There was definitely a time in my life where I shuddered at the thought of wearing Ugg boots. In high school, it seemed like everyone — and I mean everyone — owned a classic brown or black pair of Uggs, and, priding myself on not following the crowd, I vowed to just skip that entire trend. But then, college came around and comfort became a priority for early morning and night classes. So, I caved and bought a gray knit pair (you know, to be different), and from that point on, I became a big fan.

I've since accumulated multiple pairs of Uggs, from the most outrageous platform slingbacks to my personal favorite, a navy blue Classic Mini II. And, while more traditional options have come in and out of style (at least outside the house), the most iconic boot options are back in a big way, with tons of models and celebrities wearing them with everyday outfits.

I, too, have been experimenting with working my Minis into my looks, and I'm telling you, Ugg boots look cute as hell with skirts and dresses. Just take a look at how many outfit ideas I've come up with, dressier options included (and there are plenty more where these came from).

As many of us wonder how to find that happy medium between dressed up and casual this winter, Instagram is also providing tons of inspiration for how to wear Ugg boots. Take a look at a few skirt and dress outfits worth trying, ASAP.

Schoolcore

The pleated skirt and sweatshirt combo is everywhere right now, and perhaps there's no better way to finish off the outfit than with a simple pair of black Classic Mini II boots, styled with sheer knee-high socks.

Comfy Cozy

You've embraced the teddy coat, now stick to the earth tone color scheme and style it with an olive shirtdress and chestnut Ugg boots.

With a Maxi

Bring on the blanket dresses! While sleek (especially when paired with a long overcoat), this combination is also comfy enough to cuddle up in.

With a Print

I personally love breaking out a bold pattern or two, especially during the dark and dreary winter months, and these classic, neutral boots will provide some balance to your look.

With Seasonal Staples

'Tis the season for preppy, plaid outfits, chunky knit sweaters, and shoes that are easy to slip on while running errands.

With Socks

Letting longer lengths peek out of the top of our boots is a celebrity-approved fashion trick that will add a little something extra to your outfit.

As Part of a Theme

What better way to complete an all-blue look than with boots that fit the same color scheme?

With a Set

In case you don't want to go full matchy-matchy, try a more versatile, short black pair of Ugg boots.

To Create the Perfect Combo

Throwing on a loose dress is an easy, year-round outfit solution, but if your go-to seems a bit too fancy for your plans, classic chestnut boots will help to dress it down.

With a Bodycon

So, you might not be going out-out in the pandemic, but if you're feeling the urge to chill in your favorite, tight design, it'll still look extremely cute with some Uggs.

Mini Skirt

There isn't much difference between your most reliable black booties and this warm, soft shoe, so dare yourself to swap 'em out (and yes, they're great for wearing with tights, too).

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