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What Shoes To Wear With A Shirt Dress? 12 Seasonal Styles

What Shoes To Wear With A Shirt Dress? 12 Seasonal Styles

We never had an ounce of doubt that our favorite fashion royals, Kate Middleton and Meghan Markle, would show us the beauty of wearing a good quality, structured shirt dress to pretty much any occasion. We’re bringing you a rundown on how to style and what shoes to wear with a shirt dress, everyone’s favorite wardrobe staple.

We’re, of course, hinting at the fact that Kate and Meghan happen to lead the way when we’re talking about rocking different styles of shirt dresses for different seasons.

Whether they’re traveling for business, making appearances, attending meetings, or even spending weekends with friends and family, they can never go wrong with a simple, button-up dress.

And, we never shy away from looking at them for fashion-forward advice on how to wear these basic pieces without looking… Basic.

Kate Middleton, for example, recently attended a tour of numerous Caribbean countries. On that tour, she managed to wow everyone with an Alexandra Rich shirt dress with a rounded neckline, puffed-up sleeves, and a peplum embellishment on the waist.

Meghan Markle, on the other hand, tends to gravitate toward simple, minimalistic designs such as the Veronica Beard dress she wore on the royal tour with Prince Harry.

Oh, the blue dress made an impression on everyone present on the tour! And the fact that Meghan wore the same dress even after the tour attests to that.

Therefore, we’re suggesting you take a page out of the royals’ book and style your shirt dress in a way that’s elegant, timeless, and chic. However, with the right shoes, accessories, and accents, there’s no reason why you wouldn’t be able to wear your shirt dress whichever way you prefer.

What makes a shirt dress a timeless, investment-worthy, works-for-every-occasion clothing piece?

What Shoes To Wear With A Shirt Dress? 12 Seasonal Styles

Sure, a shirt dress doesn’t necessarily scream “you need me in your closet!”

Now, we’re used to running toward statement pieces, trends, and clothing bits and bobs that snatch our attention for one reason or another. We’re drawn to designers, celebrities, and content creators that challenge our perspective on what’s fashionable and what’s not.

But, we can be fashionable without falling prey to trends that come and go. Capsule wardrobes have been trending on Instagram, TikTok, and Youtube for ages because they encapsulate everything great about knowing how to style basics without looking basic.

Of course, a shirt dress seems pretty basic when you don’t know how to elevate your look the right way. First things first, what does a shirt dress even look like? Don’t worry, you’re not the only one who thinks of those men’s white button-ups combined with sheer, black tights and stilettos.

While Zandaya (and some other celebrities) mastered the effortless look we’re talking about, that’s not the only definition of a shirt dress. A shirt dress can pretty much be any button-up dress, regardless of the length, the style, and the embellishments.

Anything that buttons up and goes past your… khm… bottom constitutes a shirt dress. And, a shirt dress makes for the best basic piece because you can build whatever outfit you want around one.

You can, for example, go with the Kate Middleton signature look and choose a button-up dress that’s already a statement and add a pair of pumps to complete the elegant ensemble.

Or, you can add an edge to your outfit with chunky combat boots and a leather blazer (as long as you don’t go for a feminine silhouette of the dress like the one Kate wore). Or, experiment with whatever feels right at the moment.

What shoes to wear with a shirt dress in spring?

As you might have noticed, when you’re styling something simple you’re depending on the shoes and the accessories to make or break your outfit.

So, we’re bringing you a guide on what shoes to wear with a shirt dress to make sure you’re on point regardless of the season

Spring fashion, to begin with, means you’re ready to ditch the chunky knitted sweaters and the woolen trousers. Replace them with core classics designed with modern twists for work wear, or with leather pieces for after-work drinks and date nights.

Don’t worry, shirt dresses belong to your spring wishlists as they can be dressed up and dressed down. While you’re free to wear them in whichever way works for you, here are some of our stylish suggestions to make the most out of your button-ups and basics.

1. Ballet flats

For an easy one-step outfit, combine your favorite (preferably striped) shirt dress with comfortable and chic ballet flats, an over-the-shoulder bag, and bold, red lipstick.

FYI, you absolutely can’t go wrong wearing such a statement outfit to work, to a get-together with friends and family, or to a weekend getaway with your significant other.

Ballet flats have been on a hiatus for the past couple of years. But, now they’re back and they’re better than ever (ask Kate Moss who can attest to the fact that they never really left the throne, anyway).

Designers have been fighting to rework the classic ballet flat by coming out with leather, shearling, and kitted alternatives.

Therefore, on the off chance that you didn’t like the timeless combination we suggested, don’t shy away from experimenting with different fabrics, patterns, and embellishments.

Shearling ballet flats would work great with a knitted button-up dress, a trench coat, and a shearling handbag (take a look at Rosie Huntington-Whiteley’s recent Insta posts).

2. Platform pumps

What Shoes To Wear With A Shirt Dress? 12 Seasonal Styles

Ballet flats would be a “safe” way out of a fashion dilemma. But, platform pumps are bound to add an edge to whatever dress you’re going with.

