Hello TOGS readers! Kellyn here.
We’re all thinking it: could 2026 get any weirder? Well, turns out it can. Gauchos are back.
The one article of clothing that I thought was banished to purgatory of the early aughts has returned on the wings of zellenials, and you know what? They’re kinda chic. And now I find myself sitting with 10 tabs open on Chrome, each with cart of varying inseams to compare. How did we get here?? What are we doing? (For those also chronically online, please read that in Jeremy Culhane’s SNL voice)
Will this sick twisted trend cycle ever not catch me off guard, no matter how predictable—down to year—it is?
I’ll preface as I always do: we all know blindly following trends is lame. I don’t need to waste your precious time waxing on about that. We at TOGS, us who write and those who read, are interested in style. We’re curious about what folks with strong personal style are wearing while being true to themselves and keeping their finger on the cultural pulse. We’re interested in the things feel stylish and function well—clothing that can carry us from the city into the outdoors.
And before we jump into today’s letter, I want to splice in a bit of real time here:
This week I was tasked with a true TOGS challenge. I was home visiting my parents in Colorado, so I packed casual mountain garb and athletic wear. I unexpectedly (and thrillingly) got two tickets to see Stephen Colbert’s show in NYC. So, on a whim, my mom and I decided to go. But I couldn’t go all the way home for cuter, more city-appropriate clothes. SO! I had to put my money wear my mouth is and style my mountain togs for the city! Here’s what I pieced together:
Lovely plaid coat is from Sèzane. Recycled cotton denim jacket and trouser set from Finisterre. Lace t-shirt is old from Mango, layered over a cream t-shirt from Cos. Navy barrel pants are the Jumper Pants from Rudy Jude, black and white heels are vintage Prada from The Real Real, and sunglasses are Poppy Lissiman. And black cashmere sweater as a scarf!
I also pinned up the coat collar to create more interesting peter pan style collar with this Scottish thistle pin—
Now, on to this week’s letter. I’m going to chat a bit about what the styles were 20 years ago, why that’s relevant to today’s style, and how to wear the current trends du jour yourself.
Back in 2006, during what historians refer to as the Gaucho Dynasty, I was in 5th/6th grade and wearing some variation of this outfit:
