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.

Courtesy of the Brands

Shoes: Cole Haan Vandam Mules, $160 at; shirt: Anine Bing, $199 at; pants: Victoria Beckham, $590 at; belt: Emme Parsons, $98 at; bag: Cole Haan, $280 at; earrings: Jennifer Fisher, $450 at

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; sweater: Nili Lotan, $795 at; skirt: Frankie Shop, $175 at; bag: Cole Haan, $328 at; socks: Comme Si, $38 at; watch: Breda, $160 at

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; coat: Massimo Dutti, $629 at; top: Dôen, $228 at; jeans: Khaite, $420 at; bag: Cole Haan, $320 at; ring: Kinn, $820 at

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; dress: Staud, $343 at; necklace: Stone and Strand, $4,100 at; bracelet: Saint Laurent, $395 at; coat: Babaton, $348 at

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