My version of a truly timeless shoe is the Ugg boot. As a millennial, I can say that I have lived through every era of the beloved, albeit controversial, boots. (Insert mental image of Y2K outfits here.)
I was a fan of the shoes as a preteen because they were on-trend, but as a fully fledged working adult, I appreciate both the comfort and the casual style so much more. They've become my go-to shoes simply because they are so easy to style with everything. And it seems I'm not the only one who thinks that, as endless Instagram Reels of people styling variations of Ugg boots have inundated my feed. This was all the convincing I needed to head over to Bloomingdale's for my next pair. The moment I cast my eyes on the patterned mini boots, I knew they were coming home with me! I'm also intrigued by the platform boots—a new style introduced last year. Below, take a look at all the pairs that caught my eye.
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I Asked an AI Shopping App For the Best Winter Boots—Here’s 15 Pairs It Told Me to Style With JeansYes to them all.
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Leopard Boots Are Cool, But Rihanna Knows This Alternative Animal Print Looks Better With JeansI need her entire outfit.
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Taylor Swift Made the Most Fashion-Girl Choice by Wearing These Bag and Boot Color Trends TogetherThey clash in a good way.
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Amal Clooney Made Simple Ankle Boots Look Elegant for a Michelin-Starred Lunch in ProvenceIt's so French.
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From Paris Hilton to Addison Rae, Hollywood Royalty Is Loyal to This Controversial Winter Boot TrendThey're back.
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Not Black, Not Brown: The 2026 Boot Color Trend That Makes Every Outfit ElegantJust like that.
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Winter's Just Around the Corner—13 Standout Zara Finds I Predict Will Sell Out Before the End of the MonthAffordable funnel-neck jackets, argyle knits, and rich-looking flats inside.
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My Stylish 56-Year-Old Mom Is a Picky Shopper—31 Chic Under-$100Replica Store Finds She Approves OfFunnel-neck coats, Fair Isle knits, and Levi's jeans inside.
