Ten Things I Wish I’d Known About Style, 10 Years Ago: NEW YEAR’S RESOLUTION — 30 DAYS OF WRITING. EPISODE 6/30

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
  8. watchesAccessories / 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.

Ankle Jewelry

sox4 What do you call a thin band of color that you wear around your neck?

  • A necklace.

What do you call a thin band of color that you wear around your wrist?

  • A bracelet.

What do you call a thin band of color that you wear around your finger?

  • A ring.

What do you call a thin band of color that you wear around your ankles?

  • Socks.

 Socks are ankle jewelry.

Many men are hesitant to wear jewelry because, well, whatever. No need to go there. In any case, colorful-but-classy socks can be a styley substitution for  bracelets, necklaces, and rings.

Here are some rules of “thumb-toe” for socks.

Crank it up, but keep it under control. Yes,  there is a bit of a “Happy Sock” thing going on out there, you don’t need goldfish, moons, or MC Escher on your socks.

You do not want to be "the guy with the socks," so avoid Bat-Man, the Benjamins, and over-the-top colors.

You do not want to be “the guy with the socks,” so avoid Bat-Man, the Benjamins, and over-the-top colors.

Determine what color-palette you are wearing.

A) blue, red, black, white, and grey B) purple and grey C) Green, tan, brown, orange, and other autumn colors

Stick With Cotton

It breathes and the colors pop. Avoid polyester-blend “dress socks” – the thin, wrinkly things sold at department stores and menswear stores.

Now, pick your pattern:



Stripes: go with one color, and wear with grey, blue, black, or red pants.

Keep the stripes simple. We’re going for a bit of pizzazz, not “hey, look at my socks.”

steven allen

Polka-dots: stick to one color.

Polka Dots

Only if they’re ONE color.

Argyle is Awesome


Argyle: Wear with wingtip shoes.

Try purple and grey with a grey suit or red and blue for…anything.



Gingham: Great with jeans, grey dress pants, or red/blue chinos (casual pants)!


Will net you compliments. Stick to blue, red, brown and purple.

Now that you’re a sock-maven


Cool shoes. Perfect cuff. Now, swap in some color. (Picture from

Consider getting your pants tailored so there is no “break” – (“break” is the word for what normal people call the sag-fold that forms under your knee or near your cuff when your cuff hits your shoe).

Have the tailor hem the pants so just a sliver of sock peeks out. Not only does this give you a streamlined, clean shape, but also, it shows your ankle-jewelry. I’ve learned from experience that socks are an amazing “just because” gift. They’re fun and don’t cost much.

Next time you’re being dragged around a mall, try buying your girl-friend a pair of “just because”  earrings; if you’re lucky, she may surprise you with a little “bling” of your own.

Some sock brands to check out:

Banana Republic: Get some nice stripeys.

Richer / Poorer: Small company, great designs.

Lifetime Collective: Never heard of them? Fix that.

J.Crew: Yes, you’ve heard of them. But did you know they can be your sock purveyors?

Happy Socks: Now that I’ve criticized them…if you keep the colors and patterns under control, they can be kind of amazing.

Quiz time: which of these Happy Socks are a little too much of a good thing?

Quiz time: which of these Happy Socks are a little too much of a good thing?