Maximize Your Look: Top Picks for Shoes to Wear with Maxi Dress

As a dedicated maxi dress fan, I’ve spent years experimenting with different shoes to find the styles that truly complement these flowing, feminine garments. Through trial and error, I’ve learned which shoes help maxi dresses look their absolute best for any occasion and season.

In this comprehensive guide, I’ll share the wisdom I’ve gained on pairing shoes with maxi dresses. You’ll discover genius shoe options like ankle boots that elongate legs, perfect pumps to dress up formal maxi dresses, casual sneakers that add a laidback vibe, and flirty strappy sandals fit for date nights.

I cover every scenario – from beachy summer weddings to winter holiday parties – and provide tips to choose shoes that properly balance and proportion your frame. You’ll even find styling suggestions for on-trend shoes like gladiator sandals, cowgirl boots, and menswear loafers.

If you love maxi dresses as much as I do, this is the ultimate guide to help you choose shoes that pull together your look seamlessly. Let’s dive into the perfect footwear to complement your favorite maxi dresses!

Best Shoes to Wear with Maxi Dress

  • Ankle Boots – Ankle boots are a perfect choice for maxi dresses. They add some height and elongate the legs. Go for heeled or flat ankle booties. I love wearing slouchy suede ankle boots with casual jersey maxi dresses for a model-off-duty vibe. Pointy-toe ankle boots also look sleek with satin maxi dresses.
  • Sneakers – Sneakers add a casual vibe to maxi dresses. Opt for clean white or neutral colored sneakers. Chunky high-top sneakers also look great with maxi dresses. I like to wear my white slip-on Vans with floral maxi dresses for a weekend brunch look.
  • Sandals – From flat sandals to strappy heels, sandals pair nicely with maxi dresses. Gladiator sandals and flatform sandals are on-trend. I traded in my flip flops for a cognac leather strappy sandal last summer and love wearing it with all my maxi dresses.
  • Chelsea Boots – Chelsea boots are sleek and stylish with maxi dresses. Try a neutral suede pair. I found an amazing pair of black suede Chelsea boots at a vintage shop that I now wear with midi and maxi dresses in colder months.
  • Loafers – Loafers add a polished touch for work or formal occasions. Penny loafers or oxfords work well. I bought a pair of menswear-inspired loafers for my office job and get compliments whenever I wear them with maxi dresses or skirts.
  • Strappy Heels – For evening events, strappy heels dress up maxi dresses. Go for a heel height you can walk in comfortably. I wore rhinestone strappy heels to a wedding reception last fall with an ankle-length black maxi and felt so glamorous.
  • Wedges – Wedges are perfect for a beachy vibe. Espadrille or cork wedges complement maxi dresses. I lived in espadrille wedges the entire summer I spent studying abroad in Spain. They paired perfectly with all the maxi dresses in my suitcase.
  • Ballet Flats – Ballet flats provide all-day comfort. Go for a pointy toe style. My go-to ballet flats are buttery soft black leather with a pointy toe that works with everything from jeans to maxi dresses.
  • Block Heels – Block heels are walkable and on-trend with maxi dresses. Opt for a 2-3 inch heel. My favorite block heels are neutral snakeskin print – they make any outfit, especially maxi dresses, look instantly more stylish.
  • High Top Sneakers – For a sporty look, high top sneakers add flair. White or colored sneakers work. I love the contrast of feminine floral maxi dresses paired with white high top Converse sneakers.

Shoes to Wear with Maxi Dress by Season


Springtime is my favorite season to break out maxi dresses. The weather is ideal for transitional shoe options like loafers, sandals and ankle boots.

  • Ankle Boots – In spring, I like to wear cut-out or mesh ankle boots that show a peek of skin. Ankle boots with a wood stacked heel also give off great spring vibes.
  • Sneakers – Low-top sneakers in white or pastel colors complement spring maxi dresses. I also like slip-on Vans when the weather is nicer.
  • Loafers – For work in springtime, I wear a lot of loafers with maxi dresses or long skirts. Metallic or animal print loafers add flair.
  • Chelsea Boots – Chelsea boots work year-round but tan suede pairs nicely with the earth tones prominent in spring.


