Sizing is often my issue as well, except that it's usually more about either "outdated" cuts (baggy where now more tailored/fitted is fashionable) or where decent looking stuff in my fairly average size is often snagged, leaving only the very small or very large sizes behind.

Still, I occasionally find some decent stuff and I still hit up the Goodwill anytime I'm out running errands and pass near one. It's just a matter of luck so the more often I look, the better my odds.

I tend to have less luck with the common stuff like nice wool pants or well-fitting button down shirts but I've gotten some really nice jackets and at three pairs of Allen Edmonds shoes ($250-350 MSRP) for $20-25 each with only a cleanup and polish needed.

It's nice because even though I'm still buying the occasional $20-40 shirt, I've got a few pairs of shoes that are much nicer than anything I'd be able to justify buying at retail.

Large is pretty standard size for tall men. Pretty much required over 5'11.

I'm 6'2" and 180lbs and large still fits baggy on me most of the time. Which is annoying for gifts because most people think the same way and gift large or extra-large clothes without gift receipts so I end up having to drive them over to the salvation army.

Large, non bespoke shirts off the rack, are longer. Which is required for taller people. I have the same issue, which is why I look for fitted shirts in large. 6'1 175lb.

Depends where you are? I'm in the UK and 189cm tall and I always wear medium.

Then somehow your mediums are very long. Medium is just way too short stateside. While it fits the chest, it doesn't lengthwise.

Yeah it is lucky. I have a odd body type, I'm 6'3" but only weight 170 pounds, so I really wear a XL-Tall but a lot of the XL clothing works pretty well. It's also a hit or miss every time I go in. Sometimes I will find 10 things that fit and are great, other times I leave empty handed.

Buy the big sizes then get the shirts tailored to fit for roughly $20-$25. You'll be wearing nice brands that fit perfectly.