Our days of going back to school may be long gone, but that desperate desire for a new fall wardrobe never leaves us. And nothing speaks of fall like plaid, tartan, and checks. Join the Ivy League with a satchel that exudes the feel of those crisp days. Think prep school-inspired, but not your typical preppy, and mix them up with nubby knits, rich wools, and juxtaposing prints.
1. Vivienne Westwood Coated Canvas Derby Top Handle: It doesn’t get more classically British than plaid Westwood. This bowler gets an enticing upgrade in an unlikely sunset-inspired palette.
On Luisa via Roma for $637.
2. Marni Plaid Wool and Leather Hobo Bag: We usually think of plaid as hard, pleated, or structured, but I’ll take mine with a little bit of slouch for a modern spin.
On Net-a-Porter for $950.
3. Jas M.B. Large Bomber Checked Cotton Backpack: Channel your inner Catholic schoolgirl (not in that naughty way!) with this ultra-preppy backpack. Rough it up with moto boots or a leather mini.
On Luisa via Roma for $425.
4. Christian Louboutin Sweet Charity Plaid Shoulder Bag: Sometimes the Sweet Charity works better than others, and tartan plaid suits the style so well. Especially amped up with bright gold detailing.
At Saks Fifth Avenue for $1,395.
5. Fendi Daisy Clutch: Plaid gets the royal treatment, as the Daisy gets a chic upgrade. Somehow, this mix of studs, mink, snakeskin, and patent leather works together in perfect plaid harmony.
On My Theresa for $1,551.