This time of year can be tricky to dress for. Do we wear summer clothes? Fall clothes? The short answer: both! Temperatures are fluctuating, and so is your mood. Some days, you want to soak up the last of summer and let your outfits reflect that. Other days, you’re ready to pull on a sweater and lean into the cozy fall vibe.
In late summer, I took a trip to England, and here’s a glimpse at what I wore during this in-between season to inspire your own outfits. Mornings and evenings were cool, while the days still felt like summer. Some leaves were already starting to change, and at times I could feel fall in the air. Balancing both seasons, here’s how I dressed—hopefully inspiring your own transitional looks, too!
1. white maxi skirt + cardigan + flats + straw bag
cardigan | skirt (similar) | shoes | bag
You’ll notice that white skirts and dresses make up the majority of my late summer/early fall outfits – and for good reason! Effortlessly balancing the two seasons is all about mixing summer and fall pieces, and what screams summer more than a white skirt or dress?
Fresh, crisp, and breezy, they’re perfect for layering with moodier hues and richer fall textures. I balanced the summery vibe of this skirt with a cozy mohair and alpaca sweater. Its light beige color is the perfect in-between shade – exactly what you need for transitional weather. A straw bag adds a touch of summer, while woven chocolate brown flats bring in a subtle fall feel.
2. white t-shirt + black pants + green trench coat + sneakers
coat (similar) | pants | sneakers | bag
An olive-green trench coat is the perfect way to add a fall touch to your outfit! On a cooler morning or evening, this piece instantly brings an autumn vibe. Too warm for a layer? Simply take it off… your outfit underneath is still casual-chic! The white T-shirt balances the look with the pants, keeping you from overheating. Transitional style is all about layering and pairing the right colors with the right silhouettes!
3. floral blouse + white skirt + straw bag + flats
shirt | skirt (similar)| shoes | bag
You don’t have to pack away your florals just yet! While bright-colored florals may lean more toward spring and summer, darker or more muted prints can easily work for fall. It’s a great way to add a sweet touch without looking out of season.
A white maxi skirt keeps the outfit breezy for warmer days, while a straw bag adds texture and transitions the look seamlessly. In summer, you might pair this outfit with sandals, but swap them for black or brown ballet flats instead. The darker color, along with the extra coverage, gives it that perfect fall touch.
4. striped shirt + linen shorts + knee-high boots
shirt | shorts | boots (similar)
Summer on top, fall on the bottom! Transitional looks for early fall don’t need to be drastically different from your usual outfits. Sometimes, something as simple as a shoe swap can make all the difference. In fact, simple swaps often make the best late-summer looks!
The combination of a striped shirt and linen shorts is something I’d wear all summer long (especially somewhere like Italy), and to bring it into the fall season, simply swap your strappy sandals or espadrilles for boots.
5. white blouse + white maxi skirt + crop trench coat + boots
coat | shirt | skirt (similar) | bag
When a full-length trench coat doesn’t make sense, go cropped. This silhouette is not only a modern, updated take on a classic piece, but it’s also perfect for transitional weather. I love this Sézane one for the peek of plaid – nothing says fall quite like that -but you definitely don’t need this exact coat to recreate the look.
The white base of the shirt and skirt creates a fresh, feminine foundation for layering. For shoes, ankle boots or leather Chelsea boots are both great options to complete the outfit and add a rugged, autumn look.
6. romper + riding boots + trench coat
romper (similar) | coat (similar) | boots (similar)
Live out your English countryside dreams with this look! A romper – with shorts and long sleeves – is a perfect piece for transitioning between seasons. It’s both summer and fall in one! To lean into the fall vibe, slip on a pair of knee-high boots. Skipping tights or leggings lets a bit of exposed skin balance the outfit. To complete the look, add a trench coat for extra-chilly days, and if it gets too warm, simply remove it!
Related: 10 English Countryside Fall Outfits You’ll Want to Recreate
7. white dress + crop trench coat + boots
dress (similar) | coat | boots (similar)
Not only does a cropped coat pair proportionally well with a midi or maxi skirt, but the contrast of summer and fall is also perfect for this time of year. I leaned into a countryside aesthetic for my look, but you could easily pair this outfit with flats instead of boots. Whether you’re frolicking through fields or enjoying a slightly crisp walk, this combination gives you the best of both worlds!
8. white dress + brown flats
A summer dress paired with fall shoes is one of the best (and easiest!) ways to create a late summer outfit. Simply pick your favorite midi or maxi white dress and pair it with closed-toe flats in a darker color that screams fall. Whether you choose black, chocolate brown, or burgundy, this simple shoe swap is an effortless way to blend the seasons. Want to add texture to your look? Opt for woven shoes or add a beautiful woven or suede handbag to your outfit.
Outfits That Capture the Best of Both Seasons
It doesn’t have to be complicated. Think of dressing for this season as simply mixing summer pieces with fall pieces. It makes everything much easier! And when you’re in a pinch, reference these outfits to inspire your own looks.
Want more tips on how to balance this time of year? Here are 9 Summer to Fall Transition Outfits With Your Favorite Basics
Dear Carolyn,
I discovered you during Covid, loved your book and , happily,
have followed ever since. Beautiful home.
Bless you and your family.
Thank you so much, Mary! I am so happy you are here.
Please include outfits for plus sized ladies – using plus sized models so that we can see how the outfits really look on us. Also, if you have the sales info for any of these pieces, that would be amazing if you could include it. I’ve found the older I get, the less I enjoy physically shopping. Maybe the pandemic had something to do with it…
Thank you, Cheryl, for your feedback! I completely understand where you’re coming from and we’ll keep this in mind.