Every September I pull out the same beat-up pair of overalls I bought years ago at a little shop in Portland. My sister makes fun of them. She says I look like I am about to paint a barn. But to be honest, guys – I don’t care one bit.
There is something about the cooler weather that makes me want to layer everything, throw a knit over my shoulders, and just feel COZY for a few months. Fall dressing is my favorite kind of dressing, in fact I think about it all summer long.
So I made a list – a big one. Some of these are overalls, some are jeans, and a couple are dresses because, well, my friend Dana is throwing a baby shower next month and I had that on the brain.
My Favorite Fall Outfit Combos to Try This Season
Denim Overalls With Striped Knit
This is the one. The overalls outfit fall look that started this entire post, if I am being honest with you.
A classic pair of denim overalls with a red and white striped knit peeking out underneath is just so easy and so charming, and it works whether you are running errands or heading to a pumpkin patch with the kids.
Barrel Jeans With Suede Jacket
Barrel jeans took me a minute to warm up to. My husband asked why my jeans looked “confused” and I nearly threw a throw pillow at him. But now I am obsessed. They have this curved, roomy shape that feels so current.
Top them with a soft suede jacket in a warm caramel tone. It’s the kind of jacket that makes any basic jeans outfit fall into place instantly. Add a plain tee underneath and some loafers and you are done.
Floral Midi Dress With Brown Boots
I am not ready to give up my dresses just because the leaves are turning. A dark little floral midi, the kind with tiny flowers on a deep background, is perfect for this in-between weather.
Slip on a pair of tall brown boots and suddenly it feels seasonal instead of leftover from July. This is honestly one of my go-to autumn dress outfit choices when I want to look like I tried without actually trying very hard at all.
Foldover Leggings With Funnel Jacket
Some days call for comfort and nothing else. On those days I reach for foldover leggings, the ones with the wide waistband that you can flip down.
Pair them with a funnel-neck jacket that zips up high around your face for those cold morning school drop-offs. Warm, easy, and you can still bend down to tie a small child’s shoe without any wardrobe drama.
White Jeans With Chocolate Blazer
Yes, you can wear white after Labor Day. I will die on this hill. A crisp pair of white jeans looks so fresh in fall, especially against darker layers.
A rich chocolate brown blazer over a cream shell is my favorite way to style them. The white jeans outfit autumn combo feels unexpected and a little polished, and people always ask where I got the blazer (thrifted, of course, but I let them think it was fancy).
Corduroy Overalls With Mary Janes
Corduroy overalls are peak autumn. The little ridges, the warmth, the way they just SCREAM October. I found a rust colored pair last year and I have not shut up about them since.
I like to wear them with a fine-gauge turtleneck underneath and a pair of black Mary Janes on my feet. The Mary Janes keep it from looking too much like a costume and add a sweet, slightly retro touch that I love.
Bootcut Jeans With Pointed Boots
Bootcut jeans are called bootcut for a reason, and that reason is a pointed boot slipped right underneath. The flare skims over the top of the boot and makes your legs look about a mile long.
I keep mine in a medium wash and pair them with a tucked-in sweater. Simple. But there is something about a pointed toe peeking out that makes the entire look feel intentional.
Burgundy Dress With Camel Coat
This might be my favorite color pairing of the season. A deep burgundy dress under a camel coat is the combination I think about when I think about fall, capital F.
The dress can be a simple knit or something with a bit of drape. Add brown accessories, maybe a leather bag, and walk out the door feeling like you belong on one of those foliage maps I check every August. Warm, rich, and endlessly wearable.
Black Leggings With Oversized Knit
The uniform of every cool aunt everywhere. Black leggings and a big slouchy sweater that hangs down past your hips.
My sister lives in this combination from October straight through to March. Add ankle boots and a long necklace and it looks put together even though it took roughly ninety seconds to assemble. Some outfits earn their place by being reliable, and this is one of them.