Come on, platform pumps have been taking the world by storm ever since Versace came out with those Medusa Aevitas ones. We would be crazy to overlook the world of possibilities such statement shoes offer.

Oh, that’s the thing with shirt dresses, by the way. Whenever you’re wondering what shoes to wear with your shirt dress, always go with statement shoes.

Whether you’re a fan of chunky combat boots, platform pumps, or thigh-high, glittering booths like the ones Victoria Beckham wore for her Cinderella moment, you can’t go wrong with eye-catching footwear.

And, that’s exactly what a simple, monochromatic button-up dress needs. Because platform pumps became super, super popular quite quickly, you can’t find them pretty much anywhere you look.

Zara, Mango, and H&M came out with more affordable alternatives, and Steve Madden, Michael Kors, and Nine West have a couple to choose from, too.

3. Sneakers

Sneakers are the comfortable shoe you turn to when you’re tired of strutting around on your stilettos. But, for the past couple of years, we’ve witnessed sneakers going from a sporty shoe to a shoe everyone wears with everything.

And, we couldn’t be more stoked to suggest you combine your stripy, white, or even denim shirt dress with a pair of sneakers. Now, you can go two ways when wearing sneakers.

First off, you can always go for white sneakers that look great with tailored trousers for work and dresses for weekend strolls around the neighborhood.

White sneakers would look stunning combined with a white, oversized shirt that goes past your bottom, a cardigan draped over your shoulders for some warmth, and a bunch of gold accents.

What shoes to wear with a shirt dress in summer?

Now, swap those white sneakers with strappy sandals, add some sunglasses, a raffia handbag, and some statement earrings and you have the ultimate summer look.

When summer starts knocking on your door, you know you need to start stacking up on sandals, slides, and espadrilles. Truth be told, these shoes happen to go wonderfully with a simple, button-up dress.

We know we’ve talked your ears off with Kate Middleton and Meghan Markle… But, these two fashionistas know how to style espadrille wedges better than anyone we’ve looked into for inspiration. And, we’re happy to take a page out of the royal books.

What are you waiting for, then? Take a peep at what we’ve gathered and uncover numerous ways you can wear summer shoes with a button-up dress. Right off the bat, strappy sandals are our favorite fashion hacks to make you stand out wherever you go.

1. Strappy sandals

What Shoes To Wear With A Shirt Dress? 12 Seasonal Styles

Oh, there’s something comforting about the start of the summer season and the moment you swap your chunky, combat boots with dainty, delicate sandals.

While you’re putting away your sweaters and scarves, hold on to those button-up dresses and oversized shirts a little longer. With some fashion-forward tips and tricks, you can keep on wearing all of them.

A structured shirt seems to be a staple whatever season we’re talking about. And, a shirt dress falls under the same category which means you get to wear and style one however you want to (versatility for the win, always).

Strappy sandals are a great way for you to elevate a simple shirt dress. Gladiator sandals or even sandals that can wrap around your legs to your knees add a little somethin’ somethin’ you can’t get with other shoes.

While you don’t need to go the designer route, we can’t help ourselves but mention the Gianvito Rossi strappy metallic sandals as a guideline for what you should strive for.

2. Block-heeled sandals

Shopping for the right style of sandals can be exhausting. Whether you’re looking for something that’s going to make everyone gasp or something that’s going to be comfortable (and cute) enough for work, block-heeled sandals are a great show to start with.

Sure, they don’t have the stilettos’ appeal. But, they don’t make your feet bleed or sweat which makes for appropriate summer footwear.

When you’re wondering what shoes to wear with a shirt dress, don’t shy away from the obvious choice that’s bound to make your life a lot better and easier.

Combine block-heeled sandals with a structured button-up dress that ties around the waist and adds some definition to your figure. Complete the look with a claw-clipped bun, fresh makeup, and a handbag that fits everything you need.

3. Espadrille wedges

What Shoes To Wear With A Shirt Dress? 12 Seasonal Styles

Espadrille wedges aren’t a novelty when we’re talking about summer footwear. But, why would we want to change something that works?

Though that might sound strange, espadrilles are the only shoe you’re going to need over the summer and there’s nothing wrong with that.

For starters, espadrille wedges are comfortable enough to wear to work, for a walk, or even to a garden wedding. They’re lightweight and breathable, and they add a vintage vibe to whatever you’re wearing.

Therefore, we suggest you wear espadrille wedges with a retro button-up dress. A flowy, floral pattern, puffed-up sleeves, and a cinched waist would make you look like a dream.

And, when you’re looking for something that’s not that dreamy, you can always go with a monochromatic, minimalistic number.

What shoes to wear with a shirt dress in fall?

We don’t always turn to celebrities when we’re trying to figure out what to wear. But, when we do, we make sure we turn to some of Hollywood’s A-listers like Rihanna, Hailey Beiber, and Zendaya.

When they start stepping out on the streets wearing suit sets, leather blazers, and chunky boots, you know fall fashion’s here to stay.

