Honestly, I don't think you should listen to your tailor for style advice. He will give you the Saville Row Handbook answer. He's hemming your denim the same way as he does your grandfather's? Or you want to look like Steve Jobs? I have a true 30 inseam. In theory a 30x30 jean would fit me perfectly. However, I always go for 32 or even 34 length. 32 is usually too short to cuff, but still doesn't show any sock. 34 allows the option to cuff if I feel like it, and has slightly more bunching. I hate showing socks when sitting down. Sorry if that sounds dumb to some older people here, but that's what I think. 30 is too short, period, unless it's slacks. BTW, I hate dragging pants, I never EVER drag my pants on the ground. I think it's unsanitary. And lastly, many cult denim repros are 36 length. I think that's overdoing it for someone who has a 30 inseam, I won't wear 36 length, thats too much bunching. I pass on those.