Boot Outfits | Which Styles Go the Best with What You’re Wearing this Winter

Cool boot outfits are everywhere right now, but all the different jeans and boot style combinations are overwhelming. If you’re wondering which boots will go the best with what you’re wearing, they’re in this post. I’m breaking down and sharing the best styles that will go with the most outfits so you don’t have to stress over getting dressed.


When women start to put together their fall and winter outfits the first place they usually get hung up is their boots, literally! All the different jean and boot style combinations are overwhelming. The wrong boots can ruin an outfit by bulking up your leg line or fighting with your jeans. The best boot style you can buy is one that is fitted to your foot.

Boot styles that are narrower at the ankle and tighter across your instep and back the back of your heel always look the best. My personal pick this winter was the Nixie from Jeffery Campbell, but it’s almost completely sold out in black neoprene. You can still get the black patent and some cool fashion colors on sale HERE.

Leather Might Be Better

If you have wider feet or bunions, suede is sumptuous and soft otherwise, a leather boot is better. Leather won’t stick to your straight-leg jeans but will tuck nicely up under them, especially styles with a tall stance. Styles like the first two, with an elastic side panel, like the first two in this lineup, fit close to the foot.

Sock Booties

If you’re petite or have small ankles try a sock-style fabric boot. Sock booties are elasticized so naturally have a more fitted and feminine silhouette.


Lug-sole boots with a heel are trending alongside wide-leg and bootcut jeans this winter. Styles with elastic at the opening will fit closer to the foot.

Lug-sole With a Heel

Flat Lug-sole Boots

Flat boots with a lug sole look best with loose-leg pants, joggers, or leggings

Unless you wear a lace-up pair of boots like this over modern skinny jeans flat boots with a lug sole tend to look too bulky with most jeans.

Pull a pair of stylish sweats over the top of these.


I love black opaque tights with any black boot in the winter, but sometimes If you’re not wearing black, tights don’t look quite right. That’s when you can reach for a nude boot. Completing an outfit with a nude shoe is a styling trick I’ve used to make outfits that work every time. Typically we think about wearing nude shoes when it’s warmer, but I love the idea of a nude boot all year long. They will elongate your leg and won’t start and stop the eye. Nude boots are also an unexpected way to break up an all-black winter outfit. For a great go-to outfit match them to a timeless trench or camel coat.

Nude Boot Outfits


Here is a breakdown of which boots go with the most popular jeans right now.

Low Heel Boots

Long Straight Leg Jeans

Stiletto Boots

Flare Leg Jeans

Block Heels

Bootcut Jeans

Flat Lace Up Boots

Modern Skinny Jeans


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