Enzo Angiolini Boots Exposed zippers give flat leather boots some edge. To buy: $99, piperlime.com.
3 of 6Jason Brownrigg
A Herringbone Blazer
Tucker for Target Jacket Menswear herringbone looks feminine when it comes in a surprising color and takes the form of a hooded acrylic-and-wool wrap style. To buy:Unfortunately, this item is no longer available.
Victor by Victor Alfaro Sweater A cowl neck, like this one in a viscose blend, makes a cozy sweater seem more sophisticated. To buy: $58, 800-233-7626.
Miraclebody Jeans Skinny jeans that make you look skinnier? Yup. Thank the secret built-in control panels. To buy: $68, 877-836-4610.
4 of 6Jason Brownrigg
Chic Skinny Jeans
Kenneth Jay Lane Earrings Oversize gold-plated hoops perfectly round out your look. To buy: $45, 877-953-5264.
Sequin Bracelet Gold-plated brass links lend instant polish to an everyday outfit. To buy: $58, 212-398-7363.
Old Navy Jacket A cotton utility jacket in army green looks even better the more it gets beaten up. To buy: $39.50, 800-653-6289 for stores.
Petit Bateau Shirt A navy-and-gold striped tee gives off a collegiate, let’s-hang-out-in-the-quad vibe. To buy: $83, 212-988-8884.
The Limited Jeans Slim denim is slightly dressier in black. To buy: $69.50, thelimited.com.
L.L. Bean Flats Navy shoes in patent leather and suede are less expected than black but also good at hiding wear and tear. To buy: $69, llbean.com.
5 of 6Jason Brownrigg
A Patterned Scarf
H&M Scarf This earth-tone cotton wrap plays up all of fall’s rich colors. To buy: $25, hm.com for stores.
Velvet by Graham and Spencer Top No basic tee, this smooth cotton pick has a draped neckline and tab sleeves. To buy: $75, 888-862-4121.
Calvin Klein Jeans Belted Khakis The pleated, ankle-cropped cut makes these chinos more modern than most. To buy: $59.50, macys.com.
Freebird Bag Leave hands free for leisurely autumn strolls with a cross-body leather bag. To buy: $79, 866-290-1350.
R.J. Graziano Bangles These gold-plated bracelets are intertwined, so you’ll never lose one. To buy: $35 for nine, 212-685-1248.
6 of 6Jason Brownrigg
A Floral Dress
Loft Necklace This strand of brass links has a timeworn quality. To buy: $39.50, loftonline.com.
Gap Cardigan Whisper-thin, lightweight cotton makes for bulk-free layering. To buy: From $20, gap.com.
H&M Dress For the person who lives in dresses, even on lazy days: this floral pick in no-fuss cotton. To buy: $30, hm.com for stores.
Ariat Belt This leather belt has a unique buckle and rip-resistant reinforced holes. To buy: $35, 800-899-8141.
Donna Karan Tights Heather brown hosiery provides the textured look of a nubby knit without the heft. To buy: $30, 800-777-0000.
Unisa Boots Running around all day? Pull on this faux-suede–and-leather pair with extra-cushiony rubber soles. To buy:Unfortunately, these boots are sold out in brown, but you can find them in black in limited sizes here:amazon.com.