Somehow I am ugliest when I am on a trip. And I’m not talking about the inescapable, ever-present Plane Pimple that pulls the trigger every time I set foot in a terminal — I’m talking about the grueling outfit/body/skin/hair/personality dysmorphia that emerges the second I hear I have to leave town. My carefully curated and heavily debated outfits always sit a little frumpier despite being the same clothes I wear at home. It never looks like what I want it to look like.
Perhaps the pressure comes from not wanting to look like a tourist. Of wanting to feel “special” — like I’m having a singular main-character experience among the collective crowd who are all wondering, “Who is this mysterious, supremely stylish, gorgeous, delectable young woman? She couldn’t possibly be from here and yet she is better than the rest of us!”
It’s a grown up version of the Harry Styles fan-fiction trope: Boy sees different Girl in audience, strikingly beautiful, reading—at a concert—and is so mesmerized by her that he invites her backstage so they can fall in love. It’s possible that its just my own niche brand of travel narcissism and a desperate attempt at a continuation of the Best Dressed high school senior superlative.
Best Dressed in the Office. Best Dressed on the BART.
Or maybe it’s as simple as the water in the hotel is making us uglier and the government doesn’t want us to find out.
Whatever the cause, my weeks of work travel are often a closet conundrum. What does one wear when she has to be corporate casual/work appropriate and foot traffic friendly — but is also going to be on a boat, on a bike (for work—no less), meeting clients for nice dinners, having cocktails in jazz bars and attending an opera, with weather varying from 40-70 degrees, and also feels like a scary, ugly travel troll?
The answer: apparently denim. And while I’m not here to play influencer or persuade you to buy anything, I am here to say that a good jean is the solution to most of my outfit riddles. It’s nothing groundbreaking, and yet it’s a reminder for both of us, in case you need it too.
I’m purposefully omitting a Monday outfit because that was my travel day. There will be no further questions, your honor.
These are the Free People Mid Rise Barrel Jeans in Ian Indigo. I’d recommend sizing down— these are a 25 to my typical 26/27. You can see these everywhere now, but while I’m exercising my narcissism muscle I’d like to formally declare that I’ve had my eye on this denim shape from Citizens of Humanity since late 2022— and I had them before my friends did.
These are the Val 90s Mid Rise Straight Jeans in Colorado — I sized up for a bit of a baggier feel. There’s definitely room in the waist but they were perfect for biking around Angel Island.
This is the Belted Jean Midi Skirt from Oak and Fort. It’s on sale (!!!!!!) for $48. I often feel that denim skirts are reserved for those of us above 5’6. That’s a taller woman’s garment because the rigidity of the fabric leaves me waddling like a penguin. BUT! I will say this skirt is quite a bit softer than others I’ve tried, which makes it a little friendlier.
These are also the Free People Mid Rise Barrel Jeans in Rambler. I believe these are a size 26 — they sit considerably lower on the waist but are the perfect on-a-plane-from-SF-to-NY jean. Pair with a sour melon crossbody and a fun textured shoe for a little more zest.
What are you wearing when you feel the Travel Uglies? Do you get the Travel Uglies? Am I an egomaniac or do you also exercise Main Character Syndrome when you touch down on the tarmac?
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