The logical and obvious answer to this seemingly simple question: when the weather cools down after the heat of Summer. That first hint of crisp Autumn air signals us to dust off our boots and incorporate them into outfits. That’s why shooties, booties, mid-calf boots, knee-high boots, and over-the-knee boots start to get a lot of attention this time of year. 

But it really isn’t quite that simple. First of all, seasonally confused combinations are trendy. Booties with shorts, harem pants or skirts are fun looks. Pairing mid-calf boots with short Summery dresses is a fab throwback to ‘90s fashion. Leave off the hose and show skin as a way of compensating for the coverage of the boots. And bootcut jeans worn with cowboy boots and just about any top combination is in style across the seasons, especially in places like Texas.

Leith V-Back Sweater & J.O.A. Midi SkirtSandra Shirttail Hem Tunic DressChelsea28 Open Shawl Collar JacketPendleton Buffalo Plaid Barn Coat

Secondly, Summers aren’t always too hot for boots. Although we’ve had two years of glorious hot weather in Seattle, our Summers are usually mild at best. Sometimes even chilly — like having the fire on in August chilly — which makes boots a cozy and comfortable option. It can also cool down at night if you live by the sea, making boots a great option for evenings out. And of course, the arctic air conditioning of some office environments makes wearing boots a comfortable option despite the scorching heat outside.

So just like you can wear white after Labor Day, wear boots at any time of the year if it makes sense for your climate, environment and style. Fashion definitely doesn’t dictate a correct season for boots.

Personally, I typically wear my boots in Autumn, Winter, and early Spring. I try to not wear them in late Spring and in Summer so that I can give my warm weather footwear a workout. Over to you. When does boots wearing season start and stop for you?