The Ultimate Guide To Pairing Shoes With Dresses: From Casual Chic To Red Carpet Ready

Have the perfect dress hanging in your closet, but aren't sure what shoes to wear with it? You're not alone! This common fashion dilemma can turn excitement into frustration. The right pair of shoes can truly transform your entire outfit, enhancing your look effortlessly and setting the tone for any occasion. Whether you're heading to a wedding, a summer night out, or just a regular day at the office, the perfect pair can elevate your style.

To help you navigate the endless possibilities, we've tapped into the wisdom of fashion experts. We asked five fashion experts to help with shoe pairings for every dress style and length, including top tips from New York-based stylist Anny Choi on how to pick out the perfect pair of shoes for any dress, from short and simple to full-length and glamorous. This article offers a step-by-step guide on how to pick the perfect pair for any dress and occasion, covering different types of dresses and seasonal considerations. So, let’s dive right in!

The Golden Rules: Occasion, Season, and Personal Style

Before you even think about specific shoe styles, remember that the right shoes to wear with dresses depend heavily on three key factors: the occasion, the season, and your personal style. Any type of dress can go with any type of shoes, but to make your combination more flattering, embrace versatility and mix and match stylishly. Don’t know what shoes to wear with a dress? Tune into the vibe!

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• Occasion: Are you going to a black-tie event, the office, a casual brunch, or a beach party? The formality of the event dictates the formality of your footwear.
• Season: Open-toe sandals are perfect for summer, while boots are ideal for cooler weather. Consider the weather and comfort.
• Personal Style: Ultimately, your shoes should reflect who you are and make you feel confident. Whether you’re going for classic elegance with pointed-toe pumps or keeping it casual with white sneakers, there are endless possibilities.

Matching Shoes to Dress Style and Length

The length and style of your dress play a significant role in determining the best shoe pairing. Here, we’ll cover different types of dresses to help you make the best choice.

Minidresses & Short Dresses

Minidresses are playful and show off your legs, offering a wide range of shoe options. For a classic, feminine look, wear ballet flats with minidresses. They keep the outfit light and youthful. For a more modern and edgy vibe, consider the best sneakers to wear with dresses as your unstoppable, power pair. They’re incredibly chic combinations that are oh-so-effortless, perfect for running errands or a casual day out. If you're looking to add a little height without going overboard, low block heels or even stylish ankle boots can create an interesting silhouette, especially for transitional weather.

Mididresses

Mididresses, which typically fall anywhere from below the knee to just above the ankle, are incredibly versatile. They can be dressed up or down with ease. For a sophisticated and elegant pairing, open-toe kitten heels work beautifully with mididresses, adding a touch of grace without sacrificing comfort. Mules, with their slip-on design, also offer a chic and effortless option. For a more structured look, especially with A-line or pleated midis, block heels can provide stability and style. And don't shy away from stylish ankle boots, which can give a midi dress an unexpected, fashion-forward edge.

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Maxidresses & Floor-Length Dresses

Maxidresses and floor-length gowns exude an air of effortless elegance or bohemian charm, depending on their fabric and cut. When it comes to footwear, block heels match floor-length dresses perfectly, providing height and comfort, especially for events where you'll be on your feet for a while. Heels or pumps can help to elongate your legs and make you look taller, making them ideal for formal occasions like weddings or galas. For a more casual or bohemian maxi dress, one fail-proof pair is any type of casual sandals. From earthy Birkenstock outfits with dresses to sporty Teva sandals, they offer comfort and a relaxed vibe. For cooler weather or a touch of edge, boots, including ankle boots or even knee-high boots, can add a surprising yet stylish element to a long dress.

Exploring Popular Shoe Styles for Dresses

I've found eight stylish shoe styles to wear with dresses right now, from trainers and boots to heels and flat sandals. Below, you can see a good choice of shoes from flats to heels, rounded to pointed toes, ankle straps, wedges, peep toes, and menswear-inspired styles. Plus, of course, you don’t have to stick to just one!

