I picked up a pair of 1880 Chesters from Woolridge Shoes in Toronto and I'm very happy with them. I like AE but with the recent deterioration of the Canadian dollar, the value proposition with them is not quite what it used to be when after shipping and taxes I'm looking at $500 Cad versus almost $600 for a pair of Loake 1880s tax in purchased locally and Loake is much nicer than AE.
$600? That is insanity!!! Look into one of the online retailers from the UK. Pediwear and Herring are 2 I know of.
My last purchase of 1880s from pediwear cost me 144 GBP with free shipping. VAT gets removed since we are outside of the UK, and pediwear gives you a permanent 10% discount on Loake shoes after your first purchase.
Out of 5 orders never once have I been hit with duties/taxes. Very unlikely since they ship them with Royal Mail (Canada post)
$300 ish CDN all-in to my doorstep - no other shoe can come even close to this.