The boxer short has long been a men’s underwear staple. First emerging in 1925 after Jacob Golomb, founder of Everlast, designed these elastic-waisted trunks to replace leather-waisted ones worn by boxers, the modern boxer short has never truly lost its popularity.
Boxers are the perfect underwear choice for men who don’t want to be gripped and squeezed by their underwear. They are light, airy, and loose fitting, and vary in length, but usually sit around the mid-thigh, providing ample coverage if you want to wear them to simply lounge about the house or garden, or even sleep in (many men own boxers solely for this purpose). The design of men's boxers allows you to hang loose and free, whilst providing good coverage on the leg for those of you who are turned off by ‘tighty whities’.
Whilst boxer shorts aren’t the best underwear to pair with tighter-fitting clothing, any classic cut trousers or shorts will make a good match and provide you with ample room. Oh, and a handy bonus: the extra airflow and freedom provided by boxers have been scientifically proven to improve your sperm count. Cashback.
Naturally, there are several different brands, styles and types of boxer shorts to choose from, so we at Pants and Socks have once again enlisted the aid of our lord and master, the Pantsman, to guide us through the very best of men’s boxers.
While they all have common features, there are subtle differences that make each of these wonderful boxers unique. So, read on and discover a new world.
Our best men’s boxers top picks
- Derek Rose Amalfi/Gingham/James/Savoy (Best luxury boxers)
- Polo Ralph Lauren Slim Fit (Best slim fit boxers)
- Calvin Klein Woven Boxer Shorts (Best ‘big name’ boxers)
- Tommy Hilfiger Woven Boxer Shorts (Best classic boxers)
Derek Rose Amalfi/Gingham/James/Savoy
Best men’s boxer for men looking for true luxury
From the best value boxers to the absolute final word in boxer short quality. Derek Rose is a world-famous British luxury brand specialising in nightwear, loungewear, and underwear. And it shows.
Derek Rose has a very functional and ‘forensic’ approach when it comes to its boxers. The company’s designers know that all you want to do at the end of a long, tiring day is slip into something comfortable and relax. And boy, do they know how to make some comfortable boxer shorts.
The Amalfi, Gingham, James, and Savoy boxers are all crafted from the softest lightweight cotton possible. The fit is generous and loose (as traditional boxer shorts should be), and the elastic waistband can even be adjusted for a more snug or looser fit using the two buttons on the fly.
The difference between their 4 styles is simply that - style. Whether you’re looking for a cornflower blue, plain white, checks, or stripes, they all deliver the same level of amazing quality and luxury that you’ll want to wear all day and night. They’re also perfect for wearing on long-haul flights where you really want that added level of comfort (speaking from experience).
They don’t have a logo on the band because the company ethos recognises quality of material and construction over a name. So if you’re not concerned about branding and want a plain and understated design, these are the perfect choice.
Scratch that.
These are just the perfect choice full stop. If you want to splash a little more cash, these are the most luxurious boxer shorts that you can be. We highly recommend them.
Polo Ralph Lauren Slim Fit
Best men’s boxer for a slimmer fit
Not all boxers are extremely loose and flowing. Polo Ralph Lauren demonstrates this with its slim fit boxers as a slightly modern take on a classic design, without entering the fitted territory of the boxer brief.
These are definitely the shorts for you if you want something more streamlined and don’t have large thighs. They’re designed to fit comfortably under slightly tighter clothing, so they’re perfect for many more modern cuts,
They have an open fly design for ease of access, sit comfortably at your mid-thigh, and are made using a cotton-elastane blend (97/3%) for the slightest touch of stretch when necessary. This also aids in durability. For greater ease of movement, they also include a curved side vent, so sitting and stretching in these should be no issue either.
They have the Polo Ralph Lauren branding across the waistband for those of you who are conscious of your branding, and also sport the signature polo player on the lower left leg.
These are a great choice if you have slimmer thighs or prefer something just a little less loose from your boxer shorts, without entering the territory of boxer briefs.
Calvin Klein Woven Boxer Shorts
Best ‘big name brand’ boxer shorts
Calvin Klein is perhaps the biggest name in underwear around the globe - and for good reason. It uses high quality materials and crafts stylish underwear, building from classic designs.
The Calvin Klein woven boxers are no exception to this rule. They comprise a woven cotton blended material for strength, durability, and flexibility. They have the classic elasticated waistband, complete with a subtle CK logo at the front and an open fly for ease of access. The fit is designed to sit at your mid thigh.
Conveniently, they also come in a great value pack of 3, with a mixture of designs to suit your mood or style. This 3-pack also makes them an excellent choice if you’re a boxer shorts fan and need to quickly stock up your drawers after a clear out.
If you like your big brands, favour the loose feel of a boxer short, and need to stock up on a classic design, then you really can’t go wrong with these woven boxers from Calvin Klein. Just an all-round excellent choice.
Tommy Hilfiger Woven Boxer Shorts
Best classic boxers
These boxers from Tommy Hilfiger are the perfect choice if you just want one pair of boxer shorts in a classic style and you don’t want to spend heaps and heaps of cash doing it. They’re solid, they’re reliable, they’re classic.
In a woven cotton blend and with the Tommy Hilfiger logo on the waistband (as well as on the lower left leg), these shorts are comfortable as well as appropriately stylish. For added security they also include a single button on the fly. They come in a plain navy blue for a classic, minimalist look.
The perfect choice for a single pair of boxer shorts in a classic style without breaking the bank.
So which men’s boxer is best?
As the Pantsman loves all of his children equally, he could not possibly say that one single boxer short is better than any other. As he says, it depends entirely on your needs, your budget, your brand preference… many factors.
The best picks for those of you who appreciate solid branding are definitely Calvin Klein, Polo Ralph Lauren, or Tommy Hilfiger. These are big name brands, with solid, classic designs, and the quality to match. They are all great choices for anyone who doesn’t want to break the bank on their boxers, without compromising on style or quality. Ralph Lauren’s slim fit boxers are also great as a more modern cut.
In terms of value, Jockey takes the undisputed crown. Its boxers are such incredible value. Sure, they’re not the fanciest boxers, but they’ll more than get the job done without hurting your bank account. They’re also the perfect choice for anyone who hasn’t tried a traditional boxer short before and wants to give them a go before they commit to spending any more cash.
As for the most luxurious and top quality - it’s got to be any of the boxers in the Derek Rose collection. They are the epitome of what a comfortable, loose fitting, classic boxer short should be. They are designed purely for comfort, so if this is what you prize above all else, then Derek Rose is your best bet.
If you’ve read this and you’re thinking ‘perhaps boxer shorts aren’t for me’, then don’t fret. We have you covered with this handy guide on underwear styles.
If you have been bitten by the boxer bug and you want to grab yourself a pair right now, then be sure to check out our sizing guide to ensure that you walk away with the absolute best fitting boxers possible.
If you’re waiting for me to shush and leave you to browse, then you can shop our full underwear range. And, of course, if you have any questions, our fantastic team is on hand, so drop them a line.