I Overthink Every Outfit, So You Don't Have To | 06
Airport Outfit Overthink & Zara's Break-Up Email: A Round-Up of Last Week’s Looks
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I was getting ready to go to the airport and caught myself in the ultimate overthinking moment. I feel like you guys have to relate. I was laying out all of my clothing for the next morning—or night? I’m not even sure because the driver came at 2:50 a.m. I mean, yeah, it’s technically a.m., but in college, that was still p.m.… so I’m confused.
I had ordered the cutest linen trousers from Zara along with a few tops and some last-minute items for our trip. Then, out of nowhere, Zara sends me an email on the day my order was supposed to arrive saying I’ve been refunded. No explanation, no reasoning. It felt like a bad breakup over text.
I pivoted and found another cute, trendy outfit to wear. This was going to be my year. My year to not look homeless at the airport… my year to be a “cool girl.”
I laid out my outfit—oversized button-up, satin pants, sandals, accessories—all ready to roll. Then I sat on my bed and started to ponder/unravel:
DO PEOPLE WEAR SANDALS ON THE PLANE???
I usually do on the way home out of sheer laziness and a refusal to accept that I’ll be back in shoe jail once I hit the tundra of the Northeast. But honestly, I feel like I’m one of the few who actually wear them?
Before you judge me—walking barefoot on an airport floor really doesn’t faze me. I know, some of you are mortified and want to hit the unfollow button so bad. But I lived in an athletic locker room for 89% of my college life. I’ve seen it all. I’ve experienced it all. Sometimes, I wish I was more freaked out by this sort of stuff. I know my husband definitely wishes I was.
It reminds me of the time (pre-kids) when my husband and I were out walking. All of a sudden, I felt something smack me in the face. I touched it and—well—lucky me, a bird had pooped right on my head. Yeah, it sucked. Yeah, it was gross. But what was I supposed to do? I turned to my husband and said, “I think a bird just pooped on my face.” I’ll never forget the disgusted, mortified look on his face. I wiped it off, wiped it on my pants, and kept the train moving. I was far from home, I didn’t have a napkin, and there was obviously no shower in sight. He was shook to the core at how blasé I could be about something so utterly disgusting. Maybe this is my superpower… or maybe I’m just weird. I have this eerie ability to stay creepily calm in chaotic situations.
Okay, so back to the airport outfit. I started googling: Is it appropriate to wear sandals on an airplane? The answers were wild. They ranged from “absolutely not” to “yes, as long as it’s a supportive sandal.” The main reasoning? If there’s an emergency, you need to be mobile. Which, honestly, makes sense. I’ve also been watching Yellowjackets, so I now need to be prepared at all times for potential survival in the Canadian wilderness—even though I’ll be nowhere near Canada.
So, my adorable cool-girl outfit had to change… in the name of SAFETY. I went with my usual uncool-girl look: T-shirt, leggings, crew socks, and sneakers. I made it slightly better by throwing on an oversized polo and a cute hat. But I definitely went from “influencer in the wild” to the untucked version of Carlton from The Fresh Prince of Bel-Air.
That’s the degree of overthinking that goes on here. Safety > fashion, I suppose.

Monday
Monday was meh. I feel like it’s been raining here for like 4 days straight. The goal of this outfit was to get as close to wearing pajamas to the workplace as possible. These Amazon trousers are IT. They’re comfortable, flattering, and pajama-like. I paired them with a beige bodysuit to give it a polished look. For shoes, I went with a brown boot to match the brown belt. This was a good example of using the three-color rule with an outfit. All rules are meant to be broken, but sometimes this rule helps me focus on an outfit.
Color 1: Beige - bodysuit
Color 2: Chocolate Brown - trousers
Color 3: Rich Brown (?) - belt and shoes
Links: Bodysuit (Similar) // Brown trousers // Brown belt // Brown boots (Similar)// Gold earrings
Tuesday
I do love that polos are having a comeback moment. I’m grateful it’s a more stylish version of how I used to dress in high school. WHY DID WE LAYER LIKE THREE POLOS ON TOP OF EACH OTHER? Who decided that was a good idea? I blame Hollister and Abercrombie. When I used to shop there, my mom would literally refuse to go inside. She said it felt like she was having a seizure—between the loud music, the pitch-black store, and the overwhelming perfume smells. I knew that if she didn’t go into the store, my chances of convincing her to buy me something dropped to zero. Thirteen-year-old me would die inside—convinced my life was basically over.
This red cashmere polo is so good. I love tucking it into my jeans for a polished, put-together look. I paired it with pearl drop earrings and my two-toned ballet flats. I joked that it’s giving “Jake From State Farm-Chic” vibes.
Links: Red polo // Red polo (option 2) // Red polo (option 3) // Red polo (option 3) // Dark denim // Earrings // Ballet flats
Wednesday
Just a good fashion day. I love a printed boyfriend blazer—they’re so versatile. You can wear them the way I did for the office, toss one over a tee for a night out, or channel the cool girls and layer it over a hooded sweatshirt with leggings and sneakers. I’ve had this one for a few years, and every time I pull it out, I remember how much I love it.
The linen shirts I love from H&M really come in handy on days like this. They give the look of layering without making me too sweaty. I went with a black belt and black loafers to finish the look. If I could go back and tweak the outfit, I’d probably swap in a more feminine loafer—something like this.
The jeans are a cropped flare—different from my usual straight cut, but a fun little change-up. Press play to watch me “get ready” in action.
Links: Blazer (similar) // Linen shirt // Jeans // Black belt // Black loafers // Earrings
Thursday
Thursday wasn’t my best fashion day of the week. I wasn’t feeling my best, so this was the best I could put together: what appears to be an all-black jumpsuit, white sneakers, oversized sunglasses, and crew socks.
What made me even more “basic”? The black sweatshirt layered over it is a Zach Bryan concert sweatshirt. Call me basic, but I will hyperfixate—no, literally, I’ll listen to the same song on repeat for two solid weeks until I can’t stomach it anymore—on anything that man puts out.
Most recently, after watching the Menendez Brothers documentary on Netflix, I spiraled into a “Blame It on the Rain” by Milli Vanilli phase. My poor family. My poor Amazon Alexa. I feel like even the dogs howled in despair. Everyone was so over it.
Links: Black sweat pants // Sneakers // Socks // Black sweatshirt // Black sunglasses
Friday
Sweater vests are the most underrated way to diversify an outfit. I have a few that I’ve kept and restyled over the years. This is a cashmere one from Anthropologie — I’ll share similar options. I love the way it drapes.
I usually wear boots with my super-wide leg jeans, but I saw some ladies out there rocking ballet flats with them, so I took the risk. The fashion girlies in the social media world know their stuff. They looked great together.
I also love how people wear sweater vests under a blazer. Again, this gives the look of layering without committing to the full sweater. It prevents your sleeves from making you feel like Ralphie’s brother Randy from A Christmas Story. Press play on the video to watch me style this baby live.
Links: Chambray shirt // Denim // Sweater vest (similar) // Sweater vest (option 2) // Sweater vest (Amazon option) // Ballet flats
Saturday
As you read above, Saturday was my airplane outfit debacle. Maybe I should see if Milli Vanilli can perform a live version of “Blame It on Zara” instead of lip-syncing “Blame It on the Rain.” Stay tuned—I might just write them some fan mail. Also, fun fact — you may have to board your dogs, but dog hair will still travel with you. They’re called “German Shedders” for a reason.
Links: Oversized polo // White tee // Leggings // Socks // Hat (Similar) // Hat 2 (Similar) // Sneakers
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