How to Spend a Saturday in the City

In partnership with our friends at Stuart Weitzman

There are few feelings that top waking up after a particularly hectic workweek and realizing that you have…absolutely nothing to do. When this happens, here’s how to make the most of it: Get dressed for a go-with-the-flow day—soft separates, practical layers, and the kind of curb-hopping, cab-hailing boots (hiii, Stuart Weitzman) that can keep up with you. Then get yourself to the city (any city will do) and spend a few hours rediscovering all the reasons you fell in love with this place to begin with.

MARIA MCMANUS TRENCH COAT (worn throughout), goop $850; STUART WEITZMAN BOOTIES, Stuart Weitzman $625

The best thing about big cities this time of year—that is, aside from the spectacularly decorated worth-the-wait window displays—is the weather. Sublime in the sun, shivery in the shade, it calls for strategic styling (ABL: always be layering), modern interpretations of the classics (an evergreen suit is a power move, while an oversize cable knit is peak cozy), and hyper-walkable boots that will take you uptown, downtown—all over town.

TOTEME SWEATER, goop $800; STUART WEITZMAN BOOTIES, Stuart
Weitzman $625

GANNI COAT, goop $475; G. LABEL YANG HIGH-CUFF TURTLENECK SWEATER, goop $595; STUART WEITZMAN BOOTIES, Stuart Weitzman, $695

FROM TOP: G. LABEL MAXINE RIBBED CARDIGAN, goop $595; STUART WEITZMAN LOAFERS, Stuart Weitzman, $450

Catching a matinee? Meeting a friend for lunch? Whatever the plan, you can’t go wrong with a timeless silhouette in a luxe, unexpected material, like a slip dress knit from ultrafine merino wool. Or pleated trousers with punk-rock DNA. Or, say, platform boots or perennially-in-style penny loafers—choose your fighter—crafted from water-repellent and lacquered nappa leather, respectively.

ANOTHER TOMORROW COAT, Another Tomorrow, $1,600; G. LABEL VILAN TANK SWEATERDRESS, goop $625; STUART WEITZMAN BOOTS, Stuart Weitzman, $795

Browsing quaint bookstores, trying new coffee shops, meandering through charming cobblestone streets: Exploring a not-yet-discovered-by-you neighborhood is most enjoyable in comfortable pieces that can hang all day. The hype beasts have their sneakers; we prefer lightweight lug-sole boots that make easy work of 10,000 steps.