I Overthink Every Outfit, So You Don't Have To | 07
Fashion Fails & Vacation Mishaps: How I Survived Palm Beach with Style, Laughs & Bulbasaur
*Warning: This post may be too long for your inbox to handle. If it gets clipped, blame my inability to self-edit, not your email provider. Click 'View in Browser' for the full experience—because my ramblings deserve the spotlight they were born for.
Spoiler: there’s a giveaway buried in here—but you’ve gotta read to find it 👀
One of the things I know my family can’t stand about me is how the most minor inconvenience can ruin my entire day. It could be something so small and inconsequential, and yet—day derailed.
I had the privilege of teaching with my best friend as my co-teacher (God bless her soul). We spent every single day together, all day long. Honestly, I’m not sure how we’re still friends.
She knows every single quirk about me. One time, I tried to tell her I’m easygoing and just go with the flow. I think she almost spit out her lunch laughing. I am anything but go with the flow. I’m rigid. I like things predictable. If she even tries to make a dinner reservation at any time other than 5:00 p.m., she knows I’m quietly dying inside.
One of the things that always makes me laugh is remembering how these minor inconveniences would send me into an epic spiral—and she was usually the one tasked with talking me off the ledge.
Once, I spilled salad dressing on a beautiful floral chiffon dress. I must’ve asked her 72 times if she thought the stain would come out. She’s never worked in the laundry business, so I’m not sure why I decided she was the expert. I remember saying at least 4,521 times that I wanted to leave work early to bring it to the dry cleaner. Randomly throughout the day, I’d just walk up to her with a sad face and point at it.
Another time, I accidentally marked the string of my white peasant top with an Expo marker. I almost fainted. I spent the entire day talking about that stain and strategizing how to get it out.
And for some unknown reason... she’s still my friend. Blessings.
On our recent family trip to Palm Beach, a few of these minor crises popped up again. First was at airport security. For some reason, they needed to re-check my carry-on. This included my adorable straw hat. The TSA agent started trying to fit these weighted brick things around my stuff until she got frustrated—and tossed the bricks right on top of my hat.
She dented my hat. Dented is a nice word, she CRUSHED my hat.
Listen, I’m all for safety. I even wore sneakers on the plane in the name of it. But this was not how I wanted to start my trip. I stared at that dent obsessively. I tried to fix it—no luck. Eventually I told my husband it was damaged goods and needed to stay in Palm Beach. He assured me the dent wasn’t that bad and that I was being ridiculous. But the next day, the first store we passed in town? I immediately found a replacement straw hat. That dent was just unacceptable. I would’ve perseverated on it the entire trip.
This was a big fashion trip for me. I was ready to be decked out in my all-linen-everything. I couldn’t wait. I told my husband I wanted to iron my linen outfits (I’m becoming such a Big Girl!). He pulled out the ironing board, plugged in the hotel iron, and then I asked him for a full demonstration. Yes, I’m 37 years old and I’ve never used an iron. I either steam things or just wear them wrinkled. Luckily, I married a U.S. Marine who can iron perfect corners blindfolded while hanging upside down from a pull-up bar.
I took strong mental notes as he walked me through it. I was ready.
I started ironing my linen set. The whole process was very aesthetically pleasing… until I noticed the wrinkles weren’t really budging. Then I noticed what looked like black marks. I told myself I was imagining things. I pressed on (literally). Then I saw tiny specks where the color seemed to be fading. I knew I wasn’t imagining it. My husband came over, took one look, and suggested I stop ironing immediately.
So, I pivoted. I’m a grown-up. I would not let this ruin my trip.
I changed into a different linen set—one that seemed less sensitive to the aggressive iron. But then I realized I didn’t pack a pivotal undergarment for this specific top.
My. Life. Was. Ruined.
I stood in the bathroom doorway with both hands over my eyes, seconds from rage and tears. Everyone in my family knows not to speak or make eye contact during these moments.
But good news: I prevailed. I did the unthinkable. I wore the original linen set—with what looked like a little burn and color loss. I didn’t talk about it incessantly. I didn’t point and pout. I actually forgot about the damage until I started writing this.
And for me—that’s massive progress.
Just a reminder that even at the ripe age of 37, we can evolve. I can remain eerily calm in true emergencies (remember when my daughter threw up all over my lap on a plane?). But the smallest setback—a stain, a dent, a burn—can still send me to the brink. So if you spill something on me, dent my straw hat, or take an Expo marker to my white shirt, I will tell you it's all good, no worries. But please know there’s still a chance—hopefully a small one—that it’s not good, and I have a lot of worries.
Today I made even more progress. I wore the cutest lobster sweater (can’t wait to show you on Saturday!). I took it out of storage, put on my whitest outfit to show off my tan, and… there it was. A stain.
I took a deep breath. I didn’t redo my entire outfit. I didn’t immediately go online and buy a new one. I just wore it to work and went about my day.
