10 Pieces to Dress Like You Mean It

You already know you’re supposed to dress for success or dress like your boss’s boss. I say, dress like you mean it — even on the weekends. If you aren’t hearing, “Looking good!” on (at least) a weekly basis; you’re not looking good. And that’s no good.

A lot of people don’t want to be overdressed. They are worried they will stand out. I cannot see how this is a bad thing. Standing out because of being under-dressed in my nightmare, but if you’re not ready to look good, let’s think through the benefits of dressing well:

You’ll feel like a million bucks. When I wear my best suit, I walk tall. Nothing boosts self confidence like loving the way you look.

You’ll get noticed. I don’t mean that you’ll be ogled or admired (though that wouldn’t be a bad thing). I mean that you won’t blend in and disappear whether you’re in the boardroom or the bar. People will want to know you, and they’ll remember you.

So, you’re ready to dress well, but you’ve never been into fashion? Don’t worry, this is about style, not fashion. Do these things:

  • Learn what works for you. Basically, you need to discover what colors, styles, and cuts look best on you. Variables to consider: height, weight, complexion, and hair color.
  • Purge your wardrobe. Lose everything that doesn’t work with what you learned in Step 1. Everything! Comfort, nostalgia: these things do not matter now. We are trying to look good, aren’t we? Trash or donate stuff that won’t be part of your new look.
  • Launder and press. Take care of your stuff. It’s as simple as that.
  • Seek out classic pieces. There are several lists out there claiming to share the “Ten Essential Items” for your wardrobe*.

Here are mine:

  1. A trim, tailored 3-button suit. If you can afford more than one; have navy, black, gray, tan, and a chalk-stripe (in that order).
  2. White Oxford dress shirts. French cuffs (and understated links). No collar-buttons. No monogram.
  3. Ties. Get them in the colors that work for you. Then in stripes. Tie them well — with a dimple.
  4. Fine leather shoes (and matching belt). Wingtips or brogues. Longer toes to make you look taller. Own black first. Then brown. Brush each night. Tree them. Shine each morning.
  5. An amazing watch. Keep it elegant and simple. Single gents, this will be your only jewelry.
  6. Polos. Collars down, please. Get creative with color.
  7. Cashmere sweater. Subdued tones are best. Standalone or worn between our oxfords and suit jackets.
  8. Overcoat. Save the Goretex for the slopes. My favorite is a slim, thigh-length pea coat.
  9. Dark jeans. No holes. No fading. Some distressing is okay, but why pay for something you’ll do anyway?
  10. Dark socks and boxer briefs. Skip the KMart 12-packs and shop for these items. Socks should match your pants (though always a darker shade) and stay above the calf. Boxers look careless, and briefs look creepy.

Weekends count too. Picking up the mail, going to the store, and other simple activities are times to look amazing too. You don’t have to don your tux (Item #11), but you should be groomed and pulled together no matter what day it is.

This is going to take time, energy, and (let’s face it) money; but it’s worth it. Dressing well will pay for itself.

*Sorry this section only pertains to a man’s wardrobe. Women’s fashion is much more fickle. Good luck stocking up on the classics, ladies.


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