Something I’ve been learning in the last six months: What makes an outfit? Where is the line drawn between simply dressing, and dressing well? What seems to be the keys to style?

Robert Henri says in The Art Spirit, and I’m paraphrasing badly here, that beauty is in the form and function of a thing made well.  I’ve come to believe that an outfit is no different than a Swedish-designed chair or new luxury car. A thing made well is a thing made with care, and time, and probably effort.

It takes effort to “look good”, whether that be through gelling up your faux-hawk just so, choosing the silver watch instead of the brown leather watch since you’re wearing black boots today, or deciding to add another layer just for color. The femmier-ones among us know how much effort it takes to put on makeup every day and shave and pluck and all sorts of other nonsense.

I struggle with this effort on a daily basis. The grooming stuff I’ve got a handle on – it’s the clothing part that’s still a bit up in the air. (Damn seasonal changes.)  It takes a lot of pre-planning for me to see beyond the limitations of “not-dirty-tee-shirt” and “not-dirty-jeans”.  God forbid it if I owned more than three pair of shoes.  And I know there are quite a few fashion-savvy butches out there, but for the rest of us, I’ve made a little cheat sheet.

  1.  A tee shirt and jeans is not an outfit. Add a hat and a watch and it can be.
  2.  A cardigan over a tee shirt is probably not an outfit, but if you layer two shirts under the cardigan, then it is.
  3.  There are few looks that can’t be improved by the right blazer. A black blazer makes any outfit sharp.
  4. A belt, a watch, a chunky bracelet, a hat, and good sneakers: accessories always look dashing.
  5. A white tee shirt under a button down ranks a ten on the masculinity scale. Make it a tee that gives a splash of color and you’re metrosexual. Lose the tee and add a blazer or vest for a more feminine twist. Layer two tees with soft colors under the button down for that J. Crew look.
  6. You can pull off almost any shoes, as long as they’re in good condition. Save the dusty vintage kicks for actual vintage shoes, and learn about shoe polish.
  7. On that note: Men’s vintage oxfords look amazing with almost any outfit. I’ve seen femmes pair them with baby-doll dresses. Look for ones that still have a good shine and aren’t too broken down on the soles.
  8. A graphic tee shirt and jeans worn with an open suit vest will catch you a lot of compliments, and you’ll look like an 80s teenage dream king.
  9. Never wear a belt AND suspenders. And always try for suspenders with braces. Learn to sew the buttons on your trousers yourself. It’s good be a handibutch.
  10. Colored or patterned socks can really finish a look. I only wore argyle socks for years (before they came back into style) and called myself “grandpa-chic”. Leave the white sport socks for the gym.

I can certainly name more, but these are the notes that are getting me through right now. Have any other quick, style-setting fixes you can share?