Choosing underwear can present itself as a daunting, tedious and frustrating task. There are copious amounts of underwear and apparel brands vehemently advertising their skivvies, word vomiting buzz words faster than a vegan at Whole Foods. But whether or not the fabric is organic and locally sourced, the design is patent protected or a dollar of all proceeds go to a heterosexual in need (likely wearing ill-fitting boxer shorts) – what underwear ends up in your pants is completely up to: you.

As an owner of an underwear company called, Dirt Squirrel and also having some life experience under my belt, I can sympathize with it sometimes being tough to decipher through all of the marketing razzmatazz which underwear options are going to best suit you and your lifestyle. While everyone’s preferences and needs are going to be entirely subjective there are some rules of thumb that will help you in finding your best fit. 

First thing is dressing for the body you have and not the body you want. Body dysmorphia is alive and well thanks to modern society, social media, bullies and best friends making some people afraid to be seen with any “L’s” on the tags of their apparel. Most underwear sizing goes by waist size, butt, cocky, thick thighs make the size rise and Shakira has informed us that hips most definitely, do not tell lies. So, if you’re gifted in one or more of those areas, consider going up a size in order to prevent cutting off circulation to your extremities or risk looking like you’ve been baking at 350. Well fitted underwear is half the battle, because you have to be comfortable in order to be fully confident and transform into the cheeky little minx you are at heart. 

Second: Don’t limit yourself! Consider different styles and cuts for various activities or circumstances. I find that there is a time and place for *almost* every style of underwear including: boxers, boxer briefs, briefs, jocks and long johns. I excluded trunks from that, because they are tacky and (in my opinion) are basically the sweaty, smelly, ungroomed armpit of the gay world, which is some people’s preference, but most people wear deodorant and I’ll leave it at that. A well-structured and sized boxer can be super sexy as pyjamas, briefs are great for shorts or dress pants, boxer briefs work wonders at the gym or while travelling and jocks are great for the gym or when a total stranger opens your bedroom door only to find you blindfolded in a precarious position, but I digress. The point is, the most exciting underwear drawers are the ones with diversity – try mixing things up once in a while. However, if you’re the person who just loads up on twenty pairs of black boxer briefs from one company and calls it a day, that is wildly respectful in its own right. 

Third: Fabrics, colors and pockets, oh my! In the wise words of Heidi Klum, “You have to treat yourself every once in a while, get to the fun stuff”! There are plenty of fabrics out there, but some are more comfortable than others and may even offer health benefits such as bamboo fibre, a fabric that is not only soft, but also known for its eco-friendly, anti-bacterial, sweat absorbent and insulating qualities or pima cotton, which is a smooth fabric that’s soft to the touch, wrinkle-resistant, and ultra-durable. When it comes to color, black is a sleek, sexy and safe choice, but nobody should shy away from adding some colors or prints to their repertoire! That being said, people’s preferred colors can be very subjective and the prints department can be a tricky one, because while there is a time and place for just about every pantone color, some prints are hideous and are literally the trash that’s killing the buzz, the planet and probably your sex life. For example, unless it’s a gag, maybe avoid the SpongeBob Square Pants graphic print. Lastly, if there are pockets, additional features or accoutrements to the underwear in question, make sure they’re tactful and not just a cheap attempt at enhancing certain areas – it’s always more obvious than you think!


Hopefully these pointers help guide you through your next underwear purchase! At the end of the day, choose a pair that is going to make you feel comfortable and confident, pampered and provocative. Avoid trunks. Don’t be afraid to try something new and find yourself a style or brand that works best for you around the clock. After all, underwear is typically the first thing you put on and the last thing you take off, so it’s important to start your day strong and finish on a high note. If you choose wisely, maybe someone else will even take them off for you! 


Article by Wade Hopwo of Dirt Squirrel