Fall may be calling, but we’re not quite ready to put down our lobster rolls — so we’re doing all we can to keep the warm-weather vibes going. Case in point: these end-of-summer looks worth revisiting when the calendar says September but the temps claim otherwise. Grab your A/Os and soak in the season until the last ferry leaves the island. (And then come back when you’re looking for winter getaway packing inspo).
We love a look that could set sail on a moment’s notice — and nothing says seaworthy like a classic stripe. The quarter sleeve on this one offers a nice transitional twist, and the denim shorts and A/Os keep things cool for these last days of boating and beaching. Tote along a little texture with a woven bag to carry your offshore essentials with room (and style) to spare.
After the season of the shoulder, we still can’t get enough — especially in a tailored silhouette like this one that nods to classic Oxford style. The asymmetric dropped shoulder and cropped short keep the look feeling fresh and of-the-moment, while the grey A/O Vida puts the prep back in. Pair it with a classic red lip and shades to keep those end-of-summer rays at bay.
A look like this proves that downtime comfort can be seriously chic. Emily plays it cool and crisp by balancing her tee with a warm-weather-ready white pant. (Though we’ve added length for the seasonal transition, you’ll find us solidly in the white-all-year camp.) The blush A/O keeps things rosy, while the woven hat caps off the carefree vibes.
Found: a fall-ready, four-season neutral that’s universally flattering without the weight of black. Lisa works in the moment’s “it” color with a tapered drawstring pant that’s ready for anything — jet-setting, or an afternoon on the jetty. A streamlined white cami on top keeps color in check, and the neutral boat shoe adds an unexpected twist. End-of-summer adventures are calling.
Shorter days and cooler nights are just on the horizon—and denim feels so right. This pair is torn to (im)perfection, edging up the dressiness of the dark wash. A Breton-style stripe is always a good idea, as are the brown A/Os, which add a bit of dimension and a chic school-day vibe to the look. Try this look for those in-between weather days — whether you’re seafaring or sea-gazing.
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A/O stands for Authentic Original. Explore The Sperry Boat Shoe Buying Guide, and find yours.