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Whether you’re a Boomer, Gen X, or Millennial, chances are you’ve come across the phrase “dress for success” like it’s a gospel of adulthood. Someone – perhaps a family member, school guidance counsellor, or boss – doled it out with a straight face, ignoring its often-Working Girl connotations and Horatio Alger-esque message of putting on clothes to strive for the job above you. While it’s not an entirely negative sentiment, the phrase is a tad misguided, often glossing over its classist core and style-over-merit symbolism. Yet, “dress for success” still holds water, even in a world where Silicon Valley’s deceptive dressing down has permeated all but the most formal and stodgy occupations.