How To Layer Your Summer Dresses for Fall

This morning when I stepped out into the AM light, I was met with something unexpected, yet entirely welcome: Crisp air. 66 degrees is by no means frigid, but it got me excited for what lies ahead; those breezy, fresh days of early autumn and all the sweaters, boots, and jackets that come with them.

But just because the days are beginning to cool doesn’t mean I’m packing away my summer clothes just yet – in fact, one of my favorite outfit combinations is a soft and cozy sweater thrown over an airy summer dress. Contrast and warmth, perfection. But there’s more than one way to layer up for the seasonal transition …

Layering Summer Dresses

Layering Summer Dresses

Layering Summer Dresses

Get the look: Shaggy Knit Pullover, Circle of Flowers Slip, Breton Heeled Boot, Osiris Necklace.

I love how the raw edge of this dress plays against a super soft pullover, with the raw hem peeking out just so. Open-back booties in oxblood can be worn now, and paired with socks as the temperature gets colder.

Layering Summer Dresses

Layering Summer Dresses

Layering Summer Dresses

Get the look: Harry’s Babe Dress, Exploded Plaid Buttondown, Shark Hem Cotton Cardigan, Amazing Pointelle Thigh High, Truemay Lace Up Boot.

Cooler weather offers the perfect excuse to play with color and pattern. Top your airy crepe dresses with a menswear flannel and an oversize sweater to stay warm in the morning; if the weather gets hot, all you need to do is remove a layer. This is also the time of year to start experimenting with thigh-highs and cute ankle socks!

Layering Summer Dresses

Layering Summer Dresses

Get the look: Elise Pintuck Mini DressFireworks CardiHigh Rise Roller SkinnyPebble Madison Flat.

For reasons having to do with the polar vortex, this past winter, I began layering dresses over jeans and fell in love with the look. To keep things from throwing too far back (think: 1996) toss a simple slip-dress over dark jeans and top with a sweater jacket, slipping on low profile flats to complete the outfit.

More fashion posts from the BLDG 25 Blog.

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Ha, thank you for avoiding 1996. Dark denim with a slip dress is lovely and actually a style I have been wearing a lot of lately.

Most people don’t actually like this ‘in between’ season but I love it. Putting summer dresses with thick knitted jumpers and boots is my heaven. Love all the layers!

Hypnotica Vintage

When I was falling asleep last night I was thinking “guess I need a new jean jacket”
fall is coming, the apples are appearing at the farmer’s market

The juxtaposition of textures is absolutely stunning. This post definitely has convinced me to delay putting away my summer dresses until the end of fall!

Love all the textures!

Pretty! I’m all about the cardigans, knee socks, and riding boots!

Warm regards,

SO so excited about this! Dying for fall.

Hi freepeople, how do I layer my short overall this fall?

great inspiration, thanks! i was just wondering how should i style my summer dresses for the colder days ^^

Autumn is my favorite season, because dressing in layers is so fun! It’s such a great inspiration to make my favorite floaty summer dresses into a fall wardrobe staple. Great inspiration post!

<3 dani

LOVE this, might try it myself! <3

Love all these looks. Thanks for the great tips!


Wow. I love the colourful shrugs over pretty floral prints.

Layering cute summer dresses is a great way to transition from summer to fall. And you never know when that brisk autumn day will happen, so having a sweater handy is a great way to stay warm while still looking fashionable.


Love this article! I’m in love with the dress/slip you put with the first outfit. I have looked everywhere for it, do you know of anywhere that might still sell it?


Do you happen to know if there is anywhere to get the white floral slip dress that you wore in the first picture?

Hi Raven, unfortunately that is an older style we no longer carry. Here are a couple other options that would be great under a chunky sweater though: (a Classic FP style) (our newest slip!)
Thanks for stopping by! :)