Part One: Fashion Guide to Dressing Like You Give a Damn


Take a look at that photo up there. Take a long, steamy gawk at that image. Those are supposed to be men, or at least what passes for men these days. Maybe we should say they’re adult, post-pubescent males.

The morning I took this photo, these three otherwise sensible people got out of bed, showered, pretended to shave and decided to dress like teenage girls from the 1980s. While I took this picture, I was wearing a light suit (casual, no tie), a bespoke dress shirt and $300 shoes. So, there was obviously a gulf of communication.

I suppose they think this is a sharp, modern and fashion-minded look. Or, perhaps they just don’t care. Unfortunately for them, women do care how a man dresses. If they don’t get a sense that you are concerned with how you look, they assume you don’t prioritize attracting them. Expect to be treated accordingly.

Whether you stumble out of the door in sweatpants and a dirty t-shirt, or you choose to dress like like Bananarama up top there, you’re sending the image that you’ve given up on the opposite sex.

Related: Improve Your Online Dating Chances

To get you back on target, I’ve put together some fine tuning points to get your public image on track. Some tell you what to do. Some tell you what to avoid. You’re free to pick and choose what speaks to you.

You never know who’s watching. Leave the house looking like other people will see you – because they will. You simply can’t predict when your ideal human female will catch sight of you. This sounds obvious, but too many guys stumble out of their door the way they dressed to knock around the house. Maybe it’s the weekend after a long stretch at work. Maybe they only plan on seeing their guy friends in a given day. But, they leave the house dressed to embarrass.

As you leave, make sure you’re free of sweat pants, flip flops and cut-offs. No wife beaters. No cargo shorts. No Army surplus came unless you’re going hunting. (I confess I’m guilty of that last one.) No hoodies, unless you’re the eternally bitter coach of a football team in Massachusetts.

Finally, carrying through on that athletic point, no jerseys. You’re not a professional athlete, and you never will be, You might as well go out dressed like Boba Fett. There’s just as much reality to your dress sense.


You are safe to mix and match. There’s one popular formula for dressing to attract the ladies that any many can manage – “high/low.” The idea is to blend a little underdressing with a touch of class to shoot for that Goldilocks zone.

Most daily social events are too casual for suits, but show up dressed embarrassingly as discussed above and you’ll look like a lazy clown. So, you split your body off at the waste and dress well on one half, more casually with the other. For example, you can get away with a good pair of jeans if you go dress shirt and sport coat. You can get away with the solid color t-shirt if you go dressier pants and upmarket shoes.

You’re not 12. If there’s one male fashion failure that annoys women the most, it’s the inability or unwillingness of men to dress their age. As if it’s some extended case of Peter Pan Syndrome, many grown up men still walk around looking like they haven’t hit puberty yet. (See every other “man” in Los Angeles – even in the workplace.)

So, playing off the no jersey note from earlier in the piece, get over the baseball caps. There’s nothing wrong with a little millinery effort, but maybe try that short brim Fedora or the classic driver’s cap. Also, give the non-stop jeans a rest unless you’re blending it high/low.

That should hold you for now. Keep an eye out for part two of our “dress to impress” tips tomorrow. Now, go and clean yourself up, for chimp’s sake.