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15 Shoes That Flatter Maxi Dresses & 5 That Make Them Look Frumpy

15 Shoes That Flatter Maxi Dresses & 5 That Make Them Look Frumpy

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Pairing the right shoes with your maxi dress can make or break your entire look. As a fashion stylist who’s seen countless outfit disasters and triumphs, I’ve compiled the ultimate guide to maxi dress footwear. Let’s explore which shoes will elevate your flowing frock to goddess status and which ones should be banished from your wardrobe immediately.

1. Strappy Flat Sandals

Who What Wear

Ever notice how the most fashionable women at beach weddings seem effortlessly chic? Their secret weapon is often delicate strappy sandals.

The minimal design creates a barefoot-but-better look that complements the breezy nature of maxi dresses without competing for attention. They’re especially magical with bohemian or casual cotton maxis.

2. Wedge Espadrilles

© Vessi

Where height meets comfort, wedge espadrilles reign supreme! The natural texture of the rope sole adds earthy charm to any maxi ensemble.

Unlike skinnier heels, these distribute weight evenly, preventing those awkward moments when you sink into grass at outdoor events. Plus, they visually lengthen your silhouette while remaining supremely walkable.

3. Sleek Ankle Boots

© The Fox & She

Transitioning your summer maxi into fall becomes effortlessly stylish with the right ankle boots. Opt for pairs with minimal hardware and a slightly pointed toe.

Though seemingly contradictory, the edgy-meets-feminine contrast creates a magnetic look that turns heads. For maximum effect, choose a boot that hits right at the ankle bone—not higher!

4. Block Heel Sandals

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Hallelujah for the block heel renaissance! These sturdy beauties offer height without the wobble of stilettos.

The substantial shape creates visual balance with voluminous maxi skirts, while remaining surprisingly comfortable for all-day wear. I recommend a 2-3 inch height for optimal proportion—anything higher risks looking clunky rather than chic.

5. Metallic Strappy Heels

© ThredUp

Nothing transforms a daytime maxi into evening-ready glamour faster than metallic strappy heels. Gold, silver, or rose gold—they’re like magic wands for your outfit!

The reflective finish catches light beautifully while the delicate straps maintain visual lightness. When wearing these showstoppers with printed maxis, choose a metallic tone that appears somewhere in the pattern for cohesion.

6. Streamlined Gladiator Sandals

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Forget those knee-high gladiator nightmares of seasons past! Today’s ankle-height versions offer just enough edge without overwhelming your maxi.

The horizontal straps create interesting peek-a-boo moments as you walk, adding movement and dimension. Stick with slimmer straps rather than chunky versions—they’re far more flattering and less likely to visually chop your foot.

7. Refined Flip Flops

InStyle

Banish thoughts of rubber beach flip-flops! I’m talking about their sophisticated leather cousins with slimmer profiles and quality materials.

These elevated versions maintain casual ease while looking intentionally styled rather than thrown-together. Perfect for resort wear or weekend brunches, they offer that rare combination of extreme comfort and genuine style.

8. Pointed-Toe Flats

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Sharp as they are comfortable, pointed-toe flats add unexpected sophistication to flowing maxis. The angular shape creates wonderful tension against the dress’s soft lines.

Unlike rounded ballet flats (which often look childish with maxis), these elongate the foot elegantly. For maximum versatility, invest in a neutral pair with minimal embellishment—they’ll work with every maxi in your collection.

9. Western-Inspired Ankle Boots

© Pinterest

Howdy, unexpected style combo! Western boots with subtle nods to cowboy heritage—think stacked heels and minimal stitching—create delightful contrast with feminine maxis.

This pairing works especially well with solid-colored dresses in earthy tones. Keep the boot shaft height at or just above the ankle to maintain proportion and avoid cutting your leg line awkwardly.

10. Simple Canvas Sneakers

© Jess Keys

Who says comfort can’t be chic? Clean, low-profile canvas sneakers (think Converse or Superga) add youthful charm to maxi dresses.

The juxtaposition of casual footwear with a flowing dress creates that coveted “I’m not trying too hard” vibe. White sneakers offer the crispest look, but don’t be afraid of colored versions that pick up a hue from your dress.

11. Minimalist Mules

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Slip-on sophistication at its finest! Backless mules with clean lines add instant polish to any maxi dress without feeling fussy.

The exposed heel creates a subtle sexy element that balances the modesty of a floor-length dress. For summertime, leather or suede versions in lighter colors feel especially fresh, while darker tones transition beautifully into fall.

12. Delicate Lace-Up Sandals

© eBay

Ribbons and laces that wrap around the ankle create romantic whimsy that perfectly complements flowing maxi silhouettes. They’re like ballerina slippers for grown-ups!

The vertical lines of the laces visually extend your legs, creating a longer line. My pro tip: choose laces that match either your skin tone or your dress color for the most harmonious look.

13. Sleek Platform Sandals

© ROOLEE

Height without the heel—what’s not to love? Modern platform sandals with clean lines offer elevation while maintaining stability.

Unlike chunky platforms of decades past, today’s versions feature streamlined profiles that don’t compete with your maxi’s flow. They’re particularly fantastic with solid maxis that hit right at the ankle, creating a peek-a-boo effect as you walk.

14. Chunky Hiking Sandals

© Vox

Oh dear, where do I begin? Those practical but painfully ugly sandals with thick straps and molded footbeds create a visual disaster with delicate maxis.

The heavy, orthopedic look creates jarring contrast against flowing fabric. Even the most expensive maxi dress looks like a bargain bin find when paired with these functional but fashion-backward options. Save them for actual hiking, please!

15. Running Sneakers

Who What Wear

Performance athletic shoes have their place—the gym, not beneath your beautiful maxi dress! Their technical design elements and neon accents scream “I’m heading to spin class.”

The bulbous shape and excessive cushioning create awkward proportions with flowing dresses. This combination sends mixed messages about your destination and suggests you grabbed the first shoes you found in your closet.

16. Oversized Platform Sneakers

PureWow

Those trendy massive platform sneakers that add four inches to your height? They’re overwhelming beneath maxi dresses, creating a clown-like silhouette.

The exaggerated proportions make your feet look enormous compared to the dress’s flowing lines. This combination creates a visual bottom-heaviness that throws off your entire silhouette and makes the dress look oddly short.

17. Square-Toe Pumps

© DHgate

Despite their cyclical returns to trend status, square-toe pumps create an awkward visual endpoint for flowing maxi dresses. The abrupt geometric shape fights against the dress’s organic movement.

The truncated appearance of square toes visually shortens your feet, creating odd proportions. This shoe style seems to cut the visual flow exactly where you want it to continue, creating a jarring full-stop effect.

18. Ankle-Strap Flatforms

© SilkFred

While flatforms themselves aren’t always problematic, versions with thick ankle straps create an unfortunate visual effect with maxi dresses. The horizontal strap cuts across your ankle at precisely the wrong spot.

This creates the illusion of shorter, wider legs—exactly what nobody wants! The chunky silhouette fights against the maxi’s graceful lines, making even expensive dresses look awkward and proportionally off.