For the first time in many years, heels aren't trending (thank goodness)! Everyone's swapping pumps and stilettos for this comfy boot style that pairs perfectly with dresses. Chelsea boots are the trendiest shoes this season, and these 19 picks deliver on every front. Plush, stylish and affordable, these chic boots are the easiest 'yes' for comfort connoisseurs and fashionistas alike. On our list below, find secretly affordable picks and options from big name brands like Dr. Marten's, Steve Madden, Toms and more. And while the boots stun with dresses, they're equally chic with jeans, skirts and anything else in your wardrobe. Trust Us, you'll wear them with everything. 19 Comfy Chelsea Boots to Wear With Dresses - From $13 1. Simple Stunner: You'll wear these suede booties with everything from dresses to jeans. Plus, the low heel gives them a sleek, modern flair. 2. Total Classic: A chunky outsole, low profile and elastic side panels make these suede kicks a fail-proof pick. 3. New Heights: Combine multiple looks with these block-heel Chelsea boots that never go out of style. Over 7,300 shoppers gave them five stars! 4. Expensive Appeal: People will think you splurged on Dr. Marten's with this comfy boot style. We especially like the intricate stitching that seals the deal. 5. Beige Beauty: In case you missed it, winter beige is the hottest thing lately. Nail the look with these creamy pull-on boots. 6. Box-Checker Alert: Not only are these ankle booties waterproof, but they have a wintery-approved fur lining and a playful cheetah print option. I Ditched My Jeans for This Fall Trend That's Comfier and Much Classier 7. Dr. Scholl's: Save up to 50% on these timeless leather-style boots that are enhanced with supportive insoles, algae-infused foam and even anti-odor technology. 8. Like Uggs: These $16 mini boots feature a 1.57-inch platform, chestnut shade and white fur lining that scream 'Ugg' - without the hefty price tag. 9. Go Bold: Turn heads while wearing this edgy option that makes a major fashion statement. The mid-calf height and chunky block heel are just a few other highlights. 10. Luxe for Less: These lug sole boots have a polished, refined aesthetic that makes even casual outfits look high-end. 11. Hunter Boots: The best gift just entered the chat! Whether you're shopping for yourself or a loved one, these waterproof booties are sure to impress. 12. Slight Wedge: On the short end? These modish leather shoes have a two-inch wedge to boost your height and confidence. 13. Comfy Cozy: These pull-on boots feel like slippers, thanks to the warm fur lining and dreamy memory foam insole. 14. The Biggest Trendsetter: We can't believe these crocodile-embossed Chelsea boots are just $13, but we're taking advantage of it! 15. Wear-Everywhere Boots: These luxurious low-heel boots dress up nicely for holiday parties and down for errands, so you'll never take them off. 16. Aspen Chalet: Steve Madden nailed it with these fur-embellished suede booties. They channel pure Aspen millionaire vibes for just $43. 17. Secretly Flattering: Wear these heeled Chelsea boots with a maxi skirt for a lean-looking silhouette and model-long legs. 18. Effortlessly Elevated: We're obsessed with these camouflage-style Toms that style well with dresses, denim and everything in between. 19. Splurge-Worthy Find: These fleece-lined ankle boots are the definition of quality, so don't be afraid to splurge a little for your new favorite pair. Martha Stewart Calls These Slip-On Sneakers 'Essential' for Busy Days - On Sale Us Weekly has affiliate partnerships. We receive compensation when you click on a link and make a purchase. Learn more!