The ‘Worst Dressed’ City Gets Redemption: Anchorage is Everywhere this Fall!

Jasmine Alleva
4 min readDec 7, 2022
(1). Kendall Jenner in North Face, 2022. (2). My brother and me in North Face and Carhartt hat (bonus, the mittens are from ARITZIA!), 2012. (3). Family members and myself, pictured in pink North Face and Birkenstock Boston clogs, 2011. (4). Kendall Jenner in Birkenstock Boston clogs, 2022.

They always come back around. Ex-boyfriends, ants, fashion trends… they’re all cyclical, baby! And today, sitting in my Los Angeles apartment, I’ve got some things to hash out with a little publication called Travel + Leisure. While I’m not the biggest fan of my hometown, T+L ranked Anchorage, Alaska as the ‘worst dressed city’ in 2012. An unfair shot — even if it was decided by the polls of its readers. Anchorage is like a sibling to me at this point. I grew up with it. And even though it’s made some questionable choices and can be kind of embarrassing sometimes; no one gets to make fun of it but ME.

As previously mentioned, I now live in Los Angeles. Yes, the city of angels — home to Hollywood’s elite, Rodeo Drive, and Melrose Place. Recently, I was at some supposedly bougie shindig, a guest list ornamented with household names and other unknown plebes like me. However, if you had told me that I was at the N Gates in SeaTac about to board a direct flight to Anchorage, I would have believed you. All around me were Carhartt’s, North Face jackets, Uggs, and — to my shock and awe — a pair of Xtratuf boots scuffing the floor. What was happening? Unkempt hair, sweatpants, and flannels, too? Did we enter a wormhole or was Anchorage ahead of the trends? I’ll go with the latter.

When the world had to pull into neutral and idle its ass at home for a little less than a couple years at the beginning of the pandemic, no one wanted to be wearing uncomfortable jeans or shoes with laces. Who were you really seeing at the grocery store, especially under a mask? Slip on your Uggs and your North Face down jacket and get that toilet paper before it runs out again! This ‘style’ or (according to T+L) lack-there-of, is Anchorage, Alaska’s magnum opus. Carhartt hats? Been there, done that. Birkenstock clogs? Come on! Is this middle school? Don’t even get me started on Crocs. Every Alaskan should be Miranda Priestly in The Devil Wears Prada going over new spring/summer lines: “Florals? For spring? Groundbreaking…”

I’m not saying we started these trends, either, because surely the Upper Midwest and other cold parts of the country are ALSO feeling the sting of inflation on their beloved Carhartt overalls and winter hats (and not just because of the economy, but because demand has gone up!). I’m saying that the very things we were absolutely roasted for are now popular and I’d like a recount on that T+L poll.

A recent photo in one of the tabloids that graces checkout stands showed Brooklyn Beckham (celebrity spawn of David and Victoria Beckham) rocking a Carhartt jacket. I, too, have a Carhartt jacket. It’s purple. My dad bought it for me when I was in high school (circa 2009), and I wore it religiously until the same, exact jacket was worn on by Michael J. Fox’s daughter on the short-lived Michael J. Fox show and he told her she looked like a Zamboni driver. I was MORTIFIED. To see a Carhartt jacket worn by the likes of Brooklyn Beckham feels like vindication but also envy — how the hell is this kid getting away with it and has he ever shoveled a driveway in his life? Please!

I’m not here to gatekeep. But I’m no one if not a hipster to the hipsters and Alaskans seem to have been ahead of many of the popular trends of the past few years. Oh, you made sourdough starter? Yeah, I did that in 3rd grade! Oh, you have Seasonal Affective Disorder? Yeah, so does every Alaskan. And now our fashion staples have made it into the mainstream. Or maybe people are just waking up to the fact that comfortable, warm, and cozy is better than anything else.

It has been a decade since Travel + Leisure’s ranking of Anchorage as the “worst dressed city” came out. That decade has seen some of the greatest changes in our world in recent history. A pandemic, the political pendulum swinging like a county fair amusement ride, and maybe most shocking of all: Anchorage, Alaska’s redemption. Sure, it can be argued that the rest of the country started dressing worse, but what fun is that? I guess the Alaska state motto was right, after all, NORTH TO THE FUTURE! I’ll be waiting on the Travel + Leisure recount.

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Jasmine Alleva

I was born and raised in Anchorage, Alaska, growing up in a warehouse in Anchorage's industrial district. Now I live in airports and stand in front of cameras.