a conversation about ranking our past outfits episode artwork

EPISODE · Jun 7, 2026 · 31 MIN

a conversation about ranking our past outfits

from Little Miss · host Ryley Gale

This week, we're doing something equal parts nostalgic and embarrassing: ranking our most questionable outfits from the past. From cringeworthy trends and ill-advised accessories to fashion choices that should have stayed buried in old Facebook albums, we're revisiting some true style disasters and deciding which looks were the absolute worst.But this episode isn't just about roasting our younger selves. As we scroll through the evidence, we're also reflecting on what it was like growing up online—and how social media has completely transformed since then. From the era of awkward photo dumps and unfiltered posts to today's carefully curated feeds and constant content creation, we explore how the internet shaped our fashion choices, self-image, and memories.Join us for a trip down memory lane filled with laughs, secondhand embarrassment, and a conversation about how both our wardrobes and the online world have evolved over the years.

This week, we're doing something equal parts nostalgic and embarrassing: ranking our most questionable outfits from the past. From cringeworthy trends and ill-advised accessories to fashion choices that should have stayed buried in old Facebook albums, we're revisiting some true style disasters and deciding which looks were the absolute worst.But this episode isn't just about roasting our younger selves. As we scroll through the evidence, we're also reflecting on what it was like growing up online—and how social media has completely transformed since then. From the era of awkward photo dumps and unfiltered posts to today's carefully curated feeds and constant content creation, we explore how the internet shaped our fashion choices, self-image, and memories.Join us for a trip down memory lane filled with laughs, secondhand embarrassment, and a conversation about how both our wardrobes and the online world have evolved over the years.

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a conversation about ranking our past outfits

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This episode was published on June 7, 2026.

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This week, we're doing something equal parts nostalgic and embarrassing: ranking our most questionable outfits from the past. From cringeworthy trends and ill-advised accessories to fashion choices that should have stayed buried in old Facebook...

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