Popsugar Fashion Fashion Trends Stylish and Comfortable Heels to Wear to Work The Most Comfortable Work Heels For Fall 23 October 2019 by Avery Matera Image Source: Getty / Edward Berthelot As POPSUGAR editors, we independently select and write about stuff we love and think you'll like too. If you buy a product we have recommended, we may receive affiliate commission, which in turn supports our work. You work hard enough. Give your feet a break. While many consider heels a nonnegotiable for the workplace, there are many chic ways to make that style choice a reality without killing all 10 of your toes — and your back at the same time. Sure, we love a sky-high stiletto moment, but if you're on your feet all day, running back and forth from your desk to meetings and maybe even outside for an appointment or two, they're not your friendliest choice when it comes to office footwear. If you're into a high heel, consider options with a bit more gravitas, like a chunky style or a more closed loafer silhouette. And, what's more, skinny heel lovers might want to choose something with fewer inches on them, like a kitten or ankle bootie. Ahead, find five huge Fall shoe trends that also happen to be among the most comfortable work heels of the season. 1 Heeled Loafers Image Source: Getty Images Go preppy with a pair of loafers — with a heel — this Fall. The closed-foot shape works wonders keeping your feet in place, allowing for a more comfortable way to wear everything from kitten heels to sky-high stilettos without fuss. 2 Prada Image Source: matchesfashion.com Prada Block-Heel Logo-Jacquard Loafers ($900). Prada Block-Heel Logo-Jacquard Loafers $900 from matchesfashion.com Buy Now 3 Leqarant Image Source: farfetch.com Leqarant Block Heel Loafer Pumps ($230). Leqarant Block Heel Loafer Pumps $230 from farfetch.com Buy Now 4 Anthropologie Image Source: anthropologie.com Anthropologie Harlow Loafers ($130). Anthropologie Harlow Loafers $130 from anthropologie.com Buy Now 5 Gucci Image Source: matchesfashion.com Gucci Marmont Fringed Suede Loafers ($807). Gucci Marmont Fringed Suede Loafers $807 from matchesfashion.com Buy Now 6 Short Block Heels Image Source: Getty Images Whether you love a pump, slingback, or mule, shorter heels will nearly always equate to a more comfortable wear. Channel your grandmother's chic-as-anything workwear wardrobe when you slip into a pair of retro-looking short block heels this season. 7 Loeffler Randall Image Source: loefflerrandall.com Loeffler Randall Emi ($325). Loeffler Randall Emi $325 from loefflerrandall.com Buy Now 8 Chanel Image Source: chanel.com Chanel Slingbacks ($875). Chanel Slingbacks $875 from chanel.com Buy Now 9 Margaux Image Source: margauxny.com Margaux The Heel ($245). Margaux The Heel $245 from margauxny.com Buy Now 10 Raid Image Source: asos.com Raid Rumie Heeled Shoes ($48). Raid Rumie Heeled Shoes $48 from asos.com Buy Now 11 Heeled Mules Image Source: Getty Images If you're seeking a little more coverage on your foot (i.e. a way to steady yourself for running in heels) without going for a fully closed loafer style, consider the well-popularized mule style. It has a retro feel, but will easily take you from day-to-night — and keep those toes happy as well! 12 J.Crew Image Source: jcrew.com J.Crew Sophia Kitten Heels ($148). J.Crew Sophia Kitten Heels $148 from jcrew.com Buy Now 13 Club Monaco Image Source: clubmonaco.com Club Monaco Saydee Suede Pump ($298). Club Monaco Saydee Suede Pump $298 from clubmonaco.com Buy Now 14 Cole Haan Image Source: shop.nordstrom.com Cole Haan Ophelia Mule ($150). Cole Haan Ophelia Mule $150 from shop.nordstrom.com Buy Now 15 Mansur Gavriel Image Source: shopbop.com Mansur Gavriel 40mm Mules ($395). Mansur Gavriel 40mm Mules $395 from shopbop.com Buy Now 16 Heeled Ankle Booties Image Source: Getty Images There's no arguing that a classic ankle bootie is a wardrobe must-have for Fall, but consider kicking it up a notch this Fall by opting for a style of the heeled variety. With some slight elevation, it will quickly become your comfortable go-to for the office and beyond, all season long. 17 Tibi Image Source: shopbop.com Tibi Theo Booties ($750). Tibi Theo Booties $750 from shopbop.com Buy Now 18 & Other Stories Image Source: stories.com & Other Stories Leather Pointed Ankle Boots ($179). & Other Stories Leather Pointed Ankle Boots $179 from stories.com Buy Now 19 Madewell Image Source: madewell.com Madewell The Kelci Heeled Boot ($198). Madewell The Kelci Heeled Boot $198 from madewell.com Buy Now 20 Mango Image Source: shop.mango.com Mango Heel Leather Ankle Boot ($80). Mango Heel Leather Ankle Boot $80 from shop.mango.com Buy Now 21 Kitten Heels Image Source: Getty Images For a Grace Kelly-inspired look this coming Fall, seek a practical yet completely elegant kitten heel style. In pumps, slingbacks, and even sandals, it's the workwear shoe you need for those long days where you're going nonstop through the morning, noon, and night. 22 Dior Image Source: dior.com Dior J'Adior Slingback Pump ($890). Dior J'Adior Slingback Pump $890 from dior.com Buy Now 23 Charles by Charles David Image Source: shop.nordstrom.com Charles by Charles David Addie Pump ($100). Charles by Charles David Addie Pump $100 from shop.nordstrom.com Buy Now 24 Manolo Blahnik Image Source: neimanmarcus.com Manolo Blahnik Carolyne Kitten-Heel Flannel Pump ($745). Manolo Blahnik Carolyne Kitten-Heel Flannel Pump $745 from neimanmarcus.com Buy Now 25 Giuliva Heritage Collection + Le Monde Beryl Image Source: Net-a-Porter.com Giuliva Heritage Collection + Le Monde Beryl Venetian Pinstriped Wool Mules ($550). Giuliva Heritage Collection + Le Monde Beryl Venetian Pinstriped Wool Mules $550 from net-a-porter.com Buy Now ShoppingFashion TrendsFallFall FashionShoesHeels