Todd Herriott

Forty Years of Losing Oakleys

One brand has been on my face for basically every meaningful mile I've ridden since 1986 - from Factory Pilot Eyeshades to the Meta Vanguard. What I kept wasn't the glasses.

My dad handed me my first Oakleys

My dad bought me my first pair of Oakleys in 1986 — white Factory Pilot Eyeshades, the same style Greg LeMond and Andy Hampsten were racing in that era. I'd just started wearing contacts, and those things wrapped my whole eye socket. Perfect coverage.

I didn't know it then, but that was the beginning of a forty-year relationship with a brand that's been on my face for basically every meaningful mile I've ridden since.

A garage, $300, and a dog named Oakley

I got my first pair of Frogskins around 1988 — pink and white, no idea why I picked that color, but I followed them up with a black frame/purple lens pair not long after. Since then I've owned nearly every colorway Oakley's ever made in that model, and I've lost or misplaced almost every single one. I actually traded a pair of pink Frogskins for a skateboard once, which I then gave to my cousin. Different era, different priorities.

I had Blades in the mid-80s — black on black, thought I was the coolest guy in Nebraska. Moved into M Frames in the early 90s, blue frame, black lens, still one of the cleanest looks Oakley's ever made. In 1992 my buddy Ed, who worked at the Bike Rack in Omaha, got me into a pair of Sub Zeros. I sold those a year or two later for fifty bucks to a guy in Boston because I needed the cash more than I needed the shades in that moment. Still one of my real regrets in this sport — not the losses, the money you leave on the table. Those Sub Zeros were beautiful and completely impractical, which is probably why I loved them.

Nearly every colorway. Almost every one, gone.

I got my first pair of Frogskins around 1988 — pink and white, no idea why I picked that color, but I followed them up with a black frame/purple lens pair not long after. Since then I've owned nearly every colorway Oakley's ever made in that model, and I've lost or misplaced almost every single one. I actually traded a pair of pink Frogskins for a skateboard once, which I then gave to my cousin. Different era, different priorities.

I had Blades in the mid-80s — black on black, thought I was the coolest guy in Nebraska. Moved into M Frames in the early 90s, blue frame, black lens, still one of the cleanest looks Oakley's ever made. In 1992 my buddy Ed, who worked at the Bike Rack in Omaha, got me into a pair of Sub Zeros. I sold those a year or two later for fifty bucks to a guy in Boston because I needed the cash more than I needed the shades in that moment. Still one of my real regrets in this sport — not the losses, the money you leave on the table. Those Sub Zeros were beautiful and completely impractical, which is probably why I loved them.

I've made my peace with being a guy who loses things. Forty years of Oakleys and what's still in a drawer would fit in one hand. What I kept instead was who handed me each pair.

Repping the brand with no deal to show for it

Funny enough, I didn't actually wear Oakleys through most of my racing career — none of the teams I rode for had an Oakley deal, and the guys getting their own contracts were winning bigger races than I was. My amateur career was much longer than my professional riding career. Being named Amateur of the Year by VeloNews in 2002 and being the first American to win the Univest GP gives me some good story lines when I'm riding with my club guys — but none of my "major" achievements in road racing saw me in Oakley eyewear.

From 1987 to 1991, while I was in college in Boston, I worked as a bike messenger, and I like to think I was repping the brand hard through that stretch — dodging cabs on Comm Ave in a pair of Oakleys deserves some kind of extreme-athlete classification, in my opinion. No payout ever came. I was ahead of my time, I suppose.

Twenty-two years later, I was the one handing them over

By 2006 I was in Radars, and I stayed in that shape for close to fifteen years — through my last pro season, through the move to Seattle, through opening the shop.

In 2008 I opened my Oakley dealer account. That felt like a real milestone at the time and it still does, honestly. My dad bought me a pair in 1986; twenty-two years later I was the guy handing them to somebody else's kid.

Then I put on a pair of Vanguards

When Holbrooks came out in 2010 they became my everyday pair, and true to form I lost them constantly. I went through Jawbreakers, Sutros, most of the cycling-specific lineup over the years. Before the Vanguards, I'd settled into Sphaeras — I liked how they sat on my face and the way they looked off the bike as much as on it.

Then I put on a pair of Meta Vanguards, and I haven't wanted to ride without them since.

"Hey Meta, play some Echo and the Bunnymen"

My first reaction was that they looked too big. Then I remembered I wear hard contacts, and for me, more coverage is always a win. I'll also admit I'm not a big fan of Meta as a company generally, so skipping this whole category would've been the easy call.

But I've always ridden with music, and the ability to say "Hey Meta, play some Echo and the Bunnymen" while I'm grinding up one of Seattle's uglier kickers on a cold morning — and still hear cars, still hear the person riding next to me — changed my mind fast.

The stuff I never thought I'd want

They're tethered to your phone, which I was skeptical of, since half the reason I ride is to not deal with my phone. But taking a call through them is easy and the audio's clear both ways. Asking Meta to snap a photo or start recording is just as easy, and the quality is legitimately good — a traffic incident, a near miss, a street name I want to remember later — that's real utility, not a gimmick.

And having an AI assistant to just ask things while I ride is something I never thought I'd want. Turns out I have a lot of questions. From a training standpoint, being able to set timers and reminders to eat, drink, or start an interval hands-free is genuinely useful — even though these days I keep my efforts pretty modest.

Somebody's dad comes in with a kid. Somebody who's been racing twenty years tries on a shape they swore they'd never wear. I've been on both sides of that counter.

Oakley Meta Vanguard

For anyone who wants the specs: a wraparound shield built to stay put no matter how hard you're working, with the camera, audio, and assistant tucked in where they don't get in the way.

Lens

Prizm Road

Tuned for medium light · 20% transmission

Durability

IP67 Rated

Sealed against sweat, rain, and dust

Audio

Dual open ear

Holds up in wind to 30 mph — you still hear traffic

Training

Garmin Sync

Real-time data on the ride

Fit

Three-point fit

Unobtainium temple tips — grip increases with sweat

Camera

12MP - up to 3k

Stills and video, hands-free capture

Battery

9 hours daily use

6 hrs continuous audio · +36 hrs from the case

Recording

Strava connected

Rides logged the way you rode them

There are a lot more eyewear brands today than there were when my dad handed me those Factory Pilots — but none of them carry the story, the culture, and the style impact that Oakley does. I've been asking "what's next" for decades now, and they keep answering.

In 1986 I'd have asked my dad that question. Now I'm asking the glasses. I'm not sure what to do with that, but I noticed it.

Hey Meta — who's going to be the next rider to win the Tour in a pair of Oakleys?

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