25 Outfit Ideas To Help You Transition Your Summer Wardrobe To Fall

25 Summer To Fall Outfit Ideas

Are you mentally checked out of summer fashion and ready to put on a pair of jeans and a chunky sweater? I know I am, but the weather has a different plan. I know in the PNW, we’re in a bit of heat wave these next couple of weeks. Getting dressed during this summer to fall transitional phase can be tough. You want to wear layers and the stores are only selling fall pieces, but it’s blazing outside. There’s also those summer pieces you’re not willing to give up just yet – white embroidered dresses for me! Well, today I’m talking all about transitional dressing and sharing tips and tricks to help take some of your favorite summer pieces and make them fall appropriate. Scroll to the bottom to read the rest of the post.

Leather jacket outfit ideas

Old Navy tunic (old, similar), Zara biker jacket (old, similar), Rag & Bone jeans 24 (new version), Soludos espadrilles 5, Givenchy small Antigona satchel, Brixton hat (old, similar), Ray-Ban black aviators 58mm

Best faux leather pants

T by Alexander Wang tee, J.Crew denim jacket, Blank Denim faux leather pants, 3.1 Phillip Lim mini pashli satchel, Soludosespadrilles, Le Specs sunglasses

How to style a bomber jacket 2

Mural varsity bomber jacket (sold out, similar), Topshop tank (sold out, similar), Rag & Bone jeans (new version), Marc Fisher booties, Rebecca Minkoff Love bag, Ray-Ban round sunglasses

Transitional lightweight jackets

Caslon tee petite xs, Caslon peplum twill jacket petite xs, AG legging jeans 25 (sized up for the bump), Kristin Cavallari mules 5 (TTS, super comfy), Ray-Ban aviators, J.Crew tote

Jeans – Eager to wear jeans? Pair them with off the shoulder tops, embroidered blouses, or a cute tank top. As long as you balance out the the rest of your outfit, jeans are a great way to transition some of you favorite summer pieces.



Blank NYC suede moto jacket styled

Blank NYC moto jacket xs, Caslon tee petite xs, One Teaspoon shorts 24 (old, similar), Soludos espadrilles 5, 3.1 Phillip Lim mini pashli satchel, Ray-Ban aviators 58mm

Leather jacket and white dress

ASTR the Label dress, Zara leather jacket (old, similar), Steve Madden Born sandals (under $80), Cult Gaia acrylic ark bag, Ray-Ban rounded sunglasses

Tee Shirt – You can’t go wrong with a classic tee. They’re honestly the easiest thing to throw on and really serves as a base piece for the rest of your outfit. Want to wear a jacket or cardigan, pair it with a tee shirt to keep your outfit from looking like you’re trying to force fall.


Leather Jacket – Leather jackets are a staple in the fall and one of my favorite pieces I look forward to wearing. Once September hits, I’m ready to pull it out and wear it with everything. If temps are still high, reach for them during your nights out or for dinner dates. You can take your summer day outfit, throw on a leather jacket, and you have an easy transitional look.



Striped tees and distressed jeans

Old Navy stripe top (old, similar), Old Navy boyfriend jeans (old, similar), Old Navy boyfriend shirt-jacket (old, similar), Old Navy lace up flats, Rebecca Minkoff bag, Ray-Ban aviators

Drape front trench with shorts

Banana Republic tee (old, similar), Azalea trench (old, similar), Target shorts (old, similar), Sam Edelman Gigi sandals, Rib & Hull tote (sold out), Ray-Ban original aviators 58mm, Bianca Pratt initial necklace, Daniel Wellington watch

White summer top with ankle booties

Kimchi Blue top (old, similar), Zara leather jacket (similar), One Teaspoon shorts (sold out, similar),  Rag & Bone booties (old, similar), Urban Outfitters clutch, Daniel Wellington watch, Ray-Ban silver mirrored aviators

Drape Trench – Fall is all about the trench coat, so this more relaxed style is a great way to transition your favorite summer outfit to cooler weather. They’re lightweight and flow nicely. Pair them with jeans and opened toed heeled sandals, dresses, and even shorts.


