Review: Stylish underwear for the mature man

For the longest time I’ve harboured a, mostly unexpressed, jealousy towards women. That’s women in general, not really any specific females, at least not in this case. You may wonder why I’m jealous (or not, in which case I’ve probably lost your interest anyway)? Now, I’m quite certain I’m not alone in feel a little jealous, although I’ve resisted Googling it, as I just know it will throw up a gazillion hits of a very dubious nature, so I feel no shame in discussing it front of untold numbers of readers. It’s all about underwear.

Why is it that the female gets all the fancy, frilly and expensive underwear? Surely it can’t only be a case of men wishing to adorn the female form? Well, maybe it is, but how unfair is this? Why is there so little effort expended on making some really smart, proper, attractive and well… tempting underwear for men? Is it because all men are slobs, cheapskates, satisfied with simple cotton underwear, and their partners have no interest in dressing them up a little? It may well be, but I’m happy to say that there are options out there for those that wish to put a little effort into it. I know I’m no example to hold forth when it comes to interesting underwear. For the past 4 years I’ve basically had a huge selection of boxers from Fat Face in rotation. Plenty of different colours and designs, and provably heard wearing, but totally shameful compared to all the finery WellDressedGirlfriend wears.

sunspel boxer

Sunspel cotton boxers – 90 pounds of … unremarkable?

So, you say, where is all this talk of undulating undergarments leading? Well, I asked on Twitter about suitable underwear for a stylish man and the resonse was underwhelming to say the least. I probably shouldn’t be surprised, as I’ve already surmised that your average gent does really worry too much about what’s underneath, as long as it does the job. Of the 3 suggestions I received though, the first is a company by the name of Sunspel. Not a company I’d come across previously, although they’ve been in business since 1860. Not too hot on the social media, I guess? In any case, from what I can tell, it’s quality stuff, although the design is as traditional (read: boring) as I feared. While some of their underwear appears to be made in the UK, I suspect it’s only the most expensive pieces. And by expensive I’m talking 90 pounds for a pair of boxer shorts. No kidding. And they’re plain white as well. I’m sure there is a market for this, but it’s not ticking any of my boxes!

So, what else do we have? Well, there’s a new company making a splash when it comes to men’s underwear at the moment (and I realise this can be understood in many ways, but I mean it in a proper and positive way, so be good and behave now). I’m thinking of Hamilton & Hare. With a name like that, it sounds like they’ve been around since the dark ages, creating sartorial excesses for noblemen and Royals, but the truth couldn’t be further away. They’ve been in business since 2012, and they make one garment and one garment only: Tailored boxer shorts for men. And to be honest, I was a little sceptical of their claims. The boxers are designed by a Savile Row tailor, from top quality materials, superbly presented, with a team that arguably know what they’re doing when it comes to sales and marketing. For the record, as an admittedly middle-aged man, I’m not really that taken by all the advertising material showing various studly young men wandering around in their boxers. This may be aimed at younger men and women, but I suspect it’s missing the mark a bit when it comes to guys like me. Or maybe I just don’t like being reminded of what I could have looked like 20 years ago!

hamilton hare package

Hamilton & Hare packaging

In any case, what are Hamilton & Hares 38 pound boxer shorts like? As I mentioned above, they are superbly presented. They come in their own little bag to keep them safe until you’re ready to wear them. My first impression was that they were very light, almost a little dainty? This makes a nice change from the usual heavyweight thick cotton men are used to. The sewing is very fine, the pattern and colour a welcome and stylish change. The waistband is designed with the elasticated parts only on the sides, unlike most others that have the elasticated waistband all the way round. This does allow the boxer to fit better on the sides and front than is usually the case. Nice double buttons and faux buttonholes add a little interest to the front, though why not working buttons? The fly is lined with silk, which is a nice touch and surely appreciated by tender parts. All in all, pretty nice shorts! If I could make one deduction it is for the fly. While I’m hesitant to start any rumours as to my endowment, I did find the fly has a tendency to pull open. Unless this is a feature engineering into the shorts, I feel this is an area that could be improved upon. If there was one other point that could be improved it would be to produce the shorts in the UK rather than Portugal. Not an issue of quality per say, as Portuguese seamstresses are certainly competent enough, but Made in Britain is very strong now, and a pair of boxers selling at 38 pounds needs all the justification it can get.

hamilton har frontside

Front side of H&H boxer shorts

hamilton hare backside

And the logo on the rear

Our final contender in this short review is Sir Plus, a company I first covered a while back. They, or rather he, makes a great contrast to Hamilton & Hare, being different in almost every way, yet also producing boxer shorts for the discerning man. The idea behind Sir Plus is to up-cycle offcuts, or “cabbage” if you speak tailor, into a variety of products. Of most interest to us right now is boxer shorts (though we’ll be looking at waistcoats for Waistcoat Wednesday soon!). This means Sir Plus also has a Savile Row connection, albeit in using excess shirt material rather than being finely tailored by a Savile Row tailor. Using shirt material means we’re talking about fine 100% cotton boxers, in actual material deemed fine enough for the fine Savile Row shirts. Without a doubt that is a good backstory, and it adds interest to a type of garment that probably doesn’t get it’s fair share of attention around the coffee tables. The sewing is nicely done, contrasting waistband is a nice touch, though the waistband is elasticated all round and general fit does feel a little inferior after trying on the H&H shorts. Of course, actually talking about how boxers may have a tailored fit is such a leap forward from where most of us are today that it feels strange to even mention it!

