October is harsh in that in takes the clothes you worshipped a mere month ago — airy silk dresses, linen blouses, twill shorts — and turns them into raggedy monsters that have no place loitering among the dreams of your future closet, a closet of soft sweaters and pants that fit well and shiny-ass loafers that will not make you bleed because you are responsible and bought socks for the break-in process. But it takes a minute to ease into a new month, especially when it’s at the top of a new season. And it is never right to shop for fall before you’re actually in it.
I know this to be true because I have done it and regretted it. Every time. So to inaugurate the Most Awkward Dressing Month of the Year, here’s your guide of what to buy and when to buy it. As always, though, these are mere suggestions and I encourage you to reject the F out of them if you feel like they don’t fit with the story you’re writing about who you’ll be this season. After all, you’re a grown-ass woman. But on that note, everyone of us could probably benefit from a pair of stirrup leggings.

Can you practically feel your feet inside the loafers already? The kitten heels actually belonged to Belle from Beauty and the Beast. Believe it.
They’re going to look so cool with your leggings and oversize shirt! Which you’ll be wearing a full month before Thanksgiving! How cool.
As for the accouterments?
Frigging maraschino cherries atop your hamburger.
Guide designed by Emily Zirimis.

