5 Popular Boot Styles from the 90’s: Hot or Not?

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Last Updated on July 19, 2022

Footwear trends from the 90’s still have an incredibly apparent grip on today’s shoe designers, for better or for worse. While authentic 90’s style is predominantly defined by its signature leather jackets, baggy dark-wash jeans and tattoo chokers, the shoes that accompany those nostalgic separates are just as illustrating of the aesthetic. Today we’ll focus on one specific category of the footwear world: boots.

Combat boots, moon boots, knee-high boots… it seems like there is a never-ending list of boot sub-categories to choose from. As a shoe lover myself, I’m definitely not complaining! Additionally, I marvel at some of the shoe trends that were born from the 1990’s, especially when it comes to boots (and chunky dad sneakers, but we’ll have to save that for a later date). In this article, we’ll deep dive a few of the most iconic and popular boot styles from the 90’s and see whether they remain on-trend.

Disclaimer: for some of these styles, I’m going to be interjecting my own personal opinions here. However, each of these boot styles are seriously flattering in their own unique way. Just because Timberland boots don’t look great on my short (and pasty) legs does not, in any way, mean that they don’t look fabulous on you. With that being said, take my thoughts with a grain of rice and wear the sh*t out of your vintage boots, babe.

#1. Doc Martens / Combat Boots


If you’ve read any of my articles thus far, you already know how much I adore Doc Martens. Every style, color, height… In my opinion, Doc Marten has absolutely nailed it when it comes to quality leather products that can both excite and be relied upon. (Example: I’ve had my Jadon’s for nearly 6 years, and they still look as good as when I purchased them.) Doc Martens were wildly favored by young people in the 90’s, but more broadly, combat boots as a whole captivated an entire generation and helped complete their style. But why? Well, probably because they’re the perfect grunge boots. Let’s learn a little more about these cultural icons.

As the UK and the US alike started to experience a new wave of grunge and punk-rock music fanatics, trends and styles adjusted accordingly. Combat boots could be seen sported with patchwork denim jackets, chains, and limitless self expression to match. These shoes represented rebellion and a departure from the status quo, and it helped that the chunky soles and high-quality structure of the shoes allowed for as much stomping and dancing as the younger generation could handle.

Today, combat boots (and more specifically, Doc Martens) come in hundreds of styles and colors, remaining true to its alternative roots while creating pieces that fit everyone’s personal style. That’s why today, these shoes get the HOT stamp of approval. Combat boots from the 90’s like these will never get old.

Check Out: Doc Martens: Off-Duty-Model Look Style Guide for Women

#2. Pointed Kitten Heel Boots

…Not 🙁

Kitten heels as a concept were popularized in the 1950’s, and were considered a practical and comfortable alternative to higher heels or platforms. In the 90’s, household name supermodels began wearing shorter heels in the form of sandals, mules, and stilettos. Much as the combat boot became popular during the rise of the grunge era, pointed toe kitten heel 90’s ankle boots grew in popularity as a feminine alternative to the chunky platform boots.

Many of these styles were offered in shorter lengths (like the picture shows), while some brands went for a half-calf length. All the stars were wearing them on the streets, and many women embraced the kitten heel boots by incorporating them into office attire.

So why don’t they get my personal stamp of approval? I can answer this with one simple word: balance. I know we’ve all been in the situation where we’re dancing a little too passionately and suddenly… a heel breaks (and, if you’re not dancing till a heel breaks, I need to take you to some different parties).

Coincidentally, I have only experienced this phenomenon with kitten heel boots. Unfortunately, I consider the heel to be too thin for the structure of a boot, therefore distributing the weight in an uneven manner. And on a personal note, if a shoe is going to elongate my foot in the way pointed boots do, I prefer to have a bit more height to stabilize the look of my feet. But again, friends, this is all subjective!

#3. Square-Toed Knee Highs


Now these are some 90’s style boots I can get behind. The square-toed, knee-high black boots were especially popular in the 1990’s, with icons like Kate Moss and Naomi Campbell embodying the true “model off duty look” while sporting these ultra-chic boots. And though the hunger for knee-highs was prevalent then… I would argue that they are even more sought after today!

What’s great about this boot style is that they come in so many different flavors. Since I have shorter legs, I tend to gravitate towards styles that are a bit shorter (i.e. mid-calf). If you have longer legs, then you may want to opt for the full knee-high effect like the photo to the right!

These shoes can be difficult to break-in, I must admit. The square toe style definitely squeezes everything together, but after a few wears, they are comfortable and the perfect addition to your fashion collection. My favorite way to wear these are with black mini skirt and colorful mesh top (preferably one with a fun print). With black boots like these, the opportunities are truly endless.

Check Out: 5 Stunning 90s Skirt Outfits that Inspired the Y2K Style

#4. Fold Over Boots

…Not 🙁

Fold-over boots are yet another example of a quirky silhouette that immediately attracted a boatload of young fashion enthusiasts in the 90’s. I don’t particularly blame them, because these boots are definitely distinct in their shape and structure. In my opinion, another part of this style’s allure was its effortlessness. The slouchiness of the upper portion of the boot allowed for it to maintain the grunge spirit of the 90’s, while also conveying a more formal attitude. So, why is this a miss for me?

Slouchy boots, in my experience, end up widening the calf area (which I do not have time for, years of basketball have made my calves too large to even fit into some pant legs, but I digress). Especially if you are interested in wearing flowier material (i.e. a dress, a longer skirt, a loose pair of slacks) it is my recommendation that you choose footwear that provides a tapering effect down the body.

We don’t see many fold-over boots like these anymore, though we do see the styles that look like a whole pant leg is covering the body of the boot (see the photo to the right). Much like everything else, fashion and design choices evolve and adapt as the years go one. What do we think about this reimagining of the fold-over boot?

Shoe designers and fashion houses alike clearly knew what they were doing in the 90’s, and each brand discovered their own unique style that set them apart from the competition. While not every boot style was a hit that found its way back to the 2020’s, we still have to respect and cherish the funky design choices that we loved so dearly in those years.

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Madison Gile
Madison Gile is a young professional living in the United States with a passion for all things fashion, trends, and sustainable style. She works in the legal field, but has a lifelong love of fashion and writing. Throughout her college career, she ventured to understand how to influence her peers to view fashion in a different way, one that promotes inclusivity and social responsibility. Madison loves all things vintage; specifically vintage Chanel and Prada. As a 90’s baby and someone who is deeply appreciative of the aesthetic, Madison upcycles 90’s pieces from thrift stores and incorporates the edgy and adventurous style into her intriguing makeup looks.