• Pumps & Heels: These are the quintessential dress shoes. Pointed-toe pumps offer classic elegance, while open-toe heels, wedges, and mules provide variety for different levels of formality and comfort. They are perfect for elevating any dress, whether it's for a formal event or a chic dinner out.
• Flats: Don't underestimate the power of flats! Ballet flats are timeless and comfortable, ideal for minidresses or casual midi dresses. Loafers or other menswear-inspired flats can add a sophisticated, edgy twist to your dress look, especially for the office or a smart casual outing.
• Sneakers: The sneaker-and-dress trend is here to stay because it's incredibly chic and oh-so-effortless. White sneakers, in particular, are a versatile choice for keeping it casual with almost any dress style, from flowy maxis to sporty minidresses. They offer comfort without sacrificing style, making them your unstoppable, power pair for everyday wear.
• Boots: Ankle boots are incredibly versatile and can be paired with minidresses, mididresses, and even long dresses for a fashion-forward look. Knee-high boots can make a bold statement with shorter dresses or add warmth and style to midi dresses in colder months.
• Sandals: From casual sandals like Birkenstocks and Tevas for a laid-back summer vibe to elegant strappy sandals for evening events, this category offers endless possibilities. Wedges and espadrilles are also fantastic for summer dresses, offering height and comfort.

The Power of Color and Material

Beyond style, the color and material of your shoes can significantly impact your outfit. Colors: Pair bold and patterned clothes with beige or cream shoes to let the dress shine. Conversely, with a denim dress or jeans and a shirt, deep purple, bold orange, or metallic shoes can add a vibrant pop of color and personality. Metallic shoes, in particular, are incredibly versatile and can act as a neutral while adding a touch of glamour. Consider materials like leather for a polished look, suede for softness, or canvas for a casual feel.

Shoes for Every Occasion

No matter where you're going or the vibe, there are the best shoes to wear with dresses! Our guide covers styles and tips to match your outfits and enhance your look effortlessly. Here, I’m sharing footwear styles that work every single time to take the stress out of getting dressed, whether you’re heading to the shops or to a black-tie event.

• Formal Events (Weddings, Galas, Black Tie): Opt for elegant pumps, strappy heels, or sophisticated open-toe heels. Classic colors like black, nude, silver, or gold are always safe bets.
• Office & Professional Settings: Closed-toe pumps, refined ballet flats, or low block heels are ideal. Choose classic colors that complement your dress and maintain a professional appearance.
• Casual Outings (Brunch, Shopping, Park): Sneakers, casual sandals (like Birkenstocks or Tevas), or comfortable ballet flats are perfect. Comfort is key here, but don't shy away from stylish options.
• Summer & Beach Vacations: Flat sandals, espadrilles, or wedges are your go-to. Light, breathable materials and open designs are best for warm weather.
• Dinner & Night Out: Depending on the venue, you can choose anything from chic block heels to daring stilettos or even stylish ankle boots for an edgier look.

You'll find must-have picks from Schutz, Zara, Steve Madden, and more when you shop the best shoes to wear with dresses for 2023, no matter the occasion. Buy trending styles of pumps, flats, open-toe heels, wedges, mules, sandals and more from your favorite brands.

Final Thoughts

Choosing the right shoes to wear with a dress doesn't have to be daunting. The key is to know which shoes complement your dresses, and in this round-up, we’ve discussed the best shoes to wear with dresses whether you’re headed to dinner, the office, the park, or the beach. Remember, any type of dress can go with any type of shoes. But, to make your combination more flattering, embrace versatility and mix and match stylishly. This article has offered a step-by-step guide on how to pick the perfect pair for any dress and occasion.

By considering the occasion, season, and your personal style, along with the dress's length and style, you can confidently select footwear that enhances your look. From casual days to special occasions, the perfect pair can transform your style. Experiment with different shoe types—from trainers and boots to heels and flat sandals—and don't be afraid to mix and match. Ultimately, the best shoes are the ones that make you feel comfortable, confident, and stylish, allowing you to step out with poise and flair.