At this point in my life, I’ve grown accustomed to spending far too long deciding among three nearly identical black cover-ups for my next long weekend getaway. Yes, three cover-ups. For four days. While my luggage is already overflowing with an excessive amount of clothing to outfit a small army, and while I have exactly eight hours until my flight departs. This apparently is what my adult life has evolved to – a corporate professional able to dissect and interpret market data, create financial models, and yet utterly lose her mind when faced with the simplistic task of packing suitable clothing for assuredly 85-degree temperatures.
I would think that after years of traveling for business, I would have mastered the art of packing by now. But, there is something about packing for vacation that transforms me — and honestly, every woman I have ever spoken to — into an entirely illogical individual. It’s as if we forget how to dress ourselves as soon as sunshine and relaxation enter into the picture.
My friend Maya recently called me from her bedroom floor, where she had spread out clothes for her impending trip to Barcelona. “I’ve laid out fourteen different outfits,” she exclaimed, sounding somewhat frantic. “For six days.” This comes from a woman who typically dresses in virtually the same way each and every day — a tailored blazer, silk blouse, tailored pants, and voila. But, somehow, as soon as a vacation occurs, we need as many wardrobe changes as a Broadway musical.
The fact is, I am aware of exactly why we do this. Because we are packing for the vacation we hope we will have — not the one we will ultimately have. That Barcelona trip Maya is planning? She’s going with her boyfriend to eat tapas and walk around looking at architecture. Extremely casual. Yet, her suitcase contains outfits for high-end dinners that won’t occur, cocktail parties she wasn’t invited to, and what she referred to as her “Sexy Pool Look” although the hotel she’ll be staying in does not have a pool.
Peak Vacation Packing Delusion is the name of this game and we all participate. I packed a silk slip dress for that Miami weekend even though my itinerary simply consisted of brunch, beach, repeat. At what point did I believe I’d wear a delicate silk dress? Sitting in sand? Eating fish tacos? But there it was, neatly folded with tissue paper as if I was headed to the Met Gala rather than a very casual girls’ trip.
I’m starting to pay closer attention to this phenomenon because it’s quite intriguing from a psychological standpoint. And costly. How much money do you think I’ve wasted on vacation clothing that I only wear once — if at all? The silk dress cost $180 and spent the whole weekend in a hotel closet while I lived in the same two sundresses I always wear.
There’s a special subcategory in the handbook of women’s irrational behavior regarding the cover-up situation. I currently own seven beach cover-ups. Seven. For someone who travels to the beach approximately three times annually and spends almost the entire time either in the water or lying on a towel. However, I seem to have talked myself into believing that various forms of beach activity necessitate various cover-up approaches — something casual for walking on sand, something slightly dressier for a beachside lunch, and something “refined” for the hypothetical scenario where I need to appear well-dressed while simultaneously ready to jump in the water at a moment’s notice.
Last summer in the Hamptons, I watched my friend Jessica go through four different cover-ups in one day. Four. We were at the exact same beach club for the entire day. When I asked her about it afterwards, she simply shrugged and said, “I don’t know, they all felt right for different parts of the day?” This type of logic is perfectly logical when you’re on vacation, but has no basis in reality upon further examination.
And don’t even get me started on vacation footwear. I packed five pairs of shoes for that Miami weekend. Five pairs of shoes for a trip where I knew I would primarily be walking on sand and sitting near water. But what if we decided to go somewhere formal? What if the restaurant had a dress code I wasn’t aware of? What if my flip flops broke and I needed additional options? These are the late night thoughts that cause us to make completely irrational packing decisions.
The weather anxiety is probably my biggest vacation packing weakness. I’m originally from the Northeast, therefore I have this instinctive distrust of warm weather occurring, even in areas where it’s literally been 80 degrees every day for six months consecutively. I always pack at least one sweater “just in case.” For Miami in July. Where the nighttime temperature was 78 degrees. That sweater sat in my suitcase the entire time, but I felt slightly more secure knowing it was there.
My colleague Sarah has this thing where she packs multiple swimsuits for shorter trips based on 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 takes the same lunch to work every day for efficiency, but apparently vacation swimwear necessitates a multitude of options.
