I am medium-tall, and fat to the point of having the same troubles. It took me months to find a jacket that fits, even, and the one I finally found says "Honda Racing Team" on the back in great big letters. I wear it anyway, with gratitude. It's better by far than the ordinary windbreaker I'd been using.
I've pretty much accepted after long looking that the answer is custom gear, but it doesn't have to be _hugely_ expensive. Try looking at the stuff from Gerbing's. Yes, it's significantly pricier than off-the-shelf stuff, but is _heated_ for winter riding. I ride down to forty degrees with their stuff comfortably, and I don't even have a full set of gear yet.
I plan to buy a pair of Gerbing's Ultimate pants this fall, then a matching Ultimate jacket later. The pants (again, heated) are $299, and every pair is custom-fitted.
Try http://www.newenough.com/ they give a good idea of how a jacket will fit. Also Paul the owner is not a small guy himself and a phone call will set you up pretty nice, last but not least close out prices and a return policy that's great.
Both him and his wife run the show and ride, I got a leather riding jacket & a textile summer mesh both fit my then 56 inch gut
The personal service over the phone & email is what made the difference, they remember you days latter.and I am not that easy to please.
I just bought my wife a mesh riding jacket through New Enough. The Joe Rocket jacket that I ordered first did not fit. We returned it and got a First Gear Mesh-Tex II jacket for her. They shipped the new jacket right away (same day that I shipped the first jacket back to them). They just charged my credit card for the difference in price & shipping cost. The First Gear jacket fits her well, and is also a better quality jacket.
Like many Internet vendors, they do not stock items. But they do have the item drop shipped directly to you from the manufacturer or distributor, which speeds up the process. They respond promptly to emails, and are helpful on the phone. Overall, a good experience dealing with them, even though we did have to suffer postage fees on the return.
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