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.

New Years Resolution: Episode 3/30: Where Not to Cut Corners

We, like Tony Hawk, shall do a 180.

We, like Tony Hawk, shall do a 180.

This is day 3 of a New Years Resolution.

Recently, I wrote about aspects of Style where cutting corners is not only advisable, it’s downright admirable.

Now, we’re going to do a 180 like the dude in Tony Hawk’s Pro Skater.

Where not to cut corners.

My first pair of non-cheap footwear. Purchased nearly five years ago. Cost more than all the shoes I owned at the time, combined. Guess which pair I still wear and cherish, today?

My first pair of non-cheap footwear. Purchased nearly five years ago. Cost more than all the shoes I owned at the time, combined.
Guess which pair I still wear and cherish, today?

1. Grown-ass Shoes

I completely understand that you’re not accustomed to spending $100 on anything style-related. You’re used to getting away with something from Target or Old Navy. You have bills. Priorities. You’re a family man. You’re playing of zillions of dollars in college-debt. You’re putting away all your pocket money so you can knock down a giant retirement-domino like the guy in that Prudential ad.

That said, the time has come to dig deep. Dig deep into the pockets and buy a pair of grown-ass man shoes. They will not cost you $75. They will not cost you $100. They will be probably around $200. Put your eyeballs back into your skull, and go see if you have $200 in your rainy-day fund. And I bet you anything, your loan-officer / girlfriend / wife / Prudential domino-dude will not scowl when you say: I’m splurging on a proper pair of shoes.

They will say: you’re a grown-ass man. Walk like a grown-ass man.

Wear a pair of grown-ass shoes.

Allen Edmonds' "McTavish" shoe. A heritage of kick-assery.

Allen Edmonds’ “McTavish” shoe. A heritage of kick-assery.

Here are five brands that will treat you right. 

1. Allen Edmonds. Made in America. You will leave them to your progeny.

2. Cole Haan. Dressy shoes with the sole/soul of a running shoe. My Style-Up clients try them on and sprint out the door. I have to run after them to remind them to pay. It’s all very awkward.

3. Timberland Boot Company. Different than Timberlands. Don’t confuse them. So damn comfortable. And sorta badass.

4. Red-Wings. Unquestionably cool. Pair them with jeans or a suit.

5. Johnston and Murphy. Styley. A little bit dandy in a very cool way.

Lastly: how to cut corners with shoes? Get a good brand on sale.

I mean, if you want to cut corners on your haircut, be my guest.

I mean, if you want to cut corners on your haircut, be my guest.

2. Proper Haircut

Many men talk about how little they spend on their hair-cuts as if that’s admirable. It’s not. Sometimes in life, you get what you pay for: fresh produce vs. frozen. Fresh herbs vs. dried. Fresh haircut vs. Supercuts.

It’s your head. It should look good.

Some men say: “My hair is thinning. No point in an expensive cut.”

No. Wrong. A good cut by a talented stylist will make whatever hair you have (or don’t have) look better.

How to find a good stylist?

  • 1. Ask some dude at work with good hair where he gets it cut.
  • 2. Check Yelp.
  • 3. You know that small salon (or hip barbershop?) around the corner from where you work, where the cuts are $60? Try it. Just TRY it. You will feel amazing.

"Small-batch" ties like those made by The Hill-side are much more expensive than department store ties. And guess why? They're made of excellent fabric, and excellent die, and they're gorgeous.

“Small-batch” ties like those made by The Hill-side are much more expensive than department store ties. And guess why? They’re made of excellent fabric, and excellent die, and they’re gorgeous.

3. Non-department store ties

You already know that I’m a Tie-vangelist, and that I think that dudes should wear ties way more often.

The thing is, while you can cut corners with ties, in terms of not spending tons of money on them, you cannot walk into:

and expect to find a non-expensive, styley tie. Most of what you find will be those shiny, silk things which you will have no use for — except to wear to your job at a bank. But you don’t work at a bank, and you don’t want to drop a lot of money.

Here’s the thing: though my previous post declared that you can cut corners with a great $20 tie, you have to go out of your way to get it. To find it. To pick it out. Sure, you can order one of the ties I suggest in my previous post, but let me put it this way – you cannot run out and buy whatever ties you find. You need to pick one. Thoughtfully. Invest the time and energy.

Here are some great places to browse for non-banker ties:

ebay: lots of options. Lots of digging needed.

The Hillside: a little more expensive. Worth it.

The Knottery: gourmet. Delicious.

Dandy’s: a small store in Austin, Texas, with a vintage look. Everything they have is gorgeous. Even a fabulous tie is very affordable.

This suit is about double the cost of a mass-produced suit. And it's triple the quality, and looks a million times better.

This suit is about double the cost of a mass-produced suit. And it’s triple the quality, and looks a million times better.

4. Suit

If you don’t want to spend the money required to buy a decent suit, don’t wear a suit.

Ooh, jeez. That sounds so harsh. Let me back up.

You can get a cheap suit (even two for one) at Mens’ Wearhouse, but it will look like you got two suits for the price of one.

Instead, do one of three things:

  • Conclude that you can get through life with a great blazer and dressy pants. Don’t get a suit.
  • Decide that you need a suit, and bite the bullet. Get something nice. Look amazing.
  • Do the in-between. Go to a discount place that carries last year’s overstock like Nordstrom Rack. Have it tailored.

But even in the third case, it will cost you money. It will be more expensive than Men’s Wearhouse, H&M, or Zara. And guess what? It will be a grown-ass suit you can feel good about wearing to, you know, grown-ass events like weddings, gala banquets, and James Bond parties.

Top 5 Styley-Casual Shoes for Men.

There’s what men think impresses women, and there’s what actually impresses women.

It’s worth paying attention to this; some things, men worry about unnecessarily. And other things, men forget to pay attention to.

In a recent interview with a very talented SF style-genius, there was a lot of good news for normal, non-superhot guys:

“Shoes. Shoes are very important. A guy can have a belly, he can be sort of so-so looking, but if he smells good and has great shoes, game on. We can totally make something work.”

So the good news is you don’t need mega-lottery genes. Just like the caveman dorks who defeated the alpha-males through using their higher brain functions, you can make a smart shoe choice that might earn you a genetic legacy.

The “bad news”: there are no “Whateva Whateva shoes.”

Shoes always count.

What do you wear when you want something comfortable. Casual. That won’t call attention to your feet. That you can wear with a t-shirt or with a blazer?

One of these five. I list them below with level-up options for extra flair. (For a deeper dive on how to avoid too much flair, click here.)

Before you feast your eyes, some food for thought: every casual shoe below looks pretty much the way it has since it first emerged – 40, 50, or 60 years ago. The update is in the material and the color. This means that the best outfits to wear with your new kicks follow the same rules.

1. Chuck Taylor All-Stars: white, black, or blue.

+1 Flair: leather or herringbone.

2. Clarks’ Original Desert Boots: Beeswax Leather

+1 Flair: blue canvas

3.  PF-Flyers

+1 Flair: PF-FLyers Ebbets Field from Brooklyn Circus

4. Adidas Originals Superstar 2

+1 Flair for sticking to all white. But if you gotta get your flair on, keep it simple and pick one. Red. Blue. Black.

5. Pro-Keds by J. Crew

Perfect as is.

Perfect as is.

+1 Flair: Keep it simple, keep it white.

6. Boat Shoes: brown or blue

+1 Flair: Really blue. Or blue linen.