Transition season is upon us, and while I’m enjoying the cooler mornings and warm afternoons, this can be a challenging time of year to dress for, so I’ve rounded up 15 transitional outfits for your style inspiration!
Most of these looks are easy to copy or adapt with items you already own, and of course, you can always add elements or swap out pieces to make these simple outfits better suit your personal style.
My lifestyle is pretty casual, so that’s reflected in these outfits, but most of these looks can be adapted for the work place or dressed up for date night by swapping the jeans for pants and wearing a dressier shoe.
I did my best to link similar styles for the items that have sold out, but the idea here is to shop your closet, so hopefully it’s not too frustrating when you can’t purchase the exact pieces.
15 Transitional Looks to Copy Right Now
#1. A lightweight skirt in fall colors like this Yara Midi Skirt from Evereve pairs easily with a tank top and sandals or sneakers, and you can throw a denim jacket on top for those cool mornings and evenings.
printed skirt (S) // white tank (O/S) // denim jacket (S) // gold slides (8)
#2. Sweater vests are trending right now, and this is the perfect piece to segue from summer into fall. They look great paired with jeans, pants, or skirts; and if you tend to get cold indoors, you can always bring a lightweight jacket to throw on top. I wore mules to keep this look more fall than summer, but sandals or sneakers would work too.
Evereve Reese tank // Pistola Monroe // Splendid Liza
#3. Here’s a similar look with a sleeveless sweater and slingback pumps.
sleeveless sweater (S) // Pistola Monroe cigarette jeans (29) // JW PEI bag // Veronica Beard pumps (8) (similar for less)
#4. Wearing darker colors helps your outfits look more seasonal, even if it’s still too hot for sweaters and boots. I love this Lara Twist Musle Tee from Evereve; I’ve also worn it with a similar pair of wide leg jeans and Birks, and with dark wash straight ankle jeans and black leather espadrilles.
KUT from the Kloth Meg in Exhibited (6) (also at Zappos) // Evereve Lara Twist Musle Tee (S) // black boots (8) // earrings
PAIGE Anessa (29) // Birks (39) // MOTHER Rider straight ankle jeans (29) // similar espadrilles
#5. White pants after Labor Day are no longer a taboo fashion choice, and I love how these ecru wide leg jeans pair with the olive utility top for a transitional look. The brown accessories keep it looking more fall than summer, although I might swap out the raffia sandals for leather.
PAIGE Anessa Utility in Tonal Ecru (29) (also at Evereve) (similar for less) // bobi Utility Tee (M) // Sam Edelman raffia slides (8)
#6. Pairing boots and short sleeves is an easy way to incorporate juxtaposition into an outfit, and I think this is a really fun neutral look. This top is a little heavier than a typical t-shirt, making it a nice transition piece. I’ve also worn it with my Birks, for a lighter look.
Caroline Seamed Muscle Top (M) // MOTHER The Hustler Roller Skimp Flare Jeans (29) (similar for less) // rag & bone Walker Chelsea Boot (39) (similar for less)
#7. Here’s another short sleeve sweater with full length denim combo I’ve been loving all summer long, and I’ll continue wearing it into fall.
tie dye sweater (S) // MOTHER Weekender (29) (similar for less) // Birks (39)
#8. This Oakley Mesh Top pairs so nicely with off-black and dark wash denim, to create a slightly edgy vibe that’s perfect for date nights this fall.
Oakley Mesh Top (S) // MOTHER Rider High Waist Ankle Slim Straight Leg Jeans (29) // Vince Pia Wedge Sandal (8) (similar for less)
#9. Denim skirts are trending big time this fall, and they’re a great way to transition your looks. I styled a button-front style with this black tank and wedge sandals earlier in the summer, but I would wear this right into a warm September. I’ve also worn a similar look with a midi length denim skirt and brown shoes and accessories.
Sarina V Neck Tank (S) // KUT from the Kloth denim skirt (8) // Vince Pia Wedge Sandal (8) (similar for less) // Mika Smocked Tank (S) // RAILS Highland Midi Skirt (29) // Vince Camuto slides (8)
#10. Here’s a classic yet modern look with a rust colored sweater in a lightweight knit paired with medium wash jeans. The cigarette leg style works well with loafer mules, as shown here, and with sneakers as shown with the stripe sweater.
Pistola Monroe High Waist Crop Cigarette Jeans (29) // Treasure & Bond Relaxed V-Neck Sweater (S) //  Dolce Vita Havan Loafer Mule in Brown Crinkle Patent (7.5) // JW PEI Joy Faux Leather Shoulder Bag // Faherty stripe sweater (S) // P448 sneakers (39)
11. I’ve been saying all summer how this Sunkissed Graphic tee will be perfect to wear into fall. The colors really lend it to the transition season. The Birks are nice for now, but I’ll swap them out for sneakers or ankle boots when the weather turns cooler.
Michael Stars Sunkissed Graphic Tee (S) // MOTHER Weekender (29) (similar for less) // Birks (39) // AllSaints Half Moon Bag
#12. This one is from last year, but it will be easy to recreate with current items. I love the way the wide leg jeans and clogs update the classic utility jacket outfit.
similar jacket (option) // white tee (option) // wide leg medium wash blue jeans (option) // brown clogs (option) // brown belt // brown handbag
#13. This is another sweater vest I recently found, and I think it’s so fun with the red slingback pumps.
Sanctuary Stripe Sweater Tank (S) // KUT from the Kloth Meg in Exhibited (6) (also at Zappos) // Sam Edelman Bianka Slingbacks (8)
#14. This is one of my favorite looks from last year. The cap toe slingback pumps make it, in my opinion. Unfortunately, it’s all sold out except the tote, but I did find similar items.
similar sweater vest // similar jeans // slingbacks (similar) // AllSaints tote
#15. When in doubt, I love to put together an all-black outfit. I will swap out the linen pants for washed black jeans as we get deeper into fall, and the flip flops for a sandal with more foot coverage or some type of ballet flat or slingback pump, but I still love the overall vibe of this look.
similar jacket (similar for less) // Sarina V Neck Tank (S) // KUT from the Kloth linen pants (denim option) // Staud flip flops (option) (option)
