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This grungy ensemble from 1999 would totally work today

De la Haye and Tucker note the connection between sportswear and the more casual styles of the decade writing: The prevalence of urban sportswear in male dress can also be directly correlated to the increasingly informal approach to workplace clothing

Medium volume in the lace ups and high volume in the Chelsea Birchbury Wide But Not Barefoot Leather | Sizes EU 39-49 | Ships from US These are an in-between barefoot shoe option they have a much wider toe box than is typical in mens dress shoes, but they still retain a mainstream aesthetic and they come with a lightly supportive and cushioned insole

Sits at approximately the high mid thigh