HOW TO WEAR BOOTIES
One of the most popular fall outfits on my blog features a pair of gorgeous and perfect brown ankle boots from Sole Society. I wore an oversized turtleneck, matching blazer, belt, and distressed jeans. Overall this outfit is very cozy and can be worn on a casual date or hanging out with friends. The blazer balances the distressed jeans, so there is outfit has a relaxed feel but not too casual. The oversized sweater is soft and relaxed, so the blazer works to bring structure to the look.
Note that the brown booties end near the thinnest part of my leg, this creates the illusion of longer and leaner legs. You don’t want booties to cut you off any higher than a couple of inches above your ankle because it can make you appear shorter.
Below are 20 CUTE FALL & WINTER OUTFITS WITH BOOTS
The Dos and Don’ts of Boots
DON’T overdo it
If you’re going to go for the gold (boots), you should keep the rest of your, um, ensemble simple.
DO try the equestrian look
It’s both cozy and cool to pair your favorite riding boots with a tailored blazer and slim-cut jeans.
DON’T be a rubber maid
Yes, we know that rainy weather is sometimes fun for your puddle-stomping inner six-year old, but that’s no excuse to wear childish cartoony rain boots. As an alternative, try the equestrian look from slide 1. It’s just as chic (and waterproof!) in the rain as in the sunshine.
DO remember the classics
A classic rain boot is just as important as a classic trench: Both are timeless pieces you will wear proudly—and stylishly—for the rest of your life.
DON’T double up
Yellow boots and a yellow slicker? Not unless your style icon is a rubber ducky. Plaid boots and a plaid sweater? Um, no. Fur-trim boots and a fur-trim parka? No way, Jose, and the same goes for any other matchy-matchy look
DO watch your hemlines
Don’t wear a dress or skirt that hides just the top of your knee-high boots—unless, of course, you are trying to achieve that boots-as-pants look. (Which, last time we checked, wasn’t a good look.)
DO shift into neutrals
When shopping for a new pair of boots, look for a pair you can wear with everything you own. Choose a neutral color to get the most mileage out of em.
DON’T be afraid of the mid-calf boot
While the trendy calf-hugging boots can seem scary, if you pair them with a sleek and simple skirt or coat that hits at the knee, they can actually have a sveltering effect.
DO know that a little color goes a long way
Bright red boots like these spice up a simple outfit in mere seconds
DON’T let your boots dictate your whole look
Lady, don’t get us wrong: We love your pinks boots—we just kinda wish you hadn’t worn pink everything.
DON’T get sucked in
Don’t bunch your too-wide jeans into snug boots, much less snug booties. Opt for leggings or opaque tights instead (under a long tunic or dress).
DO show some skin
So how DO you wear booties with denim? Just pair the boots with tailored, ankle-length jeans and show a little (emphasis on little) skin, like you would with a pair of pumps.
DON’T underestimate the power of a boot
Most of the time, a good pair of boots can make (or break) an outfit. Unfortunately, this woman’s boots don’t do much to keep her busy patterned dress and wild lace tight combo from looking wacky. If she’d paired her basic black boots with opaque tights and a simple sheath, she’d have been all set and super stylish.