I keep coming back to how unlikely the UGG boot is. In 1978 Brian Smith, an Australian surfer living in Santa Monica, noticed that his new California friends had nothing like the sheepskin boots Australians pulled on after a cold morning in the water. He and Doug Jensen started Ugg Imports that year and sold 28 pairs in the first season. UGG's own history says Smith went door to door to more than 150 Southern California shops, and every one told him sheepskin would never sell next to flip flops and board shorts. So he sold them from the back of his van at Malibu instead.

The construction has barely changed. A classic UGG is twin-faced sheepskin, fleece on the inside and tanned suede on the outside, on a light synthetic sole. Deckers bought the company in 1995 and took it worldwide, but the shape Smith sold out of that van is still the one everyone recognises.

What changed is the height. UGG introduced the Classic Ultra Mini in 2020, the boot dropped below the ankle, and it suddenly looked new again. By the first quarter of 2022 it was the second hottest women's product on the Lyst Index, and that September Bella Hadid wore the platform version in New York and Lyst saw searches for the style jump 152 percent in a day. So that is where I'm starting: the minis first, then the tall and short classics, then the Bailey Bows and the boots built for real winter.

The Classic Tall is the boot I picture when someone says UGG, and the brand still describes it as a style originally worn by surfers to keep warm after early-morning sessions. It is also the pair that went worldwide in the mid-2000s, when Deckers put UGG on celebrities and into Sex and the City. Wearing one now is less about nostalgia and more about proportion.

Below, the Classic Tall II comes in chestnut and black, and the Classic Ultra Tall climbs higher on the leg for anyone who wants sheepskin right up to the knee. The Classic Short II is the middle height, and the Spillseam version turns the seams out so a line of fleece shows along each edge. Then the more designed ones: the Bailey Bow Tall II with its ribbon ties down the back, the Sunburst Tall with shearling trim running down the front, the Whipstitch Knit in charcoal, the Classic Tall Western with three silver buckles, the Uptowner Tall in light bronze and the Moxy Knee-High on a chunky heel.

My rule with a tall UGG is to keep everything above it narrow. A short skirt, denim shorts with bare legs on a dry autumn day, or straight jeans tucked in all work. A wide trouser bunched over the shaft does not.

What I would skip: the suede classics on a day of slush. Sheepskin and suede hate standing water, so save these for dry cold and reach for the waterproof pairs further down.

UGG makes a serious winter boot, and it has been doing it for longer than most people realise. The Adirondack is 25 years old, and the XXV versions mark the anniversary: waterproof leather and suede, Xerogel insulation, a Vibram outsole with an ICETREK rubber compound and a cold-weather rating down to minus 32 degrees Celsius. The chestnut Adirondack Boot XXV laces up over a curly UGGplush lining, and the Adirondack Boot Tall XXV in black adds a taller shaft for deeper snow.

Next to those, the Classic Mini GTX keeps the familiar mini shape on a lugged sole, the Classic Tread Boot laces up over a shearling collar, and the Neumel is the lace-up chukka I wear on in-between days. The Moxy Chelsea and the Uptowner Short are the city boots of the group, both on chunky treaded soles.

The Bailey Bows sit here too, because the ribbon ties down the back are the softer side of the same idea. The Bailey Bow II, Mini Bailey Bow II and Ultra Mini Bailey Bow come in chestnut, black and sand.

My test for a winter UGG is simple: if the sidewalk is wet, I want a rubber outsole and a waterproof upper.

What I would skip: the Bailey Bows in a storm. They are classic sheepskin with ribbon, so treat them like the Classic Short, not like the Adirondack.

If I could only own one pair, it would be the chestnut Ultra Mini. It is the shape that brought the brand back, and it works with everything from leggings to a long skirt. If you already have one, a tall classic is the next pair, and the Adirondack is the one to add if you live somewhere with a real winter.

On fit, UGG's own guide says the Classic Boot is cut with a relaxed comfort fit, and that shearling compresses slightly with wear, so a snug first try often softens after a few uses. Many styles come in whole sizes only, so check the product page before you order.

For care, a protector spray before the first wear does most of the work, and UGG makes its own. When a pair gets caught in the rain, let it dry slowly and away from a radiator.

The funny thing about UGG is that the most famous boot in the line is still the plainest one. Nearly fifty years after Smith's first 28 pairs, the classic is the reason the rest of this list exists. If you want to keep browsing, I also put together UGG Boots and Chanel Boots, From Quilted Combat Shapes to Tall Two-Tone Lines.