
We’re in the homestretch of summer and close to entering fall bliss. The heat waves are long gone, but now, another dressing issue has risen: The awkward weather makes building outfits a bit difficult. It’s cool in the morning, warm during the day, and very chilly in the evening. You can layer, but not too much, and getting dressed feels more like a chore than an adornment ritual.
That’s why I did some digging in search of the best transitional outfits to wear for the in-between season. Each look is chic, elegant, and quite expensive looking, and they’re all very fitting for the weird weather we’ll experience until fall hits full force. Think warm tonal outfits, pops of color here and there, and clean lines. Light layers, versatility, and functionality without compromising style are always the goal for my outfit inspiration, so keep scrolling to see pre-fall transitional outfits and shop each look.
Monochrome Butter Yellow
Butter yellow is a color trend that keeps on giving. It rose in popularity last year, as it blends beautifully in outfits for all seasons, particularly fall, IMHO. While we’re still in a liminal space with this weather, a full butter-yellow outfit is just right. To break up the color, try layering a sweater over a lace-trim top. It’ll add a delicate texture to your monochrome outfit.
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TOTEME
Oversized Organic Cotton-Blend Sweater
Open Edit
Lace Trim Satin Camisole
FRAME X Amelia Gray
The Gray Relaxed Bootcut Jeans
Dark-Wash Jeans
Now that the weather is finally shifting, it’s totally safe to wear dark-wash jeans with your outfits again. If it’s still warm enough, style a printed sleeveless top or tank top with your jeans, and slip on a pair of flip-flops. To accessorize, add a woven leather bag for some texture and an eye-catching detail.
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Madewell
Cinched Double Layered Mesh Top
Levi’s
721 High Rise Skinny Jeans
Madewell
The Signature Woven Mini Zip Shoulder Bag
Shopping_NonBrand_PMax_NCA
Long Shorts + Long Trench
A pair of long shorts is perfect for both summer and fall. It’s just the right length for a casual or dressy outfit. If you’re leaning more dressy casual like the look below, add a flowy trench coat over your V-neck tank top and a pair of thong-heeled sandals, and play around with your accessories to zhuzh it up. If you’d like to dress your look down, just trade your heels for flats, and ditch the trench coat.
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Lioness
Penny Trench Coat in Ash
ZARA
Cotton V-Neck T-Shirt
Reformation
Amelia Croc Embossed Leather Heeled Thong Sandals
Crochet Hat + Trousers
Crochet hats have had a big moment this summer, but there are also fall-friendly ways to style them. This in-between weather is the perfect time to try out the trend if you haven’t. It looks especially chic with a pair of trousers and pointed-toe shoes. If it’s not too cold, a breezy top is highly recommended, but if you’d rather layer up, swap your top for a lightweight sweater.
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Madewell
Embroidered Lace-Insert Top in Jet Black
Norma Kamali
Tapered Pleated Trousers
Tony Bianco
Sicily Black Vintage Heels in Black
Warm Tones
As you can see, I’m a big fan of monochrome outfits. This one below incorporates warm tones of tan and brown. Beige doesn’t have to be boring, and this look is proof. Wear a long-sleeve top with a long column skirt in similar colors for this tonal effect. Your flats don’t have to be brown; they can be black to break up the colors just a bit. Accessorize with a deeper brown bag, and you have yourself the perfect monochrome pre-fall outfit.
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Eloquii
Layered Cape Sweater
Nordstrom
Maddox Ballet Flats
Strathberry
Kite Suede Hobo Bag
Pop of Blue
Listen. Fall colors don’t have to be limited to black, white, beige, and burgundy. We can expand as much as we want, which is why the look below resonates so much with me. An oversize button-down is an essential for fall. Wearing one in bright blue with white pants is still a fall-friendly outfit—trust me. Slip on a pair of red kitten heels for an even more striking detail.
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Madewell
The Easy Shirt in Poplin
Shopping_NonBrand_PMax_NCA
Leset
Kyoto Cotton Carpenter Pants
Jamie Haller
The Kitty Point Heels in Red Snake
Classic Trench Coat
It’s never too early to pull out the trench coat. If it’s really chilly, layer yours over a black sweater and black pants. Then slip on a pair of white flats, rather than black flats, for an interesting touch. Add a big, slouchy bag if you’d like to accessorize. If it’s not too chilly but not particularly warm either, swap your sweater for a simple baby tee instead.
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J.Crew
New Icon Trench Coat
J.Crew
Cashmere High V-Neck Sweater
ZARA
Cropped Wide-Leg Trousers
Staud
Maude Croc-Embossed Leather Tote Bag









