Orange leaves on the trees. Frost on the ground. Little buds blooming on the branches. Here at KEEN, we love all the seasons equally, and we especially love comfortable boots that transition with you through seasonal changes and unpredictable weather — the kind that keep feet warm when it’s chilly out, grip to slippery sidewalks, and have all the style you need for harvest-season dinner parties, wintry days, and dewy spring mornings.

Whether you’re road-tripping, reading a book on the porch, or enjoying friluftsliv living, three-season boots are the ones you can always grab for the moments in between epic adventures. They’re the boots you throw on at the ski lodge, keep by the front door for walking the dog, and never think twice about wearing into the city.

So which boots are the ones you want for not just one season but three? Consult this handy KEENparison to find out:

How Much Insulation Do You Need?

Before we get to the shoes, let’s talk about insulation. Specifically, how much of it do you need? KEEN three-season boots come with 100g insulation rated to -4ºF or 200g insulation rated to -25ºF. If you live in a mild climate like the Pacific Northwest, 100g insulation might be just what you want. If you always have to wear a parka over your Halloween costume, 200g may be a better choice for you.

KEEN tip: Some folks' feet tend to naturally run hot. If that sounds like you, you might find that the amount of warmth contained in waterproof boots with no insulation is enough to keep your feet comfortable.

Our Go-To Boots for Three-Season Versatility

Women’s Kaci III winter boot: This one is a fan favorite. Cozy, casual, and endlessly comfortable, the women’s Kaci III winter boots keep feet warm and dry while you run errands or explore around that cabin you rented for the weekend. An environmentally preferred premium leather upper is paired with a super-cozy ankle collar and tongue, so your feet look every bit as good as they feel.

Great for: everyday around town and weekend getaways

Kids’ Knotch Chukka: Whether they’re searching for slugs in the backyard or skipping through a corn maze, the kids’ Knotch Chukka shoes keep kids’ feet warm while kids play. Half of what makes these shoes so cozy is the 100g of KEEN.WARM insulation inside. They’re also lined with fleece. The low-profile outsole has the feel of a favorite pair of sneakers, so kids can stay active and warm at the same time.

Great for: adventurous kids who want to make the most of chilly days

Men’s Anchorage III waterproof boot: Exploring a pumpkin patch. Taking a screen break. Cruising around the city. Whatever you’re up to on cool days, the men’s Anchorage III waterproof boots wrap your feet in the ultimate combo of warmth, style, and waterproof coverage. There’s simply no arguing with the wear-it-anywhere good looks of a full grain leather upper. KEEN.FREEZE rubber grips ice and snow, so even a midwinter freeze won’t slow your roll.

Great for: all-season, all-occasion versatility

Men’s Targhee II winter waterproof boot: From enjoying a walking meditation to crunching across frosty sidewalks on your way to the local coffee shop, there are a lot of reasons to get outside on cold days. While you’re out there, the men’s Targhee winter waterproof boots keep your feet dry and toasty warm. They have the famous fit and feel of our iconic Targhee hiking boots, plus insulation and a KEEN.FREEZE outsole that can handle ice and snow. If you were looking for rugged hiking boots to wear casually around the city, you just found them.

Great for: sitting around a backyard campfire and trekking through the city

Women’s Greta Chelsea waterproof boot: The boots you keep by the door because they’re just so easy to slip on and go, the women’s Greta waterproof Chelsea boots pair rugged durability with total ease and style. Feet stay cozy thanks to 200g of KEEN.WARM insulation, and the rugged outsole ensures a solid grip when you’re walking on soggy leaves and muddy park trails. In other words, these are the boots you’ll wear every day for three seasons straight without even thinking about it. (KEEN tip: The Betty waterproof boot has the same warmth and pull-on style with a little more height.)

Great for: dog walks, car camping trips, and city outings

It’s fun to have a closet full of shoes, but doesn’t it feel great to have one pair of boots that works for three seasons? Whether you’re U-picking fall produce, crunching through snow, or enjoying a foggy spring morning, there’s a pair of casual KEEN boots with all the insulation, style, and weather protection you need to transition with ease through the changing seasons.