How To Wear Boots
Sophie Diego
Table of Contents
The athleisure sneaker hogs most of the limelight. Yes, everybody needs a lax outfit for hump days, but you shouldn’t stick to what’s comfortable. After all, the antithesis of fashion is stagnation.
In an effort to jazz up your closet, a staple boot is absolutely necessary. Whether it’s a pair of platforms or a stiletto heel, a standard set of closed-toe booties can help elevate an outfit.
Compared to the average summer sandal and Oxford loafer, this variety of footwear provides that touch of ‘boss-babe’ attitude that no other shoe can provide.
Of course, there are hundreds of boot designs to choose from. Depending on your preferred aesthetic, styles can range from Victorian-style cottage-core to MySpace emo chick. I swear, there’s no other shoe more powerful than a pair of booties. Could you even imagine a world without them?
But, for those who consider themselves a veteran sneakerhead, chances are that they don’t know the basics of boot styling. If so, there’s no need to stomp in frustration.
Instead, we’ll teach you how to wear boots by providing 11 outfit ideas. From vintage excellence to TikTok cybergirl, there’s definitely no shortage of OOTD inspo online.
What is a Boot?
Before we address how to wear boots, it’s important to answer the ‘what’ question first. A boot is a type of footwear that’s traditionally worn in the cold season.
Most varieties feature an ankle cut silhouette, lace-ups, and added traction. People typically wear them for function and fashion, depending on the occasion.
History of Boots
Boots involve a long-winded history that dates back to the prehistoric ages. Depicted in cave paintings and murals, animal skin booties were popular among trend-setting neanderthals.
Centuries past, ancient civilizations such as those in Egypt and Persia adopted the shoes as an intrinsic part of royal garb and military uniform.
At an early age, boots became synonymous with the upper class, considering that underprivileged communities could not afford such costly materials at the time.
Boots were a wardrobe staple in the middle ages, as cobblers reinvented the classic animal skin cover-up to embody multiple styles, such as the poulaine, the Crakow, and the ever-so-famous Goodyear welted shoe.
In the 1800s, boots were slowly integrated into the working class and, most notably, the United States Cavalry during the Civil War. Spats, cowboy boots, and Wellingtons made their official debut at the time—and have continued to hold a dominant place within the fashion industry.
Today, boots have long lost their symbolism to class. Anybody can wear them, ranging from the super famous to plain jane.
When to Wear Boots
While most associate boots with fall and winter, there is no set season when it’s appropriate to wear them. You’re free to style Dr. Martens, Demonias, and Chelseas at any given time.
With that being said, there is a clear difference between the strictly fashionable and the exclusively functional. In short, you can’t wear Lamoda boots during a snowstorm.
In the Venn diagram of fashion, I think it’s fair to say that brands like Stella McCartney, Uggs, and Jeffrey Campbell are worn as fashion statements. Companies like Arctic Fox, North Face, and Sorel are typically recommended for extreme weather conditions due to the amount of support and traction.
Regarding occasions, boots are typically worn as streetwear. They’re synonymous with casual cold-season fashion. We don’t recommend wearing them to weddings, galas, or black-tie events.
How to Wear Boots
The best way to tackle the ‘how to wear boots’ question is to assess your personal style. Do you prefer romantic silhouettes, or are you a stickler for vintage grunge? No matter the aesthetic, boots can easily blend into your daily look—all you really need is some confidence and outfit inspo.
From jeans to frilly dresses, we’ll help you answer the ‘how to wear boots’ query using 11 different outfits. Don’t worry; we’ll offer ideas for both men and women.
6 Outfit Ideas with Boots for Women
You’d be surprised how a simple pair of Dr. Martens can transform a simple and sweet ensemble to a hardcore grunge moment. Take, for instance, this outfit, which features a playful red button-down, a black accordion-pleated skirt, and a matching hat.
The boots provide that needed ‘edge’ to the look, something that a pair of stilettos can’t offer. Aside from being stylish, it’s a solid outfit to consider if you hate walking in heels.
Own a pair of ‘daddy long legs?’ Honestly, it’s a flex worth showing off—but I understand if you feel self-conscious of showing too much skin. For those not keen on wearing tights or leggings underneath, you can definitely make do with some knee-high cowboy boots.
Not only does it provide ample coverage, but the heels help in accentuating your figure. Paired with a loose white button-down and cute mini skirt, this is how to wear boots that compliment your body shape.
