Side Order: Back To School

But for grown ups

It’s that time of year where, despite the forecast telling me it will be 80-plus degrees through Thanksgiving, I become laser-focused on living an autumnal life. I might be less pumpkin spice and more Love Story, but there’s no fooling anyone: I am basic, and this is my time to shine.

It’s been over a decade since the phrase “back to school” has meant anything to my schedule, yet I still find myself ordering fresh pens (Le Pens, of course) and re-upping my trouser sock stash. After listening to American Ivy, a podcast about the history and evolution of Ivy League-inspired style by Avery Trufelman that I can’t shut up about, I am convinced that I’ve always been a prep at heart and it’s time I lean all the way in.

I know you’re in the mood for a little Ralph Lauren-adjacent styling too; when I asked the folks of Instagram for loafer recommendations the other day my DMs were flooded with enthusiasm around patent leather and chunky soles and other not-safe-for-summer shoe details (I’ve included the most-recommended loafer down below, by the way.) So, this month’s Side Order is a preppy little assortment of clothing, accessories, and desky things that are hitting the spot for me right now. Per usual, I’ve searched all corners of the internet for high, low, new, and vintage items, so enjoy your curated stroll through my findings.