In looking at past years' 60 DoD about style, the focus was usually on clothing, shoes, and accessories, which I'll call "fashion." They covered the issue well, especially this one, so I'm going to be brief regarding fashion.

Fashion you can buy, but style you possess. The key to style is learning who you are, which takes years. There's no how-to road map to style. It's about self expression and, above all, attitude. —Iris Apfel

I don't know or care who Iris Apfel is, but this quote captures the point I want to get across -- your style is more than your clothes. It is your grooming, clothes, shoes, posture, eye contact. Its how you move and how you speak.

Your style is the integrated package you are presenting to the world, and it signals to others who you are, what you are about, and whether you are worth a shit or not. And signaling matters.

The rest of this post is broken down into (1) fashion, (2) grooming, and (3) how you carry yourself. I'll leave speaking style and any other aspects for another day.

1) Fashion

Like I said above, other posts cover this topic well, so I'll keep my comments relatively brief.

Don't Be Unattractive

This is most of the job here.

  • Step 1: Anything that has holes, pit stains, no longer fully covers your gut, has lost elasticity, or shape, etc. should be trashed.
  • Step 2: Anything that you haven't worn in the last year should likely be donated.
  • Step 3: Anything that doesn't fit *well* any more should be donated or put up in an appropriately labeled bin.

Ex: I've had to retire all of the button-down shirts, polos, and suits I've owned for more than two years because they no longer fit in the chest. I donated half and kept the higher quality half if it was within one size, but put them in a bin and labeled them as such.

Fit Is Paramount

Not only should you not look like you are wearing your father's (or son's) size clothes, you should only buy clothes that truly fit. Be exacting about it. If it doesn't look like it was made just for you when you try it on, keep looking.

Ex: I bought a dress shirt recently, but I'd look ridiculous if I just bought an off the rack shirt because I'm a 17.5" neck, 41" chest, 31" waist, and I'm 5'8". The shirt would be worthless to me if I hadn't gotten it tailored, but now it looks like a million bucks.

Also, find a brand / fit that works for you and buy a couple different styles. For example, Peter Millar's Crown Crafted button down shirts are tailored enough for me and I've found a few styles of those that I like. For athletic shirts, i found a brand on Amazon that fits me well, and they are 3/$25, so I have 12 of them in a handful of colors.

Quality Is Also Paramount

You know that shirt or outfit that you look great in, so you wear it half of the time you have an occasion to? It is probably the right combination of fit, style, and quality. If it's not a "fuck yea" it's a "fuck no."

Dress Up a Notch, Not Down

Early in my career I worked at a bigger company that had Casual Friday. It devolved to the point there were some young guys who wore tank tops and flip flops. No one respected them. Don't be them.

Instead, be the guy who takes it up a notch -- a sport coat when slacks and a shirt will do.

Shoes Are A Giveaway

If you look good but your shoes are scuffed and tattered, it ruins the look.

Also, don't wear sneakers unless you are working out or its an intentional look.

If I'm wearing slacks or jeans (my day-to-day and/or office wear), I either wear a pair of nice suede or leather "driving shoes" (moccasins?) or cowboy boots (ostrich). Yes, they are expensive, but (for example) I've had those boots for 12 years and wear them 1-3 times a week. That's absolutely a better value than cheaper shoes I wear once a quarter.

Jewelry

I don't wear any rings, necklaces, etc. That's just not my style. You do you.

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2) Grooming

This is somewhat covered by the hygiene DoD, so I'll also be brief here.

Obvious stuff:

  • Nails clean, trimmed, and smoothed (no sharp edges)
  • Clip, trim, or pluck the errant ear, nose, and eyebrow hairs

Hair Style

Do you even have one? When did you last update it? Does it fit your face? Does it fit who you are? I had the same style for 18 years. Updated it about a year ago. It's still professional, but it's got more of a confident edge now.

Beard / Shaving

Be intentional.

  • If you are clean-shaven, be clean shaven.
  • If you have stubble, have it because you wanted it and maintain it at whatever the right length is for you.
  • If you have a beard, keep it neat, clean and maintained.

3) How You Carry Yourself

This is an area that I think gets overlooked a lot, but what is the point of spiffing yourself up if you still hunch over, avoid eye contact, and generally project weakness instead of strength?

Posture

Two tips that stuck with me:

  • Act like you have a massive set of antlers.
  • Imagine balancing a quarter on your chest (chest up and shoulders back).

Eye Contact

Maintain it. Don't stare at someone who isn't looking at you, but if eye contact is established, maintain it for 4-5 seconds. If you need to, look near the eyes, or at one eye. Don't dart away or move from eye to eye, and when you look away, look away slowly (but not down).

Movement

Do you move quickly and nervously or confidently and intentionally. Do you act or react?

You know why Sean Connery got cast as the first James Bond despite his limited resume until that point? Because he moved like a jungle cat -- and because "Connery put on an assertive, reckless and masculine act at lunch". How is that for presence?

An easy way to start being more intentional about how you move is just to walk more slowly (and ffs, don't be looking at your phone).

Smile

This should be obvious.

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Action Steps:

  • Fashion
    • At a minimum, take the three steps I mentioned above to be less unattractive.
    • Next, focus on fit and quality
    • Get Classy, San Diego
  • Grooming
    • Address the basics
    • Be intentional about your hair and facial hair.
  • How you Carry Yourself
    • Address posture (antlers)
    • Practice sustaining eye contact
    • Move like a fucking jungle cat, not the nervous prey.