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Conventional wisdom dictates that we should bias towards optionality, the more options we have, the better our overall welfare. The paradox of choice aside, I have come to realise that we ought to seek constraint and restraint for another reason: creativity.

I often apply artificial constraints when I decide what I want to wear. My go-to is to choose one (or two) articles of clothing and designate them as my statement piece(s) around which I will build an outfit. Generally, the things I consider in ascending order are:

  • Shoes
  • Socks
  • Pants (+ belt?)
  • Shirt (+ jumper?)
  • Outerwear
  • Scarf
  • Headwear

By locking in one of those sections, it makes the process of finding complementary pieces of clothing not only easier but a lot more fun. There is no stress associated with the thought that I could wear anything today. Plus, I find myself finding fits that I wouldn’t have otherwise thought of because sometimes if I choose an my olive-green pair of shoes as the statement piece, it really makes me dig into my wardrobe to try every combination. Making an olive-green pair of shoes work in an outfit is not as easy you think, at least not with the aesthetic I have grown to admire.

This has reflected my shopping habits, I often splurge on items that do well to catch the eye e.g. basically anything corduroy, sleek outerwear, funky shoes, vibrant scarves. For 99% of the rest of my clothing –– the shorts, dress shirts, sweatshirts, and other wardrobe essentials – I shop almost exclusively at Uniqlo where I know the the quality is top-notch. While I would never label myself as a designer, I do think I have a good eye for what looks aesthetically pleasing.

While some make a hobby out of thrift shopping (or even just shopping), I feel as though I have made a hobby of the art of choosing an outfit. I am as far away from the Silicon Valley trope of buying 10 of the same outfit and wearing that everyday as you can you can get.

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