I consider September 1st the beginning of fall. I don’t care when the actual autumn equinox is, okay? The weather is definitely starting to cool here in Seattle, and the mornings are crisp and fall-like. I particularly love this time of year for dressing because you can pair long sleeves with shorts and tank tops with jeans or pants. This weather only lasts for a short window so I’m enjoying it while I can. In this post, I’m rounding up several summer to fall transitional outfits I’ve worn recently. You’ll see many repeated items in these outfits and a good mix of high and low pieces.
Summer To Fall Transitional Outfits
Vest Top + Straight Jeans + Mary Janes
Outfit Details:
Target Vest Top (runs small; size up)
Sézane Jeans (exact color is sold out; similar linked; I sized up)
Madewell Flats
Sézane Bag
I had to place a Target order, and this little vest top ended up in my cart (along with this skirt.) It’s an adorable little top, but it runs quite small so I recommend sizing up. I paired this black top with some brown jeans (a color combo I’m loving right now) and black ballet flats. These ballet flats are a favorite of mine since last spring, and I own them in the brown color as well. They are so comfortable.
Denim Button Down + Straight Jeans + Red Mary Janes
Outfit Details:
Sézane Button Down (runs big; I sized down)
Everlane Jeans (this is the mid-indigo wash)
Frēda Salvador Flats (STITCHANDSALT15 for 15% off)
Sézane Sweater (I sized down)
Old Canvas Tote (similar)
Le Specs Sunglasses
This button down is one of the most worn pieces in my closet. I also own it in white, and I can’t recommend it enough. As for the rest of this outfit, I’ve very into pairing red and denim right now (two very trendy colors) and plan to make more combinations like this during the fall season.
Cream Tee + Black Shorts + Ballet Flats
Outfit Details:
Sézane Tee (similar)
Everlane Shorts (I sized down)
Frēda Salvador Flats (STITCHANDSALT15 for 15% off)
Clare V. Bag
Le Specs Sunglasses
This is more of a warm weather transitional look. If it’s still hot where you live, try switching out your sandals for flats for more fall vibes. This is such a simple look, but it is taken up a notch with the woven flats and crocheted checkered handbag.
Sweater Tee + Ecru Jeans + Ballet Flats
Outfit Details:
Everlane Sweater Tee
Everlane Jeans
Frēda Salvador Flats (STITCHANDSALT15 for 15% off)
Madewell Bag
Quince Sunglasses
Another way to transition to fall during these in between weeks is with sweater tanks and tees. This one from Everlane comes in a few color options, but this striped version is giving 70s vibes which I love. I paired it with my favorite off white jeans, woven flats, and a crocheted bag.
White Tee + Slip Skirt + White Sneakers
Outfit Details:
Sézane Tee (I sized up)
Parallel 51 Skirt (code ASHROHR15; similar option)
Frēda Salvador Sneakers (STITCHANDSALT15 for 15% off; affordable option)
Abby Alley Sling Bag (ASHLEYR15 for 15% off your first purchase)
I wore this outfit to my son’s 7th birthday party at the arcade. I thought the cactus print skirt was so fun and youthful. To keep it casual, I wore a plain white tee and slim white sneakers. I really loved this look!
Gray Tee + Ecru Jeans + Ballet Flats
Outfit Details:
Everlane Tee
Everlane Jeans
Madewell Flats
Madewell Sling Bag
Quince Sunglasses
A simple jeans and t-shirt outfit will always be my go-to when I don’t want to think about what to wear. I love pairing white and gray together; I don’t wear this combination enough. I added some chocolate brown accessories to complete the outfit.
Striped Tee + Maxi Skirt + Sambas
Outfit Details:
Everlane Striped Top
Target Maxi Skirt
Adidas Sambas
Everlane Sweater
Madewell Bag
I shared this outfit in a reel recently! The combination of a feminine skirt and sneakers was unexpected but I was very into it. I also loved the olive green accents and sweater over the shoulders for extra interest.
Striped Tee + White Pants + Sandals
Outfit Details:
KULE Tee
Everlane Pants (I sized down)
Tkees Sandals
Abby Alley Sling Bag (ASHLEYR15 for 15% off your first purchase)
Quince Sunglasses
Another casual chic outfit with a tee. This time, I wore these white pants that I received from Everlane as part of a collaboration. See more details here. If you’re someone who needs to dress business casual, I can’t recommend these pants enough. They come in a few different styles, too. I paired them with a striped tee, a sling bag, and thong sandals.
