The 7 Types of Boots Always Worth Investing In

You'll have these pairs for life.

Street Style: February 28 - Milan Fashion Week Fall/Winter 2016/17
(Image credit: Melodie Jeng)

Just like you can never own enough white tees, you can never own enough boots. But before you refresh your fall/winter wardrobe with new footwear, check your styles. Do you have all the classic silhouettes? By this, we mean the kind of boot that stands the test of time. Chelsea boots meet this criteria, as do your rain boots, and even your new designer ankle booties.

It doesn't matter if these boots have been given a makeover in trendy colors or different textures—you can still tell they're classics by the shape and overall fit. But if you're not sure what types of boots you need or are even out there? We have a short, digestible list of ones to own (or try—no peer pressure here) ahead.

Chelsea Boots

Street Style - Paris - January 2017

(Image credit: Edward Berthelot)

This classic boot comes in all heel heights and toe shapes, but the most distinguishable feature of a Chelsea boot are the black elastic side panels. The shoes often have a tab on the back of the boot, making it easier for you to pull on. Fun fact: The first of this style was made by J. Sparkes-Hall for Queen Victoria in 1851 because she wanted a pair of non lace-up boots, though the Chelsea boots as we know them today didn't become popular until the '50s and '60s. They were considered trendy and "mod" in the United Kingdom when they first came out, and over time became a timeless wardrobe staple for both men and women.

Combat Boots

Street Style - Berlin Fashion Week Spring/Summer 2019 - July 5, 2018

(Image credit: Christian Vierig)

The army combat boot was initially designed to be worn by soldiers in combat, as the name suggests. While the style is still worn by members of the military today (soldiers are getting upgrades in the designs), civilians tend to look for more fashion than function (I, personally, mostly wear my combat boots to and from the office). Fashionable combat boots still have the same original army elements, such as a rounded toecap, laces, a chunky sole, and a high collar. But the designs are more flexible, coming in various textures, from faux croc to smooth leather, and in every color imaginable.

Weather Boots (Rain/Snow)

Street Style - Berlin Fashion Week Autumn/Winter 2019

(Image credit: Christian Vierig)

Speaking of functional shoes, you'll always need a pair of waterproof boots, whether that be snow boots or rain boots, to carry you through the winter storms. Waterproof footwear, thankfully, has come a long way in terms of stylish designs, with many companies like Hunter giving the shoe a more fashun look. (Just check out the Chanel rain boots in the street style photo above.) You no longer need to choose between an ugly rain boot that leaves your feet dry or a boot that leaves you with soaked socks—you can cover all your bases with the weather-appropriate options below.

Thigh-High Boots

Street Style : Paris Fashion Week Womenswear Spring/Summer 2019 : Day Three

(Image credit: Christian Vierig)

Unlike ankle boots, which sometimes leave parts of your skin exposed to the nippy winter elements, thigh-high boots has you covered—literally. The classic style features a shaft that hits mid-thigh and is often fitted to your legs, leaving no weird ripples and bumps. Thigh-high boots can be worn with tights, jeans, skirts, dresses, and more as you've seen on your favorite fashion bloggers and celebrities. Not completely sure how to rock them? Good news: I've come up with foolproof outfits for this season here.

Stiletto Heel Boots

Street Style : Paris Fashion Week Womenswear Spring/Summer 2019 : Day Nine

(Image credit: Christian Vierig)

A stiletto-heeled boot will never be out of date, even though the kitten heel style has made a comeback in recent seasons. The skinny heel can be included on any shoe style from the Chelsea boot to thigh-high options and look best when worn with tailored pieces. Think of the stiletto heel boot as an alternative to pumps at the office for fall/winter. You still retain that confidence you get from your normal heels as well as the height boost. Be right back, trading in my slingback pumps for one of these picks, below.

Riding Boots

Street Style - Paris Fashion Week - Haute Couture Fall/Winter 2017-2018 : Day one

(Image credit: Edward Berthelot)

You don't need to be an equestrian to pull off a pair of riding boots. This knee-high with a flat or low heel style comes in many colors and finishes, but typically brands will offer them in standard shades like brown, black, navy, or grey. Some riding boots come in suede, others in leather, and overall give off a very posh vibe. For a more classic look, go with an option like Tommy Hilfiger, below. For a more vintage meets modern minimalism feel, Zara's "Tall Leather Boots" hit the spot.

Cowboy Boots

New York Fashion Week - Street Style - Day 1

(Image credit: Christian Vierig)

The further we move from the past, the more designers are looking back to the archives for shoe silhouette inspiration. One of them is the cowboy boot, which has been continuously remade every season. Cowboy boots now come in all prints, colors, and textures outside of cowhide leather. For this season specifically, you'll find everything from a kitten heel option to a pointy-toe shape metallic design. Here's to channeling the Wild Wild West the 2019/2020 way with the Western-inspired footwear picks ahead.