One tight-to-the-body turtleneck later and you’ve transformed this light-as-air seersucker dress into a chic, fall-feeling outfit. ($170, ganni.com)

Caftans: the all-in-one, WFH-to-wherever solution. Season-proof this roomy pick with a thermal tank and biker shorts once the temps dip. ($180, sidiathebrand.ca)

Big shy-’90s-movie-heroine energy over here. Give it a generously sized grandpa cardigan for some back-to-school vibes. ($120, cosstores.com)

When you think about it, slip dresses are pretty much made for the fall. No-sweat conditions means it’ll actually slip over your curves, not stick to them. ($155, parkandfifthco.com)

A pair of sheer black tights converts this picnic-y frock to a full-on ’60s-era look. ($199, elizafaulkner.com)

Equipped with a high slit and short sleeves, this body-con T-shirt dress is a transitional foil for those confusing, cool-in-the-morning-warm-by-noon days. ($165, michaelkors.ca)

Linen gets a ton of play in the summertime, but thanks to its warm oatmeal hue and maxi length, this minimalist dress leans fall-appropriate when matched with a trench. ($185, esserstudio.com)

We’ll admit it—an oversized tee dress has less practice once the true fall climate settles in. But paired with tennis socks and an oversized windbreaker, you can sneak in a few more September wears before some closet hibernation. ($63, nike.com)

Breezy wine country look on the weekend, buttoned-up (virtual) boardroom piece come Monday. It’s called versatility. ($119, frankandoak.com)

Don’t let this spot-on wedding guest dress sit idle until your next matrimonial invite. A boxy denim jacket – perfect for extending it to an early autumn patio date – helps narrow the cost-per-wear calculus. ($418, thereformation.com)