Bomber Jacket + Jeans + Mary Janes
Outfit Details:
Old Navy Tee
Old Navy Jacket
Everlane Jeans (this is the Vintage Indigo wash)
Madewell Flats
Clare V. Bag
I recently picked up some affordable finds from Old Navy including this bomber jacket and this tee (see more here.) I was super impressed! I styled these more masculine pieces with some Mary Janes for contrast and a cool checkered bag. I LOVED this look.
Striped Sweater + Barrel Jeans + Sandals
Outfit Details:
Sézane Sweater
Everlane Jeans
Tkees Sandals
Madewell Bag
I wore this outfit to our back to school night! This sweater is another favorite from Sézane; I’ve worn it so many times. It is made of cotton so it works well if you’re sensitive to wool. I paired it with some trendy barrel jeans. This color is sold out, but they also come in an ecru color, and I also just received them in the Ocean color as well.
Polo Sweater + Overalls + Mary Janes
Outfit Details:
Gap Sweater
Gap Overalls
Frēda Salvador Flats (STITCHANDSALT15 for 15% off your first purchase)
Abby Alley Sling Bag (ASHLEYR15 for 15% off your first purchase)
Quince Sunglasses
I surprised myself when I added these overalls to my cart. I think they are adorable! I love them paired with something more fancy or feminine like this polo sweater tee or some kind of blouse. I added some red Mary Janes and a sling bag for this look. I plan to style these overalls a lot more this fall.
Oversized Button Down + Cotton Shorts + Ballet Flats
Outfit Details:
Gap Button Down
Everlane Shorts
Frēda Salvador Flats (STITCHANDSALT15 for 15% off your first purchase)
Abby Alley Sling Bag (ASHLEYR15 for 15% off your first purchase)
Quince Sunglasses
This is an outfit combination I wore a few times over the summer. I love the look of an oversized button down with these super casual cotton shorts. It was cool yet so comfortable. As the weather cools, I’ll swap these shorts for some elastic waist pants.
Oversized Button Down + Jeans + Ballet Flats
Outfit Details:
ABLE Button Down
Levi’s Jeans (wash is sold out; similar linked)
Everlane Flats
Sézane Bag
Quince Sunglasses
Can you tell I like oversized button downs? This is another one of my go-to outfit combinations. This button down from ABLE is so soft, but it runs quite big. I paired it with one of my favorite pairs of straight jeans, some ballet flats, a tote bag, and sunglasses. This is an everyday look you’ll see on repeat this fall.
Tee + Elastic Waist Pants + Sandals
Outfit Details:
Everlane Tee
ABLE Pants
Dolce Vita Sandals (similar)
ABLE Sling Bag
Sézane Tote Bag (not available)
I apologize for the low quality photo, but I liked this outfit so much, I wanted to share it. I wore this look on a weekend day of running a few errands. It was so comfortable. As we transition to fall, you could add a third layer like a denim jacket for more warmth.
Striped Tank + Blazer + Straight Jeans + Mary Janes
Outfit Details:
Sézane Striped Tank
Everlane Blazer
Everlane Jeans (this is the Vintage Indigo wash)
Madewell Flats
ABLE Sling Bag
I wore this outfit recently to a doctor’s appointment. During the fall, I wear some combination of a blazer and jeans at least once a week. If you go to the office, you could swap the jeans for pants.
Bomber Jacket + Hiking Pants + Sneakers
Outfit Details:
Gap Bomber Jacket (old; similar)
Outdoor Voices Pants
New Balance Sneakers
This is what I wore recently on a long walk and coffee run. I bought these pants in white and black for hiking, but I like wearing them for a casual every day outfit, too. They are also very petite-friendly! I paired it with a bomber jacket and comfy sneakers. You may not see these sneakers much on the blog, but I wear them all the time for school drop off or on our after dinner strolls around the neighborhood. They are a classic sneaker that will always be in style.
Read More:
28 Fall Pieces From My Closet I’m Excited To Wear Again
My 2024 Fall Wishlist
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