Last month I spent forty-five minutes trying to decide between three nearly identical black cover-ups for my long weekend in Miami. Three cover-ups. For four days. While my suitcase sat there already bulging with enough outfits to dress a small army, and my flight was leaving in exactly eight hours. This is apparently what my life has become – a corporate professional who can analyze market trends and build financial models but completely loses her mind when faced with the simple task of packing appropriate clothing for guaranteed 85-degree weather.
I mean, you’d think after years of business travel I’d have this figured out by now. But there’s something about vacation packing that turns me – and honestly, every woman I know – into a completely irrational person. It’s like we forget how to dress ourselves the moment sunshine and relaxation enter the equation.
My friend Maya called me last week from her bedroom floor, literally surrounded by clothes for her upcoming trip to Barcelona. “I’ve laid out fourteen different outfits,” she said, sounding slightly hysterical. “For six days. And I still don’t think I have enough options.” This from a woman who wears essentially the same thing to work every day – blazer, silk blouse, tailored pants, done. But throw in some vacation time and suddenly we need enough wardrobe changes to rival a Broadway production.
The thing is, I know exactly what’s happening here because I do it too. We’re packing for the vacation we want to have, not the one we’re actually taking. That Barcelona trip Maya’s planning? She’s going with her boyfriend to eat tapas and walk around looking at architecture. Very low-key, very casual. But her suitcase contains outfits for fancy dinners that aren’t happening, cocktail parties she hasn’t been invited to, and what she called her “sexy pool look” even though their hotel doesn’t have a pool.
This is peak vacation packing delusion, and we all do it. I packed a silk slip dress for that Miami weekend even though my itinerary literally consisted of brunch, beach, repeat. When exactly did I think I’d wear a delicate silk dress? To sit in sand? While eating fish tacos? But there it was, carefully folded with tissue paper like I was heading to the Met Gala instead of a very casual girls’ trip.
I’ve started paying attention to this pattern because it’s actually fascinating from a psychological perspective. And expensive. Do you know how much money I’ve spent on vacation clothes that get worn exactly once, if at all? That silk dress cost $180 and spent the entire weekend hanging in a hotel closet while I lived in the same two sundresses I always wear.
The cover-up situation alone deserves its own category in whatever manual they write about women’s irrational behavior. I currently own seven beach cover-ups. Seven. For someone who goes on maybe three beach trips per year and spends most of that time either in the water or lying on a towel. But somehow I’ve convinced myself that different beach activities require different cover-up strategies – something casual for walking on sand, something slightly dressier for beachside lunch, something “sophisticated” for the imaginary scenario where I need to look put-together while also being ready to swim at a moment’s notice.
Last summer in the Hamptons I watched my friend Jessica rotate through four different cover-ups in one day. Four. We were at the same beach club the entire time. When I asked her about it later, she just shrugged and said, “I don’t know, they all felt right for different parts of the day?” This is the kind of logic that makes perfect sense when you’re on vacation and absolutely no sense when you examine it later.
And don’t get me started on vacation shoes. I packed five pairs for that Miami weekend. Five pairs for a trip where I knew I’d be walking on sand and sitting by water most of the time. But what if we decided to go somewhere fancy? What if the restaurant had a dress code I didn’t know about? What if my flip-flops broke and I needed backup options? These are the midnight thoughts that lead to completely irrational packing decisions.
The weather anxiety is probably my biggest vacation packing weakness though. I’m from the Northeast originally, so I have this deeply ingrained inability to trust that warm weather will actually happen, even in places where it’s literally been 80 degrees every day for six months straight. I always pack at least one sweater “just in case.” For Miami in July. Where the overnight low was 78 degrees. That sweater sat in my suitcase the entire time, but I felt somehow safer knowing it was there.
My coworker Sarah has this thing where she packs multiple swimsuits for short trips with very specific reasoning. “This one is for actual swimming, this one photographs better, this one is more comfortable for lounging.” I counted six suits in her bag for a five-day trip to Turks and Caicos. Six. She’s a financial analyst who brings the same lunch to work every day for efficiency, but apparently vacation swimwear requires extensive options.
The reading material situation is another place where vacation logic completely breaks down. I always pack at least three books for any trip longer than two days, despite knowing I’ll probably spend most of my time scrolling Instagram or napping. Something about vacation makes me think I’m going to become this sophisticated person who reads literary fiction while sipping wine and looking contemplatively at the ocean. In reality, I read maybe fifty pages total and spend most of my time taking photos of my breakfast.
What’s really interesting is how this extends to trying new styles that I’d never wear at home. That Miami trip included a bright yellow dress that I bought specifically for vacation because “bright colors feel more tropical.” Yellow is not my color. I don’t wear bright colors to work, or anywhere else really. But vacation me was apparently going to be someone who could pull off sunshine yellow. Spoiler alert: she was not. The dress looked just as wrong in Miami as it would have in Boston, but somehow I needed to travel 1,200 miles to figure that out.
