10 Best Fall Shoes and Boots Starting at $28

Fall carnivals, pumpkin patches, and farmer’s market trips galore. It’s safe to say that our excitement over the beginning of fall has officially hit its peak. Outside of daydreaming about apple cider donuts and colorful fall foliage, we’ve been happily anticipating the return of fall fashion, too. With cooler temperatures quickly approaching, now is the right time to fill any gaps you might have in your fall shoe rotation, lest you get caught in a sleet storm sans proper footwear. 

Lucky for you, we shop online for a living and, naturally, have already collected a bevy of on-trend fall shoes to obsess over. Ahead, dive into 10 of the best fashion-forward picks, including neutral-toned walking sneakers, waterproof boots, timeless loafers, and comfy ballet flats. The brands on this list are ones you likely already know and love, like Madewell, Ugg, and New Balance. With prices starting at just $28, you’re sure to find a pair to suit whatever events line your fall itinerary. 

Free People Liv Loafer 

If you’re in need of more fall-appropriate work shoes, look no further than these gorgeous Liv loafers from Free People. The thick rubber outsoles and slight block heel give it a platform appearance without adding tons of height, while the coin-filled slot nods to the aesthetic of vintage men’s penny loafers. With some of the four color options discounted down to just $45, these gorgeous loafers make a perfect addition to your fall business wardrobe. 

Sorel Joan Now Chelsea Boot

We’re obsessed with the perfectly-chunky bottoms of these Sorel Chelsea boots. Currently on sale for just $57, these boots marry style and function thanks to their stretchy elastic side panels, ankle pull tabs, and waterproof uppers. The interior hosts a removable cushioned EVA footbed, while the molded Evertread rubber outsole provides traction on slippery surfaces, making them a great option for winter evenings out.

Madewell The Greta Ballet Flat

The “balletcore” trend is still going strong. If you’re wanting to jump in on it, we love these Greta ballet flats from Madewell. Available in 14 colors, they have a rounded square toe that mimics pointe shoes. The elastic Mary Jane strap secures the foot, and a cushioned insole is made with the brand’s patented Cloudlift Lite padding. Plenty of five-star reviewers report they’re super comfortable and, thanks to their classic silhouette, these pair well with just about everything in their wardrobe.

Dream Pairs Knee-High Stretchy Boots

These chic, tall boots from Dream Pairs are budget-friendly and stylish. Available in seven different colorways, the boots hit right below the knee and come with a chunky mid heel, round toe box, and rubber outsole for added stability. The shafts feature a full zippered closure and have elastic backs that stretch up to 17 inches at the highest point, a width that one reviewer said made them work for their wide, plus-size calves.

Junayuan Slingback Heels 

For comfort, we’re eyeing these pointed-toe slingback heels, which are $50 on Amazon. Available in seven beautiful neutral shades, they come with a chunky block heel and adjustable ankle strap that provides plenty of stability for long periods of wear. One five-star reviewer attested to that, saying these “fit like a dream” and “provide great support.”

Steve Madden Brixton Motorcycle Boot 

These viral harness moto boots from Frye are currently taking the internet by storm, and while we admit that they’re gorgeous, the price point does give us pause. These Steve Madden motorcycle boots deliver a similar grunge-y vibe to the luxury item for nearly $400 less. Crafted with distressed leather and brass hardware details, these come with a slight block heel and roomy square toe box. Five-star reviewers say they’re perfectly comfortable to walk in, too, with one reviewer sharing that they were a great fit for their wide feet. 

Ugg Classic Mini II 

Ugg remains one of our go-to footwear brands for cooler weather. While it’s hard to pick a definitive favorite from their collection of cozy boots, slippers, and slides, these Classic Mini boots are certainly a top contender for us. They deliver all of the best features of Ugg boots with a plush sheepskin lining, durable outsole, and water-resistant suede exterior. Available in eight different colors, these boots have garnered over 5,600 five-star reviews on Zappos alone for their comfort, convenience, and quality. 

Madewell ​​The Ingrid Chelsea Boot 

This Chelsea boot from Madewell delivers a hint of vintage-Western flair.

It features 100 percent leather uppers and a recycled rubber sole. These boots pair beautifully with classic denim jeans, flowy skirts, and bodycon dresses alike. The chunky mid heel adds just enough height to add style without sacrificing comfort. 

New Balance Women’s 237v1 Sneaker

Upgrade your sneaker game with these ultra-comfy New Balance sneakers. Currently available in a wide array of fall color palettes (we love the colorways Copper, Dark Vintage Rose, and Dark Olivine, specifically), these casual sneakers are made with a durable rubber outsole, cushioned midsoles, TPU heel insert for extra support, and removable foam insole. Complete with a foam-padded tongue and collar, these make a stellar daily sneaker option.

Asgard Ankle Rain Boots 

We love footwear styles that work overtime, and these Chelsea boots are up for the job. Made , with waterproof rubber uppers, they’re technically rain boots, but they have a classic and understated design that will complement a wide array of outfits. Available in 15 colorways, they also feature a heel pull tab and EVA foam insole for added comfort. Currently on sale for just $28, these boots have garnered over 17,500 five-star reviews from Amazon shoppers. 

Love a great deal? Sign up for our T+L Recommends newsletter and we’ll send you our favorite travel products each week.