If you’re wondering how to wear boots with jeans, we suggest copying from style icon Emily Ratajkowski. In our opinion, the best way to wear cowboy boots is to pair them with form-fitting jeans.
I know most trendsetters usually don a set of skinnies to help prevent bunching, but we feel that a bit of ‘creasing’ can help embody those Shania Twain vibes.
The addition of the white turtleneck and the oversized black blazer works to counterbalance the chunky silhouette of the boots. Of course, shades are an absolute must for this look.
The ‘how to wear combat boots’ question is a highly searched-for term in Google. Naturally, it would only make sense for us to share our own answers within this lineup.
If you’re up for showing a lot of leg, a pair of platform stompers blends perfectly well with matching biker shorts. Paired with a white oversized zip-up, a cross-body bag, and some cool shades, it’s certainly a more hardcore version than Princess Diana’s iconic look.
For those wondering how to wear ankle boots with jeans, we recommend taking inspo from Gigi Hadid. Here, she’s rocking a pair of retro-themed heels with light-wash cigarette jeans, a vintage tee, a beige mohair sweater over top, and a fun set of shades.
Who says that you have to opt for black when it comes to boots? These vibrant beauties are certainly the highlight of the outfit, especially when it’s paired with the bag and the graphic shirt.
Perfect for brunching, bookstore-hopping, and Instagram-modeling, this romantic ensemble is the fit to opt for if you’re feeling adventurous.
This OOTD features a preppy brown sweater, a brown leather skirt, and matching knee-high booties. Accentuated with a handbag and a pair of stylish sunnies, it’s getting a complimentary chef’s kiss from us.
5 Outfit Ideas with Boots for Men
The ‘how to wear ankle boots’ debate can easily be settled with a pair of form-fitting pants and a relaxed crew-neck long sleeve. It’s a fairly basic outfit, but it comes with a few attributes to help avoid monotony.
For instance, the sharp-pointed booties help elongate the legs while the coral hue of the tee works to unearth the blush tones in your skin. We don’t recommend any accessories, but we do suggest layering the look with a suede black leather jacket on top.
If you own a pair of sock boots, wearing a loose set of trousers can easily swamp that form-fitting illusion. Instead, we recommend tucking your pants into your socks to help create that vintage pilot look.
The addition of the black turtleneck and leather jacket work wonders in accentuating the brooding, charcoal tones of the shoes. In our humble opinion, this is how to wear boots in a casual, charming way.
This outfit is totally giving me Harry Potter vibes. Composed of plaid trousers, a forest green trench coat, a brown collared duster, a burgundy turtleneck, and a pair of Dr. Martens, it’s the super-sophisticated look to go book-shopping in.
If you’re wondering how to style ankle boots in a more elegant manner, this is definitely the ensemble to go. Don’t forget to finish off your OOTD with a pair of glasses and a stylish leather satchel.
The safest way to approach the ‘how to wear boots’ question is to go full monochrome. There’s a good chance that your lace-ups are black, which is the go-to shade for many trendsetters.
We recommend wearing a basic pair of trousers, a comfy cable knit top, and a crochet cardigan for added texture. To avoid monotony, you can always opt for a pattern for the over-layer. The addition of the white beanie helps to lighten up the entire look.
Soft boys like boots too. Instead of opting for grungy black, you can always go for white as well. For those into pastel shades, we recommend a pair of ocean-blue pants, a light-colored sweater vest, and a relaxed crew-neck tee underneath.
The baseball cap and the crossbody bag help marry the whole look together. The dog, of course, isn’t an added ‘accessory,’ but it definitely pushes the cuteness vibe up to a 10.
What Type of Boots Can You Get?
Boots come in all sorts of shapes and sizes. From cowgirl chic to Victorian-inspired silhouettes, the options are literally limitless. Before you settle on a design, it’s important to consider your shoe preferences.
Do you opt for slip-ons or lace-ups? There are also cuts to consider, as boots can vary from knee-high styles to cropped ankle length.
As we previously mentioned, boots are typically divided into 2 different categories: fashion and function. Of course, you’re free to intermix styles, but we’re just here to lay out some ground rules. To keep things simple, we’ll provide a list of common boot brands organized by style.
Fashion:
- Dr. Martens
- Demonia
- Uggs
- Jeffrey Campbell
- Franco Sarto
- Lamoda
Function:
- Sorel
- Arctic Fox
- L.L Bean
- Merrell
- Baffin
- Columbia
How to Choose The Best Boots
Unless you’re a high-balling trendsetter, boots are usually treated as an investment purchase.
