I picked up a couple pair of wool BR "tailored fit" pants a while back with a 40% off coupon. Seems to be about their slimmest model. I'm not a fan of BR stuff but they're tough to beat for around 40 bucks after discount.
Custom is slimmer than classic fit. In their polo shirts, I size down to a small which fits almost exactly like a custom medium but without the rediculously short sleeves.
Did the shirt you bought have the embrodoidered polo player? That's one of the biggest reasons I don't buy more Polo button up shirts.
I love reading all the over the top criticisim. Especially fom people who have never posted a picture of their own.
The OP looks way ahead of 99% of the general population and likely looked as good or better than most people he'd run into wearing it.
There's good advice in this thread. Brown shoes, darker jeans and a tucked shirt would make for a much better outfit. If you resolve to not buy anything black from now on you'll be a lot better off too.
Your shirt sleeve has to wrinkle somewhere when you lift your arm up like that. My shirts with tighter arm holes do the same thing.
I would agree it looks like you need more slope to the shoulder and reduce the point to point slightly.
I got those same chukkas from Steven at Leffot recently and they don't have nearly that much "pilling". I'd personally want a bigger discount on a pair of shoes that looked like that. I'd have a hard time paying more than half the original price for a used pair of shoes myself though. To be fair they don't look bad for being worn 10+ times.
Thanks so much for the suggestions everyone. I missed that thread on Florence in my initial search. This is my last day in Florence so I'll check out as much as I can while I'm here. I should have even more time in Rome over the next few days.
If anyone has any other suggestions on Rome feel free to chime in. Unless someone posts in the next hour I may not be able to check the thread until in Rome.