Targeted Clothes and Footwear Purchases

Tim Ferriss once passed along the advice, “Buy the most comfortable bed and pair of shoes you can afford. If you’re not in one, you’ll be in the other.”

Prioritize comfort if you’re going to be wearing something every day. Only recently have I appreciated the wisdom of this advice. Growing up I wore more or less the same thing: jeans or sweatpants, t-shirt, and if cold (California cold) a hooded sweatshirt. I hated shopping and had no interest in fashion per se so my wardrobe was a hodgepodge of clothes I received as Christmas gifts, whatever my Mom picked up at Mervyns for me, and whatever I purchased at the outlet stores in Vacaville, CA.

It’s still 90% a hodgepodge of hand-me-downs, and I still hate shopping and still wear that combination most days, but in the last few years I’ve made a handful of targeted, strategic purchases of clothes and footwear that have dramatically increased my comfort, style, and by extension, projected self-confidence.

Shoes — I found via the Boulder Running Store Asics Foundation running shoes. I buy the maximum support version of the shoe so I can easily hike in them too. (I wore them all through Patagonia.) I buy a new pair, exact same kind, every year. I used to never spend more than $100 on shoes. These cost me about $120 and they’re totally worth it. Gretchen Rubin says a true secret to happiness is to wear running shoes all day.

Sandals — I upgraded from my usual Nike or Adidas sports sandals and purchased Reef sandals. More durable, more comfortable, thicker base.

Socks — Any brand is fine, but Thorlos are supremely comfortable, easy to get on and off, and absorb sweat.

T-Shirts — I bought a few American Apparel tri-blend basic t-shirts. So so so comfortable, especially if you’ve only worn “free” t-shirts. They look good. I highly recommend having a couple of these in your closet.

Outerwear — What to wear on the outside that’s not too formal (sports coat) nor too informal (hoodie)? For years I wore my San Francisco Giants fleece to all sorts of business meetings. Now I have two better options: The cashmere sweater from Land’s End (a bit pricey but super soft and comfortable and versatile for both formal and informal) and the lightweight Nike Dry Endurance Jacket which is great for walking outside in chilly/crisp weather or trekking outside in light rain environments.

Pants — I have not found anything better than basic, cheap, loose-fitting jeans and basic sweatpants. Same goes with hoodies.

Travel Clothes — I own a couple button down travel shirts like this one which absorbs sweat, dries quickly, breathes in hot weather, and contains two breast pockets which is helpful for storing things. I own two pairs of super light weight and fast drying boxers.


Here’s The Onion’s magazine cover Heterosexual Men’s Fashion, spoofing the NYT fashion issue. People who buy fake clothes / merchandise are more likely to cheat in other ways. The end of the hipster? (I hope so.)

16 comments on “Targeted Clothes and Footwear Purchases
  • The School Boy Pant (also called the Welt Pocket Pant) from American Apparel would fit nicely into your criteria. It was designed to be a staple or basic. I think I have 5 pairs. It’s all I wear.

  • If you invest in a pair of high-end jeans (about the same price as your running shoes, or a bit more) you will feel just as comfortable and will look extremely stylish for the same amount of effort. Of course, this may or may not matter to you šŸ™‚

  • Ben: Love those tri-blend t-shirts. Seriously, has a better fabric ever been invented, save maybe merino wool?

    Ryan (and ben): Right on with those Nike Free’s. Shoes that simulate being barefoot may seem odd for the first few days, but they quickly become more comfortable than any padded sneaker out there. Brands producing these sort of shoes include Terra Plana and Vibram.

    Kirsten’s right about the high-end jeans. Assuming you have a little extra cash, you’ll get a positive style return with no sacrifice in comfort or durability. If they’re a darker wash, they’re even more versatile- you can pair them with a button-down for all but the most formal business situations.

    Hector: Allen-Edmonds or Florsheim. They’re $250+ new, but you can find them used at thrift stores or on ebay, and they’ll probably last longer than you do. Even if you pay full price, divide their retail price by your current life expectancy and they’ll cost you dollars a year.

  • You want to be comfortable, stop wearing shoes with thick heels. Most running shoes are a con, I kid you not. The more cushion you have on your heel, the straighter your leg is when it hits the ground, leading to ankle, knee & hip problems. Nike Frees are an improvement, but there are several excellent kinds of shows that approximate bare-foot walking, such as these:

    I have nothing whatsoever to do with this company, and they are not the only ones who do something like this. I’m tempted to send Gretchen Rubin a pair, she’d revise her idea of happiness.

  • I wouldn’t be caught dead in a pair of running shoes of any kind– they are hideous, bad for your feet, and too reminiscent of that disgusting asshole Tucker Max and his doppelganger Spencer Pratt. You’re better off to run in a pair of Reefs.

    It’s not good for your body to run on concrete anyway– far too much pounding on the skeletomuscular system.

    I don’t buy anything from American Apparel on the principle that it’s too popular with hipsters.

    I always wear as little as possible, board shorts and flip-flops will usually suffice. I write most of my comments in the nude, sitting on a flokati rug draped over my chair.

    For the record, I shoot hipsters on sight from the comfortable perch of my swivel chair (you have to turn fast. I like the way they sound when they fall).;-)

  • Good call with the tri-blend shirts.

    I’m not the hiker/outdoorsman you are Ben, but for lounging around, I recommend some Sperry Topsiders – the authentic original boatshoes version. They’ve got a some new ones with actual support, but I enjoy the traditional Topsider. Preppy, yes, but you can wear them with just about anything.

  • Kirsten, I’ll give you a pass since you’re female but for men, there is no such thing as “high end…stylish jeans.” If a man thinks he has a pair, he’s a douchebag.

  • Ben, how do you get clothes that fit your height? Or are you big enough that you can fit an XL comfortably?

    I’m 6’5″ but 190, so the only place I can get shirts that fit without special order is Eddie Bauer, which has LT (large tall) in the store. Otherwise, it’s either too baggy or bare stomach.

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