The 6 Boots Every Woman Needs over 40 (and what to wear them with) - Nada Manley

If you don’t have them, you can’t wear them.

These words of wisdom ring through my head every time I consider a new pair of shoes. You can’t wear them if you don’t have them. This is equally true when talking about boots, because there are so many options and each style brings something different to an outfit. From the edginess of a chunky boot to the cool-girl trendiness of a modern cowboy boot, they’re a key accessory for winter that are as stylish as they are practical. And, seriously, how often do we truly get to combine style with practicality? Not very.

I am so excited to be partnering with Dream Pairs on today’s video because their shoes are accessible, affordable, and most of all, comfortable. If you’re not familiar with Dream Pairs, prepare to be shocked by the prices, the variety, and the style.

Since we’re smack in the middle of boot season, I thought that highlighting the 6 different styles of boots that every woman “needs” would be a timely topic. If you’re looking for a new style to get you through the winter, or simply want some ideas on how to style your boots with clothes, you’ll find some ideas here.

Now, you don’t TECHNICALLY need 6 pairs of boots when one boot can, for example, check multiple boxes. The black lug-sole boots I show in this video, for example, are both CHUNKY (box one) and WATERPROOF (box two). But who am I to limit you? :)

Before I introduce you to the 6 pairs of shoes that every woman needs, let me give you a very general, often broken rule of thumb:

Short boots with pants. Tall boots with dresses.
VERY General Rule

I break this rule all the time, and so should you, but the combinations above always work.

4 Tips For Pairing Boots With Outfits

Functionality: Do the top of the boots interfere with the hem of the clothing item? Do they “work” together?
Scale: Does the scale of the outfit “go” with the scale of the boots?
Style: Do the styles/dressiness levels/details of the boots and the outfit go together?
Season: Do both pieces look like they belong in the same season?

As always, keeping elements the same creates a CLASSIC look, while pairing contrasting elements results in a more CREATIVE look.

And now, the 6 pairs of boots that every woman needs. And you can shop them all right here.

Booties

Possibly the most versatile boot style, these pair easily with pants and dresses. If you have the dark neutral box checked, try a light neutral like white or beige for an unexpected touch. If your legs are short, a color close to your skintone will lengthen them, especially when worn with dresses.

My Pick: The Sianna Chunky High Heeled Ankle Booties, Use code nada20 for a discount.

Best With: Medium-scale boots work well with fitted and flowy dresses alike, as well as pants.

Tall Boots

The classic choice in this category is the riding boot, but any mid-calf, knee-high, or even over-the-knee style fits here. Cowboy boots and even rain boots are also fun and practical options. They also offer an easy way to update skinny jeans or pants.

Mid-calf Western cowboy boots, $49.99. Use code nada20.

Tall boots work best with skinny bottoms (skinny jeans and leggings) or dresses of all lengths. When worn under longer dresses, keep the dress flowy to avoid a bulky look under the skirt.

Chelsea Boots

This fairly unisex style often features a flat heel, round toe, and elasticated sides for easy on-and-off, and are usually worn with pants. I chose a slightly dressier style with a small heel and elongated toe.

Pointed-toe Chelsea ankle boots, $49.99. Use code nada20.

Chelsea boots are typically best with pants, although this style with it’s elongated toe and slight heel works well with dresses too, especially in this leg-lengthening color.

Weatherproof Boots

From rain and snow boots to snuggly faux shearling styles, these are as practical as they are cute. The shorter style shearling boots are back in style, and if you love them, style them with leggings, loungewear, or very casual dresses.

Suede mid-calf snow boots, $49.99. Use code nada20.

These work best with very casual dresses, leggings, joggers, and skinny jeans.

Chunky Boots

Lug sole, platform, combat and moto boots all fall into this category, which combines edgy style with practicality, as they are usually flat and also slip-proof. This specific style features a sock-like top that molds to your leg for warmth and comfort.

Stride lug sole platform slip-on booties, $42.99. Use code nada20.

The chunky scale of these boots makes them a better pairing with flowy dresses and non-skinny pants.

Dress Boots

This sleek and polished boots are a great alternative to a pump in colder weather. They have all the dressiness of your favorite dress shoe, but with more warmth and practicality.