12 Summer to Fall Fashion Transition Outfit Ideas

Anyone else have whiplash from the weather lately?

It’s been going from chilly to warm faster than you can say “September’s here.” Summer to fall fashion transitions can be tough, because mornings are in the 50s, then by mid-afternoon it’s in the 70s. Yesterday was a high of 60, and today it’s anticipated to reach up to 90 degrees. It certainly makes dressing for the day a bit of a challenge, no? Not quite ready to put away our warm-weather gear, but definitely ready to bring out the layers.

This time of year is always such a funny one in terms of feeling too. It’s still technically summer until September 23, but with school in session and a crispness in the air, summer is essentially long gone from all of our minds. And judging from the fact that I’ve already embraced my inner #Basic and had a Pumpkin Spice Latte, I think it’s safe to say that fall has arrived!

But don’t fully switch out your closets just yet! You’ve still got a few weeks left until your booties and sweaters will feel like appropriate options on the daily. In the meantime, here are 12 summer to fall fashion transition ideas for how to bring hints of fall into those crisp-yet-warm September days!

12 Summer To Fall Fashion Transition Outfit Ideas

A FEW NOTES: As always, I try to stock my closet with wardrobe essentials that I can wear year round! Most of the items below are still available, however, some are not. I’ve tried to find similar options in all cases. Many of the summer items are currently on sale so don’t overlook the summer items if you like the item!

Add a chunky sweater + platform sneakers

SUMMER OUTFIT // Belted Twill Shorts (Currently $21!) + Everlane Slides (No longer available, however these Steven ones are identical!) + Silk Button Down Cami (Currently on sale from $78 to $54!)

FALL OUTFIT // Belted Twill Shorts (Currently $21!) + Platform Sneakers (These are past season but I’m loving this pair + this pair for fall! Also – this Keds + Kate Spade pair is too cute.) + Signature Fisherman Sweater (An absolute closet staple!) + Baseball cap

Add Over The Knee Socks + Heels + Beret

SUMMER OUTFIT // Fitted Black Dress. Would you believe me if I told you this is from Old Navy?! Under $20, yall! + Black D’Orsay Pumps

FALL OUTFIT // Fitted Black Dress (Old Navy & under $20!) + Over The Knee Socks + Black D’Orsay Pumps + Beret (This is past season, however this + this are similar!)

Add A Classic Trench + Over The Knee Boots

SUMMER OUTFIT // Fitted Black Dress. Would you believe me if I told you this is from Old Navy?! Under $20, yall! + Black D’Orsay Pumps

FALL OUTFIT // Fitted Black Dress (Old Navy & under $20!) + Over The Knee Snakeskin Boots + Classic Camel Trench Coat (Similar here + here)

Psst – How To Wear Snakeskin Boots

Add Leather Jacket + Jeans

SUMMER OUTFIT // Graphic Tee (This Rolling Stones one is similar, and I also LOVE my Anine Bing Tee) + Agolde Jean Shorts (FAVES of the summer) + Veja Sneakers

FALL OUTFIT // Graphic Tee (This Rolling Stones one is similar, and I also LOVE my Anine Bing Tee) + Veja Sneakers + Leather Jacket (Mine is vintage but this + this are similar) + Skinny Jeans (Grey is very on trend right now! Love this pair from Citizens of Humanity.)

Psst – VEJA Sneakers Review: The “Next Big Thing” Shoes You Need Now

Add Blouse + Leather Jacket + Socks + Heels

SUMMER OUTFIT // Blush Mini Skirt (Past season, however THIS ONE IS SO CUTE + this is similar!) + Embroidered Button Back Top + Similar Nude Flats

FALL OUTFIT // Blush Mini Skirt (Past season, however THIS ONE IS SO CUTE + this is similar!) + White Blouse (Similar + similar) + Ankle Socks (These + these would be cute with heels) + Black D’Orsay Pumps + Leather Jacket (Mine is vintage but this + this are similar)

Add Blouse + Trench Coat + Socks + Heels

SUMMER OUTFIT // Blush Mini Skirt (Past season, however THIS ONE IS SO CUTE + this is similar!) + Embroidered Button Back Top + Similar Nude Flats

FALL OUTFIT // Blush Mini Skirt (Past season, however THIS ONE IS SO CUTE + this is similar!) + White Blouse (Similar + similar) + Ankle Socks (These + these would be cute with heels) + Nude Pumps (Similar + Similar) + Classic Camel Trench Coat (Similar here + here)

Add Faux Leather Leggings + Heels

SUMMER OUTFIT // Free People “Kiss Kiss Tunic” (Currently sold out, but you can shop similar looks here!) + Agolde Jean Shorts + Dolce Vita Raffia Mules

FALL OUTFIT // Free People “Kiss Kiss Tunic” (Currently sold out, but you can shop similar looks here!) + Spanx Faux Leather Leggings (Got these during the Nordstrom sale and love them! They fit really well and look adorable paired/layered with items for fall) + Black D’Orsay Pumps

Add Chunky Sweater + Booties

SUMMER OUTFIT // Polka Dot Dress (Mine is years old however this + this are similar and adorable finds) + Steven Greece Sandals

FALL OUTFIT // Polka Dot Dress (Mine is years old however this + this are similar and adorable finds) + Ankle Booties (Similar here + here) + Signature Fisherman Sweater (An absolute closet staple!)

Add Jean Jacket + Booties

SUMMER OUTFIT // Silk Button Down Cami (Currently on sale from $78 to $54!) + Midi skirt (Mine is past season Antro – shop similar finds here!) + Everlane Slides (No longer available, however these Steven ones are identical!)

FALL OUTFIT // Silk Button Down Cami (Currently on sale from $78 to $54!) + Midi skirt (Mine is past season Antro – shop similar finds here!) + Similar Black Chelsea Booties + J.Crew Jean Jacket (Have had this for years – absolute closet “Must!”)

Add Jean Jacket + Casual Tee + Slip On Shoes

SUMMER OUTFIT // Embroidered Button Back Top + Utility Joggers (Also love this pair!) + Steven Greece Sandals

FALL OUTFIT // Madewell Whisper Cotton Tee + Utility Joggers (Also love this pair!) + J.Crew Jean Jacket (Have had this for years – absolute closet “Must!”) + Sofft Slip Ons (SO COZY!)

Add Leather Jacket + Leopard Ankle Booties

SUMMER OUTFIT // Free People “Love Of My Life” Dress (One of my favorite purchases of the year!) + Dolce Vita Raffia Mules

FALL OUTFIT // Free People “Love Of My Life” Dress (One of my favorite purchases of the year!) + Leather Jacket (Mine is vintage but this + this are similar) + Leopard Ankle Booties (Similar finds here + here)

Psst – The Most Lovely Free People Dress

Add Utility Jacket + Jeans + Booties

SUMMER OUTFIT // Madewell Whisper Cotton Tee + Agolde Jean Shorts + Maya Huarache Sandals + Similar Belt Bag

FALL OUTFIT //Madewell Whisper Cotton Tee + Flare Jeans (Similar here + here) + Utility Jacket + Ankle Booties (Similar here + here)

Psst – Here’s one of my outfit go-to’s for chilly weather – so cute!

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What’s your favorite summer to fall pairing? Any other easy outfit builds to make your summer staples work in the fall? Leave your suggestions in the comments below!

PS – 5 BeautyCounter Products That Made Me A Believer + Easy Tips On How To Wear A Shift Dress