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.

“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 wryly compared her pandemic state to a “walking pharmaceutical commercial” whose list of symptoms included crying in the shower and sending emails at 4 a.m. Ms. Smilovic believed a good outfit could help with that too.

Tibi designs clothing for “creative pragmatists,” a term Ms. Smilovic, 52, coined late last year to describe a style she had long struggled to describe. The look is about balance — being modern but not edgy, she says, and chill but not bohemian. As she once advised on Instagram, where she also occasionally ribs Lululemon moms, Bravo stars and yogurt-straining yogis: “when u dress interesting u will feel interesting.”

From a design perspective, this usually means adding unusual twists to familiar closet staples: an oversize blazer with slits at the elbows; jeans that look as if they’re being worn backward; a crew-neck sweater with rounded shoulder pads. Ms. Davis called the weird accents “Tibi Easter eggs.”

As the summer continued, the styling sessions evolved. Instagram Live had become a popular feature in the pandemic as people (or brands, mostly) sought new ways to connect with homebound followers. At the beginning, Ms. Smilovic and Ms. Davis streamed from their homes, splitting the screen

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