Cheekster vs. Hipster Underwear: The Differences

 person wearing black underwear

When it comes to underwear, figuring out the difference between types is a fine art. From cheeksters to hipsters and everything in between, TomboyX is here to help you make sense of it all! 

In this post, we'll explain the differences between cheekster and hipster underwear. Then, we’ll go over other popular styles so that you can feel confident picking out undies that are perfect for you. 

What Are Cheeksters?

Let's start with cheekster underwear. 

Cheeksters are a type of low-rise underwear that sits below your natural waistline and provides full coverage of the backside. Think of them as an updated version of classic briefs.

They come in a variety of styles, from comfortable cotton ones to more luxurious lace options. Not only do they look great under any outfit, but they also provide extra support and comfort throughout the day. 

Any Benefits?

Cheekster underwear is designed to provide superior comfort, support, and style. Whether you're pumping iron in the gym or lounging around the house, cheeksters are sure to keep you feeling cozy and looking chic.

Check out a few of the many benefits of wearing cheekster underwear:

  1. Breathability

Cheekster underwear is typically made with breathable fabrics that are strong and long-lasting. This means that they will keep you comfortable and dry, even during the most intense workouts.

  1. Snug Fit

Cheeksters are designed to fit your body seamlessly. More often than not, they use stretchy fabrics that can conform to your body, providing a secure and comfortable fit.

  1. Support

Featuring a snug but comfortable fit, cheeksters offer support and coverage where it counts — giving you confidence all day long.

  1. Variety

With different colors and designs, cheekster underwear can be dressed up or down for any occasion. Cheeksters are there for you when you need a reliable, confidence-boosting base layer under your hottest outfit. Cheeksters are also your BFF when you’re simply chilling at home and need something as cozy as your go-to sweatpants.

  1. Style

Cheeksters come in a range of fun styles and designs, so you'll have no problem tracking down the perfect pair to reflect your personality!

What Are Hipsters?

Next up, we have hipster underwear. 

Hipsters are mid-rise undies that sit slightly higher up than cheeksters and end just below your belly button. In addition, this type of underwear provides more coverage on your hips and thighs than cheeksters do, making them perfect for wearing with tighter-fitting clothes like leggings or yoga pants. Since they come in a wide range of prints, detailing, and colorways, you can easily find a pair that suits your personal style. 

Any Benefits?

If you ask us, hipsters are one of the best underwear options out there. Not only does it provide the right amount of support, but it also looks fantastic!

Here are just some of the benefits that hipster underwear has to offer:

  1. Comfort

With its ultra-soft fabric and snug fit, you won't find a more comfortable pair of underwear than hipsters. That means no more uncomfortable bunching or digging into your skin. We are partial to combos of materials like OEKO-Tex-Certified cotton, Spandex, and the similar. 

  1. Coverage

Hipster-style essentials offer moderate coverage in the front with a low-rise waistband, providing maximum support without sacrificing comfort. 

  1. Versatility

With its versatile style, hipster underwear can easily transition from day to night. You can wear it under jeans during the day and dress it up with a skirt for evening wear. 

  1. Moisture-Wicking

With their breathable fabric design, our hipster underwear is great for keeping you cool during the summer months. You can even wear them for workouts without worrying about excess sweat or chafing! 

  1. Support

Whether you're looking for extra support from your underwear or want something comfortable to lounge around in, hipsters provide just the right degree of support without being too clingy. 

Factors To Consider When Choosing Cheeksters vs. Hipsters

When it comes to choosing between cheeksters or hipsters, there are a few things to consider. So, if you’re an underwear-shopping pro or a novice, here are some factors to keep in mind:

Comfort Level

The first and most important consideration when deciding between cheeksters and hipsters is your comfort level. Both styles offer a more breathable fit than traditional underwear, but you might find that one fits better than the other. Consider what fabric you prefer, and make sure to read the care instructions before purchasing.

Pro Tip: On the hunt for a pair of comfy-cozy undies? Check out our snazzy line of Hipster Underwear. With a fit between a boy short and bikini, these cheeky undies are made of the same oh-so-soft cotton but with a slightly higher stay-put waistband. 


Cheeksters and hipsters both have their own unique functions. If you're someone who likes to move around during the day, then a cheekster style may be best, as they are designed for action. 

On the other hand, if you're looking for something that stays in place when lounging or catching Zzzs, then a hipster style might be the better option. Alternatively, if period underwear is what you're after, look no further than our Leakproof Period Hipster.


Cheeksters are low-rise undies that offer a lot of coverage, usually sitting slightly above the hip bone. This style is a must-have for those who prefer less fabric around the waist and more coverage at the back. 

Hipsters, however, are slightly higher on the waist and often sit right below the navel. This style is waiting if you want more fabric around your hips and tummy in a fashion-forward silhouette.

Other Types of Underwear To Shop for

Although cheeksters and hipsters are two incredibly popular types of underwear, they aren't the only ones out there. With this in mind, here are some other styles of undies to fall in love with:


Briefs are the traditional boy short-style of underwear with a higher waistband that sits at or just below your natural waistline. They provide medium coverage of your bottom and provide more support than other styles. 

For a pair that feels second to none, check out our collection of Iconic Briefs — designed to move and fit comfortably wherever your day takes you.


Boxer shorts are loose-fitting shorts with an elastic waistband that typically come in cotton or polyester fabrics. They offer full coverage for the bottom and are usually longer than other styles. 


Trunks are a hybrid of briefs and boxers, offering more coverage than briefs but less than boxers. They have a more relaxed fit with short legs, making them great for everyday wear. Look for trunks made with breathable fabrics, like our 4.5" Trunks, that will keep you comfy while you're making big moves and relaxing on slow days.

Boxer Briefs

Boxer briefs are also a hybrid of briefs and boxers but with a tight fit and longer legs. They provide full coverage for the bottom and often come in moisture-wicking fabrics like our deliciously velvety TENCEL™ Modal, making them great for workouts or everyday wear. 


Thongs provide minimal coverage with a cut-out at the back, making them great for wearing under tight-fitting clothing. They can come in a variety of materials and offer moderate support. 

To ensure long-lasting quality and uncompromising comfort, we recommend checking out our comfy-cozy line of Thong Underwear. Made with unbelievably smooth fabrics like TENCEL™ Modal and OEKO-TEX-Certified cotton, these thongs feel like a cloud and fit like a dream. 


Bikini underwear is a low-rise style of briefs with a thin waistband and sides that sit at the hips. Like thongs, they provide minimal coverage well-suited for wearing under tight clothing.

Boy Shorts

Last but not least, boy shorts are a low-rise style of undies with wide sides and full coverage in the derriere. They provide medium to full coverage and are often more comfortable than other styles. 

Here at TomboyX, we design our fan-favorite boy short collection with comfortable fabric and a silky waistband — perfect to wear under work clothes, at the gym, or while lounging around the house. 

A Final Word

No matter which type of underwear you prefer — cheekster or hipster — it's essential that they fit well and are made from high-quality materials for maximum comfort and support throughout the day. 

Whether you love bold colors or prefer something more subtle, there's an option out there for everyone! So go ahead and explore all the different styles until you find one (or two) that work flawlessly for you. 


Don’t Sweat It: How Moisture-Wicking Fabrics Keep You Cool and Dry | inChemistry

What Is Period Underwear and Does It Work? | Cleveland Clinic 

Man-made fibre | Britannica