In late April, Amy Smilovic began streaming live from the Instagram account of her fashion label, Tibi. About once a week, she and Dione Davis, her styling director, would put on Tibi outfits and talk — easily, authoritatively — about how the clothes made them feel.

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“When you feel good about the outfit that you’ve put on, your confidence just can go through the roof,” Ms. Smilovic said in one early episode, after Ms. Davis modeled a pair of tailored bloomers. In the same session she…

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