What shoes do you wear with a shirt dress during the fall season, you wonder? Comfort, common sense, and practicality seem to be the motivation behind some of these designer pieces we’ve been witnessing on the streets.

Mules, loafers, and boots work wonders with puffy, baggy silhouettes – hence, they’re some of our top picks for fall footwear.

1. Mules

We’re obsessed with mules and we’re not scared to combine them with pretty much anything. When the weather starts getting colder, we start looking for something that covers our feet (at least a little bit).

Sneakers are great but they’re too sporty. Boots are beautiful but they’re too much for days that aren’t that cold. But, mules are perfect because they’re the right combination of comfort, elegance, and practicality.

For that signature fall fashion ensemble, combine an earth-toned shirt dress with suede mules and a suede handbag. Tory Burch leather mules with gold accents or Birdies shearling mules would work great for the season.

2. Loafers

What Shoes To Wear With A Shirt Dress? 12 Seasonal Styles

On the other hand, there are times when you’re not looking forward to bearing the back of your feet for the world to see. That’s when you ditch the mules and decide to wear loafers with whatever outfit you already planned.

And, that’s when you figure out that loafers go with everything. Actually, we appreciated Haile Bieber’s determination to make leather loafers with socks work.

And, they work better than we would’ve ever pictured. As a matter of fact, we suggest you wear them with some sheer black tights, a shorter button-up dress, and a cardigan draped over the shoulders.

Switch the short dress for a longer one, throw a leather blazer over everything and you’re ready for work. We don’t even know what’s more versatile when we compare the two – that’s probably why they’re a match made in heaven.

3. Ankle boots

“Ankle boots. For fall? Groundbreaking.” We couldn’t skip out on the opportunity to (kind of) quote Meryl Streep and our favorite fashion movie ever.

We’re hoping you get the reference as we move on to discuss why you shouldn’t dwell on wearing ankle boots and dresses during the pumpkin spice Lattes season.

Ankle boots combined with button-up dresses are what dreams are made of. Whenever you’re wondering what shoes to wear with a shirt dress, listen to your gut feeling that’s screaming, “Ankle boots! Always wear ankle boots!”

Because you already know that’s the shoe you’re going with when the weather starts getting wet and disgusting. We’re leaning toward the Gucci ankle boots with gold accents (of course we are), but you can get ankle boots pretty much anywhere you look.

Zara and Mango always have your back with affordable alternatives, and Nine West, Steve Madden, and Free People offer some of our favorite styles.

What shoes to wear with a shirt dress in winter?

Winter fashion often gets shunned away for the sake of warmth, comfort, and the opportunity to wear something that won’t cause pneumonia. However, that doesn’t mean that you can’t look your best while keeping your toes happy and healthy.

Quite on the contrary, winter fashion offers a great chance for you to experiment with different fabrics, textures, and styles.

Knitted dresses, chunky cardigans, and “boots with the fur” make sure you’re fashionable and protected. We don’t know what Flo Rida’s wearing these days, but we’re bringing you a couple of shoe suggestions to wear with a button-up dress he would probably approve of.

1. Chunky combat boots

What Shoes To Wear With A Shirt Dress? 12 Seasonal Styles

Choosing what shoes to wear with a shirt dress during the winter doesn’t sound that easy.

First off, you’re not even looking forward to wearing a dress when you remember the temperature (and the frostbite) that awaits you when you step outside. But, that doesn’t have to be the case when you learn how to style what you already own.

Now, you can always turn to layers when you’re out of other options. Chunky combat boots are a no-brainer when we’re talking about winter fashion.

Wear woolen socks under them and style them with a white button-up dress, a knitted sweater, and a shearling coat. We suggest you add a scarf for some additional warmth – and, don’t forget the TikTok famous, fleece-lined tights.

2. Knee-high leather boots

Chunky, combat boots are great for when you’re running errands, walking around the town, or doing something that requires you to be comfortable.

And, they’re even better when there’s snow everywhere and you’re clumsy enough to end up on your bottom whenever you try to take a walk.

But, when you’re wondering what shoes to wear with a shirt dress that won’t make you look like a high schooler, you might want to go for knee-high leather boots.

High-heeled, of course. Knee-high boots are bound to make you stand out wherever you go (not only because they make you look taller, but because they make you look like you actually tried).

Steve Madden Ally knee-high boots, Vince Camuto Alinkay knee-high boots, and Dune London knee-high boots would work wonderfully for what we pictured.

3. Moon Boots

Winter boots are one of the most necessary purchases when we face cold weather. Sure, stiletto booties and Victoria Beckham’s thigh-high booties make you look like you came straight from the runway.

But, they aren’t a realistic choice for someone who has work to do and places to be. A good-quality winter boot needs to be water-proof, slip-resistant, and insulated.

And, Moon Boots seem to be everything a winter boot needs to be. Other than that, they’re chunky, fashionable, and seem to make a statement when combined with something as simple as a kitted button-up dress. Oh, you don’t need to sacrifice fashion for comfort after all.

Read more: What Shoes To Wear With Rompers? 14 Stylish Ideas