WAYWRN: Classic Menswear, Casual Style - Page 953
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^ This is awesome - but in terms of style, there is a world of difference between NOBD's hiking boots and the Keens of CP (as much as I like CP's fit otherwise). Mind you, I am perfectly fine with wearing the Keens with what people usually wear hiking these days (fleece, hiking pants, waterproof jacket etc.). But OCBD + shetland sweater call for something more traditionally styled IMHO.
As for the shoes, do you critique running shoes for being ugly? Not sneakers. RUNNING SHOES for people who are running in them? Fit and function are king for activity shoes. I don't give a flying if my running shoes are ugly if they work.
On the day of the picture, I spent two hours in a university library where the temperature was freezing. Hence, the sweater.
After my research was finished, I walked about 6 miles, across the town, mostly through the trails and (fairly steep) hills of the Arboretum. The Keens were perfect for this. While on the walk, the sweater went into my knapsack. Earlier, this year, I underwent 6 months of grueling physical therapy so that I could run and walk (normally) again. At one point, I could not even climb stairs. For a walk like this, the Keens gave me the support that I needed. When I arrived at my destination, for a lunch date, I switched to the weejuns that I had in my knapsack.
I posted the picture of the (despised?) Keens only out of fun.