The marriage between denim and boots is legendary; it is the “match made in heaven” combo of the fashion world and one of the most-sought-after looks in colder temperatures. The most common perception about this union is that it affords a “macho/tough” look to women, or that is only intended for casual settings, but with the vast assortment of jeans to choose from as well as a plethora of boot options, even feminine and professional looks can be achieved with this pairing. There are certain intricacies associated with this styling as well, such as the folding technique of your jeans i.e. the cuffing of your jeans (which can add another dimension to your outfit). All of this is discussed below.
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No matter the season, pairing a great pair of jeans with a stylish pair of boots is definitely the way to go.
When pairing boots with jeans, you can dress up, dress down, and accommodate whatever weather happens to strike that day.
This fashionable dynamic duo is a comfortable and versatile wardrobe must-have.
But perhaps most important is learning how to wear boots with jeans to show off your own personal style.
Best Jeans To Wear With Boots
You can never go wrong with the winter classic look, boots and denim.
Not surprisingly there are endless combinations you can create to innovate a new style and overall look that will make both your jeans and your boots be the statement of your outfit. We’ve curated a selection of 5 drastically different pairs of jeans that will look fantastic with various different styles of boots.
From straight leg bootcut denim to the more modern and trendy flared crop, we’ve got it all in this one stop shop for all the latest denim styles you’ll need to rock this season.
WASHED DOWN PAINTER SKINNY JEAN
The cut of these jeans is perfect for those who want to go the extra level and pair them with knee high or calf high boots. These black denim washed jeans with a modern twist of white splattered paint, really add a subtle but creative touch to any outfit. They can easily be dressed up or dressed down.
Earnest Sewn Blue Victoria Jeans
Adding some regular washed jeans with two rips in the knees, keeps your outfit looking tasteful while still adding a bit of an edgy flair. These are also cropped so you can pair these with an ankle boot of your choice!
McGuire Denim Valetta Straight Jeans
Black denim with black boots of any height and style always look fantastic. These McGuire Denim jeans are the perfect staple pair of jeans to add to your winter collection. Not only will they look fantastic with any boot, but they will be a great transition into spring and summer as well. Also with any denim classics, it can easily be dressed up for a more chic look, and it can be dressed down for a cozy and casual feel.
The Simple Crop
Blank Denim The Straight Up Jeans
These high waisted distressed jeans might come off a bit summery, but they can easily be warmed up to make a regular wash look fantastic with a pair of neutral colored suede or velvet boots. Add in a bit of wear and tear and you’ll have a great casual statement look that will turn heads anywhere you go.
The Classic Straight
Khaite Vanessa High Rise Straight Jeans
You can never go wrong with a classic regular washed denim high waisted jean. These look fantastic with any style of boot, cuffed, or even tucked. They can really make any outfit look perfect by adding a bit of brightness to your outfit.
These 5 drastically versatile styles of jeans will bring some fashion innovation into your life this season. Whether you choose to opt for a cropped and modern look or a more traditional style, the choice is yours. The good news is, they all look amazing on anyone of any shape or size.
How To Wear Boots With Jeans
Before we dive deep into the various ways you can pair denim and boots, there are some basic styling rules that should be explained.
Although it is the most convenient option, never opt to pull your straight-cut or jeggings over your boots (the case is different for boot cut or flared jeans). And so, here is an all-encompassing guide to mastering boots with jeans.
It may be surprising to some, but it’s not enough to simply throw on your favorite pair of jeans and slip your feet into a comfortable pair of boots.
To get this stylish combination right, you first need to pay attention to the length of your jeans.
If your jeans are long enough to drag on the floor, they’re too long.
When looking for jeans to wear over boots, unless you’re shopping for a specific type of jeans (skinny, boyfriend, etc.) you want to go with boot-cut denim.
Boot-cut jeans should be 1-2 inches from the ground so that they lay over your boots properly.
That being said, boot-cut jeans are really only best to wear with boots when you plan on wearing the boots under the jeans, as opposed to tucking them in.
When selecting a pair of boot-cut jeans, you’ll likely want to go with a darker pair.
Lighter-washed denim can make your legs look bigger than they are, while dark denim is more slimming overall.
As for the rest of the ways to pair jeans and boots, check out the list below and see which ones appeal most to you!
How to Wear Booties and Boyfriend Jeans
To sum up this style using just one word, we’d go with “trendy.”
A great pair of booties is practically a closet staple and boyfriend jeans are all the rage!
Booties are essentially boots that cover your ankle bones but don’t reach the calf.
You want to look for a pair of booties that don’t come up any further than a couple inches above your ankle or else you’ll look too short.
They can have a heel but not all do!
Booties are one of the most versatile boot styles and are comfortable enough to wear all day long!
The most popular way to wear booties with boyfriend jeans is to cuff the hem of the jeans by rolling them up twice.
Be sure to avoid making the “roll” more than an inch wide.
You want to show just a little bit of skin above the booties!
This style is absolutely perfect to wear all year long!
How to wear Black Boots and Black Jeans
To some, this style may sound “edgy” but to others, it sounds “chic.”
No matter how you describe it, it’s pretty clear that black on black is bold but stylish.
Creating a solid silhouette of the same color can help make anyone look both taller and leaner.
This is certainly ideal for most women.
Black jeans and black boots can be styled so many different ways, it’s a pairing that’s perfect for just about any occasion.
Whether dressed up or down, paired with a chunky sweat or a flowing tank top, you truly can’t go wrong with this dynamic duo.
How To Wear Riding Boots and Jeans
Classic riding boots with a stylish pair of jeans may be the most traditional look on this list.
A great pair of riding boots are timeless and look great paired with just about any top, whether dressed up or down.
Black and brown are definitely the most popular colors when it comes to the boots, which means your denim selection can range from white to black and everything in between.
You can find a great pair of riding boots ranging from around $50 to over $300, so don’t feel like you need to splurge unless you want to!
They even make wide-calf pairs to accommodate your calves if necessary!
As for the jeans, skinny jeans tend to be the easiest to wear with riding boots, but you can wear boot-cut or even flared jeans if you know how to tuck them in properly.
How To Tuck Jeans Into Boots
Tucking in the jeans inside the boot is a classic yet casual and care-free method to wearing the two together. This technique ideally requires you to don skinny or straight cut jeans (with no excess bulking around the ankle) and then pair that with ankle boots with heels or western-style ankle boots. The added height of heeled boots offsets the tomboyish look of slouchier straight-cut jeans. A pro fashion tip would be to tuck in your jeans into your socks so that your outfit stays streamlined throughout the day.
Some stylish looks with this technique require combining embellished biker boots with skinny distressed jeans (this combination is also the ultimate tough chick look). For a funkier look, opt for jade green skinny or straight-cut jeans and black or tan hiking ankle boots with heels.
First, look for the slimmest pair of jeans you have.
Then, roll up the hem to create a sizable cuff, but not one long enough to show when your boots are on.
You then need to grab the extra material at the cuff and fold it over to create a tight hem.
Then either roll the cuff again to hold the crease in place or put on a tight pair of socks over the cuff and slide on your boots!
How To Wear Over-The-Knee Boots and Skinny Jeans
Thigh high boots seem to be making a comeback and for good reason!
Over the knee boots (with or without heels) and super skinny jeans make for an effortless style hack to long, endless legs. Because there is no visual break between boots and jeans, you can extend your silhouette and look fierce at the same time.
This stylish but sexy look is great to wear during cooler weather, especially when paired with an oversized sweater.
You can go with black jeans and black boots or mix things up with brown boots and dark denim.
Even white jeans and black boots would work for this style!
The key is to choose slim-fitting boots and skinny jeans.
No, skinny jeans and boot-cut jeans are not the same!
Over-the-knee boots are perfect for dressing up for a date night or a night out with the girls.
They typically have a heel but it’s entirely possible to find thigh-high boots without a heel, like these that you can purchase at Macy’s.
They also make thigh-high boots with straps at the top to help them stay up as you move around.
The hardest part will likely be finding a pair of over-the-knee boots that fits your leg all the way through because it can be hard to accommodate both the calf and the thigh of the majority of people.
How to Wear Biker Boots and Destroyed Denim
Now if you’re looking for edgy, this is the look for you!