White Jeans With Plaid Shirt
Back to the white jeans, because they earn a second spot on this list. This time throw a soft flannel plaid shirt over the top, worn open with a tank underneath or buttoned up and tucked in.
It is casual, a little bit lumberjack, a little bit weekend-at-the-cabin. I wore this apple picking with my kids and only got one small handprint on the leg, which for us counts as a WIN.
Dark Overalls With Lace Blouse
Here is where overalls get a little dressed up. Take a dark, almost inky pair of overalls and wear a delicate lace blouse underneath, with the sleeves poking out.
The contrast between the sturdy denim and the pretty lace is just so lovely. It’s unexpected. You could genuinely wear this to a nice lunch and no one would blink, which is more than I can say for my paint-the-barn pair.
Straight Jeans With Barn Jacket
A barn jacket is having a real moment and I am here for every second of it. That waxed cotton, the corduroy collar, the roomy pockets big enough for a phone and a granola bar.
Wear it over straight-leg jeans and a chunky sweater. It’s the outfit I put on for long walks when the air finally turns crisp and the trees start doing their thing.
Brown Boots With Knit Dress
A sweater dress and tall boots is such a no-brainer that I almost did not include it, but then I remembered how often I actually wear it, so here it is.
A ribbed knit dress in oatmeal or camel with a good brown boots outfit fall pairing underneath is warm, forgiving after a big meal, and takes zero thought in the morning. Add tights if it dips below freezing where you live.
Baby Shower Dress With Cardigan
This one is for Dana, who is due in November and asked me what on earth she should wear to her own party. A soft empire-waist dress with a long cozy cardigan over the top is comfortable and still feels special.
The cardigan means she can take it off if the room gets warm, or bundle up if it gets drafty. A pretty fall baby shower outfit does not need to be complicated, it just needs to let the guest of honor sit down comfortably and eat cake.
Flared Leggings With Leather Blazer
Flared leggings are leggings that think they are pants, and I mean that in the best possible way. They have a little kick at the bottom that reads more polished than your standard pair.
Wear them with a structured leather blazer for a look that goes from the office to dinner without a single change. This flared fall leggings outfit is what I reach for when I want to feel a little bit powerful on a Monday.
Ecru Jeans With Quilted Jacket
Ecru is just white jeans with a warmer heart, if you ask me. That soft cream color is so easy to wear once the light goes golden in October.
A quilted jacket, the diamond-stitched kind that looks like it belongs on a country estate, is the perfect topper. Add a scarf and some ankle boots and you look like you own horses (I do not own horses).
Plaid Dress With Knee Boots
Plaid is the print of autumn, full stop. A plaid shirtdress or a plaid midi is such a simple way to lean into the season without much effort.
Pull on knee-high boots and belt the dress at the waist if it has any volume to it. I wore something like this to a fall festival two years ago and my friend Dana still brings up how “very New England” I looked. I took it as a compliment.
Wide-Leg Jeans With Rugby Shirt
Wide-leg jeans and a rugby shirt is such a fun, sporty combination. The rugby, with those bold horizontal stripes and the little white collar, adds instant preppy charm.
Tuck the front of the shirt into the wide jeans, add clean white sneakers, and there you have it. It feels youthful without trying too hard, and it is honestly so comfortable that I keep wearing it two days in a row (do not tell anyone).
Maternity Midi Dress With Ballet Flats
For the mamas-to-be, a stretchy maternity midi dress is a gift from the heavens in fall. Soft, forgiving, and it grows with you week to week.
Pair it with ballet flats because, let’s be honest, feet swell and heels become the enemy pretty quickly. Add a denim jacket or a cardigan on top and you have an outfit that carries you comfortably through those last cozy months.
Brown Boots With Denim Skirt
And to close things out, a denim skirt with brown boots. A midi denim skirt, the kind that hits below the knee, feels so current right now.
Tuck in a warm sweater, add tall brown boots, and throw a coat over the top if the wind picks up. It’s the little bridge between summer and full-on winter, and I find myself reaching for it again and again on those middle-of-October days.
