Less Is More: The Handful of Items I Wear Most Often

Flat-lay of menswear basics

Earlier this week I jotted down a few tricks I’ve learnt in order to save on shopping and ultimately make better clothing purchases. In a similar vein, I’ve been thinking a lot recently about the clothes that I wear most often. 

If you spend any time reading high-minded content online, you’ve likely come across the notion of the 80-20 rule, also called a Pareto distribution. It describes a scenario in which a disproportionate 80% of the output in a given system is attributed to a comparatively meagre 20% of the input. Originally used to map the distribution of wealth in a society, the 80-20 rule can be applied to any number of other phenomena and pursuits — including, I would argue, the workings of the average wardrobe. 

In other words, if you were to open the doors of your closet right now, chances are that most of the things you wear on a day-to-day basis account for just a small fraction of clothing you’ll see. You probably reach for your favourite jeans or trainers way more than you do the novelty jumper you wear at Christmas or that one super expensive jacket you probably regret buying.

I reckon there’s a lot that can be gained from reflecting on the clothes we wear most often. Not everything you own has to be in use all of the time — dinner jackets, winter coats, swimsuits, and any number of other items come to mind — but having a clear sense of the things we actually end up putting on most often can help us make better decisions in future. To this end, here are the 20% of items in my closet that I end up wearing 80% of the time. (Also, in this same spirit of simplicity and discernment, I’ll limit the product recommendations included below to just the handful I’m most interested in). 


There is no question about me owning too many shirts, but the ones I wear most often comprise a half dozen or so collared candidates: blue and white Oxford button-downs, a small selection of flannels and chamoises, and a single hard-working denim number. I find most of my bases are covered by this modest team of tops. The flannels and chamoises keep me warm throughout the year, the OCBDs cover everything from beach-bound casual to coat-and-tie type scenarios, and the denim shirt variously fills in as a slouchy overshirt, a characterful accessory to a blazer or sport coat, and just about everything in between.

Regardless of the season, I also usually wear a T-shirt — almost always in white — sometimes on its own, sometimes as a visible undershirt, and (more often than not during the current winter season) hidden under various seasonal layers.

In my particular case, I have historically bought OCDBs made by Spier & Mackay, Drake’s, and Brooks Brothers (the ones I wear most are from the former, given they were the cheapest by some margin), flannels and chamois shirts mostly from L.L. Bean, and a denim shirt from Wrangler. Most of my tees currently come from Hanes and Uniqlo. And when my current batch needs replenishing, I plan to go to Jake’s for button-downs, Pendleton for the more outdoorsy kit, Bryceland’s & Co. for another denim shirt, and Merz b. Schwanen for tees. 


My everyday trouser rotation comprises a simple trifecta: a single pair of jeans, some military-style chinos, and a pair of olive military fatigues. I find this straightforward blue, green, and tan combo to work with just about anything I throw at it, be it a pair of trainers and a T-shirt or some loafers and a tweed jacket. Heck, I’ve even seen the namesake proprietor of the aforementioned Jake’s wear his drab fatigues with a dinner jacket. If I were only allowed to own three pairs of casual trousers, these are the ones I’d go with every time. 

I own half a dozen pairs of jeans, but there is one that reigns supreme: a set of Orslow 105s I bought from Dick’s a year or two ago. They are probably my favourite trousers and I feel tangible happier whenever I put them on. I also have a couple of different pairs of chinos, some of them gotten from thrift stores over the years, but my favourite has long been Uniqlo’s regular fit model. My old fatigues probably have about another year or so in them, at which point I plan to replace them with a new pair from Stan Ray. Then as far as other chinos go, I might try something from Real McCoys, Rubato, or Casatlantic next. And for jeans, I’ve been wanting to try some of Levi’s Vintage Clothing’s retro 501 offerings for long enough now that they will almost certainly be the next ones I buy.

Layering and outerwear

From here on out, I found the selection process to be a tad more challenging than the shirts and trousers mentioned above. I suspect that’s because I mostly wear the same shirts and trousers regardless of season whereas jumpers, jackets, and shoes vary greatly based on time of year. That said, a few clear candidates presented themselves without too much difficulty.

The first no-brainer is a grey sweatshirt, which I wear on a weekly basis nearly year-round. Again, it goes with just about any casual ensemble, plus it can take a real beating only to look better for it. I wear it while out and about, lounging around my house, while exercising, and it’s among the first things I pack on holiday or grab if I’m running out the house in a hurry. To this I would add one or two crew neck sweaters, a fleece, a work jacket, and a waxed-cotton jacket. Crew neck jumpers are menswear staples for a reason: they are simple, stylish, timeless, and reliable. I find I use a fleece all year round either as a just-in-case jacket when it’s warmer out or as an infallible bit of layering when it gets colder (that’s what they were made for originally, after all). Then, nearly regardless of season, I find I regularly either wear either my trusty denim jacket or chore coat (I currently have just one of each). And, though the last-named candidate above might be a quirk of living in Scotland, there is no question that the jacket I wear most often of all is my Barbour Beaufort. I would be permanently soaked without it.

The provenance of the remaining items are as follows: My longest-serving sweatshirt is from Russell Athletic, who invented the style, although when that one needs replacing I’ll definitely want to go for a more vintage styled version from RRL, Mister Freedom, or similar.. Most of my knitwear is currently from thrift stores and (again, you guessed it) Uniqlo, though when I’m next in need of a Shetland I plan to head over to Dicks and get a Harley jumper or similar. I own a frankly embarrassing number of Patagonia fleeces, so I should probably never buy another one of those. That said, as a layering option I could consider adding a sleeveless Retro Pile to the fold. Both of the aforementioned work jackets I got second hand, through I would like to get either a Lee Stormrider or their equivalent chore coat and I’ve long been tempted to get a Carhartt chore coat, a L.L.Bean Field Coat, or a J.Crew Barn Jacket.


Novesta New Balance Kleman and Clarks shoes

As with the previous one, this proved another tricker category. Probably the only shoes I wear equally often regardless of the time of year are my Kleman Padrors and Blundstones 500s, partly because of their stylistic versatility but mostly because they stand up to the year-round meteorological challenges posed by living in Edinburgh. To this end, I find some sort of derby, chukka, or work boot probably constitute the most versatile footwear styles I can think of. For me, these are followed closely by the slightly more seasonal plimsoll and comfy sneaker, which I might like wearing a tad more but am forced to retire when it gets a little too icy or rainy out. 

Apart from the styles already named, I most often wear a nearly kaput pair of New Balance 574s (which I plan to replace with some garden-variety 990s when they finally give up the ghost), one in a quickly-worn-out conveyor belt of canvas sneakers (either Converse, Sperry, Vans, Jack Purcells, Novesta, or similar), and a pair of Desert Boots or Wallabees from Clarks. In terms of heavy-wearing leather shoes for both foul weather and outdoor trekking, I have long had my heart set on some Danner Mountain Lights, Red Wing Roughnecks, or Paraboot Avignons


Finally, I nearly always leave the house wearing a hat, be it a baseball cap when it’s warm out or a beanie when it’s cold. The headgear I wear most of all, however, is made by Ebbets Field Flannels. And when I next upgrade my winter hat rotation I’ll probably look to Heimat as my first port of call. I also always wear an affordable watch, usually either a first gen Casio G-SHOCK or my Seiko 5, but when it comes to watches I’d like to buy, all talk of wise and restrained purchases go out of the window…which makes this feels like the right moment to bring things to a close. 

So I’ll end with an obvious but worthwhile prompt: What are the select few pieces of your wardrobe that end up pulling most of the weight? 

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