What Lies Beneath: A Stylish Man’s Guide To Underwear Skip to content
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What Lies Beneath: A Stylish Man’s Guide To Underwear

What Lies Beneath: A Stylish Man’s Guide To Underwear

What Lies Beneath: A Stylish Man’s Guide To Underwear

It may not be an exciting purchase in quite the same way as a new winter coat or pair of boots is, but what’s underneath your trousers is of equal importance. After all, can you ever really claim to be well dressed if your underwear isn’t up to par? Arguably not, which is why it deserves the same level of attention as all other aspects of your wardrobe.

The good news is that once you find a style, fit and brand you like, there’s little reason for you to ever have to change. However, getting there often requires years upon years of battling through uncomfortable designs to secure the ones you like.

This considered, we’ve decided to take the difficult part out of the underwear equation and bring you everything you need to know in order to find the boxers, briefs or trunks of your dreams.

Key Types Of Men’s Underwear

There’s more than one way to cover your nether region. That’s okay, options are good. But if you aren’t familiar with the terminology, choosing suitable undergarments becomes a whole lot more difficult. Here are the key styles you need to know before you start shopping.

Boxer Shorts

Boxer shorts are elasticated around the waist, but airy and loose-fitting everywhere else. This makes them great for the summer, worn under shorts or wider trousers to promote air circulation and keep you cool. However, if you’re usually found in slim- or skinny-fit jeans, you’ll find that boxer shorts can quickly bunch/ride up and become uncomfortable. Plus, no-one wants to see you adjusting yourself constantly “down there”.


Unless you’re blessed with the torso of a Greek god, these are probably best left well alone. Briefs are the smallest and most revealing of all the underwear styles we’ll mention here today. They usually feature an elasticated waist and an elasticated-cotton construction. The leg openings sit as high up as possible, offering an extremely secure fit and leaving all of the wearer’s leg exposed.

Boxer Briefs

As the name suggests, if boxer shorts and briefs were to somehow produce offspring it would probably look a lot like this. This modern classic takes the shape of a boxer and the stretchy comfort of a brief and merges them together to create one super-comfortable wonder garment. If you’re unsure where to start, this is a foolproof option for the majority of men.


Like the idea of boxer briefs but find the legs a little too long for your taste? No problem, there’s a name for what you’re looking for: trunks. Just like boxer briefs, trunks boast a comfortable, stretchy construction – the only difference is they end slightly higher up the thigh.


There are few things more distracting while on a run than having your underwear ride up and become twisted as you try to beat your personal best on Strava. But with specially designed pants, it ceases to be an issue.

A relatively new product category – driven in part by the rise of sports luxe and the athleisure movement – sports underwear tends to offer slightly less stretch, is cut longer in the leg and made from moisture-wicking fabrics. These features combine to keep you comfortable and secure so that you can perform to the absolute best of your ability without having to pay any attention to what’s going on downstairs.

Buying Considerations

Before you go splashing out, you’ll need to establish exactly what you want from your underwear. In order to do that, there are a number of factors you should be paying close attention to.


First and foremost, the material your underwear is constructed from will have a big part to play in how they feel. Synthetic materials are common in cheaper undergarments, but for best results, stick to cotton.


You need to think about how you want your undergarments to fit. Do you like them tight enough to keep everything locked in place? (Keep an eye out for styles blended with a touch of elastane.) Or are you more of a free spirit who isn’t averse to a bit of a breeze flowing around down there? (Try 100% cotton versions in a looser cut like a boxer short.)


You’ll have no doubt noticed that many underwear styles come with a button closure or some other form of opening at the front. While this isn’t hugely important when you wear casual clothing, anyone who wears a suit on a daily basis will know it can save a great deal of time in the bathroom.


The color and/or pattern you choose is completely up to you. After all, only the people you’re most intimate with will ever see you in your underwear. That said, it’s worth bearing in mind that lighter colors – brace yourself – show up stains more than darker versions, and can also lose their luster quicker after repeated washing.

The only non-negotiable: no grown man should ever wear “novelty” or “fun” underwear.

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