My Worst Looks: A Definitive Ranking

I don’t look good naked.

This shouldn’t be news, but I’ve finally accepted it. I always thought I was too skinny, or too chubby, or too white, or too sunburned, and if I could only eat more protein/do more crunches/get more sun/stay locked in my basement, I would suddenly have a sexy body. Well, after lots of effort and several attempts at the LGN diet, I’m not expecting that result anymore.

Fortunately, I live in the 20th century, and we have reached a nice place in history where we can fully cover our bodies at will with “clothing.”

Unfortunately, I have never really cared enough to develop good taste in said clothing, and my hair is in a state of constant experimentation. Some people like to say I have a “unique” style (thanks Mom!), and I appreciate their kindness.

Where am I going with this? As you may know, I love making lists, so I decided to make a list of my worst style choices ever, and then I ranked them! We’ll go through them from last to first (first being the worst, are we on the same page?). I won’t bother to explain the point system; you will understand.



Honorable Mention: The Handlebar

What is this face. That’s not a question. I think I was going for a dead-eyed, dissatisfied plumber about to call in a bomb threat. But the mustache is noice. Does it matter that I look stoically unhinged? Not at all, that’s how good the mustache looks. But wait, you think this handlebar picture is good? Hold on to your hats.


Cowboy Up

Bam! There it is. I know what you’re thinking. “Sterling, this is the ‘Worst Looks’ list. You look too good in this picture to be on this list!” Hey, I appreciate it. I do look pretty dang good in this outfit. Sam Elliot better watch out.

Clothing= +10. A trucker hat and a cowboy hat? Many men have tried, many men have died.

Hair= +15. Did you think ten was the maximum? That mustache is the maximum.

Face= -5. Looking aloof isn’t good in a trucker hat, but quiet cowboys are city girl catnip.

Selfie Bonus= -5. No self-respecting man takes selfies except when his girlfriend needs to know what he’s wearing so she can tell him to change.

Total Worst Score= +15. You’re right, these shouldn’t even be on this list.


Tyler Durden

#5. The Tyler Durden

The black-dyed hair. The wispy goatee holding on for dear life. The pink shirt collar thrown over my leather jacket like a maiden in distress. Yeah…my Fight Club phase wasn’t that great. If you think you’re freaked out, you should have seen the look on poor Irene’s face when I went to pick her up for our date. She couldn’t wait for the whole thing to be over.

It only got worse once I started an actual fight club. Nothing is more pathetic than a 135-lb. white boy trying to look cool for his one true love by starting fights in the parking lot at her apartment complex. Somehow that girl never loved me.

Clothing= 0. Shirt is terrible, but the jacket is redemptive.

Hair= -7. That hair would look great on Fred Durst. That’s a bad sign.

Face= -7. Am I scared? Is she? Aren’t we all?

Hot Date Bonus= +5. Irene never loved me either, but she was cute.

Total Worst Score= -9


Thrift Store Superstar

#4. The Thrift Store Superstar

Those shorts served me well the next time I needed to play 1980’s NBA basketball. What makes this picture look even worse is the perfect alignment of that red sign with my head, looking like I’m wearing a pipe-cleaner glasses chain. I’m like a poor man’s Kurt Rambis, if that poor man’s favorite movie were Peter Pan. This picture exemplifies my personal fashion motto: Don’t Use a Mirror.

Clothing= -6. You can’t unsee those shorts.

Hair= -3. Though shapely, my legs obviously needed a Venus.

Face= -9. I should have demanded a refund from the store for not punching me in the face.

Watch Bonus= +5. What? It’s a nice watch.

Total Worst Score= -13


4142_1149465461953_347464_n#3. More Mustache

You know when you are walking from your car to your house at night, and as you approach the door you suddenly feel a dark presence behind you, so you desperately grab your keys and turn the lock, then slam and deadbolt the door? What were you afraid of? What did you feel might be behind you, but were too afraid to look and see?

This. This is what you were afraid of, and what you didn’t want following you up the porch steps. This is the face of your fear.4142_1149465621957_7272847_n

Clothing= -8. I popped the collar of a pearl-button beauty. Fail.

Hair= -5. My fading hairline (thankfully retreating at a glacial pace) is juuuuuust starting to make a name for itself.

Face= -12. Do I want to take your purse, or steal your virtue? It’s hard to say. That’s why I don’t say anything at all. I just watch.

Ad Lib Bonus= +8. Those weights + that headband = everything.

Total Worst Score= -17


#2. Shaggy Hair

Did you think the dead-eyed creeper look was gone? Nope. Did you think I had maxed out my bad hair with the Brad Pitt impression? Nope. Do you think anyone can have a wispier goatee and still call it a goatee? Nope…or yep…I can’t tell. Asking yourself questions is supposed to be easy!

There are two things that are very sad about these pictures. First of all, these pictures were taken roughly two years apart. That means that I wasn’t discouraged enough by my first attempt at looking like an Irish Setter had shed its entire pelt on my head. No no, I had to try again. The second thing is, I  asked girls out with this hair and they said yes! A good man really is hard to find.Shag 2

Clothing= -3. The 90’s were a confusing time to grow up. Why was an undershirt always required? Thanks a lot, Zack Morris. Your inept tutelage has followed me all my life.

Hair= -20. I’m…*looks down at floor, wiping tears from his eyes* …I’m sorry.

Face= -10. I don’t think my face is all that weird, but these are leftover negative points from the hair. 😦

Gay Guy Bonus= +5. The guy in the background came out awhile later. It’s not important, I just needed a bonus category. He also told me I needed a haircut.

Total Worst Score= -28. I can’t get over the hair. It’s so bad. At least I was wearing a shirt.


#1. Nearly NudeSnow + Mugsey




Porch Swing








Car Dealership


Pumping Gas

SAY ?!?!

I have more questions than answers. Why am I holding my dog in the snow?! Whose porch swing is that?! WITH is my life?!?!?!?!?!

Clothing= -10. Sometimes I get nervous that I’m not wearing the right thing, but discarding all clothing in favor of boxers is not the answer! Silver lining: I was sensible enough to wear socks.

Hair= N/A. That I didn’t have a ridiculous hairstyle back then is a damn miracle.

Face= -25. I look so happy. I’m at the “This is a good choice I’m making. There is nothing out of place here. Move along” level of happy. And that’s wrong.

Ab Bonus= +15. I NEED THIS!

Everything Else Bonus= -100. That this even exists, and that I’m sharing it with you right now, is everything that’s wrong with America and I am at least partially responsible for Donald Trump. I’m sorry.

Total Worst Score= -120

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One Response to My Worst Looks: A Definitive Ranking

  1. Michelle says:

    Oh my goodness. I needed the laugh at the end. Socks and sandals woth your boxers pumping gas. OH MY.

    That being said, maybe I am stuck in this pseudo resurgence of the 90s, but I see nothing wrong with numbers 5 and 2. The only thing that would have made either of them better would be frosted tips.

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