You can find women’s motorcycle boots or “biker boots” all over, but you’d be hard-pressed to find a pair in any color other than black or brown.
Amazon offers a variety of stylish motorcycle boots that are great for this style.
A motorcycle boot is essentially a boot with a tighter-fitting ankle that reaches about halfway up the calf.
They often feature a buckle and a heel about an inch tall. Styles and features vary depending on who makes them, but that style is pretty standard.
Because women’s biker boots tend to follow more of a “rough” and “edgy” form, it makes the most sense to pair them with destroyed denim.
Fortunately, you can find a quality pair of destroyed jeans just about anywhere that sells denim!
Asos, Pacsun, Macy’s, and 7 For All Mankind are all great brands with destroyed options available.
If you really want to complete the look, you’ll want to find a great leather jacket, pull your hair back, and go with subtle but sexy makeup that includes a smoky eye.
How To Wear Combat Boots and Colored Jeans
This style may be reserved for the bold, but if you can pull it off, you’ll be one stylish chick!
Whether you wear black or brown combat boots, or even work boots, the key to pulling off this style is in the color of your denim.
Throwing on a pair of colored jeans is a great way to mix up your personal style without going too over-the-top.
Plus, when worn with a great pair of combat boots, it’s an easy way to be both stylish and comfortable, all year ‘round!
Combat boots for women are similar to biker boots, except they tend to lace up.
They also cover the ankle and have a slim look if fully laced up.
However, some people like to wear their combat boots tied loosely, with the upper portion of the folded over for even more of a laid-back look.
Combat boots don’t have a heel larger than an inch which makes them easy to wear all day.
The Folded Up Over Boots Technique
Folding up or cuffing your jeans over your boots is a great technique to create a distinct line from pant to boot so that you can highlight both fashion item without any overlapping between the two. The best looks with this technique goads well with the pairing of Chelsea boots or high-heeled booties with boyfriend jeans or straight-leg jeans. Remember, that this technique also works with skinny jeans. The correct folding procedure is discussed below.
The vogue folding technique of 2017 is to fold along the hem of your jeans – about one to two inches – and then fold a second time by another one to two inches (or till desired length). This is the double-folding technique. Make sure to “firmly establish a crease” by folding your pants before putting them on (you can re-adjust it after putting it on) and then ironing the fold. The perfect lines give the impression of a posh, put-together look. This folding technique makes for a thick or wide cuff. You can also fold a third time for a three-fold technique.
Other than the double-fold technique, there are other folding techniques as well, namely:
- The simple, imperfect cuff (or, the messy cuff) technique: if you don’t have the time or the patience to perfect the prim and proper cuff, then opt for an imperfect one. Simply fold according to your needs, without worrying about matching fold lengths on each side, and step out with confidence. It’s fun to appear unkempt and carefree sometimes! The best look with this technique involves distressed leather boots and skinny jeans. A tip for this technique is to leave a little bit of skin exposed between the boot and the jeans to “visually elongate your leg.”
- The single large cuff technique: instead of the current trend of the double folding technique, you can do a singular large cuff (about 4 inches). However, there is one disadvantage to this technique: it would make your legs look shorter, so only use this technique if you have long, lean legs.
- The rolled cuff/ roll-it-up technique: to employ this folding technique, simply fold the jeans one inch, next, roll the jean again for a double-inch cuff (like the double-folding technique). There is no need to form a crease however and the loose cuff will give a “barrel roll-like,” casual look. The “cylindrical” fold makes it different than the wider, straight lined cuff. The best way to pull off this technique is with boyfriend or straight cut jeans and high heeled booties.
- The half cuff technique works best with baggier/slouchier jeans like boyfriend jeans. Firstly, a single four-inch fold is made along the hem of the jeans and then the top of the fold is bundled together with the bottom half of the fold by pulling it downwards for some extra “accordion-like” “dimension and texture.” Lastly, fold the top of the hem by one inch again for some added flair.
- The skinny/super skinny cuff / flip the tips technique: this differs from the double fold or thick cuff method since this method requires one-fold about one or half inches and the second fold is skipped. This works with well-fitted (super skinny) jeans for a slim-fitted, lean silhouette or you can even do this technique on “modern mom jeans” for a retro look.
