Success!!! I have found stylish and comfortable black riding boots that fit my calves! I shared the beginning of my quest with you here and for all of you out there dealing with this same issue, I'm back to fill you in on all the styles I tried, what worked and what didn't. Thank you to everyone who left a comment with a suggested style and strategy. From authentic equestrian boot brands to professional calf stretching, you guys are full of good ideas!
Here are 6 boots in a range of prices that will fit those of us with larger calves.
As a reminder, I'm 5'4, wear a 7.5 shoe in everything and have 15.5" calves. My goal was simple - to find a pair of black riding boots that I could comfortably wear with a pair of skinny jeans tucked in.
1. Ecco Hobbart
2. Frye Paige
3. Frye Melissa Button
4. Frye Melissa Button Back Zip
5. J.Crew Billie Buckle (extended calf)
6. DSW Mia Elisa Riding Boot
By combining an afternoon in the Nordstrom's shoe department with a truck full of UPS deliveries, I tried on all six of the boots pictured above. And Knox had a mountain of boxes to climb for a while. Here's the rundown on each style.
The Mia Elisa Riding Boot from DSW
Price: $99.95. I really REALLY wanted this boot to work because it's perfectly priced.
Zipper or Pull-on: Pull on (no zipper) but shockingly, they slipped right on and even fit my calf (snuggly but I assumed they'd stretch).
Verdict: The problem, sadly, was one I hadn't even anticipated. They came up really high on my shins. Like they kinda made me feel like Puss in Boots. I could feel them hitting the very bottom of my knee cap when I walked.
At this point I decided to bite the bullet and order some Fryes. I've heard nothing but amazing things about these boots and for the price, they'd better be amazing.
Price: $348.00. OUCH!
Zipper or Pull-on: Pull on (no zipper). I could BARELY get my foot into these boots. After lots of pulling and sweating I finally put my entire foot into a plastic shopping bag and was able to slip them on that way. Once on, they were incredibly comfortable and actually weren't tight on my ankle. But boy...getting them on was virtually impossible. They fit my calf great though.
Verdict: They fit like a dream once on, but I couldn't get over how impossible they were to pull on. They were just a smidge taller than I would have preferred but not nearly as tall as the Mia's.
Price: $328.00.
Zipper or Pull-on: Pull on (no zipper). These pulled right on, none of the huffing and puffing involved with the Paige's. They also have a nice dip down cut in the front and back which keeps them from creeping up too high.
Verdict: Just a little too tight for comfort on my calf. 
Price: $345.00.
Zipper or Pull-on: Pull on (no zipper). These were the opposite of the Paige's. They pulled right on but had a really slouchy look to them, especially in the ankle area.
Verdict: Not the look I was going for. Too slouchy but the calf fit great...not tight at all. And the leather was really nice. 
Price: $328.00.
Zipper or Pull-on: Zipper. I got these because I liked the Frye Melissa Button's so much but they were just a little too tight for comfort in the calf. They zip up the back and then there are 2 snaps on each boot that close over the zipper.
Verdict: OMG. I have never put on a more perfect boot. The leather is perfect, the color (black soft vintage) is the ideal "worn just so" texture and the fit is as close to a custom boot as I could image. I was in love. 
The Ecco Hobbart Buckle (ordered from OnlineShoes.com but only because they were out of stock at Zappos).
Price: $220.00.
Zipper or Pull-on: Full length inside zipper. The buckles were also functional. They could be opened up to reveal a hidden elastic gusset. They fit my calves great but even if they hadn't, there was room to expand the boot shaft.
Verdict: They fit really well. They were just a bit taller in the shaft than the Frye Melissa Button Back Zip but they were still really comfortable. I didn't love the buckle look and they were also a shiny black leather vs. a more worn in leather on the Fryes. In the end, it came down to the Frye Melissa Button Back Zip and the Ecco Hobbart Buckle. I really, REALLY wanted to go with the Ecco Hobbart and save myself $100. The leather on the Frye's was unquestionably nicer. Did you know Frye was founded in 1863 and is the oldest continuously operating footwear brand in America? I could actually see the craftsmanship that had gone into creating them.
And if I'd never put on the Frye's I think I would have been ecstatic with the Ecco boots. But there was no turning back once I had the Frye's on. Ultimately, I decided that a pair of low-heeled black boots are a wardrobe staple and one I would be pulling out for many seasons to come so I was ok investing in something great. I've worn them literally, every day since we've been back from the beach. Absurd, I know...but it's love. Plus I've gotta get the cost per wear (CPW) down on these! I'll post a photo of them soon....haven't been able to get my act together to actually take a picture!
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