Embroidered / Flowy Tops – If you’re trying to get as many wears out of your favorite embroidered or flowy top, this transitional time is perfect for you. Before we really get into the changing of the leaves and the cooler weather, pair your favorite top with jeans or layer with jackets. You have this brief transitional phase to really work your summer piece in with fall pieces.



Silk dress with maxi cardigan

Calypso St. Barth cardigan (old, similar), Cuyana silk dress (old, similar), Steve Madden Slithur sandals, Cuyana shopper tote (similar), Ray-Ban silver mirrored aviators

Cardigans – Cardigans are your best friend during this time. Mornings tend to get chilly once September hits, so you’re able to pull these bad boys out. Pair them with a cami and jeans or with your favorite denim cut offs.


.Utility jacket styed with shorts

Ever striped tee xs (old, similar), Loft jacket petite xxs (sold out, similar), Abercrombie and Fitch shorts 25, Soludos espadrilles 5, Quay sunglasses, Souer bag

Leather jacket and floral dress

Topshop dress, BB Dakota jacket, Steve Madden heels, Rebecca Minkoff shoulder bag, Ray-Ban aviators

Sweater, utility jacket, and shorts

Rebecca Minkoff sweater (old, similar), Madewell jacket xxs, Abercrombie & Fitch shorts (similar), Soludos espadrilles 5, Clare Vivier bag, Ray-Ban original aviators

Utility Jacket – This is one of my favorite transitional pieces. Utility jackets are a staple in a fall wardrobe, but you can easily throw them on with a summer look to make it more fall appropriate. Pair it with your favorite summer dress, or go super casual and wear it with denim cut offs, a white tee, and pointed flats.


.Transition your summer outfits with denim

Banana Republic wrap dress (sold out, similar), Banana Republic denim crossbody, J.Crew denim jacket xs, Zara sandals

Cardigan, shorts, and booties

Caslon tee pxs, One Teaspoon shorts 0 (old, similar), Halogen cardigan pxxs, Sarto by Franco Sarto booties 4.5 (sized 1/2 size down), All Saints tote

Denim Jacket – A denim jacket is another great way to make a summer outfit more fall appropriate. I would say, reach for your darker washes if you can. A great piece to add to a dress, leggings, or shorts.


Booties – Booties will instantly make your outfit look and feel more fall appropriate. If the weather is still a little too warm for layers, booties are a great option. Pair them with shorts or dresses!



High waisted striaght jeans styled

Old Navy boatneck tee (sold out, similar), Zara jacket (old,  similar), Topshop jeans (old, similar), Clare V clutch, Zara pumps, Ray-Ban sunglasses

AG distressed skinny jeans

Pleione top pxs, AG jeans 25 (sold out), Kristin Cavallari mules 5, 3.1 Phillip Lim mini pashli satchel, Ray-Ban original aviators 58mm

How to style sweaters with booties

 Hinge sweater, One Teaspoon shorts (sold out, similar), Steve Madden Tobii booties , Chloe Marcie small bag, J.Crew felt hat, Ray-Ban aviators, Tory Burch watch

Sweaters – Sweaters are an easy-to-wear transitional piece. You can go more lightweight or chunky and pair them with shorts, jeans, skirts, and dresses. As mentioned in my transitional dressing tips, just make sure you always have some element of summer in your outfit.



BB Dakota Faux leather drape jacket

Topshop cami petite xs (sold out, similar), BB Dakota jacket xs, Tosphop jeans, Soludos espadrilles, Rebecca Minkoff shoulder bag, Ray-Ban black aviators

Blank NYC suede moto jacket 3

Blank NYC moto jacket in Toker Midgnight, Splendid tee, Topshop jeans (same style, lighter wash), Coach saddle bag (similar color), Westward Leaning glasses (old), M.Gemi flats, David Yurman ring (sold out, similar)

Blazer and cropped flare jeans

J.Crew stripe long sleeve tee (old, similar), Banana Republic blazer (old, similar), Rag & Bone jeans 24, Madewell sandals (old, similar), Brixton hat (old, similar), Clare Vivier Alistair bag, Ray-Ban original aviators 58mm

Bomber jacket with slip dress

Mural varsity bomber jacket (sold out, similar), Topshop slip dress (old, similar), Rockport loafers (old, similar), Clare Vivier clutch, Ray-Ban black aviators

Loafers – Loafers or flat mules are a must-have fall staple and you can easily start wearing them now. You’ve swapped out sandals for closed-toe shoes, but you’re still going sockless, so you still have that summer-vibe going on. Love them paired with short skirts, shorts, dresses, and even shorts.