sirplus sturdy package

Sir Plus uses a nicely designed cardboard box to complement the up-cycle/recycle image

Sir Plus have a pleasing, and ever changing range of boxers, well designed and made. At 20 pounds a pair, they are expensive compared to your everyday cotton boxers, but can easily be justified for more special occasions. Extra credit for being made in Britain and for the idea of up-cycling Savile Row waste, and for seeming like a cool, interesting and innovative company in general.

sirplus frontside

Sir Plus boxer shorts

sirplus fabric

Savile Row cabbage, i.e. excess shirt material

One issue I have with both the reviewed boxers are the washing instructions. In my house all underwear is routinely washed at 60 degrees, but these boxers should only be washed at 30 or 40 degrees. Will this be hygienic? Will the shorts shrivel up if washed at 60?

Now, at this point I’m sure many of you are sitting there in deep thoughts, with the main thought running through your mind being: Will a truly excellent pair of boxer shorts increase my luck? Yes, we are talking about luck as in successful overtures with females. I don’t have a clue, to a asked WellDressedGirlfriend for her opinion. First I flaunted myself in each boxer short in turn, to see if she, unable to control her primal impulses, would throw herself at me. I’m saddened to report that she barely looked up from her laptop and only when prompted agreed that yes, both boxers were really nice and yes, the H&H did look more fitted. This indicated that high end boxers are probably not the magic nookie-device we might have hoped for. In the interest of Man Science, I did ask her to expand on this though and she came up with something roughly like this:

“While fancy boxer shorts are unlikely to aid in getting you laid, dressing well and taking care of yourself will make you more attractive to potential partners and hence increase your chances of gaining the life experiences you wish for. While expensive underwear won’t improve your chances to a great degree, worn out and scrappy old underwear will impress no one. Your money is better spent on the outside than the inside! Use a similar rule for underwear as for your other garments, in that if it looks good, it is good. (WDD interjects: Your raw denim selvedge jeans that you’re wearing for a year before washing for the first time should not be used as a yardstick for when you wash your underwear). In general though, as long as you have your hygiene under control and generally look smart and OK, you’re halfway there.”

Try Bamboo Underwear

If you’re looking for the trendiest men boxers, you can try bamboo fabric undergarments. Bamboo men boxers are made of natural bamboo fibres or viscose from bamboo. This fabric is highly breathable, thermo-regulating, and moisture-wicking. It’s the perfect undergarment choice for men’s underwear, softer than cotton.

I bought bamboo underwear and wore it for the first time last summer. I played tennis and felt so comfortable with it. Since then, I always made it a point to wear one when playing sports. This underwear fabric is durable and keeps me dry even in intense training.

Bamboo underwear pieces are a must-include item in every man’s wardrobe. It’s suitable for any outfit, including casual, formal, and activewear. So, you might want to try wearing new bamboo underwear to stay cool, dry, and comfortable down there.

There are factors you need to consider when choosing stylish underwear for men, such as your lifestyle or daily activities and the quality, features, and benefits of the underwear.

Of course, while you wear the best underwear pieces that brands have to offer, it’s also equally important to practice proper hygiene. Make sure to change your underwear regularly whenever you change clothes. By doing so, you’ll be able to benefit from wearing the best underwear clean and healthy.


So there you go. I’d suggest treating yourself and doing your own experiment on this. I’d appreciate you sharing your results in the comments section below. In the meantime, shower and change your underwear daily, just like your Granny told you to.

huge boxers

Is this correct? They’re huge! (In fact, yes, they fit perfectly)


  • Waistcoat Wednesday: Sir Plus, if you like your cabbage up-cycled | Well Dressed Dad 15/05/2013 at 20:30

    […] a couple of times before, firstly as a label to watch, secondly as a contributor to my acclaimed review of underwear suitable for a gentleman of taste and style. Henry Hale, proprietor of Sir Plus, is a versatile […]

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    […] Review: Appropriate underwear for the stylish man ( […]

  • Chas 28/03/2014 at 18:47

    Not sure what I was googling when I came across your blog. But my 2 cents is that to look good on the outside, you need to start on the inside. Lacking imagination and suffering from OCD, I only wear white cotton boxer shorts from Zimmerli, which aren’t made in Turkey (read: Sunspel) but doubtless the EU equivalent. Will look into findings – but being OCD, I shall probably stick with the Zimmerli (unless I start all over again…).

    • Well Dressed Dad 28/03/2014 at 18:59

      Have a look around, maybe you’ll find more if interest! 🙂

  • Steve from AZ 16/07/2014 at 22:56

    One other source to consider would be Mercer & Sons.


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