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. 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.
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. 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.