so i’ve alluded to my trouble with packing for trips before, right? about how i’m a person who likes to have options despite knowing full well that taking five pairs of pants and sixteen pairs of undergarments is not necessary for a four-day trip (two days of which will be spent on air travel). and that in needing said abundance of options, that i’m a person who also tends to have to resort to sitting on her suitcase to ensure that all contents fit because heaven forbid she have to check her baggage (stubborn, party of one).

but what can i say, i hate feeling ill-prepared. i want to know that come what may (insert moulin rouge song here) over the course of my trip, i will be more than adequately prepared. even if said preparedness only refers to my ability to whip out a hooded jacket at a moments notice when, tut, tut, it looks like rain.

well, get out your carry-ons, folks (or maybe i’ll just get out mine because), i’m going to chi-town this friday (this friday!) for a little labor(less) day vacay. and while i really couldn’t be more excited about the fact that i will get to see one of my most cherished mid-western married maidens, i am a bit concerned about the weather.

more importantly, how the weather will bode for my fashion during my stay. you see, saturday will mark the first of september (what?! that’s right september, people, have you started your christmas shopping yet? because you might as well at the rate this year is headed) meaning that the weather should all but spontaneously morph into the perfectly crisp 65ish degrees making the whole boots/skinny jeans/scarf combo completely and utterly necessary. and this goes for the entire contiguous united states and parts of canada, too. like daylight saving time, it should just happen once the clock strikes midnight on august 31st (even though daylight saving time happens at two a.m. and also not in arizona).

because fall trips are supposed to breed opportunity for fall fashion. and i know what you’re thinking. labor day isn’t technically fall, if anything, it’s the last real hoorah of summer, so i should really just step off my soap box right now and go put on a bathing suit already. i mean, i should put on a bathing suit for other reasons, like, i don’t know, to get some color on this pasty bod, but that’s a whole different issue for a whole different blog post. where was i? right, that whole hey, it’s september and football is on, so let’s all drink pumpkin-flavored things and cuddle up in our muted-color corduroys and newsboy caps. i dunno, something about traveling to the windy city at this time of year just makes me think that i should be awkwardly removing my steve madden boots while venturing through the security line (because everyone knows that if you’re going to wear boots on your trip, you wear them on the plane with you because that just opens so much space in your suitcase).

but instead, i’ll probably be slipping off some rainbow sandals (or let’s be honest, those fancy bling ones i’ve been wearing non-stop since they arrived on my doorstep in early june) because last check on the weather for chicago (and the surrounding areas which is, in reality, where i’ll be) read a balmy eighty-six degrees. i mean, i can make a scarf work in mid-70’s weather, but anything above 80? even i can’t justify that. so this packing venture is going to need a bit more attention than previously thought. because when you’re dead set on throwing a half-dozen sweaters and skinny jeans into your carry-on and calling it a day, you have to switch gears for two point five and weigh your options more closely.

and if you want to know what “weighing your options more closely” looks like for me, i’ll tell you. it looks like having half of your closet strewn across the foot of your bed with every pair of shorts and bubble necklace you own stacked neatly in a pile, awaiting your ensembling expertise. at least that’s what it looks in my eyes, to everyone else, it probably looks like a bomb went off in my bedroom and i have simply been too lazy to clean it all up.

anyway, i’m still not quite sure what to pack for my weekend away. i keep acting as if the weather is going to just appease me and drop like twenty degrees, but that’s like trying to make fetch happen (it’s never going to happen, and yes i will use this example until the day i die, it also doesn’t help that my friend just watched mean girls last night and proceeded to text me periodically throughout the evening with quotes from it). but then again, there’s that whole global warming thing that can make it snow in malibu, so in the words of bieber himself, never say never.

i’m sure whatever the four (plus) outfits that i elect to join me on my journey to middle-america will be perfect and once that suitcase is zipped up and i’m ready to give charles lindbergh a big “what’s up? it’s been a while, hasn’t it?” come friday morning, i will have all but forgotten about all of this sartorial stress i am currently harboring.

but until then, i will say that for all of the wanderlust i have and for all of the trips i have planned from here until the beginning of october, i’m going to need to get this aparrel-packing anxiety in check. if anything for the fact that it’s fact becoming harder and harder to find a pathway from my doorway to my bed.

so see you soonsies, windy city. i’ll be the one inappropriately dressed for your weather. just looking for the gal with knee-cap sweat as she has insisted on wearing skinny jeans in 100% humidity.

if only my suitcase was this organized.