When It’s Almost Fall, But Still (Technically) Summer: This Outfit

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Spring and fall are sometimes referred to as “transitional seasons,” but I think the days lingering between summer and fall (and also those between winter and spring) feel the most transitional. 

I’m talking these days, right now, in late August and early September.

This time of year carries the highest amount of tension for me — a mix of extreme excitement for a fresh, new season, with doses of guilt for not living in the moment. It’s also the hardest for me to dress for, but I think I’m finally starting to nail a few outfit combinations that are spot on for the temperatures yet still enjoyable to wear.

The Best Summer-To-Fall Outfit For My Coastal Grandmother Aesthetic

Freeing myself from the mindset of needing to completely shift into “Fall Mode” has been key to finding joy. 

I’ve decided to keep the thicker layers tucked away with the shorts staying in regular rotation, but have begun to mix in a few lighter sweaters that are cozy enough for cool evenings.

One of my favorite combinations right now is pairing denim shorts with oversized sweaters (works just as well with casual hoodies too). The pairing is incredibly comfortable while giving me a little reprieve from the skin-baring outfits that mark summer days.

1 of my fave combos right now is pairing jean shorts with oversized sweaters. The pairing is incredibly comfy while giving me a reprieve from the skin-baring outfits that mark summer days.

Shop the cardigan: Farm Rio | Neiman Marcus | Net-A-Porter
Shop the shorts: Shopbop | Revolve
Shop the clogs: Nordstrom | Backcountry | Zappos | Urban Outfitters | Amazon

While the suede clogs are becoming a rare gem to find in certain colors and sizes, I’m rounding up all options further below in this post!

Wear A Light, Oversized Open-Knit Sweater Or Cardigan

A prized sweater in my closet right now is the Farm Rio Mixed Textures Button-Up Crochet Cardigan, which has been ideal for this transitional-outfit idea I’ve been enjoying.

The silhouette of the Farm Rio crochet sweater is loose & drapes effortlessly around jean shorts. The color is bright + cheery to help me soak up an end-of-summer state of mind while still being a sweater.

cardigan | shorts

The crochet element is breezy enough while still feeling cozy. It’s very much a seaside (#CoastalGrandmother) staple. I’m so feeling the granny squares in this.

The silhouette is loose and drapes effortlessly around jean shorts. The color is bright and cheery to help me soak up an end-of-summer state of mind while still being a sweater.

The cardigan has a little of everything for both summer and fall.

Any open-knit sweater design is perfect for this summer-to-fall transitional-outfit idea while still being wearable in the heat that can be lingering this time of year.

cardigan | shorts | clogs

Any open-knit sweater design is perfect for this transitional-outfit idea while still being wearable in the heat that can be lingering this time of year.

Shop More Open-Knit Sweaters For A Summer-to-Fall Transitional Outfit

I’m eager to see how long I can rock the shorts-and-sweater combination, even if it means eventually swapping the top for a warmer, tighter-knit sweater!

Add Cutoff Jean Shorts + Trending (& Comfy!) Clogs

I’ve never been happier to see both Birkenstock Boston clogs and simple black flip-flops trending in footwear. Both shoes are an easy slip-on option that provide a minimalistic, coastal look.

Naturally, I’m obsessed. 

Birkenstock Boston clogs are an easy slip-on option that provide a minimalistic, coastal look.

cardigan | shorts | clogs

While flip-flops can be found just about anywhere (but are also coming to a close with the summer season), Birkenstock clogs have become an “It” shoe for fall on social media, making them increasingly hard to find in stock. 

I searched the internet high and low for more Boston clog options (and even found a few “alternative” brands). The shearling-lined Birkenstock clogs are a great option for those of us in colder climates!

Shop More Birkenstock Clogs (+ A Few Alternatives)

AGOLDE Parker cutoff jean shorts are my most-worn denim, & they complete this outfit with prime comfiness.

cardigan | shorts | clogs

And for the shorts? The outfit is at prime comfort when you reach for your most-worn denim.

For me, that’s good ol’ AGOLDE Parker cutoff jean shorts in wash Riptide.

Xx,
Amy

Let’s be friends on Instagram! Sharing life from my sleepy little beach town, daily style, makeup favorites, Gilmore Girl binge-athons and endless cups of coffee — all with a good dose of adorable toddler content too.

Oh, hey, Pinners!….

Oversized sweaters, cutoff jean shorts + shearling-lined clogs make the perfect summer-to-fall outfit. + they really work for my coastal grandmother vibes.

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