It's the ultimate sweet spot when necessity and fashion intersect. This season, boots of all heights and styles couldn't be more practical for taking on chilly temps.
But how do you get the right proportions? To tuck or not to tuck? We summoned our best advice and recruited a few boot-loving experts-Krista Kaur Meyers of Lakeview boutique Krista K and Trudy Robinson Foley and Matt Foley of A Pied in Roscoe Village-to weigh in. Whether you want to try out the ankle-height styles that are everywhere right now or are looking for a way to wear over-the-knee boots without looking like a lost clubgoer, we've got you covered.
BOOTIE
>>Pencil skirt and tights
>>Skinny denim (see ANKLE BOOT)
>>Midi skirt
"This length can be tricky," Kaur Meyers said. Look for a heeled or wedge bootie. "The key is to show the calf."
ANKLE BOOT
>>Skinny denim
Ankle-length or longer-anything goes. "Longer skinnies can be rolled at the bottom so they hit just above the top [or] just tuck inside," Kaur Meyers said.
>>Straight-leg denim
"Straight leg [jeans], not a wide boot cut, you can actually put it over the ankle part of that bootie," as long as the style doesn't feature any details--like a cool exposed zipper or other embellishment--around the top that you'd be covering up, Robinson Foley said.
>>Above-the-knee skirt or dress with tights
"The looser and bulkier the boot is, the shorter you can go with the skirt," Robinson Foley said.
ABOVE-THE-ANKLE & BUCKLED
>>Jeans or casual pants with legs just wide enough to fit over the boot
Men's boots in moto-inspired styles typically come in this height, hitting a few inches above the ankle. Frye's Smith Engineer style--with a buckle below the ankle and another at the top--is popular at A Pied, which recently added men's footwear. "The length of the jean should be short and narrow enough so you're seeing the lower buckle [when standing]," Robinson Foley said. "When you sit down at the bar for a drink or something, your pant leg will move up enough so you see some of the detail."
COMBAT
>>Above-the-knee skirt or dress with tights and socks
This layered look-a nod to '90s grunge-can be fun, especially with woolly socks that you can scrunch.
>>Slouchy jeans or pants, rolled up
>>Slim-cut or straight-leg denim
Dudes, this one's for you: Tuck in your jeans but leave the boots unlaced.
RIDING
>>Skinny denim or slim-cut pants
>>Above-the-knee dress or skirt
AVOID:Midi skirt
A longer skirt length that overlaps the boot and hides your kneecap can throw off your proportions.
OVER-THE-KNEE
>>Skinny denim with tee or silk blouse and loose, long cardigan
"I'd finish the look with a long chunky necklace," Kaur Meyers said. "The long cardi is a nice balance to the over-the-knee boot and creates a classic, chic fall look."
>>Leggings with a tunic-length sweater
"The key is to make sure you have a strong enough legging and keep the sweater a good three inches at least above where the boot ends," Robinson Foley said.
AVOID:Mini-length skirt or dress
With anything very short, tight or bare, things start looking more than a little dominatrix-y.
