4 Outfit-Making Dress Shoes to Wear All Fall and Winter Long

Blazers and sweaters get all the glory when planning your fall wardrobe. Then, once the holidays are in full swing, coats and party dresses steal the spotlight. But when it comes down to elevating any autumn look, it’s all about the shoes.

Whether you’re styling looks for the office once again or starting the winter party circuit early, sleek mules, smart loafers, killer boots, and festive platforms are cool-season cornerstones. In luxurious textures like supple leather and with gleaming finishes, each pair turns any ensemble—from down-home denim to glammed-up attire—into something special.

To sweeten the deal, some of the styles we’ve chosen are enhanced with Cole Haan’s 3D Lux Comfort design, featuring three layers of foam that deliver shock absorption, arch support, and exceptional cushioning. This makes every step softer, reducing fatigue and impact. Keep scrolling to discover four outfits whose luxurious, wearable dress shoes aren’t an afterthought, but a focal point.

Shine Bright

There’s no rule against brights in autumn wardrobes. Reinvigorate workwear with vivid color splashes, like these electric green trousers. A roomy white button-down makes the look feel even more contemporary; half-tuck it in for a not-overly-structured effect. Then, tie it all together with clean, modern accessories, including a pointed-toe kitten heel that visually elongates your legs.

fall outfits

Courtesy of the Brands

Shoes: Cole Haan Vandam Mules, $160 at colehaan.com; shirt: Anine Bing, $199 at saksfifthavenue.com; pants: Victoria Beckham, $590 at net-a-porter.com; belt: Emme Parsons, $98 at emmeparsons.com; bag: Cole Haan, $280 at colehaan.com; earrings: Jennifer Fisher, $450 at jenniferfisherjewelry.com.

Step to Prep

Lean into the preppy girl aesthetic seen on this season’s runways with a pleated miniskirt and cardigan anchored by three-tone loafers, with or without the bobby socks. A minimal carryall and gold-tone watch are smart finishes that will effortlessly carry you from the workweek to the weekend.

fall outfits

Courtesy of the Brands

Shoes: Cole Haan Geneva Loafers, $160 at colehaan.com; sweater: Nili Lotan, $795 at saksfifthavenue.com; skirt: Frankie Shop, $175 at net-a-porter.com; bag: Cole Haan, $328 at colehaan.com; socks: Comme Si, $38 at commesi.com; watch: Breda, $160 at breda.com.

Leather Weather

The ultimate approach to fall’s leather trend? A luxe trench complemented by tonal croc-embossed boots. Dark-wash jeans and a romantic blouse steer the look into a relaxed direction that feels suitable for work, drinks, or date night.

fall oufits

Courtesy of the Brands

Shoes: Cole Haan Grand Ambition York Booties, $250 at colehaan.com; coat: Massimo Dutti, $629 at massimoduti.com; top: Dôen, $228 at shopdoen.com; jeans: Khaite, $420 at net-a-porter.com; bag: Cole Haan, $320 at colehaan.com; ring: Kinn, $820 at kinnstudio.com.

Be the Drama

This look combines period drama-level romance with a nouveau Gilded Age aesthetic—two major fall/winter 2022 runway trends. It’s a surefire way to stand out at holiday parties this season. Golden platforms punctuate the look to nostalgic perfection. Enhance it further with a bedazzled bracelet and scintillating tennis necklace (we’re all for mixing metals).

cole haan fall outfits

Courtesy of the brands

Shoes: Cole Haan Grove Platform Sandals, $180 at colehaan.com; dress: Staud, $343 at mytheresa.com; necklace: Stone and Strand, $4,100 at stoneandstrand.com; bracelet: Saint Laurent, $395 at net-a-porter.com; coat: Babaton, $348 at aritzia.com.

Laura Lajiness Kaupke is a freelance writer and editor covering fashion, accessories, and lifestyle topics, including beauty, home, fitness, and travel. You can see her work across various outlets, including VOGUE, Harper’s BAZAAR, ELLE, Marie Claire, InStyle, Glamour, Esquire, Women’s Health, Brides, The Zoe Report, Popsugar, Refinery 29, Coveteur, Byrdie, Well+Good, The Editorialist, among other titles and brands. Laura has worked in the fashion industry for over 11 years and held senior fashion editor positions at Popsugar and The Zoe Report, with additional experience as a copywriter and fashion publicist.