Footwear's Perfect Pair

What to Wear with Booties 

“With booties, I personally like a thick wool sock scrunched down for a more casual look. At work, I wear patterned socks that peek out between the cuff of my jean and the top of my boots. Booties also look great with dresses and patterned tights.” —Tammy Kirks, with Harem & Company 

“[Wear] socks with short boots. A short sock that comes right above the boots. A lot have lace that will show out of the boot. [Or] take the knee socks and just scrunch them down with short boots.” —Robin Gilmore, with Ms. Gilmore’s Tea Room and Vintage Suitcase

“Tucking your bottoms, whether it’s a legging or a denim, into your ankle boot creates a lean, elongated line for the bottom half of your body. This is what all women want, so it’s my top way to style the ankle boot trend.” —Sarah Schaeffer, with The Uptown Boutique 

Qupid high fashion over-the-knee boots, $49 at The Uptown Boutique; Simply Noelle over-the-knee socks with lace, $13.99 at Ms. Gilmore’s Tea Room and Vintage Suitcase

What to Wear with Tall Boots 

“With tall boots, a knit boot sock is great. Most are made to be longer than the shaft of the boot so you can fold them over the top, or scrunch them under your knee. If I’m wearing an over-the-knee boot style, I wear a short sock just to cover my foot. You don’t want a sock sticking out that high, but tights are a great option if you want to cover your legs. Cable knit tights are also fun with skirts and tall boots if you want something different.” —T.K. 

“[For] a lot of the boots at the knee, we have a lot of socks that cuff over them. We have some that are thigh-high length that scrunch down at the top of the knee boot.” —R.G. 

“With skirts, a little leg between the top of a tall boot and the bottom of your skirt or dress looks best. You don’t want a solid silhouette.”—T.K.

FRYE Jordan Strappy Tall boot, $498 at Harem & Company; Simply Noelle tall length stud placket socks, $13.99 at Ms. Gilmore’s Tea Room and Vintage Suitcase

What to Pair with Leggings 

“I personally think 95 percent of the time, leggings should be worn with a closed-toed type of shoe, whether it’s a riding boot, sneaker, heeled bootie, etc. The easiest, and most seen pairing, is leggings with any type of boot: flat boots, rain boots, winter Ugg boots, combat boots, knee boots, ankle boots. You want the leggings to look sleek and tight with whatever type of boots you end up pairing with them. You don’t want the boot to look too stuffed.” —S.S. 

“[Try] sweaters with leggings and boots that lace up the back. It’s really comfortable in the wintertime. The leggings are so warm and you can wear them with a dress or skirt.” —R.G.

Qupid Suede with Me bootie, $36 at The Uptown Boutique

How to Pick Socks

“With booties, choose a shorter sock that you can scrunch down. I like the rag wool ones, but there are many knit cotton versions that are great. I look for colors to stand out, but if you’re not that bold, match your jeans or boot color. Thick wool socks are casual, so wearing with jeans and leggings look best. When wearing a tall boot, a long sock specifically for boots (called a “boot sock”) is great. You can scrunch it down under your knee or fold it over the top of your boot.” —T.K. 

“Socks with leggings and boots has been a fairly popular trend the past few years. You want to make sure you are doing it right since socks are just added fabric to your look and can add bulk to your ankles. I recommend going with a neutral colored sock (any shade of gray, navy or brown) and making sure it’s a shorter length of sock. You want to layer the socks over your leggings and leave them exposed a few inches above the boot. I only recommend the sock layering with leggings, not denim.” —S.S. 

How to Pair Boots and Pants 

“Personally, I always cuff my skinny jeans to show off my socks. I like them about an inch higher than the top of my boot. If your jeans are long, let them cover the boot and don’t cuff them. This is best with a flare or boot-cut style. Most skinny jeans hit at the ankle where a single or double cuff is perfectly acceptable.” —T.K.