Something about fall makes getting dressed fun again, doesn’t it?
Maybe it’s the boots. Maybe it’s finally being able to layer without sweating through your shirt. But if you’re midsize—kind of in that weird limbo between straight sizes and plus—it also means fashion starts to make a little more sense. You get to play with shape and texture in a way that actually feels good on your body.
Let’s be honest, fall style is peak comfy-cute. It doesn’t mean hiding under black-on-black just to be “flattering.” It’s about feeling good in your clothes, actually being warm, and maybe turning a few heads in the process.
So here are 15 outfit ideas that are cozy, wearable, and very “I’ve got my life together… at least fashion-wise.”
The Shacket Situation
Yes, shackets are still here. And they still work. Great with high-waisted jeans and a plain tee underneath. Toss on combat boots or chunky sneakers and you’re giving effortless fall energy. Midsize pro tip: Keep volume up top and balance it with something fitted below. Always works.
Fitted Turtleneck + Denim Midi Skirt + Tall Boots
It’s kind of 90s mom, but cooler. The denim skirt adds structure, the turtleneck keeps things sleek, and tall boots tie it all together. Toss in a slouchy bag and pretend you’re the lead in a Nancy Meyers film.
Matching Knit Set + Statement Coat
Matching sets are for the days when you don’t have energy but still want to look pulled together. Think ribbed joggers and a half-zip sweater. Then, throw a bold trench or teddy coat over it. Suddenly you’re That Girl. Minimal effort, max results.
Mock Neck + Black Trousers + Loafers
This is quiet luxury if quiet luxury was actually wearable. Black elastic-waist trousers (bless whoever invented them), a tucked-in mock neck, and a solid pair of loafers. Add a gold hoop if you’re feeling fancy. Works for office days or pretending you’re working from a cafe.
Flannel + Leggings + Puffer Vest
You’re not actually going hiking, but you could. A longline flannel that covers your butt, black leggings that hold it all together, and a puffer vest that says, “Yes, I have oat milk in my fridge.” Throw on a cap or a beanie and go grab that cider.
Knit Midi Dress + Oversized Denim Jacket
This combo is undefeated. A ribbed or soft knit dress in rust, forest green, or wine? It hugs just enough without being clingy. Throw on an oversized denim jacket and suddenly it’s a Look™. White sneakers if you’re running errands, suede ankle boots if you’re pretending to be mysterious. Why it works: It skims in the right places and gives a bit of structure up top without trying too hard.
Pleated Midi Skirt + Sweater + Boots
If you’re a shorter midsize girlie, this one’s for you. A soft pleated skirt with a slightly cropped or tucked-in sweater gives that nice proportion magic. Pair with heeled ankle or tall boots for extra length without discomfort. Optional: Make your Target run look like an editorial shoot.
Sweater Dress + Belt + Knee-High Boots
A good sweater dress is sneaky powerful. It’s cozy, it’s flattering, and with a wide belt and knee boots, you look like you had a plan today. Add a trench or cropped coat if it’s chilly. Bonus: You don’t have to think too hard about the rest of your outfit.
Faux Leather Pants + Graphic Tee + Long Cardigan
This one gives a little edge. Your favorite graphic tee keeps it relaxed, the leather pants elevate it, and the cardigan makes sure you’re still comfy. Great with sneakers or boots, depending on whether you’re heading to coffee or concert.
Oversized Hoodie + Bike Shorts + Long Blazer
Don’t ditch the bike shorts just because it’s chilly. With a cozy oversized hoodie and a structured blazer, they still work. The contrast between slouchy and tailored hits just right. Wear with chunky socks and sneakers or ankle boots if it’s cold.
Cropped Sweater + Paperbag Waist Pants
Paperbag trousers are a low-key midsize miracle. They give waist definition without squeezing. Pair with a soft sweater that ends right at your waistband or slightly above. You’ll feel cozy, pulled together, and like your proportions are working with you.
Fitted Bodysuit + Cargo Pants
Don’t knock the bodysuit. The right one stays in place and smooths everything out. High-waisted cargo pants with a cinched waist and ankle cuffs balance it out. Add boots if you want to look tough, sneakers if you’re just running errands.
Basic Tee + Slip Skirt + Cropped Jacket
This one’s soft and easy. A tee tucked into a silky slip skirt, topped with a cropped jacket. It’s that “grab a drink with friends” outfit that feels like you put in more effort than you actually did. Also looks great with minimal jewelry and clean sneakers or mules.
A Quick Word Before You Go
Here’s the thing: none of these outfits are rules. They’re ideas. If something feels good, wear it. If it doesn’t, skip it. You don’t have to dress to “flatter” or shrink yourself. You’re allowed to be bold one day and live in stretchy pants the next. That’s not indecisive—that’s human.
Fall is the perfect excuse to play with layers, lean into warmth, and try something new without having to overthink it. Whether you’re heading into the office, sitting on a porch with coffee, or just going about your regular life, there’s something here that’ll work for you.
So wear the thing. Take the photo. Show up fully as you are. The clothes are just along for the ride.