I think there’s something about vacation that makes us believe we’re going to become different versions of ourselves. More adventurous, more stylish, more willing to take fashion risks. The clothes we pack represent this optimistic transformation – vacation Jasmine is going to be the kind of person who wears statement earrings and bold prints and looks effortlessly chic while walking on the beach at sunset.
The reality is that vacation me wants to be comfortable, just like regular me. I end up wearing the same two sundresses on rotation because they’re easy and I know they work with my body and my lifestyle. All those other carefully selected options just travel along for the ride, making my suitcase heavier and my choices more complicated.
My friend Lisa just got back from Greece and when I asked what she actually wore versus what she packed, she laughed and said, “I lived in three outfits the entire week. Everything else was just expensive security blankets.” This seems to be the universal vacation experience – we pack for twelve different scenarios and then default to whatever makes us feel most comfortable and confident.
The evening wear category is probably where we get most carried away. I always pack at least one “nice” outfit for dinners out, usually something I’d never wear to dinner in my regular life but that feels appropriately vacation-special. These outfits often require specific shoes, accessories, sometimes even different undergarments. All for dinners that could easily be handled by a sundress and sandals, which is what I usually end up wearing anyway.
It’s not just the quantity of clothes either – it’s the accessories, the shoes, the “just in case” items that add up. I packed a statement necklace for Miami that I never wore because it felt too dressy for our actual activities. But I couldn’t leave it behind because what if we ended up somewhere that required statement jewelry? This is the kind of circular thinking that leads to overpacked suitcases and outfit anxiety.
The hat situation deserves special mention because it’s possibly the most impractical vacation accessory choice most of us make. Wide-brim hats look amazing in photos and provide excellent sun protection, but they’re terrible for travel and annoying for actually doing things. I’ve brought hats on multiple trips, carefully protecting them during transit, only to wear them for exactly one photo before giving up because they’re inconvenient for eating, swimming, or existing in any kind of breeze.
What’s funny is that despite this pattern repeating itself on every single vacation, I never learn. I always think this time will be different. This time I’ll wear all the outfits I pack. This time I’ll be more adventurous with my style. This time I’ll actually need seventeen different options for a week of sitting by water.
The airport fashion show is its own special category of vacation delusion. We dress for travel like we’re walking a runway instead of sitting in a metal tube for several hours. I’ve worn heels to the airport for vacation trips, as if looking cute during the flight was somehow important. Comfort should be the only consideration for travel days, but vacation brain makes us think differently about everything, including airport attire.
Maybe the most honest conversation I had about vacation packing was with my friend Rachel, who’s a lawyer in DC and definitely knows better but still can’t help herself. “I know I’m going to overpack,” she said while preparing for Portugal. “I know I’ll wear the same few things on repeat. I know most of what I bring will never leave the suitcase. But I physically cannot make myself pack less. It’s like vacation insurance – I need to know I have options even if I never use them.”
This might be the real truth about vacation packing – it’s not really about the clothes at all. It’s about possibility, about feeling prepared for whatever version of ourselves shows up on vacation. Maybe this time we will be the kind of person who changes outfits three times a day. Maybe this time we will go somewhere that requires that fancy dress. Maybe this time we will become the stylish, adventurous vacation person we always imagine we could be.
The clothes are just props in this annual play we perform, where we temporarily believe we might be someone different in a different place. And honestly? Even though it’s expensive and impractical and results in ridiculously heavy suitcases, there’s something kind of sweet about this optimism. We pack for the best-case scenario version of our trip, even when experience tells us we’ll default to our usual choices.
So yeah, I’ll probably continue to overpack for every vacation, bringing multiple options for every possible scenario while knowing I’ll wear the same comfortable favorites on repeat. It’s wasteful and irrational, but it’s also hopeful. And sometimes, maybe one time out of ten, I actually do surprise myself and wear something I wouldn’t normally choose. Those moments probably don’t justify the other nine times of vacation wardrobe excess, but they feel significant enough to keep the pattern going.
Besides, having too many options is a good problem to have, right? Right? This is what I tell myself every time I’m trying to zip an overstuffed suitcase at midnight before an early flight, surrounded by clothes that represent all the possible vacation selves I might become, even though we all know I’m going to end up in a sundress and flip-flops regardless of whatever grand style plans I’ve made.
By day, Jasmine works in finance. By night, she writes about making corporate fashion actually interesting. Her Boston wardrobe proves office-appropriate doesn’t have to mean boring, and that investment dressing can be both powerful and personal.
