13 Comfortable Shoes to Wear With Straight Leg Jeans

An ankle boot.

Don’t let a little snow stand in the way of your outfits. There’s no need to buy six pairs of boots for different occasions: with the right pair, you’ll be ready for anything Mother Nature decides to throw at you. Below is a list of thirteen shoes that will compliment straight leg jeans, which we have heard are all the rage this winter. These suggestions are just guidelines; feel free to stray from them if something else catches your eye. Consider these options as inspiration for both stylish and practical footwear items—few things can bring an outfit together like a good set of shoes!

† The boot height should hit just above the ankle; any higher could lead to discomfort if you’re walking around a lot or if it snows and covers your ankles.

† The shaft of the shoe should be slim, but not so slender as to pinch or squeeze your legs while you walk.

† Boot toes can come in various shapes: rounded, pointed, and square are all fine options (although we recommend avoiding toes that aren’t round). You can also choose between a stiletto heel (a thin heel), block heels (heels with large rectangular platforms) or thick heels (which are similar to block heels but flatter). Just make sure your boot has some kind of heel—a flat one will cause more problems than it’s worth when trying to walk through snow*.

† When selecting boots, avoid platforms and try heels that fall between two and five inches; avoid anything higher than five inches unless you want people mistaking them for cowboy boots

A sneaker like a Nike Air Force 1.

The air force 1, a sneaker first worn by basketball players at the United States Air Force Academy in the 80s, has steadily gained popularity with the American public. This can be attributed to its versatility—the simple design allows you to wear them to work or play and match them with any outfit.

What makes the Air Force 1 so excellent is that it’s simultaneously casual and dressy. They come in an array of colors, from unassuming grey and white to bolder options like red or royal blue. Better yet, they look great with jeans (especially those of the straight-leg variety) while still fitting in at formal occasions. As a versatile staple, they are perfect for pairing with any number of outfits—even those that you wouldn’t expect it to go well with!

If you’re looking for a pair of shoes that will keep up with your fast-paced life and make you comfortable wherever you go, this classic should definitely be on your radar.

A sneaker that’s just as comfortable as your favorite pair of Nikes (or Chuck Taylors, or Converse).

If you’re a fan of wearing straight leg jeans (and if you’re reading this website, chances are good that you are), your ideal shoe is one that’s simple and goes with everything. But comfort also needs to be a consideration when you’re picking out what to wear on your feet—especially if you’ve got a long day ahead of you. Luckily, there are plenty of versatile pairs on the market that meet both criteria.

If at all possible, it’s best to go into your shoe-shopping experience with a clear idea of what you want in a pair. That can mean shopping within specific brands, or even looking for certain features—if it’s available in your style preference, look for shoes that have rounded toes as opposed to pointy ones. Sharp angles will often dig into your heels and cause discomfort after extended periods of time, so keep an eye out for footwear with squarish corners along the big toe and side edges.

The same is true for the heel—flat ones will promote better overall foot health than their elevated counterparts. While elevations can be nice, they put extra pressure on joints that aren’t meant to bear weight throughout the day; particularly if you don’t take frequent breaks from walking around in them! As such, look for shoes with flat heels available in your preferred style; not only will they be more comfortable when walking around all day long, but they’ll also give off an overall appearance of being more stable and less sloppy than their heeled counterparts. You’ll still get some height without any pain!

A chunky heel boot.

If you’re looking for a shoe to wear with straight leg jeans and want comfort, choose something that has a decent heel. One of the most famous brands for this style is Steve Madden, which makes shoes that go well with au naturale outfits but can also be dressed up for more formal occasions. They offer several types of shoes in their Women’s Uptown Bootie collection, with heels ranging from two inches to over four inches. A chunky heel boot like the one pictured above looks great when paired with ill-fitting straight leg jeans, and the bootie style will flatter your calf muscles and elongate your legs.

What’s great about a pair of boots like these is that they can be worn literally anywhere: at work or play, on weekends or during the week. Wear them to a dinner party; wear them to hang out around town; wear them to stand outside during a protest (but maybe skip the protest if it’s super cold). The thin material and pointed toe make these boots easy enough to slip on in a hurry—so try wearing them when you don’t have much time to get ready in the mornings.

A kitten-heeled mule.

This season’s kitten-heeled mules have been making their way to the runway at shows like Alexander Wang and Gucci, and now they’re making their way into the catwalk as a style that you can wear anywhere. When we first saw them, we couldn’t help but be impressed with how cute they looked paired with a loose fitting silk shirt, but we also knew that they would soon be hitting the stores.

These boots are surprisingly comfortable—they’re made to fit your foot like a glove, so you can enjoy all of the fashion flair without having to worry about breaking your stride. They look amazing on everyone from casual wear lovers to those who want to look cool in even more formal occasions. We really love wearing them with our straight leg jeans for a casual yet stylish everyday look.

A classic loafer.

When I was a teenager, I was convinced that men who wore shoes with a loafer style were weak and effeminate. It seemed like such an unmanly look. It’s not because the shoe itself isn’t masculine—it’s simply because it wasn’t the norm at the time. In years past, when men wore suits to work every day, they most likely only owned one pair of dress shoes: black leather oxfords or wingtips. No matter what color pants they had on or what shirt they wore underneath their suit jacket, those oxford or wingtip shoes would go on their feet every day.

But once loafers gained popularity among young businessmen in the 1950s and 1960s, things started to change. Loafers became a subtle way for them to express themselves through their footwear while still maintaining an air of professionalism in the workplace. Today you’ll find loafers everywhere from boardrooms to art galleries—and many come with tassels if you really want to get noticed!

