Land of Oaks and Roses

Land of Oaks and Roses

At the Market // The Transition

Part 1!

Olivia Wright's avatar
Olivia Wright
Aug 20, 2026
∙ Paid

Welcome to At the Market, your place to browse what’s in season in Land of Oaks and Roses.

People are using the term “transition" instead of fall, which I can get behind. Feels gentler. So let’s go with it. The transition is my absolute favorite time of the year. I love routine. I love how the air feels. I love everything about it (I tried to name my daughter September but my husband wouldn’t go for it!!) I also really love the clothes. The combination of long sleeves + shorts, long pants + flip flops, summer dresses + jackets… Our outfits get so creative even when we’re not trying because we’re mixing things that don’t usually go together.

If you’re ready to tap into my LOVE for this time of year, here are the 3 pieces I’m most excited to wear for the transition. Going to make this a 2-part! Here’s part 1…

THE OVERSIZED CHECKED BUTTON-UP

It’s a shirt, it’s a jacket, tie it around your waist! There are endless ways to wear this, and it’s one of the first transition pieces you can mix in with what you’re currently wearing. Instantly brings out your inner cool girl (we all have one.)

A Gap Factory find! My blue checks - recommend sizing up I’m wearing a L. This green is the thickest of the bunch perfect for wearing as a jacket. The details on this brown check are really good - slightly longer in back than front. The gray has some polish that’s nice for the office. And another blue that feels surfer girl also available here.

THE SLOUCHY PANT

Wear these with your summer flip flops for that contrast (= good outfit.) Slouch is where pants are headed and I’m pretty happy about it.

This post is for paid subscribers

Already a paid subscriber? Sign in
© 2026 Olivia Wright · Privacy ∙ Terms ∙ Collection notice
Start your SubstackGet the app
Substack is the home for great culture