Maxi dresses are a staple in my summer wardrobe. I wear tons of sandals and opt for breathable fabric shoes in the heat.

  • Flat Sandals – My warm weather go-to’s are flat sandals in every color – I love how they instantly dress up maxi dresses.
  • Wedges – Espadrilles and cork wedges are summer staples. I have a pair of black espadrilles I wear endlessly in summer with floral maxi dresses.
  • Mules – Backless mules are perfect for summer, allowing air flow to your feet. I found an amazing pair of snakeskin print mules recently that I can’t wait to pair with all my summer maxi dresses.


When fall arrives, I transition my maxi dresses to warmer fabrics like corduroy, velvet and jersey. I pack away my sandals and break out closed toe shoes like booties.

  • Ankle Boots – Block heel or western style ankle boots pair perfectly with fall maxi dresses, especially in rich colors and textures.
  • Booties – My favorite booties to pair with maxi dresses are a tie between black leather pointed toe and tan suede block heel.
  • Chunky Heels – An ankle strap chunky heel adds stability and comfort for fall while still looking stylish. I have a black pair that works with everything.
  • Strappy Heels – Open toe strappy heels complement the bare leg look before it gets too cold out. I like to add tights as it gets later into fall.


Winter is when I wear maxi dresses the least, but they can still work for the holiday season paired with boots or booties. Velvet and sweater maxi dresses paired with boots keep me both stylish and warm.

  • Knee-High Boots – I have both flat and heeled options. Sometimes I’ll layer leggings underneath to really keep warm in winter maxi dresses.
  • Suede Booties – A neutral suede bootie adds texture and warmth and dresses up maxi dresses for winter dates or parties.
  • Snow Boots – Even in the snow, maxi dresses can work! I have a cozy pair of taupe snow boots I sometimes wear with winter maxi dresses and a long coat to stay comfortable.

Shoes to Wear with Maxi Dress for Different Occasions

Maxi dresses are versatile enough to wear for casual daytime activities, to the office, out on dates, and formal events. I change up my choice of shoes depending on the occasion.

Casual Outings

Weekends often call for maxi dresses paired with casual, comfortable shoes like sneakers or sandals.

  • Sneakers – For walking around town, I love wearing white slip on sneakers or Converse high tops with flowy maxi dresses.
  • Flat Sandals – Leather sandals with a backstrap are my go-to when I want to look put together but still casual.
  • Mules – I recently got a brown suede pair of mules that pair perfectly with casual jersey maxi dresses for running errands.


Many of my maxi dresses work for the office paired with closed toe shoes like loafers, ankle boots, or block heels.

  • Loafers – I have a few pairs of menswear-inspired loafers that complement maxi dresses or skirts when I want to look professional.
  • Ankle Boots – Pointy toe ankle boots with a 2 inch block heel are ideal for wearing with maxi dresses to the office.
  • Block Heels – For days when I’ll be on my feet a lot, a short block heel gives me a bit of height without sacrificing comfort.

Date Night

When my husband takes me on a date night, I like to wear stylish heels that dress up my maxi dresses and make me feel confident.

  • Strappy Heels – For warm weather dates, I love wearing barely-there strappy sandal heels that show off my pedicure.
  • Pumps – A classic stiletto or pointed toe pump pairs nicely with a silky maxi dress for elegant date nights. Red soles add a pop of color!
  • Wedges – Espadrilles and cork wedges complement maxi dresses with a flirty, vacation vibe perfect for warm weather dates.

Formal Events

Formal weddings, events and holiday parties call for more elegant shoes like metallic strappy heels, rhinestone embellished shoes, or satin pumps.

  • Strappy Heels – For my friend’s beach wedding, I found the most perfect metallic gold strappy sandal heels to wear with my maxi dress.
  • Pumps – My go-to formal pumps are nude or metallic colors with a pointed toe. I get compliments whenever I wear them to events.
  • Wedges – For a summer cocktail party last year, I wore a silky floral maxi dress with comfortable rhinestone-embellished wedges.


