1 – Frye Addie Hiker Boots.  Flat Version.  2 – Hunter Rubber Care Kit.  3 – Moncler Blanche Boot (See Below for More Colors and Sizes).  4 – Tall Charcoal Socks.  5 – Short Cable Knit Fleece Socks.  6 – Hunter Short Original Boots.  7 – Sorel Joan of Arctic Boots.  8 – Shearling Insoles.  9 – Hunter Balmoral Adjustable Boots.

1.  Best Heeled Boots: Frye Addie Hiker Booties

Available Here.  Flat Version.

Faced with a full day of bitter cold Chicago weather over the holidays, I snapped these hiker boots up to protect me from that Lake Michigan wind while still looking stylish around the city. The hiker style, weatherproof leather, and rubber lug soles conjure images of après-ski mountain activities while the 3.5 inch heel lengthens the leg and makes these booties appropriate for even the most discerning city slicker. My favorite feature? The cozy shearling that lines the opening and tongue of this boot. Style them with black or red laces; these darlings come with both. Prefer flats in the winter? Take a peek at this flat hiker style from the same brand.

2.  Hunter Rubber Care Kit

Available Here.

While I love a good wellie, the white residue these charming British boots create can be rather (rawther) frustrating. Once you’ve invested in a pair of great wellies, this rubber care kit under $25 just makes sense. The kit includes Hunter’s boot shine spray, a shine-soaked sponge, and polishing cloth to keep your wellies clean and residue-free.

3.  Best Investment Boot: Moncler Blanche Boots

Black Leather: Size 35, 38. Size 35, 36, 37.5, 39.

Brown Leather:  Size 36, 38, 40. Size 37, 38, 39. Size 36, 37, 38, 40, 41.

Tan Suede:  Size 35, 37.5, 38, 38.5, 39, 39.5, 40, 40.5, 41.

Named after the French mountain village of Monestier-de-Clermont, Moncler’s history as a luxe ski and outerwear brand goes back to 1952. Their hiking boots are designed to worn and enjoyed on all your wintry adventures for years to come. But they’re not all about function; with buttery-smooth vachetta leather exterior and a rubber tread sole emblazoned with the colors of the French flag these boots make a fashion statement as well. Despite their lofty price tag, these boots are selling out quickly everywhere. If you’ve been looking for the perfect investment boot, don’t wait too long on these beauties!

4.  Best Socks for Tall Boots: Hunter Mid-Calf Charcoal Socks

Available Here – 50% Off.

There’s something incredibly perfect about this pair of mid-calf socks in cozy two-tone charcoal yarn peeking out of a tall pair of boots. My favorite boots to pair these with are the Hunter Balmoral and Sorel Joan of Arctic options I’ve included in this collage.

5.  Best Wellie Socks for Short Boots: Cable Knit Fleece Socks

Available Here.

While the shorter wellie style is my favorite, they can be a bit chilly since there’s a gap between the leg and the boot. These cozy fleece socks fill up the gap with a delightfully charming cable knit overhang around the top.

6.  The Essential Boot: Hunter Short Original Rain Boots

Available Here.

If you add one pair of winter boots to your collection, let these short Hunter wellies be them. While these charming boots aren’t intended to be winter boots, it’s their waterproof quality and tread soles that make them the perfect boots for trudging through snow and ice. Wondering how to make them a little cozier? Add the shearling insole into the bottoms and tuck in the fleece wellie socks. Suddenly you, my brilliant darling, have both charming rain boots and cozy snow boots in your weatherproof arsenal.

7.  The Warmest Boot: Sorel Joan of Arctic Boots

Available Here.

These boots are for those of you bracing sub-zero temps this winter; I honestly don’t think I’ve ever worn a warmer boot! Their waterproof construction keeps snow and slush out and their rubber soles provide traction on icy surfaces. Faux fur cuff and washable, recycled felt inner boot provide extra warmth. And for being so functional and warm, I have to admit, they are pretty cute with leggings and a giant, cozy sweater or parka.

8.  Shearling Wellie Insoles

Available Here.

I was so thrilled when I found these shearling wellie inserts I immediately took to Instagram Stories to share my discovery with you! I’ve loved wearing my wellies for years but their one downside was, despite the easy-to-clean waterproof exterior that begs for snow and slush, they remained too drafty and uninsulated to wear in the winter. These insoles correct that problem, making our beloved wellies appropriate for all seasons and even more comfortable.

9.  Best Boots for Exploring: Hunter Balmoral with Adjustable Sides

Available Here.

My husband and I often comment that we feel so at peace when in wide-open spaces with lush trees and dogs hopping through the tall grasses beside us. Even if we’re not trudging up hills every weekend, I can still dress the part with these Balmoral boots. Though admittedly not the most feminine selection from Hunter, these boots caught my eye for both their function and British countryside style and I’ll go so far as to say they make a better investment than the original tall Hunter rain boots. Why, you ask? The more sturdy exterior and lug soles withstand a more rugged environment. Neoprene lining provide a slightly warmer, more comfortable, and definitely more water-resistant experience. Adjustable sides allow you to snug the boots up around cozy socks or let them out to provide room for wide calves (up to an extra 4″ inches of room, to be exact). Lastly, these boots have a padded footbed to make them more comfortable for all-day wear; add the shearling insoles on top and you, my dear, will find your feet outlasting even the most adventurous outdoorsmen in your group. Pair them with a cozy fisherman’s sweater and skinny jeans or leggings for a just-back-from-the-Highlands look that would impress even Her Majesty.