Another area where vacation logic falls apart is with regard to reading materials. I always pack at least three books for any trip longer than two days, despite knowing I’ll likely spend the majority of my time scrolling Instagram or napping. There’s something about vacation that causes us to believe we are going to transform into some sort of sophisticated individual who will read literary fiction while sipping wine and gazing contemplatively at the ocean. In reality, I’ll read approximately fifty pages in total and spend the majority of my time snapping photos of my breakfast.
What’s interesting is how this translates to attempting new styles that I would never attempt at home. That Miami trip included a bright yellow dress that I purchased solely for vacation because “Bright colours feel more tropical.” Yellow isn’t my colour. I don’t wear bright colours to work, or anywhere really. But, apparently, vacation me was going to be some type of individual who could pull off sunshine yellow. Spoiler Alert: she was not. The dress looked just as awkward in Miami as it would in Boston, however, I needed to travel 1,200 miles to realise this.
I believe there’s something about vacation that makes us believe we’re going to morph into different versions of ourselves. More adventurous, more fashionable, more willing to take risks with our fashion. The clothing we pack represents this idealized transformation — Vacation Jasmine is going to be the type of person who wears statement earrings and bold prints and appears effortless while strolling along the beach at sunset.
Reality is that vacation me wants to be comfortable — just like everyday me. I end up wearing the same two sundresses in rotation because they are both comfortable and I know they fit my body and my lifestyle. All the other carefully selected options simply accompany my comfort choices in my suitcase and weigh down my luggage and complicate my decision-making processes.
When I spoke with my friend Lisa upon her return from Greece, she told me that she had lived in three outfits throughout her entire week. “Everything else was just expensive security blankets.” I believe this may be the true nature of vacation packing — it’s not really about the clothing. It’s about potential, about trusting that we will be prepared for whichever version of ourselves shows up on vacation. Perhaps this time we will be the type of individuals who will change outfits three times daily. Perhaps this time we will go somewhere that demands that fancy dress. Perhaps this time we will become the stylish and adventurous vacation individual we always imagine we could be.
The clothing is merely props in this yearly performance that we undertake, where we momentarily believe we may be someone different in a different location. Honestly? I find this optimism to be rather charming. Even though it is an extravagant waste of resources, unpractical, and leads to excessively heavy luggage, there’s something appealing about the optimism associated with this process. We pack for the absolute best case scenario version of our trip, despite past experiences telling us that we will revert to our usual preferences.
Therefore, I will probably continue to overpack for every vacation, carrying numerous options for every conceivable circumstance, while knowing I will ultimately be wearing my preferred comfortable favorites. It’s wasteful, illogical, but also full of optimism. And occasionally — perhaps one in ten — I will surprise myself and wear something I wouldn’t normally wear. Those occurrences, although unlikely to justify the other nine instances of vacation wardrobe excess, are significant enough to keep the pattern alive.
Plus, having too many options is a good problem to have, correct? Correct? This is what I tell myself every time I’m desperately trying to zip up an overly packed suitcase at midnight prior to an early morning flight, surrounded by clothing representing all the possible vacation versions of myself — even though we all know I’ll end up in a sundress and flip-flops regardless of whatever grand fashion aspirations I may have.
The airport fashion show is its own unique brand of vacation delusion. We dress for travel as if we’re walking a catwalk rather than sitting in a cramped metal tube for hours. I have traveled in heels to the airport for vacation trips, as if looking cute on the plane was in some manner relevant. Comfort should be the only factor to consider on travel days, but vacation brain makes us think differently about everything — including what to wear to the airport.
Perhaps the most honest conversation I had regarding vacation packing was with my friend Rachel, who is a lawyer in Washington D.C. and certainly 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 handful of things repeatedly. I know most of what I pack will never leave the suitcase. But, I literally cannot force myself to pack any less. It’s like vacation insurance — I need to know I have options whether I use them or not.”
This may be the true essence of vacation packing — it’s not really about the clothes at all. It’s about opportunity, about trusting that we will be prepared for whatever version of ourselves arrives on vacation.
