I just started riding English, grew up riding western. Having no luck finding tall boots with a 19/20 inch calf. Does anyone know of a brand I should be looking at or do I need to start looking for custom boots? Also anyone know of a good online store to find plus sized riding breeches?
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Boots you will probably be looking at Fuller fillies, either tall boots, or half chaps.
i love my Buckwild breeches, lots of colours Nd sizes, to much colour for some.
Fuller Fillies for both. If you’re hourglass shaped, the silicone patterned fullseat breeches are phenomenal. I don’t ride in anything else anymore, grippy and they wear really well.
When measuring for the tall boots, measure your foot length in socks to get the size you need from their size guide. The foot size will be too big if you measure against your normal shoe size. Also, you can save on shipping if you order breeches at the same time since they’ll just tuck them in the boot box
Tuff Rider Plus Rider boots go up to 20", and have elastic so may even go more. They have both dress and field boots.
Dress: https://www.adamshorsesupplies.com/tuff-rider-plus-rider-dress-boot-204365
Field: https://www.adamshorsesupplies.com/tuff-rider-plus-rider-field-boot-202878
There are size charts under each type of boot, and you can choose height and calf size.
The boots are soft, have a back zipper, and the dress boots are lined (haven’t tried the field boots). The dress boots even have a suede-ish patch onthe inner calf. I use them at home every day.
If you’re apple shaped the Smartpak Piper breeches should probably fit you well. Although they seriously don’t consider that larger waist should mean more belt loops. I have junk in the trunk and added darts and extra loops to mine. For reference I ordered the largest size and I wear a 22. I had plenty of room in the waist but that size fits my ass and thighs well.
Boots I can’t help with as I have Dehners. My 6.5 XXW feet and fat calves just don’t fit into off the rack boots. Honestly my paddock boots are also custom because of the width of my foot. Though Dehners seem to be the least expensive of the custom options.
Check out the Facebook group English Plus Size Riding Apparel - you can often find like-new boots and breeches there in the larger sizes. SmartPak has the Piper breeches and the Hadley breeches in larger sizes, and you can find some of them on their clearance page right now too, so it is worth a look.
The Plus size Smart Pak Pipers just don’t fit me well – they aren’t high rise enough, but I know they work for a lot of people. You can find them used on the Plus Size Riding group and they are common enough that I had two brand new pairs, one still with tags, and couldn’t get them sold. Probably should try again!
The Tuff Rider boots linked above are amazing. I had some custom ones made four years ago, and naturally, they are too snug now, so I grabbed a pair of the Tuff Riders, and I love them. The largest ones are a little wide for me, but I’ve appreciated being able to wear thicker breeches and socks with them. The stretch panel they use is fantastic.
Happy shopping, and in a more tight-like breech, I love my Sticky Seats. Comfortable, high waisted enough, and a woman owned small business, so can’t do better than that! 
After many months of searching, I got the Ovation flex sport in x wide, and am very happy
www.paradisefarmandtack.com/products/ovation-flex-plus-field-boot?variant=31745013635
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I’ve seen boots that have been modified/customized by good boot maker/cobbler. They sew in a “dart” I guess it’s called by splitting the back. When done right it is hard to see, looks fine.
