In the late 1800s, an acclaimed journalist and lynching opponent, Ida B. Wells, was subject to criticism from the patriarchy, not on her craft, but on her appearance. Though she was clearly stylish, it should have had no bearing on recognizing her journalistic abilities. However, expressions of personal style are often deemed as frivolous for serious people, and for men, this perception can be regarded as feminine. Growing up poor in a poor community, the author saw firsthand how beauty and pride of appearance conveyed dignity in a world intent on divesting you of it. Celebration became a way of survival in these communities. The author used to scavenge antique furniture, restore it themselves, painted with watercolors and drew incessantly, and started a small clothing company. Design has always been central to the author’s life and feels like an expression of freedom. The author aspires to become one of those older men who embrace sartorial whimsy and wants to become the old man with the quirky suspenders, bow ties, and orange socks. They become emancipated in a delightful way and return to the magic of childhood when dressing up and donning costumes were the expectation rather than an aberration.