Just because the weather cools off doesn't mean your style can't be hot. When fall and winter roll around, don't throw your skirts in storage. Wear them all year round and feel free to add a boot into the mix. Your skirt/boot pairing absolutely works and can actually be downright chic.
Throw Out Those Silly Rules
Sure, for the most part, skirts are thought to be a spring/summer item and boots are thought to be a fall/winter item, but so what? These days fashion is all about having fun and trying out new things, so feel free to wear your skirt and boots. Tons of skirts come in winter fabrics like wools that are too heavy to wear during the warmer months anyway, so you should feel confident pairing them with a boot.
There are tons of different types of boots that you can wear with your skirt. The two most important things here are that you look fab and stay warm. So, make sure you pair your boots with a pair of tights. Tights are super fashionable these days so they'll totally work with your look and your legs will stay nice and toasty. This is also a good trick to making your really summery skirts last you through the fall and winter. Get a good thick pair of tights, add a sweater on top and finish your look off with a boot to keep you warm. The same styling works with heavier, more wintery skirts, too.
Type of Boots
You'll be happy to know that pretty much any type of boot will work with a skirt. The key is to make sure that you've got the right boot for the right skirt. If your winter skirt is super-dressy, you'll probably want to pair it with a heeled boot. If it's more casual, then flats totally work. If you want to look really fashionable, try a high, flat boot. Over-the-knee boots, and even thigh-high ones, are lots of fun and look great in flat versions. Not to mention they're good to your feet, so if you've got a lot of walking to do, they're really the best option.
If you want to go a little edgy, try a bootie with your skirt in the winter. You'll still need your tights here of course. If it's even colder, try your bootie with a legging and socks. Yes, socks. Find a pair that goes a little bit higher than your bootie, or slip one on that you can scrunch down a bit. Then, slip your bootie on over it and finish off with your winter skirt.