I can still remember wearing saddle shoes some 20 years ago when I worked a job that required me to wear khaki pants, a blue blazer, white shirt and a tie. The saddle shoes just seem to truly accentuate this particular outfit and made it look a little preppy and cool in my eyes.
On rare occasion I do come across other men who do wear saddle shoes for work or for casual settings. For me they must be worn with khaki pants as they seem to be akin to one another.
The problem for me is trying to find a good quality pair of saddle shoes here in Honolulu, as many of the shoe stores seem to cater to a more contemporary look.
But two years ago a colleague of mine stumbled across one of the outlet stores where they were with liquidating their entire collection of men’s saddle shoes…
…whereupon he promptly purchased six pair!
He came to work the next day wearing a brand-new pair of saddle shoes and khaki pants and I was in true envy!
While the younger generation may find saddle shoes kind of… odd, I still find them very appropriate for this particular choice of clothing as they match perfectly and give you a very preppy and upscale look.
article: Saddle Shoes to Look Upscale