Regarding the J. Crew Plain Toe boots, may I ask for advice about sizing? How do they fit?
For the only references, I wear an 11.5D in my Allen-Edmonds Clifton and a 44 in my Common Projects Tournaments.
Additionally, I once owned a pair of Alden suede chukkas. They were sized 10E or 10.5E and though I thought they fit when trying them on at the Alden store in NYC, the right shoe ended up with awkward fit, so I had to sell them.
Do I take an 11 or 11.5 in the plain toes?
You're in NYC, why don't you just go try them on at the Liquor Store?
Another route is to use the red phone inside a local J. Crew and order both pairs. Return the pair you don't want and you will get 100% of your money back since shipping will be free anyway.
I have no idea how AE sizes run, but if I were a betting man, I'd say you're a size 11.