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.
In case you haven’t checked the calendar lately, it’s technically still summer till now in New York.
Well we had some chilly days but only for few days. Love the dry Sunny , warm wether I wish could come here early and enjoy amazing Autumn full time .
Every one is warming us that we need to prepare for the cold winter but in meantime lets seat and enjoy it)))

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.

XoXo LenLenStyle