Serpui round wicker bag

J.Crew button down (old), Madewell skirt (old), Marc Fisher pumps, Serpui bag (sold out), J.Crew neckerchief (sold out), Illesteva sunglasses

Dresses and booties outfit ideas

Madewell tank dress small, Loft jacket petite xxs, Sarto by Franco Sarto booties 4.5, 3.1 Phillip Lim mini pashli in cashew, Ray-Ban original aviators 58mm

Dresses – Still want to wear your favorite summer dresses a couple more times. Other than a bold print with a bright color, you can pretty much get away with wearing any dress during this transitional time. Pair them with more fall appropriate pieces. Jackets, flats, closed toe shoes.



Leather jacket and denim cutoffs

Topshop camisole (sold out, similar), BB Dakota jacket, One Teaspoon shorts (sold out, similar), Sole Society lace-up flats, Rebecca Minkoff bag, Ray-Ban aviators

What is Transitional Dressing?

What is transitional dressing anyway? Transitional dressing allows you to seamlessly transition into a new season (summer to fall) without having to buy a new wardrobe. You take summer must-haves, pair them with fall items you already own, and voila – a transitional outfit. Seems easy enough, right? Not so fast. This transitional phase isn’t the easiest for everyone, which is why I’m sharing my tips on how to achieve chic and easy transitional outfits.


5 Easy Steps to Transition for Summer Wardrobe to Fall 3

Transitional Outfit Styling Tricks

I created this graphic in 2015, but thought it was still super relevant, so I decided to share it again. All 5 tricks are still very applicable, but I wanted to add a couple more (6, 7, 8).

  1. Add a layer – Continue to wear your favorite summer dress or top by adding a blazer, jacket, or vest. Layering might be the easiest trick to transition just about any summer piece.
  2. Swap sandals for booties – When in doubt, add booties. Boots and booties are a fall staple, so anytime you’re reaching for those summer favorites, rather than slipping on sandals, pair them with boots.
  3. Embrace denim – Summer favorites are bound to look fall worthy with a touch of denim. Think denim jacket, vest, chambray, or skirt. Honestly, you can’t go wrong.
  4. Reach for richer tones – All your whites will start looking fall appropriate once you start pairing them with richer tones. Reach for blacks, dark grays, navy, or deep red tones.
  5. Wear it with jeans – Still want to wear your summer go-to flat sandals or off-the-shoulder tops. Pair them with jeans to keep from looking like you’re headed to the beach.
  6. Pair light with warm – pair your lighter toned pieces with warmer tones (beige, camel, browns). White denim looks amazing with nude and gray.
  7. Mix textures – Think leather or suede with embroidery. The transitional phase is all about mixing textures and playing with pieces that are a little more unexpected.
  8. Create balance – If you’re baring your legs, wear something with long sleeves. If you’re showing your shoulders, wear jeans. You always want an element of summer paired with your favorite fall pieces.

The summer to fall transitional phase is actually one of my favorite times of year for putting together outfits. You get the opportunity to mix and match many different pieces in your closet that maybe you normally wouldn’t. Think blazers with shorts, sweaters with shorts, shorts and booties, summer dresses with jackets, and not to mention, textures! You’re meshing two seasons, so now’s the time to play with unexpected pairings – my favorites: dresses with jackets, sweatshirts with skirts,  blazers with just about anything, and leather with embroidered details.

And just like that, you’re ready to take your summer wardrobe straight into fall! The biggest take away from this post, create balance in your outfits during this transitional phase. Do a little summer with a little bit of fall. It’s okay to pair unexpected pieces together. The more the merrier. Happy outfit planning!