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Need some shoe recommendations.

I’m sad no one has yet mentioned good English shoe makers like Cheaney and Crockett & Jones. They should be in or very close to your price range I’d think.
Brooks Brothers used to sell a UK made line called Pearl.

I bought several 15+ years ago.

It was rumored that C&J made them.

They have been terrific!

My every day loafers are Honduran GH Bass leather sole.

They’ve been fine.
 
Since you live in an area that has real winters (knowing that you make maple syrup), I would like to suggest you look at getting one pair dress boots…they look like high-top dress shoes. They are warmer and keep you drier should you have to cross slush or stand around in an unheated area.

A lot of high end shoe makers you are looking at have them.
 
I happen to be wearing my BB/Peal/C&J’s this evening.

Don’t fear the single Monk Strap.

They can slip on/off.

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I started with AEs, but overall quality and a somewhat clunky silhouette pushed me away long ago.

I'm surprised no one has mentioned (unless I've missed it) TLB Mallorca.

I have two pairs of oxfords (black and dark brown) and one pair chelsea boots from them and I couldn't be happier.
Their "Artista" line is especially wonderful. Extremely elegant lines.

True, you can't try them on in person (unless you happen to be in Mallorca). But I had no trouble finding my correct size for my first purchase after a quick email exchange with them. With my size now set, I've used their (really reasonably priced) customizable purchase option to great satisfaction.
 
Are you thinking of Peal & Co? They were very good and my go-to recommendation in cases like this.
That’s them!

I’d get them at the BB after Christmas and Father’s Day sales. They were still $200+ but I still own them and had my desert boots resolved even. :thumbup1:
 
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