A fall brunch outfit, an apple picking outfit, and a winery outfit each want a different shoe, and most good weekends ask for all three. Pinterest searches for “fall brunch outfit” are up 1,000% this season, “apple picking outfit” is up 700%, and “fall winery outfits” are up 500%. Here is how to dress for each, starting with what’s on your feet.
What to Wear to a Fall Brunch
Brunch is a sit-down meal with a walk on either side and, often, a wait for a table. Wear a flat you’d happily stand in line in. The Tilda Loafer in Dark Chocolate is the brunch shoe: soft enough for the walk to the café, polished enough for the table. Wear it with straight jeans, a striped shirt under a navy crewneck, and a trench. Searches for “brown loafers outfit” are up 70%, and a suede loafer shows why: it makes denim look considered.
Wearing a dress instead? Swap to a ballet flat. The Meredith Ballet Flat in Mahogany warms up a gray knit midi and a cropped jacket without adding fuss.
What Do You Wear Apple Picking?
Orchards mean uneven ground, wet grass, and more walking than anyone plans for. Wear a flat boot with some height to it. The Ramona Riding Boot in Dark Chocolate sits on a 0.75-inch stacked heel with a 15-inch shaft and a tapered toe, so it handles a muddy row and still looks right at the farm stand after. Tuck in slim jeans, add a cable knit, and finish with a barn jacket. Pinterest searches for “barn jacket outfit women” are up more than 1,000%, and “riding boots outfit” is up 80%. The equestrian mood is everywhere this year, and an orchard is its natural setting.
Choose leather over suede for this one. Smooth leather shrugs off damp grass; suede would rather stay home.
Smooth leather shrugs off damp grass; suede would rather stay home.
What to Wear to a Winery in the Fall
A tasting sits somewhere between brunch and dinner: outdoors in the afternoon, often on gravel or a lawn, then inside by the fire as the light goes. Skip the stiletto. Gravel is unkind to it, and so is a sloping vineyard. A low heel and a softer boot make more sense. The Etta Slouch Bootie in Dark Chocolate sits on a 2-inch kitten heel and pairs with a knit midi dress and a suede jacket, while the scrunched mid-calf shaft keeps the look relaxed. Searches for “slouchy boots outfit” are up 100% and “dress and boots outfit” is up 70%, so you’re in good company on the terrace.
Four Fall Weekend Outfit Formulas
Screenshot these before you pack the car.
• Brunch: straight jeans, striped shirt, navy crewneck, brown suede loafers.
• Apple picking: slim jeans tucked into flat riding boots, cable knit, barn jacket.
• Winery: knit midi dress, suede jacket, slouchy low-heel boots.
• All three: wide-leg trousers, fisherman sweater, ballet flats, and a trench in the back seat.
How Many Shoes Should You Pack for a Fall Weekend?
Two pairs. A flat and a boot cover nearly every plan on a fall weekend, from Saturday brunch to a Sunday orchard. Wear the boot in the car, pack the flat, and let one neutral coat carry all three outfits. Keep the colors in the same family, brown, olive, cream, and navy, and every piece goes with every other. If the weekend means a drive north, read A Fall Foliage Weekend in New England, and the Boots to Wear for the route.
Every pair in this story is handcrafted in a family-owned factory in Brazil, from leather made to soften with wear and outlast the season. Shop Shades of Brown for the full weekend palette, then find your next read in The Journal.
