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.
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.
Mules, loafers, and boots work wonders with puffy, baggy silhouettes – hence, they’re some of our top picks for fall and winter 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
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. 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.
4. Chunky combat boots
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.
5. 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.
6. UGGs
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 cute trendy winter boot needs to be cozy and comfy.
And, UGGs 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.
7. Slingback Pumps
These versatile shoes are perfect for spring and autumn, providing just the right amount of sophistication. With pointed toes and delicate straps, you can easily transition from day to night.
Style them with a shirt dress for a chic office look, then add a statement necklace for evening flair. Whether in classic black or a bold color, slingbacks stand out.
Their design flatters the foot, making them a must-have staple. Step confidently, knowing your style is unmatched.
8. High-top Sneakers
Unleash your inner artist with high-top sneakers! Ideal for all seasons, they bring a youthful vibe to any outfit. Pair them with a shirt dress for an unexpected twist.
These sneakers provide comfort and style, making them perfect for a casual day out. Choose bold patterns or bright colors to express your creativity. High-tops add an edgy, street style look that contrasts beautifully with the simplicity of a shirt dress.
Whether you’re exploring the city or meeting friends, these sneakers are a statement on your feet.
9. Ballet Flats
Embrace grace and comfort with ballet flats! These classic shoes complement a shirt dress beautifully, offering a touch of elegance without the height.
Perfect for summer picnics or spring strolls, their understated design blends easily with any outfit. Ballet flats provide all-day comfort, making them perfect for long walks.
Slip them on for a casual brunch or a day at the park. Their versatility ensures they remain a timeless choice for any wardrobe.
10. Slides
Slide into comfort with chunky slides! These playful shoes are perfect for summer, adding a carefree vibe to your look. Pair them with a breezy shirt dress for a relaxed beach day.
Opt for neutral and timeless colors and quality materials. Slides offer easy wear and are great for quick outings. They provide comfort and style, making them a go-to choice for warm weather.
Whether you’re at a beach party or running errands, these shoes keep you comfortable and chic. Enjoy the sunshine in style!
11. Classic White Sneakers
Keep it classic with white sneakers! These timeless shoes are a perfect match for any shirt dress, no matter the season. Their clean lines and fresh look offer endless styling options.
Pair them with a casual dress for a laid-back vibe. White sneakers are a wardrobe essential, providing comfort and versatility. Ideal for a day of shopping or exploring the city, they ensure you stay stylish on the move.
Their simplicity allows for easy pairing with accessories. A staple that’s always in fashion, they never fail to impress.
12. Strappy Sandals
Dance through summer with strappy sandals! These delicate shoes add elegance to any shirt dress, making them ideal for formal events or garden parties.
Choose styles with jewels or metallic finishes for added glam. Strappy sandals offer a breezy, open look that complements lightweight fabrics. They provide the perfect blend of fashion and function, allowing you to move freely.
Team them with a simple dress for an understated elegance. Whether at a wedding or an evening soirée, these sandals ensure your entrance is unforgettable.
13. Flip-flops
Embrace relaxation with flip-flops! Perfect for hot summer days, these casual shoes bring a laid-back vibe to your shirt dress ensemble. Choose bright colors or patterns to reflect your mood.
Flip-flops offer ultimate comfort, making them ideal for poolside lounging or beach vacations. Pair them with a casual dress for a stress-free look.
Their simplicity allows for effortless styling, ensuring your day is spent in relaxation. Enjoy the sun and sand while keeping your style effortless and cool. Flip-flops are the epitome of summer ease.