The Folded Inward/Under Cuff and Above Boots Technique
This folding technique differs from the outward folding technique because the fold on the hem of jeans is done inwards to make it invisible. This is a dream pairing for skinny cut jeans and some Chelsea boots or ankle booties with or without heels. The perfectly aligned lines give the impression of a tailored, haute styling.
The Ripped Hem Technique
Yet another option is to rip the hem at the bottom of your jeans to just above your ankles (or above your ankle boots). This will enable you to show off those ankle boots of yours without any folds. When ripping the hem, remember to use fabric scissors, a tape measure and pencil (for the markings) to “cut along the outline and leave it unhemmed for a distressed finish.” Rip the hems of boyfriend, straight-cut or skinny jeans and then pair with ankle boots or any style.
The Zipper Cuff/Hem Jeans Over Boots Technique
If you would rather opt out of the folding techniques, then you can choose to don some straight-cut jeans with zipper cuffs in the bottom with any sort of ankle boots. Michonne from The Walking Dead rocks this technique mastering the ultimate bad-ass, butt-kicking chick look like nobody’s business, pairing the zipper cuffed jeans with some embellished cowboy ankle boots.
The No Tuck-In Do’s and Dont’s
If you really want to disregard all the rigid fashion techniques for the right fold technique, then go ahead! Ditch the fold and don’t tuck in your jeans. It is not recommended to go with a no-tuck look with skinny jeans but you can go ahead and go down that route as well. A very bohemian look would be to don leopard jeans with some gray heeled, suede boots (preferably of ankle length).
That’s the lowdown on the types of techniques to adapt with your jeans and boots combos and next, here are some general looks (achieved with jeans and boots) to adopt with any of the above techniques, followed by some fashion-faux pas looks to avoid as well:
- The Equestrian/Classic Riding Look: pair some tan knee-length boots (with or without heels) otherwise known as riding boots, a tailored blazer and slim cut jeans for the classic “riding” or “equestrian look.”
- The Chic Bohemian Look: for a unique look, ideal for the fall, pair a cape or cloak (also known as a poncho) with some dark, denims for a heightened chic bohemian look.
- The Winter Wonderland Look: this is a classic wintry look that will keep you warm and comfy in frigid temperatures. Pair some dark jeans (because darker colors are better suited for winter) with some knee-high boots, a knit sweater or a coat and a woolen beanie to complete this look.
- The Professional/Androgynous Look: ideal for casual Fridays at work, pair some black pieces of denim (folded inward or neatly tailored or cuffed above the knee) with a black blazer, a plain top and simple ankle boots (with or without heels).
- The Monochrome Jeans and Boots Look: you can decide to match your boots and jeans by wearing both of the same colors. The classic fall styling of caramel or tan colored pants and matching lace-up boots is an envious look. Other options are black jeans and black boots or brown pants and brown boots (preferably in the rich shade of brown).
- The Whimsical Look: don’t pick those cartoony print rain boots with your jeans because they are only appropriate if you are less than ten years old!
- The Double Up/ Unnecessarily Matchy-Matchy Look: another faux-pas includes an overly unnecessary matchy-matchy combination of jeans and boots. For example, don’t do plaid shirts with plaid boots or fur-trimmed jackets with fur-trimmed boots. It is okay to match the color of your pants and boots though (as mentioned earlier).
Rock Your Personal Style But Branch Out!
That was the definitive guide to navigating the jeans and boots combination.
When thinking about fashion, it’s most important to keep your own personal style in mind.
You don’t have to feel pressured to try to be someone you’re not.
Boots with Jeans is a timeless combination that just about anyone can pull off.
It’s up to you to find how to wear boots with jeans and which variation best fits your personal style.
Don’t be afraid to go out and experiment with the various combinations of denim and boots. If you find the look to be exhaustive and constrictive then don’t worry, make your own rules as you go along.
That being said, don’t be afraid to step a little outside your comfort zone and try something new. Nothing compares to fearless fashion confidence at the end of the day.
If you’re a little unsure, take both a pair of jeans and a pair of boots into a dressing room with you and try them on.
Pay attention to how you feel both emotionally and physically.
You should feel comfortable and confident! Good luck!
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