Fall is that tricky in-between season. One minute, you’re sweating through your shirt; the next, you’re wondering if hypothermia can set in before you reach the coffee shop. Been there, survived that. That’s exactly why I’ve perfected a few early fall outfit combos that always hit the sweet spot between comfort and style.
These looks aren’t just “Pinterest cute.” They’re the ones you actually wear on a Tuesday morning when you’ve overslept and have exactly four minutes to look like you have your life together. Ready? Let’s get into it.
1. Oversized Sweater + Midi Skirt + Ankle Boots
This is the unofficial mascot of early fall outfits. Why? Because it works on literally everyone.
- Oversized sweaters keep you cozy without screaming “I’m already hibernating.”
- Midi skirts give you that breezy movement but still keep your legs from freezing off.
- Ankle boots tie it all together like you planned your day around your outfit (even if you didn’t).
Pro tip: Tuck the front of your sweater into your skirt. It instantly makes the outfit look polished instead of “lost in laundry day.”
2. Leather Jacket + White Tee + Straight-Leg Jeans
Effortless? Check. Cool-girl energy? Double check.
I swear, a leather jacket turns any outfit into something paparazzi-worthy. Pair it with a crisp white tee and straight-leg jeans, and you’ve nailed that “I woke up like this” vibe without trying too hard.
Bonus points: Add chunky gold jewelry for that just enough drama.
3. Knit Dress + Knee-High Boots
Ever feel like you want to wear pajamas in public but not look like you’ve given up? That’s where knit dresses come in.
- Knit material = warm and comfy.
- Knee-high boots = chic and leg-lengthening.
- Together? They say, “Yes, I am sophisticated, but also, I could nap in this.”
4. Plaid Blazer + Black Turtleneck + Dark Denim
Plaid is basically fall’s love language. Add a plaid blazer over a black turtleneck and dark denim, and you’ve got yourself a timeless, Instagram-approved combo.
Why it works:
- It’s structured, so it looks professional for work.
- Swap heels for loafers, and it becomes weekend brunch-ready.
5. Trench Coat + Breton Stripes + Cropped Trousers
Whenever I wear this, I feel like I’m starring in a European rom-com. Trench coats just have that main-character energy.
Pair with:
- Breton striped top for a French touch.
- Cropped trousers to show off cute loafers or low-heeled boots.
PS: This combo is especially perfect for those early fall days when the weather can’t make up its mind.
6. Cardigan + Slip Skirt + Sneakers
Yes, you can wear sneakers with a skirt and not look like you’re on your way to gym class.
- Cardigans are the cozy best friend you need in September.
- Slip skirts add some elegance.
- Sneakers keep it casual and comfortable.
This one is my go-to when I’m running errands but still want to look put-together enough for an impromptu coffee date. :)
7. Denim Jacket + Hoodie + Leggings
This is the outfit equivalent of that friend who’s always down for anything.
Why I love it:
- Denim jackets add structure to a casual hoodie.
- Leggings keep it comfy.
- Works with sneakers or chunky boots depending on your mood.
It’s perfect for those in-between days when it’s too cold for just a hoodie but too warm for a coat.
8. Overshirt (Shacket) + Basic Tee + Wide-Leg Pants
Shackets (shirt + jacket hybrids) are basically a gift from the style gods for early fall.
- Layer over a basic tee for warmth.
- Pair with wide-leg pants for that “fashion editor off-duty” vibe.
- Finish with sneakers or ankle boots.'''
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FYI: This combo is basically impossible to mess up.
9. Monochrome Layers
Want to look instantly polished without thinking? Go monochrome.
Pick one color family—think camel tones, all-black, or greys—and layer different textures. A camel sweater, camel trousers, and camel coat? Chic. Add suede boots for depth, and you’re ready to take on the day.''
Pro tip: Play with textures so it doesn’t look like you’re wearing a onesie.
10. Bomber Jacket + High-Waist Jeans + Graphic Tee
For days when you want to look cool but not like you tried too hard, this combo is gold.
- Bomber jackets bring sporty energy.
- High-waist jeans balance proportions.
- A graphic tee adds personality.
IMO, this one’s best with sneakers, but combat boots totally work too.
11. Hoodie Dress + Chunky Sneakers
Yes, a hoodie dress is a real thing, and yes, it’s as amazing as it sounds.
- You get the comfort of a hoodie.
- You get the one-and-done ease of a dress.
- You get extra style points if you pair it with chunky sneakers and a crossbody bag.
This is my ultimate “lazy but make it fashion” outfit.
12. Wool Coat + Light Scarf + Slim Pants
Early fall isn’t technically coat season, but pulling out a wool coat early just feels right sometimes.
Pair with:
- Light scarf for that cozy fall vibe.
- Slim pants to balance the coat’s volume.
It’s the easiest way to feel instantly sophisticated while still staying warm on those chillier days.
Final Styling Tips for Early Fall
A few things I’ve learned after years of outfit experimenting (and way too many “why did I wear this?” moments):
- Layer smartly: You never know when the weather will flip.
- Mix textures: Cotton, leather, wool—mixing materials makes outfits look intentional.
- Keep accessories handy: Hats, scarves, and statement bags can transform a look in seconds.
- Comfort first: If you can’t walk in it, it’s not worth wearing.
Wrapping It Up
Early fall is the sweet spot for fashion—you get to play with layers without the bulk of winter gear. These 12 early fall outfit combos are the ones I keep going back to because they just work.
So the next time the weather leaves you staring at your closet in confusion, pick one of these. Trust me, you’ll look stylish, feel comfortable, and maybe even get a “cute outfit!” compliment before lunch. And isn’t that the real win here? ;)