It’s 6:15 a.m. on a Friday in June. All is quiet on Newbury Street, Boston’s usually bustling shopping district with its tidy rows of brownstones. Except, that is, for a dozen runners. They’ve gathered in front of the Tracksmith storefront, known as the Trackhouse. Many are dressed in Tracksmith’s clothes, which are inspired by vintage running gear from preppy college campuses in the 1960s. The runners are wearing understated singlets in navy or maroon, paired with loose fitting...

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