why can't i pack
the "skill" that's eluded me for decades
I was in Chicago last week for a private book event which was held in a stately room in the Union League Club, a few floors down from where I stayed. I checked in last Monday and spent the majority of the 48 hours I was in the city within this building (outside of an hour on a truly edifying riverboat architecture tour — 10/10 recommend!). I’ve rarely experienced a space so simultaneously disconcerting, fancy and weirdly charming.
The Union League is an old-timey (oldest timey — founded in 1879) private club with a required dress code mandated in every public space beyond the gym, a code with specific rules like how you must remove your “overcoat” in the lobby and how “dress denim” is not considered dressy enough. This should have been my first clue that I needed to pack for this trip with serious thought and care. Alas, I remain a drunk raccoon with a suitcase.
Around 9:45 on the night I arrived, I realized the error of my ways. After a solo dinner of bratwurst and vodka at Berghoff’s (the best), I made it back to my room and, with my light buzz, decided to try on every outfit I’d packed.
The options were shocking.
ONE PLEATHER JUMPSUIT
A WAITSTAFF-ESQUE BLACK VEST
FIVE TURTLENECKS, ZERO BRAS
THREE PAIR OF SOCKS (I WAS GONE FOR FOUR DAYS)
3 PAIR NON-DRESS (TBH, NON-TOTALLY-CLEAN) DENIM
My bag seemed like it had been packed by an enemy, not a lady who spent four hours pulling together disparate garments because she — ostensibly— wanted to dress appropriately.
All of which leads me to a larger question, which is: How are we supposed to pack? I’m 51. I travel at least a half dozen times a year. I’ve packed many times! And yet I still don’t really know how. There’s rarely been a trip where I didn’t have to pick up some essential item I forgot or didn’t even imagine I’d need (seriously try buying a bathing suit in the desert in December). Or, beyond an item, a whole dumb outfit because I got the weather wrong/didn’t realize none of what I packed matched/the event was “dressier” than I’d understood it to be.
I have an upcoming trip to the east coast — please, take pity on/lend me your packing tips! In return, I will share my only good one, which is this travel kettle so I can have tea (that doesn’t taste like burnt hotel coffee mold) anytime I want.
P.S. I loved Chicago. I spent little time there but quickly got the vibe and the vibe is immaculate, at least for me.
Packing is one of my few skills. I got you.
For trips with events: think, what do I want to look like at this event? Consider a bunch of options. Pick one. Ok, I know you, you can pick two. But they have to be the entirety of the outfit as you imagine it. Not elements that could cohere. Pick the shoes, bag, jewelry you want for that event.
Then, you gotta do the rest of your packing with a ratio - 3 neutral/flexible items (jeans, good trousers, a button down shirt, a good cardi) to 1 out-there item (for you I imagine sparkles, pleather). You gotta be able to imagine a bunch of ways you can mix the out-there stuff with the useful, reliable, makes you feel comfortable and put together stuff. You need to think about how much is formal work versus just hanging out.
Then you want a pair of boots, a flat, some sneakers, and a fun shoe if you want. I personally just like really good boots and flats. You want a scarf.
Jenn this reminds me of the time I let my 5 year old pack his own bag, which he filled with three pairs of socks and all the plastic dinosaurs he could jam in. :) Ok it sounds corny because it has a name, but, the 5-4-3-2-1 packing system is solid. Even if sometimes it goes more like 64322, or whatever it is a great way to build the base.