8 Shoes That Flatter Maxi Dresses & 8 That Make Them Look Frumpy

I’ve always believed that the right shoes can make or break a maxi dress outfit.

After years of fashion hits and misses, I’ve learned which footwear elevates these flowing garments and which ones sabotage the whole look.

Nothing ruins a gorgeous maxi faster than clunky shoes throwing off your proportions! I’m sharing my personal do’s and don’ts to help you nail this sometimes tricky pairing.

1. Strappy Flat Sandals

Delicate strappy sandals create the perfect foundation for a flowing maxi dress. The minimalist design doesn’t compete with the dress’s statement length, creating a balanced silhouette that feels effortlessly elegant.

I wore mine to a beach wedding last summer and received so many compliments! The thin straps elongate your legs while still showing a bit of foot, preventing that ‘floating fabric’ effect where your dress seems to hover mysteriously above the ground.

Brown leather options work with practically everything, but metallics add a touch of glamour for evening events. The best part? They’re super packable for vacations and won’t leave your feet aching after hours of wear.

2. Wedge Espadrilles

Espadrille wedges might be my favorite maxi dress companions for summer outings. The natural jute material complements the breezy vibe of a maxi while adding just enough height to keep your hem from dragging on the ground.

Unlike stilettos that sink into grass at outdoor events, wedges provide stability and comfort. The solid base creates a visual anchor for flowing fabrics, balancing the voluminous nature of many maxi styles.

My navy pair works overtime with both casual and dressier maxis. The closed toe version extends your wearing season into spring and fall too. For petite frames, a 2-3 inch wedge lifts your entire look without appearing overly dressed up.

3. Minimalist Heeled Sandals

Clean-lined heeled sandals with thin straps elevate a maxi dress instantly. The modest height prevents tripping over your hem while creating a long, lean line from head to toe.

I grabbed a nude pair years ago, and they’ve become my go-to for wedding guest outfits. The barely-there design doesn’t visually cut off your leg at the ankle, which can make you appear shorter with a long dress.

Stick to heels under 3 inches for all-day comfort. Square-toed versions feel current without being trendy-trendy, and black pairs hide inevitable scuffs from your dress hem brushing against them. Skip overly embellished styles that compete with your maxi’s pattern or details.

4. Block Heels

Block heels offer the height of stilettos with about a million times more comfort. The substantial base creates a sturdy foundation that balances the flowing nature of maxi dresses perfectly.

My cognac suede pair works magic with both casual and semi-formal maxis. The chunkier heel proportion keeps long, voluminous dresses from overwhelming your frame, maintaining visual balance between your footwear and outfit.

For summer, I choose open-toe versions, switching to closed-toe styles for fall maxis. The best height range sits between 2-3 inches – enough elevation to keep your hem clean but comfortable enough for extended wear. Unlike spindly heels, these won’t have you sinking into grass at outdoor events.

5. Sleek Ankle Boots

Ankle boots transform summer maxis into fall-worthy outfits instantly. I reach for my fitted black leather pair when temperatures drop but I’m not ready to pack away my favorite maxi dresses.

The key is choosing a streamlined silhouette without bulky details. A slightly pointed toe elongates your leg line, while a fitted ankle prevents that awkward bulge under flowing fabric. Heel height matters less than overall sleekness.

Dark colors create a seamless transition from dress to shoe, especially with darker maxis. For a boho vibe, try cognac or tan boots with earthy-toned dresses. Just make sure your maxi hits right at or slightly above the boot top – too much fabric bunching around short boots creates an unflattering, choppy effect.

6. Classic White Sneakers

White sneakers and maxi dresses create that perfect high-low mix I can’t get enough of. The crisp, clean shoes provide a modern contrast to flowing, feminine dresses in a way that feels effortlessly cool.

Canvas styles like Converse work great, but I prefer leather options that resist dirt better. The trick is keeping them pristine – dingy sneakers instantly downgrade your entire look. I stick with slim, low-profile designs rather than chunky dad sneakers that overwhelm delicate dresses.

This combo works especially well with casual cotton maxis for weekend errands or travel days. For dressier maxis, it’s all about confidence – own the unexpected pairing! Just make sure your dress hem clears the top of your shoes to avoid dirty edges dragging on the ground.

7. Embellished Thong Sandals

Jeweled or beaded thong sandals add just the right amount of sparkle to simple maxi dresses. Unlike plain flip-flops, these elevated versions feature quality materials and thoughtful details that complement rather than cheapen your look.

My silver pair has tiny crystals that catch the light beautifully. The flat sole keeps things comfortable for all-day wear, while the embellishments add interest to solid-colored maxis. The minimal coverage shows just enough foot to break up the expanse of fabric.

Look for leather versions with secure straps – nothing ruins a maxi moment faster than that flip-flop slapping sound! These work especially well for resort wear, summer parties, or even casual beach weddings. Just skip them for formal events where something more substantial feels appropriate.

8. Pointed-Toe Flats

Pointed-toe flats bring unexpected sophistication to maxi dresses without sacrificing comfort. The elongated shape creates a sleek line that balances the volume of flowing fabrics beautifully.

My red suede pair makes even the simplest black maxi feel intentional and polished. The pointed silhouette peeks out with each step, adding visual interest without competing with the dress. Unlike round-toe ballerinas that can look childish, these have an inherent elegance.

Metallic versions work as neutrals for evening events, while bold colors make a fun statement with solid maxis. The flat sole keeps you comfortable while the refined shape ensures you still look put-together. Just avoid styles with ankle straps that visually cut your leg line and make maxis feel frumpy.

