Despite their somewhat disconcerting popularity with rappers, Timberlands are still as classic and high quality as ever- and, unlike the standard tan, a darker brown can be worn with a variety of outfits very easily.
Pictured: Timberland Men's Boot in Dark Chocolate, $155
Tags: boots, clarks, desert boot, dr. martens, J.Crew, red wing, work boot
Read our Answer More Questions and Answers Ask a QuestionShould I go to a community college before I go to a 4-year college? Looks cheaper.
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