Being comfortable is something we can all agree is important in a shoe for everyday wear; however, there are different levels of comfort between individuals and different reasons why people require comfort in their footwear. For example:

I’m not overly concerned about comfort for eight hours at my office job since I sit most of the day; however, whenever I’m out walking around town on errands or meeting friends for dinner afterwards, I need my shoes to be comfy enough that my feet don’t feel like lead by 5:00 p.m.—especially if I plan to meet up with friends after work! And while some women feel fine wearing heels all day long (I am not one of these women), others prefer more minimal styles that don’t cause blisters after standing all afternoon (i.e., me again). And then there’s everyone else who just doesn’t like high heels but still wants something stylish enough where nobody will notice how flat their shoes are!

A slip-on loafer with a little bit of edge.

While most people go through life wearing the same pair of sneakers or flip-flops, there are a wide variety of shoes that can serve as additional wardrobe staples. One such shoe is the loafer, which, in addition to being comfortable and versatile enough to wear with pretty much any outfit, also has the extra benefit (for certain situations) of looking more fashionable than a sneaker or sandal.

What makes a good loafer? Well, for starters, it should be comfortable enough to stand all day in (if you’re going to replace your sneakers with loafers at work), and it should be durable enough not to get destroyed after walking around during any one particular adventure. It’s also best if a loafer is easy to slip on and off without undoing any knots or laces (especially if you plan on wearing them while traveling). Finally, it helps if they have an interesting design element—anything from a subtle pattern to an eccentric color can make all the difference in getting noticed by someone at your local coffee shop or bar.

A moccasin boot with a stacked heel.

The stacked heel is a popular feature in moccasin boots, giving them a modern look. A stacked heel can be around one inch to two inches high, and is usually made out of wood or rubber. The stacked heel gives the boot height without sacrificing comfort while the wearer is walking, which makes it ideal for urban environments.

What else do you want?

For those who like the style of cowboy boots but don’t like how uncomfortable they are on long walks, this type of boot could be an excellent alternative. It comes in a variety of colors and materials, so you can pick one that works with your wardrobe and provides your feet with optimal comfort.

Fashioned from rich leathers or suedes and finished with velvets and other fine materials, these boots provide timeless appeal while still being roomy enough to fit thick socks underneath them during the winter months. Some styles even come lined with fur for extra warmth during cold weather.

A sandal with a formal shoe feel in the toe shape and color.

You may see a lot of sandals with a nice shape or color, but what makes those the right ones to buy? You need to look for shoes that have a formal appearance: they should be low-to-the-ground and have a heel, even if they’re covered in straps. These shoes are best worn with straight leg jeans in the summer or winter as you can wear them with cropped pants, skirts, or dresses. The below sandals all feature this kind of comfortable heel that will make you feel pulled together but not overdressed.

An open-toe bootie to wear during warmer days.

If you’re looking for shoes to wear with your straight leg jeans, try a wedge or block heel. Instead of being flat, these shoes add height to your legs and make them look thinner. If you have larger calves, try a suede or leather material. It’s more flexible than materials like plastic and synthetic fabric. Try a neutral color like off-white or black so that it will match most outfits. Try to find a design that has minimal embellishment like just one strap or buckle on the shoe’s ankle. Minimal embellishment will allow the shoe to go with all kinds of outfits including casual denim and dresses!

An over-the-knee boot to wear in colder months.

Boots worn with jeans are like peanut butter and jelly—they just go together. Of course, one of the hardest parts about buying such an item is knowing what to pair it with. If you’re not sure about how to combine these two items, or don’t know which boots would look best with your jeans (and vice versa), we’ve got you covered.


Wear a loose top (or something short sleeved) under a knee-high boot. This will prevent your clothes from bunching up above the boot’s cuff, giving it that sleek look you want for your outfit. A plaid shirt works well here: it gives you the casual feel of a t-shirt, but doesn’t make things too frumpy since it’s still technically a shirt!

Keep your top in mind when choosing your boots. If you wear wide leg jeans, you can get away with wearing an extra long sweater or ribbed tank as part of your outfit without showing too much skin overtop the boot’s cuff. This makes for an easy way to dress up without having to worry too much about layering pieces—you’ll have an extra layer right there on its own!

In both cases, pick tops that give off a laid back vibe: they should be soft and warm so they complement the coldness of the weather outside instead of adding discomfort to your outfit.

A knee high boot with a heel for dressing up casual straight leg jeans.

Stylish, casual shoes are an essential part of a well-rounded wardrobe. If you’re at a party or even just going to the gym in a pair of black jeans and sneakers, you’ll definitely stand out. By contrast, wearing knee-high boots can add some interest to your outfit and help you stand out from the crowd. Below are 8 more comfortable shoes that go with various shades of straight leg denim, giving you plenty of options for how to wear them.

1 Black Riding Boots

2 Black Ankle Boots

3 Tan Ankle Boots

4 Tan Wedge Sandals

5 Dark Brown Ankle Boots (with Tan Lace)

6 Dark Brown Wedge Sandals (with Grey Laces)

7 Grey Low Heeled Wedge Sandals (with Gold Straps)

8 Grey Ankle Booties (Black Straps)

You can wear almost anything with straight leg jeans!

Although straight leg jeans are often thought of as a traditional, conservative choice, they can actually be paired with many different kinds of shoes. Straight leg jeans are characterized by a slim fit that narrows at the ankle without tapering sharply. They typically consist of five pockets and will appear to be longer in the back than in the front.

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