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.)