Raphael’sbusiness casual combination consisting of brown herringbone jacket, burgundy vest, gray slacks and brown Derby shoes with broguing. Dark brown penny loafers with red and navy socks and navy pinstripe pants. Mid brown Derby shoes with brown and blue socks and checked pants.. New-gen Chelsea boots from one of the premier practitioners of the form, a sturdier smart-casual pair of shoes you will not find. Born for wear with stiff, straight denim. 6/11
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The Best Business Casual Shoes Shopping Guide. The Best for Long, Hard Days: Kleman “Padror” derby shoes, $250 (now $200) The Best for Presentation Day: G.H. Bass & Co. “Larson “Weejuns Loafers.. Patent leather shoes. Velvet slippers. *Some work boots are dressy enough to wear with chinos or nice jeans (fitted, dark wash, no distressing). For example, the Allen Edmond Higgins Mill Boot works with a business casual outfit. However, the Dr. Martens 1460 looks very out of place.