That must be how normal people operate. Must be nice.
If you haven’t diagnosed me yet, you’re definitely not reading my work closely enough.
Alright—let’s chat vacation outfits! I worked hard to document them while enjoying some R&R. Hope you don’t hate them.
Beach/Pool Outfits
Honestly, I had a really simple formula for the beach/pool. If I break it down into mathematical terms, it goes a little something like this: Andie Swim + Hat + Sunglasses + Boxers + Button-Up + Comfy Sandals = OUTFIT. If you haven’t checked out Andie swimwear, you’re missing out (this is not sponsored, I am not important). I got a little wild and swapped my straw hat for a baseball cap—but that was pretty much the extent of the changes. Simple formulas like this make carry-on-only travel totally doable. You know you can do it!
I’m fully obsessed with these J.Crew tees. They’re a thick quality and just look so darn good. I sized up for a perfectly oversized fit and now own them in yellow, white, navy, and red. A quality tee means you’re investing once—instead of rebuying a new one every year when the cheap ones fall apart.
Also, you’ll have to pry these OG Rainbow Sandals from my cold, dead hands before I ever admit they’re uncool or out of style. I SIMPLY DO NOT CARE. Let’s run a poll—I need to know where my real millennial girlies stand.
Out On The Town Outfits (aka 5:00pm dinner crowd/in bed by 9:00pm)
We eat dinner at 5:00pm. Vacation or not. Rain or shine. Holidays included.
So if you tell me dinner’s at 7:00pm or you’re picking me up at 7:30, just know—I am not okay.
I am pretending to be fine, but my stomach has already filed a formal complaint.
I'm clearly in my linen era. Please ignore any potential iron burns on the red shirt (I think they're not visible?). I don't think Substack will let me run another poll, but report back in the comments—I trust you.
I love the shell and starfish earrings when traveling on vacation. I carry these fun styles into the summer as well. These Target sandals are, and will always be, the real MVPs. I was just sharing with a friend—I’ve had these for like 5 years now. I wear them to work ALL the time. Someone explain the science as to how they’re so cheap yet still holding up really well?
This white linen dress is awesome! I enjoyed styling it in different ways. The dress comes with a slip, but I read that the yellow one doesn’t, so be sure to double-check before you buy. I loved throwing on the button-down to give it a fun yet elevated look. I really like the GAP button-down because it’s made of cotton—Poplin material is fine, but I love the feel of a legit cotton button-up shirt.
That’s a pretty scary close-up of my face, but I’m hoping this is a safe space.
Babysitting Bulbasaur
I spent a good chunk of the trip styling these outfits and having so much fun with them. But let's be real—the majority of the time was spent babysitting my daughter’s pet Bulbasaur. This little knitted version traveled all throughout Florida, including the handrails at every airport (GAG). I’m honestly grateful to have a large portion of our family photos now featuring my third child, 'Bulby.' Walking down the main street with 'Bulby’s' head sticking out of my bag to ensure he got enough air—nothing humbling quite like feeling like you’ve nailed a look, only to be reduced to a Pokémon servant.
GIVEAWAY! The more the messier…
📩 Forward this email, share the Substack link to your stories, or drop it in the group chat. Just send me a screenshot showing how you shared it (text, DM, or email—it all counts!).
Each share = 1 entry (up to 3 total) ⌛ Deadline: Friday, 4/25/25 at 5:00 PM (EST) I’ll announce the winner in Saturday’s Substack post!
🎁 One lucky winner will get a Starbucks gift card—because you deserve nice things for spreading the good word.
DMs or emails work for sending proof—whatever’s easiest!
Let’s test the limits of my executive function together.
Thanks so much for taking the time to read my post! Your support TRULY means the world to me. I'm beyond grateful for the little community we've built. And if you're making fun of me, well, you're doing a fantastic job of making sure I’m blissfully unaware of it.
Thanks for reading my poolside ramblings—I’m so glad you’re here. Truly. You make this space what it is.
See ya Saturday! xo,
Traci
If you enjoy my work and want to support the content I create, consider BUYING ME A COFFEE ☕🍵—think of it as a virtual tip jar to keep the ideas flowing!
❤️ Liked this post? Tap that heart so the algorithm knows someone’s out there.
📩 Think a friend would love this? Share it—good taste isn’t meant to be gatekept.
📸 Want more style and unfiltered ramblings? Follow me on Instagram @timelesslytraci. Tag me if you post—I’ll be in the comments with emojis, enthusiasm, and yas queens.
Some of the links in this post are affiliate links, meaning I may earn a small commission if you make a purchase through them. This comes at no extra cost to you, and it helps support my content and allows me to continue sharing the things I love. Thank you for your support.
You always have me running to the comments, Traci! Currently perseverating on that white linen dress 🤗
Early dinner any time we can because bedtime is 9pm!!! Style for vacay was perfect! Why is it that they touch EVERYTHING gross … and touch their face 😳