9. Chunky Orthopedic Sandals

Bulky orthopedic sandals create a visual disconnect with flowing maxi dresses that’s hard to ignore. The heavy, utilitarian design fights against the graceful lines of your dress, creating an unbalanced silhouette.

I learned this lesson the hard way after wearing my comfort sandals with a beautiful floral maxi. Photos revealed how the thick straps and molded footbeds made my feet look disproportionately large and clunky. The practical shoes completely undermined the dress’s elegant vibe.

Even the most expensive comfort brands can ruin a maxi look. If foot problems require supportive shoes, look for streamlined options with thinner straps or consider wedges with built-in arch support instead. Your feet and your outfit can both be happy with the right compromise.

10. Heavy Clogs

Wooden clogs create a visual weight that anchors your look in all the wrong ways with maxi dresses. The substantial, blocky profile fights against the ethereal quality most maxis aim to achieve.

I once paired my favorite garden clogs with a breezy summer maxi for a quick errand. Looking at my reflection in a store window stopped me in my tracks – the heavy shoes made the flowing dress look oddly proportioned, like I was wearing house slippers in public.

The open heel design also creates an awkward gap between foot and shoe with each step. If you love the comfort of clogs, save them for pants or shorter skirts where they can be a deliberate style choice rather than a distraction. Your maxi deserves footwear that complements its graceful lines.

11. Platform Flip-Flops

Those foam platform flip-flops from the early 2000s should never meet your maxi dresses. The chunky, casual style creates a jarring contrast with even the most laid-back maxis, instantly downgrading your entire look.

My college-era black platforms made a brief comeback during a beach vacation last year. One look at photos showed how the thick foam made my feet look cartoonishly large beneath my breezy maxi. The height difference between heel and toe also created an awkward gait that made the dress swing unnaturally.

The loud slapping sound with each step only emphasizes their casual nature. If you need height with your maxi, wedges provide elevation with much more style. For truly casual beach days, flat leather sandals offer the same ease without looking like you grabbed the first shoes you found.

12. Worn-Out Ballet Flats

Scuffed, stretched-out ballet flats instantly bring down the elegance of any maxi dress. Once the backbone of every woman’s shoe collection, these rounded-toe classics can look downright sad when they’re past their prime.

My once-beloved nude flats gradually lost their structure, developing that telltale curl at the toe and worn-down backs. Paired with a maxi, they created a sloppy, unfinished look that made even my nicest dress seem like an afterthought.

The visible wear signals that your entire outfit wasn’t worth fresh footwear. Even inexpensive new flats look better than expensive ones that have seen better days. If you love the comfort of ballet flats with maxis, replace them regularly or opt for pointed-toe versions that maintain their shape longer and offer a more sophisticated silhouette.

13. Overly Bulky Sneakers

Chunky, oversized sneakers create a visual weight that drags down the ethereal quality of maxi dresses. The extreme contrast between delicate fabric and massive footwear makes your feet look disproportionately large.

I experimented with my chunky white trainers under a flowy maxi last spring. The result was comical – like I’d borrowed someone else’s shoes! The thick soles and padded uppers created an awkward silhouette that made the dress look like an accident rather than a style choice.

The sporty technical details also clash with the feminine nature of most maxis. If comfort is your priority, slim profile canvas or leather sneakers achieve the casual-cool vibe without the visual bulk. Save the chunky trainers for cropped pants where their substantial proportion becomes a deliberate style statement rather than a distraction.

14. Rubber Slides

Pool slides signal “I didn’t try” when paired with maxi dresses. The sporty, utilitarian design creates a jarring disconnect with the inherently feminine nature of flowing dresses, regardless of how trendy certain rubber slides might be.

My black rubber slides are perfect for post-gym errands, but when I once lazily paired them with a casual maxi, even my husband noticed something was off. The flat, wide shape visually weights down your feet, while the casual athletic vibe undermines the dress’s inherent elegance.

The molded footbed and thick straps look especially awkward peeking out from under a flowing hem. If you’re drawn to the easy slip-on style, leather or fabric slides with thinner straps offer the same convenience with a much more complementary aesthetic that won’t make your maxi look like an afterthought.

15. Thick Velcro Sandals

Velcro-strapped sandals create an unfortunate “outdoorsy dad” vibe that clashes dramatically with flowing maxi dresses. The technical, utilitarian design elements fight against the graceful, feminine qualities most maxis embody.

My hiking sandals earned their keep on mountain trails but looked ridiculous with a casual maxi during a vacation. The thick, adjustable straps and rugged soles made my feet look ready for river crossing while the rest of me appeared headed to a garden party.

The multiple attachment points visually chop up your foot, creating a busy, distracting area at the bottom of your silhouette. If you need supportive, comfortable sandals, look for versions with leather straps and minimal technical details. The right walking sandals can provide support without screaming “I prioritized comfort over everything else” when paired with your favorite maxi.

16. Square-Toe Boots With No Structure

Floppy, shapeless boots with blunt square toes create a visual heaviness that weighs down the flowing lines of maxi dresses. The collapsed shaft bunches unattractively under the hem, creating awkward bulges with each step.

My once-stylish square-toe boots gradually lost their structure, developing that sad, slouchy look around the ankles. When worn with a maxi, they created unflattering folds of fabric and leather that disrupted the clean line from hip to floor.

The abrupt square toe also creates a blunt ending to your silhouette that stops the eye rather than elongating your frame. If you love boots with maxis, invest in styles with sufficient structure to maintain their shape. A slight point or almond toe creates a more harmonious line, while a fitted ankle prevents the dreaded fabric-bunching that makes even expensive maxis look sloppy.