You bought the dress because it was breezy. It’s that perfect, lightweight cotton midi with the spaghetti straps that makes you feel like you’re starring in a Nancy Meyers movie. Then you walk into a grocery store or an office building or a wedding reception, and the air conditioning hits you like a physical wall of ice. Suddenly, that "effortless" look feels a lot more like a mistake.
Figuring out what to wear over a sundress is honestly one of the trickiest parts of summer styling because you’re trying to balance two conflicting goals: staying warm enough to function while not looking like you just threw a random lumpy hoodie over a delicate piece of silk.
Most people get this wrong. They reach for the same tired cardigan they’ve had since 2014, and it completely kills the silhouette of the dress. It’s frustrating. But if you understand how proportions work—specifically how the hemline of your outer layer interacts with the waistline of your dress—you can actually make the outfit look better with the layer than without it.
The Cropped Denim Jacket: A Total Classic for a Reason
Let's talk about the denim jacket. It's the default. Honestly, it’s probably the most common answer to the question of what to wear over a sundress, but there’s a catch. If the jacket is too long or too boxy, you lose your shape. You end up looking like a denim rectangle.
The trick is the "cropped" cut. When the hem of the jacket hits right at your natural waist or slightly above it, it creates a visual break that emphasizes your narrowest part. This works exceptionally well with fit-and-flare dresses or anything with a tiered skirt. Brands like Levi’s and Madewell have built entire summer collections around this specific silhouette. A light wash denim feels more "daytime at the farmer’s market," while a darker, raw denim or even a black denim jacket can skew a bit edgier for a dinner date.
One thing people forget? Roll the sleeves. Seriously. Exposing the wrist makes the whole look feel more intentional and less like you’re just cold. It’s a small tweak, but it changes the entire vibe from "I’m wearing my boyfriend’s jacket" to "I am a style genius."
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Why the Oversized Button-Down Is the Real MVP
If you want to look like you’re vacationing in the Amalfi Coast—even if you’re just going to CVS—you need a linen button-down. This is the ultimate "cool girl" layer. You don't wear it closed; you wear it completely open, almost like a lightweight duster.
- Linen: It breathes. You won't sweat through it, which is the main hazard of layering in July.
- Poplin: A crisp white cotton poplin shirt gives a more structured, preppy look.
- The Knot: If the dress is flowy, try tying the ends of the shirt at your waist. This creates a makeshift "top" and turns the sundress into a skirt.
I’ve seen stylists like Allison Bornstein talk about the "Wrong Shoe Theory," but there’s also a "Wrong Layer Theory." Taking a structured, slightly masculine button-down and throwing it over a hyper-feminine floral sundress creates a tension that makes the outfit interesting. It’s less "sweet" and more "sophisticated."
The Secret of the Silk Scarf
Sometimes a jacket is just too much. If you’re at an outdoor wedding and the sun goes down, a pashmina can feel a bit... dated? Instead, try a massive silk or modal scarf. You can drape it over your shoulders like a shawl, but because the fabric is thin, it doesn't add bulk. It's a very Old World approach to the problem of what to wear over a sundress.
What to Wear Over a Sundress When You’re at the Office
Work is where sundresses go to die. Or at least, where they go to get covered up by sad, grey office cardigans. Don't do that.
The blazer is your best friend here. But not your heavy winter blazer. You want something unlined. Look for materials like Tencel, linen blends, or crepe. A structured blazer over a sundress is a power move. It says, "Yes, I am prepared for this meeting, but I am also going to a rooftop bar immediately after 5:00 PM."
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Try a belt. If the blazer is oversized, putting a belt over the blazer—not the dress—cinches everything together. It’s a very specific look, often seen on the streets during Copenhagen Fashion Week, and it works best with midi or maxi-length dresses. If you try this with a mini dress, it might look like you forgot to put on pants, so proceed with caution.
