“Skiing is easy,” said no one ever.

I love skiing. Skiing is taking two boards, strapping them on your feet, pointing straight down a mountain so high only eagles should be there, and praying to sweet baby Jesus that you survive. It’s an adrenaline rush. It’s marveling at mountainous beauty. It’s drinking one beer at such an altitude that it feels like three. (Which is ironically the only cost-effective thing about skiing.)

Skiing is cool, literally.

As an entertainment guy, I live and work mostly in Orlando, where it’s hot and humid. I sweat every day. (Try wearing a suit in upwards of 98 degrees with 100% humidity. Try wearing a WB approved Wizarding Robe. It’s challenging.) Now every time I get a gig in the Denver area, like the Rat Pack Swingers at the Denver Convention Center:

I rent something with 4-wheel drive (I recommend the Mercedes SUV) and wheel up the mountain to the Breckenridge Resort.

It’s like Christmas all year there! You can wear a sweater, an honest-to-God, a nice cable knit. A turtleneck even! You know how intelligent I look in a turtle neck?!! I’m freaking Steve Jobs! You Boston folks have no idea the pressures of being swimsuit ready 365 days a year. Winter culture is amazing. You drink smokey old-fashioneds by a fireplace under a moose head and love life.

Gear Up!

Now, when I first started skiing, I would wear my jeans, a sweatshirt and a leather jacket. I looked like a thrift store Fonzie, but unlike the Fonz, I was NOT cool. I was a sweaty mess with my butt soaked through my jeans and big 80’s hair. Now in 2020, you can gear up with some of the sickest swag. The athletic clothing tech has never been better and you can look amazing even if you’ve never skied a day in your life.

The Base Layer

First, you’re gonna need a set of hot chillys -this is skin tight super-hero material that makes you look like Spiderman and keeps your butt and chest so warm, you won’t need anything else on. It’s like Tony Starke designed this stuff, it’s awesome. Then all you need are some ski pants and a jacket.

The Jacket

Your ski outfit is all about the jacket. Get a pricey, bright neon one designed by a company whose logo is a spider or a dragon. The more expensive it is, the more people will think you know what you’re doing. Plus, the brighter you stand out against the snow, the easier it will be for the paramedics to find and rescue you. Also spring for matching goggles. Again by the spider/dragon people. Make sure they are as reflective and opaque as possible. This way no one can see the fear in your eyes as you ask which trail is the “easiest”.

How to be Awesome at Skiing F.A.Q’s.

Should I listen to music with my earbuds as I ski?

Yes. But not hard rock, metal or rap. Think Rat Pack. Nothing inspires cool confidence like careening down the mountain at 60 miles an hour listening to Sinatra croon “Come fly with me.”

Should I drink alcohol while I ski?

Absolutely. A nice shot of whiskey warms the blood and calms the nerves. No one wants to break their leg sober.

Helmet or Super-fun Kermit the Frog hat?

The helmet protects you from serious injuries like concussions and brain bleeds…but the hat looks much cooler. So naturally, I’m torn.
Man wearing kermit hat in sand and snow

Can I ski in my bikini?

Yes! Fun fact: I actually saw a woman ski the Poconos in nothing but a neon green bikini back in 1982. I can’t remember where I put my keys most days, but I will never forget that.

Can I ski at night?

Yes! There are actually places that let you ski after dark. It’s thrilling and terrifying and I can’t believe they let us do it.

Check this out:

Should I take videos with my phone while I ski?

Of course not silly, that would be dangerous.

Now watch these super-cool videos I took with my phone while skiing: