooded Army Coat, size XXL, Target
Grey Stretch Circle Scarf, click here for my tutorial
Stretch Cami, Navy size XXL, Target $8
Rockstar Super Skinny Jeans, Camp Fire size 14, Old Navy $29.50

Boots: I loved the black Valencia boots so much, I immediately ordered the brown version. They fit the exact same. I wanted to show you the side of the boot, you can see the soft leather, the full length zipper, and the buckles. I have learned, pull on boots don’t really work for me, I need the zipper.

Outfit: At first, I was disappointed this shirt was weirdly wide and not fitted, but then I realized it was a great casual shirt to wear over a fitted tank top and some jeans, and now I get to walk around feeling like Marin from Men in Trees (yep, I still miss that show).

Fitzwell Valencia Wide Calf Boot, Brown size 11, Zappos $169
Plaid Flannel Shirt, Yellow Check size XXL, Old Navy $13.99
Stretch Cami, White size XXL, Target $8
Rockstar Super Skinny Jeans, Camp Fire size 14, Old Navy $29.50

Ok, so these aren’t boots, but I wanted to show y’all a different option for skinny jeans in the fall. I love rolling the bottom cuff once and pairing them with some ballet flats and a cute layered sweater.

Leopard Ballet Flat,Target
Alpaca Wool Scoop Sweater, Oatmeal Heather size XL, Gap $59.99
Stretch Cami, Nude size XXL, Target $8
Rockstar Super Skinny Jeans, Camp Fire size 14, Old Navy $29.50

Boots: I mentioned a couple of weeks ago that I had been eying some wide calf Frye boots, but I just could not pull the $328 trigger on boots that I couldn’t guarantee I could pull over my legs. I loved the worn look though, so I spent 100,000 man hours reading reviews and decided to give these Enzo Angiolini’s a try. They look a little more aged than the Fitzwell Valencia boot, and the buckles are awesome. However, they are kinda tight, half an inch more and they’d be perfect. They don’t look cheap, it’s a thick leather, and they do zip, but only due to the elastic built into the shaft. I’m going to keep them in the hopes they stretch just a bit.

Outfit: I found this dress in the plus section of Target, but it was missing the belt that it came with, so the fitting room guy gave me 30% off. That is something I learned after working at the Gap, if you find a flaw, ask for the discount, or else you’ll either end up stupidly paying full price, or you’ll put it back and someone else will get the deal. I replaced said belt with a super cute leopard skinny belt from the Gap. I am also starting to get into short necklaces that aren’t chokers, because my double chin hates those.

Enzo Angiolini Wide Calf, Taupe size 10, $119
Junior’s Plus Shirt Dress, Navy size 1, Target $27.99
Calf Hair Belt, Gap $29.95
Green Necklace, Francesca’s

And there’s more (don’t tell Andy):

RSVP Isadora Wide Calf, Black size 11, $38.70
No way, no how, do these boots fit. I can’t even zip them halfway. They feel plasticy and cheap, plus the zipper on the boot that I didn’t even try on fell off for absolutely no reason.

Fitzwell Molasses Wide Calf, Brown size 10, Zappos $199
One thing is for sure, across the board, Fitzwell wide calf boots fit me like a dream. I found a brown pair of these on sale at and scooped them up. They are a little shorter than the Valencia’s and kinda plain, but if you are going for a more businessy, less casual look with a skirt or dress, these are perfect.

Ros Hommerson Simply Wide, Black size 10, $136.66
You know how Anne Hathaway wore those tall black thigh boots in The Devil Wears Prada? I was channeling that when I ordered these, but with very low expectations. To my surprise, they totally fit, and sit just above my knee. They don’t feel as high quality as the other leather boots I’ve ordered, but they’re cute and warm with leggings and an over-sized sweater.


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