The Leather Jacket Paradox
Can you wear leather in the summer? Usually, no. You’ll melt. However, a very lightweight, cropped leather or suede jacket over a sundress is the go-to for "edgy" summer nights. Think of it as the "festival look." If you’re heading to an outdoor concert where the temperature drops twenty degrees the second the sun disappears, that leather layer is a lifesaver. It provides a heavy contrast to a light fabric like chiffon or silk.
The "Shacket" and the Rise of Transitional Layers
We have to acknowledge the shacket—the shirt-jacket hybrid. It’s usually a bit heavier than a standard shirt but lighter than a coat. For those weird days in late August or early September when the mornings are crisp but the afternoons are sweltering, the shacket is a godsend.
Flannel shackets over sundresses give off a very 90s, grunge-revival vibe. If you pair that with some Doc Martens or chunky loafers, you’ve successfully transitioned your summer wardrobe into fall without spending a dime on new clothes. It’s about utility. It’s about not shivering while you eat your overpriced avocado toast on a patio.
Sweaters: The "Shoulder Drape" Technique
Sometimes the best thing to wear over a sundress isn't actually on your arms. The "preppy" look of tying a sweater around your shoulders has made a huge comeback. It’s practical. If you get cold, you put it on. If you’re hot, it stays draped.
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- The Breton Stripe: A striped sweater over a solid-colored dress is a foolproof combo.
- The Chunky Knit: Avoid this unless the dress is very fitted. You don't want too much volume on both the top and bottom.
- The Pointelle Cardigan: These are those "holey" knits. They provide just a tiny bit of warmth but mostly act as a texture play.
The Mistakes You’re Probably Making
We’ve all been there. You’re running out the door, you grab a hoodie, and you regret it the second you see your reflection in a shop window.
The biggest mistake is the length. A mid-length cardigan—one that hits at the mid-thigh—is the enemy of the sundress. It cuts your legs off at a weird point and makes you look shorter than you are. You either want to go very short (cropped) or very long (a duster). The "in-between" length is a graveyard for style.
Another mistake? Ignoring the fabric weight. Putting a heavy wool coat over a linen dress looks "off." The textures fight each other. You want your layers to feel like they belong in the same season, even if they serve different purposes.
Real-World Examples: Celebrity Styling
Look at someone like Alexa Chung. She’s the queen of the "dress plus layer" combo. She’ll take a delicate slip dress and throw a beat-up Barbour jacket over it. That’s an extreme example, but it proves the point: contrast is good.
Or look at Reese Witherspoon. Her brand, Draper James, is basically the gold standard for the "classic" approach. She almost always pairs a floral sundress with a crisp, white denim jacket or a very specific, fitted cardigan. It’s safe, it’s clean, and it always works.
Actionable Steps for Your Next Outfit
Stop guessing. Next time you’re standing in front of your mirror wondering what to wear over a sundress, follow this checklist:
- Check the Waistline: Does your layer end at your waist? If yes, you’re probably good. If no, is it a long duster? If it’s neither, put it back.
- Evaluate the Fabric: Is the layer too "wintery"? If it’s heavy wool or thick fleece, it’s going to look mismatched with a summer dress. Stick to cotton, linen, silk, or light synthetics.
- The Shoe Test: Your footwear dictates the layer. If you're wearing sneakers, a denim jacket or shacket works. If you're wearing strappy heels, reach for a blazer or a silk wrap.
- The Sleeve Roll: Before you leave the house, roll the sleeves of your jacket or shirt. It adds an immediate "styled" feel to an otherwise basic outfit.
- Color Cohesion: You don't have to match perfectly. In fact, tonal dressing (wearing different shades of the same color) often looks more expensive. A light blue denim jacket over a navy sundress is a winner.
Layering shouldn't feel like an afterthought. It’s an opportunity to take a dress you’ve worn a dozen times and make it feel like a completely different outfit. Don't let the air conditioning win. Grab a blazer, roll those sleeves, and keep wearing your favorite dresses well into the evening.