Barn Shoes
My barn shoes change with the season and right now I am wearing a pair of very padded black leather zip up Grand Prix riding boots that I bought earlier this year from The Farm House. They do not have them anymore but they are fantastic for mucking stalls, wearing around the farm. Very comfortable. These are not pretty but so functional. See them here.
Riding Shoes
I ride in tall boots all year round. A few years ago I bought an inexpensive pair of Tredstep tall boots for everyday riding so I could wear padded inserts (for my bad feet). Ariat insoles also can be added to boots (I use these in paddock boots). When it is really cold I put my riding boots on right before I ride and take them off immediately when I am done. This way I only need one pair of boots for riding all year round.
Daily Wear Shoes
There are two pairs of shoes that I would recommend paying a lot for - Gucci Loafers and Belgians. My Gucci Loafers are at least 20 years old, bought in New York on a work trip at the Gucci store where I was able to find a 7 N in the black classic loafer. They have been refurbished at least once and are still going. Definitely worth the investment in spades. I would love to own a pair of the mules with fur lining.
The second is Belgians. These are not as expensive as Gucci and come in so many colors and patterns that you'll struggle to pick out just one pair. You may think these are frumpy but to me they are classic chic. They are the most comfortable shoes I own bar none. Each year I try to add a pair. You can only buy these at the Belgian store in New York or second hand. I have found two new or almost new pairs second hand for under $100. Not sure what color I will add this year - still trying to decide. These run TTS.
I also love my Birkenstocks for around the house:
I only wear flat or almost flat shoes. Loafers are often my shoe of choice and I am loving these for fall:
I love Tory Burch loafers and have two pairs (both somewhat flat). I love these with just a little bit of heel for fall. Big fan of Tory shoes and loafers. They fit well, last, good quality. While I typically buy hers on sale, they are worth paying full price.
I also have difficult feet, although mine are wide and not narrow like yours. I look forward to cooler temperatures when I can pull out my Haflinger boiled wool clogs. Belgians, Gucci loafers, and Haflinger clogs are my staple throughout the cooler months.
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