The beach and boardwalk is one place I wear maxi dresses year-round. I choose footwear that works on sand but still looks stylish.

  • Flip Flops – My tried-and-true beach footwear are basic rubber flip flops. They work on the sand and I don’t mind getting them wet.
  • Espadrilles – For beach vacations, a jute espadrille is perfect for walking the boardwalk while complementing a breezy maxi dress.
  • Sandals – Flat leather or rubber sandals are easy to clean after wearing on the beach and pair well with maxi dresses.

How to Choose the Right Shoes to Wear with Maxi Dress

With so many shoe options out there, here are my top tips for choosing footwear that complements your maxi dress perfectly:

Consider Heel Height

Floor-length maxi dresses allow you to choose virtually any heel height. But for ankle grazing styles, opt for low heels, flats or wedge booties to avoid disproportionately long legs.

Match Color Palette

Choose shoes that complement your maxi dress’s colors and patterns. For bold prints, solid neutral shoes balance the outfit. Shoes matching the dress color creates elongated lines.

Consider Occasion and Venue

Formal events call for heels and dressy materials like satin, sequins or velvet. Casual daytime affairs are better matched with sneakers, sandals or flats. Outdoor venues may require wedge or flat shoes you can safely walk in.

Pick Comfortable Shoes

Since maxi dresses cover your feet, you can sometimes get away with less comfortable heels. But for all day events or walking around, choose shoes you can wear comfortably for hours.

Be Adventurous and Take Risks

Don’t be afraid to experiment with shoe styles outside your comfort zone. Try menswear-inspired loafers, bright colored sneakers, or strappy heels to complement your maxi dresses in new ways.

Make Sure Shoes Fit Properly

With maxi dresses covering your feet, ill-fitting shoes go unseen. But too large or small shoes will still lead to discomfort. Make sure any footwear you choose, especially heels, fits your feet properly.

Consider Proportions

Petite frames can be overwhelmed by chunky shoes, while taller builds can handle bolder footwear. Choose shoes that balance and complement your body’s natural proportions.

Frequently Asked Questions

Can you wear sneakers with a maxi dress?

Absolutely! Sneakers add a casual, dressed-down vibe that works perfectly with maxi dresses, especially for daytime. Some of my favorite sneakers to pair with maxi dresses are slip-on Vans, Converse high tops, and white trainers.

What shoes should you wear with a floral maxi dress?

Some of the best shoes for floral maxi dresses are wedges, flat sandals, espadrilles and ankle strap block heels. These shoes complement florals nicely without covering up the print.

Can you wear ankle boots with a maxi dress?

Ankle boots not only can be worn, they are one of the top shoe styles I recommend with maxi dresses. Go for block heel, western, Chelsea or slouchy suede ankle boots. They elongate legs and add polish.

What shoes should you wear with a formal maxi dress?

For formal maxi dresses, some elegant shoe options include satin pumps, strappy heels encrusted with rhinestones or jewels, sparkly wedges, or metallic strappy sandals. Basically any shoe that is dressy enough for the occasion.

Can you wear flats with a maxi dress?

Definitely! Ballet flats and flat sandals both perfectly complement maxi dresses, especially ankle length styles. Pointy toe flats add polish while flat sandals work for casual wear.

Can you wear cowboy boots with a maxi dress?

Cowboy boots pair amazingly with maxi dresses, especially in fall. Go for traditional leather western boots or try embroidered, brightly colored, or distressed cowboy boots for an extra style boost.

What shoes should you wear with a boho maxi dress?

Great shoes for boho-inspired maxi dresses include gladiator sandals, espadrilles, ankle boots, mules, and fringe details footwear. Anything with woven textures, natural materials, or free-spirited vibes.


Maxi dresses make styling easy by allowing you to highlight your footwear. With endless options from sneakers and sandals to pumps and booties, choose shoes that complement your maxi dress perfectly for the occasion and season. Focus on comfort and proportions for the most seamless look. Don’t be afraid to take risks and try new shoe styles. The right pair makes any maxi dress outfit look pulled together.

Leave a Comment