Maxi Dresses Are Back! 5 Celebrity-Approved Styling Tricks With Boots & Heels for Fall

Maxi dresses have made a comeback in the spotlight—and for good reason. The floor-grazing frocks are both trendy and timeless, and they are flattering on most figures.

As model Hilary Rhoda says, “Maxi dresses are also my best friend. They take me from my morning coffee, to the beach, to nighttime.” With their effortless versatility, these dresses can transition from casual daytime looks to evening elegance with just a few styling tweaks.

We’ve taken inspiration from some of our favorite celebrity maxi dress lovers to deliver a list of ways to wear your maxi dress well past the summer months. Here are five ways to style this beloved wardrobe staple:

1. Stay Cozy: Long-Sleeved Maxi Dresses for Fall

Sweater maxi dresses are perfect for fall. Choose a dress with a cowl neck or turtleneck for extra warmth, or opt for a traditional V-neck or crew neck cut.

Julia Stiles glows in a geometric-print maxi dress while proudly cradling her baby bump at the Riviera launch event at London’s Halcyon Gallery on June 13, 2017 (Credit: Tony Oudot / WENN / Owen Beiny / Lexi Jones / FayesVision)

If you’re not feeling a sweater maxi dress, don’t sweat. Many long-sleeved styles are made of looser materials that are perfect for the slightly warmer fall months.

Julia Stiles looked radiant in a patterned long-sleeve maxi dress, finishing her maternity-chic look with simple black strappy sandals

Long-sleeved maxi dresses are a versatile addition to any wardrobe, seamlessly transitioning from casual daywear to elegant evening attire. For instance, Kirsten Dunst recently captivated audiences in a sparkling emerald maxi dress at Gucci’s Fall/Winter 2024 show during Milan Fashion Week in February, demonstrating the timeless appeal of this style.

If you’re looking to incorporate this trend into your own closet, consider exploring different types of dresses to find the perfect long-sleeved maxi that complements your personal style. Long-sleeve maxi dresses are a timeless staple, and Shopbop’s latest collection proves that this silhouette can be both elegant and effortlessly modern.

A stunning selection of long-sleeve maxi dresses in classic black, rich brown, and deep red, showcasing sleek, ruched, and pleated designs

2. Swap Sandals for Boots to Elevate Your Maxi Dress

As the temperatures drop, it’s time to swap out your summer sandals for something more seasonally appropriate. Transition your sleeveless maxi dress into fall by pairing it with a stylish pair of boots.

Whether you opt for sleek and versatile ankle boots or edgy and bold combat boots, the proper footwear can instantly transform your look. Luxe materials like suede or leather add warmth and texture, making your outfit effortlessly autumn-ready.

Emma Roberts keeps it effortlessly chic in a blue floral maxi dress and ankle boots in West Hollywood / Jessica Alba layers a striped maxi dress with a long vest and clog boots for a relaxed yet polished look / Hilary Duff adds an edgy twist to a sheer black maxi dress with silver-studded ankle boots while out in West Hollywood

From western-inspired flair to everyday chic, pairing maxi dresses with boots unlocks endless styling possibilities. Whether you lean toward cowboy silhouettes or sleek ankle styles, these celebrity-inspired looks prove that boots can elevate a maxi dress for any season.

3. Toughen Up Your Maxi Dress with a Chic Jacket

Maxi dresses, with their sweeping skirts and dreamy prints, exude a sense of femininity and romance.

To give the look a sharper edge, top yours with a leather jacket or a tailored blazer—both add instant structure and polish. As a bonus, the outerwear doubles as protection against the inevitable autumn chill.

Fearne Cotton effortlessly mixes edgy and bold, pairing a red tiger-print maxi dress with a classic black leather jacket and sleek ankle boots

4. Instantly Elevate Your Maxi Dress with Statement Jewelry

Accessories play a big part in the overall look of your ensemble. As Poppy Delevingne once said, “I love maxi dresses, I feel so great when I put on a maxi dress, big earrings and sandals.” The right jewelry, shoes, and finishing touches can transform a simple maxi dress into a statement look.

While heavy layers of long necklaces and stacked bangles evoke a bohemian summer vibe, serious statement baubles can bring the tone down to fit the season.

Hayden Panettiere stuns in a shimmering silver maxi dress with delicate jewelry, embracing red carpet elegance, while Kim Kardashian opts for bold statement accessories to complement her striking red two-piece ensemble

5. Add Warmth and Style with a Cozy Scarf

Whether you’re wearing a maxi dress or not, scarves are an instant way to add a bit of fall flair to your ensemble.

Miranda Kerr perfects effortless airport style, layering a bold printed scarf over a classic striped maxi dress and denim jacket, finishing the look with aviator sunglasses and a sleek black handbag

Drape a scarf over your tank maxi dress for an instant upgrade—equal parts cozy and chic. Not only does it pull your look together, but it also adds a layer of warmth against that crisp fall chill.

Miranda Kerr adds a pop of color to her striped maxi dress by layering on a vibrant printed scarf, topped with a casual denim jacket for effortless airport chic

Maxi Dresses Elevated: Celebrities Who Master the Art of Styling With Heels

Maxi dresses are a staple in every wardrobe, but the right heels can take them from effortless to elegant. Celebrities have mastered this pairing, showing us how the right footwear can transform a look. Here are some standout maxi dress and heel combinations:

Maxi dresses may be effortlessly chic on their own, but a well-chosen pair of heels adds polish, height, and undeniable sophistication.