Originally Posted by CanadaCal
If I'm in the $1500 ballpark its going to be a St. Crispins MTO. I'd probably go with a Tetbury over a Harrogate. Chukkas are so versatile and comfortable. But both are nice shoes and I'm sure will fit in the wardrobe nicely.
On the topic of St. Crispins, I would suggest also considering Antonio Mecarriello at an even lower price point. Apart from not having a physical presence in stores (i.e. no discounts, can't physically try on), the service and especially the product seems to be amazing value. I believe it's now €750 for Argentum (MTO & hand welted) and €1150 for Aurum (top line, MTO, hand welted, semi bespoke, can order fully functional trial shoes for €300 more). I don't personally own a pair yet, but am planning to order at least one soon before price gets bumped up. There will soon be a RTW line in stores, which will definitely come in at a higher price point.