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  • Writer's pictureEvan Wolkenstein

Ten Things I Wish I’d Known About Style, 10 Years Ago: NEW YEAR’S RESOLUTION — 30 DAYS OF WRIT

I've learned a few things since 2005.

I’ve learned a few things since 2005.

This is day 6 of a New Year’s Resolution.


Most of what I know about Style comes from the past five years, but I started paying attention to what I wore about ten years ago. Here’s a list of 10 things I wish I’d know about style, 10 years ago, and in this list, I focus not on the trends of the time, but of basic principles that never change.

1. When you wear a t-shirt or a polo shirt, keep it slim and don’t tuck it in.

2. Wear socks with contrasting, strong colors and regular patterns, rather than trying to find socks that match your clothes.

3. Sportcoats and blazers cannot be too long for your torso length. Long blazers make you look like you’re wearing a magician’s outfit. I know you think you know what blazer size you are, but you might not. Go to a tailor and get measured before buying anything.

4. You might go through a “buying lots of clothes” phase before you figure out your style and dial in the fit. Take the advice of people in design and “fail forward.” That means lower the stakes early on. Don’t spend too much. Buy only stuff on sale, at resale boutiques, and deep-clearance.


Socks: You shouldn’t shy away from bold colors, but that doesn’t mean they should have funny, little pictures on them, either.

5. The worst person to tell you what looks good on you is the guy in the store. Even nice salespeople are salespeople. Buy stuff you can return and show it to someone at work.

6. The order with which to #StyleUp your look is:

  1. Haircut

  2. Shoes (styley-casual)

  3. Shirt

  4. Jeans

  5. Tie

  6. Blazer

  7. Belt, Socks

Accessories / Watch

7. If you’ve had the same glasses for more than 5 years, it’s time for something new.

8. One quality garment you’ll be proud of is worth a giant mountain of sub-par garments you’ll never wear.

9. Carry a stain-stick in your man-bag.

10. Know that you won’t nail the look you want right away, and that even when you’re a little off, you’re still doing something life affirming, something which takes genuine courage: quitting the act that you don’t care how others see you.

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