The Back-to-the-City Edit

After a languorous summer, closing up the cottage, lake house, or beach bungalow for the off-season surfaces more than just mental “Could I make one more month work?” negotiations. It’s a seasonal shift that sharpens our focus back toward the daily business of building a life, day by day, goal by goal, and—because you can’t show up to the board room in board shorts—outfit by outfit. Whether you’re returning to the city, another country, or simply a more focused mindset, these outfits will ease you back in style.

For Your Last Weekend Out East

Whether you’re lighting up the social scene or laying low, a GWYN-centric uniform of East Coast classics softens the transition from bucolic bliss to business as usual. Pair a maxi done in painterly plaid stripes—the star of our September drop—with an easy tank, then slip on rubber clogs that are anything but garden-variety and tuck your farewell gifts into a leather tote greener than the late summer grass and make the rounds.

For Your First Weekend in the City

The buzz of Manhattan makes the busy season in Montauk feel like a sound bath, but someone needs to get the dog groomed and pick up the Happier Grocery order. Get acclimated in a hunter-green set with plenty of pockets for stashing receipts, the low-profile suede sneaker of the season, sunnies for dodging anyone you’re not ready to see yet, and a warm-white leather carryall with a waterproof interior (genius).  

For Getting Back to Business

This chic matching set takes notes from the streamlined workwear of the ’90s, but it’s your personal styling that drives the overall mood. With a creamy white pump, aviators, and the watch your direct reports are crushing goals for, the look reads cool boss—but add a blazer and you’re board-room-ready.

For the Best Dinner You’ve Had in Months

Come Friday, it’s time for the kind of tasting menu you dress up for. Done in fine virgin wool, this long-sleeve midi makes an ideal canvas for showing off a fall trend or two: Ink-black pumps with a V-shaped vamp, a geometric clutch, and a necklace that doubles as a personal talisman. 

For the Big Board Meeting

Your outfit in review: A single silk-tie blouse delivered twice the anticipated styling options. The split-hem skirt earned more compliments than you heard in all of H1. Your investment in sharp, diamond-studded hoops is paying dividends, and as far as your pump portfolio is concerned, we suggest you hold and consider investing in an additional colorway.

For Parental Guidance

Orientation, back-to-school celebrations, sports games, and all those fancy birthday parties call for their own kind of dress code. Ours tends to loosely follow this formula: cool cardigan + fluid trousers + bold, whimsical accessories.