Of course, it’s relatively easy to cop a pair for under $30 on Shein—but considering that fast fashion doesn’t have the best rep for quality, we suggest opting for more reputable brands instead.
Companies like Ugg, Dr. Martens, and Demonia are renowned for their boot collection, so you don’t have to worry about durability and value.
A good pair of boots should be made out of leather, merino wool, suede, felt, fur, and other resilient materials. Some brands use synthetics in place of animal hide, which is a great option for ethical and vegan trendsetters.
Before you settle on a design, we suggest weighing the cost with the fabrics used. Obviously, textiles such as crocodile leather will entail a higher fee than faux alternatives.
Fashion is another important factor to consider. After all, you don’t want to opt for an ugly boot. We suggest settling for a shoe that’s timeless in design. That way, you don’t have to worry about it going out of style.
How to Style Boots
The ‘how to wear boots’ query shouldn’t be met with confused stares. It’s not a math question—you’re allowed to have fun with fashion. For those who haven’t picked up on some common themes throughout our top 11 list, here are some general tips and tricks on styling booties.
- Play around with different textures: most boots are made out of leather. Naturally, a majority of trendsetters like to juxtapose the shiny attributes of this material by adding faux fur or suede. Of course, you’re also free to wear a leather jacket or a pair of pants—just don’t go overboard with it.
- Knee-high boots love mini skirts: This also applies to shorts and mini dresses as well. Instead of opting for showing full-blown leg, you can always count on a knee-high moment for extra style points.
- Tights: Don’t own a pair of knee-high Demonias? Don’t worry; you can easily create that full-legged look by donning some black tights. Extra points to those who opt for patterned designs such as the iconic Gucci logo.
- Cigarette pants or loose trousers: Skinny jeans? Please, this isn’t the mid-2010s. It’s time to abandon the slinky silhouette. Instead, we invite you to wear relaxed trousers with your boots.
Fashion Tips to Avoid With Boots
Boots can do no wrong, right? To be honest, there’s a fair share of ugly styles out there—but the problem isn’t so much as the shoe. It’s more so on how you plan on styling them.
If you want to stay clear of the fashion po-po, here are some outfits with boots that you should 100% avoid.
- Workout leggings: Let me be clear: wearing all-black leggings with boots is completely fine. Instead, we’re referring to the classic Lululemons with interesting cut-outs and prints. Trust us, it’s a match made in hell.
- Ball gowns: this is a bit self-explanatory, but we’ll include it anyway as a reminder. Yes, it’s a classic example of fashion juxtaposition, but you don’t want to leave footprints on your pretty dress, now do you?
- Cargo shorts: Considered a fashion faux pas for Tan France, wearing dad shorts with boots is a styling sin.
- Socks that peek over the edge: If you’re wearing ankle boots, it’s best to wear a short pair of socks. You don’t want to show off your Spongebob stockings with your Balenciaga sock boots.
How To Take Care Of Boots
Whether you own a pair of $1,200 Stella McCartney boots or a $100 set of pointed-toe booties from Zara, you need to learn how to properly take care of your shoes.
Of course, not all of us can afford to visit our local cleaner, which is why we’ll provide some tips and tricks that can all be done from home:
- Use a horsehair brush or nylon bristles to eliminate surface-level debris
- Store your boots on a wire rack with a rubber platform underneath. This helps to drain your shoes of excess water and dirt.
- Apply a damp towel to stained boots. Those damaged with salt and other debris may require more intense treatments.
- Use a leather conditioner to help restore the flexibility and shine of your shoes
- Stuff a boot shaper or newspaper in your shoes to help maintain its silhouette.
Best Places to Buy Boots
So, you finally addressed the ‘how to wear boots question.” Now it’s time to find your perfect pair. For those in need of recommendations, here are some great places to cop a set of booties:
- Sam Edelman
- Franco Sarto
- Dolls Kill
- ASOS
- Uggs
- Dr. Martens
- Nordstrom
- Amazon
Final Thoughts
Every outfit needs a solid foundation. For some, it’s the basic white t-shirt. For others, it’s a simple set of jeans. Boots are another wardrobe essential, and it’s fairly easy to create a cohesive fit around a pair of shoes.
We’ve taught you how to wear boots by offering up 11 different outfit ideas, and honestly—we think that all ensembles fall apart if they were switched with a stiletto heel or pair of sneakers.
Styling is no science, but I think we can agree that fashion entails a bit of experimentation. You don’t need to be a genius to look great. Instead, you just need some confidence and a cute pair of booties to pull it off.
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