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Maxi/Midi dresses: the perfect fall transition piece

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I don’t know about your town, but in San Diego, fall just suddenly dropped in out of nowhere.

One minute extended summer seemed in full swing; the next, clouds are covering the morning sky in a fluffy grey blanket, lingering until 2pm and even dropping some occasional drizzle. . .  (For my PNW and East Coast readers, I know this is a totally So-Cal thing to say!) Anyway, what I’m getting at is that fall is definitely here, and even though I love summer, I also love the change that comes with the turning of seasons! Fall has a crisp newness, bringing in heartier veggies, soups, warming spices, and of course, awesome new styling options!

The fall transition means that the weather turns unexpectedly warm (or unexpected cool) at various points throughout the day.

The fickle weather makes it challenging to figure out what I’m going to wear; do I layer, at the risk of having to un-stylishly stuff my sweater in my purse for 80 percent of the day? Or do I leave the sweater at home and risk feeling chilly with hunched shoulders and prickled skin all afternoon?

Enter: the linen maxi/midi dress.



Linen is the perfect transition material: it is breathable so you won’t melt in an unexpected heat spell, but it is also a substantial fabric that will insulate you better than cotton or synthetic fabrics like rayon. Also, the shape created by linen as it falls gives the maxi dress silhouette a more structured look that pairs beautifully with colder-weather footwear like boots, sneakers, or (for warmer days), slides with a bit more foot-coverage (shown in this post). Since I’m definitely reaching for neutrals this fall (see my previous post on neutrals!), I picked this perfect gingham maxi dress from Urban Outfitters.


The gingham trend was trending hard this summer and I definitely see it continuing into fall but with more understated colors, like chestnut browns, tans, creams, muted yellows, and dusty orange. I also love that this dress is a wrap-dress, a style popularized a few years ago by French cool-girl Jeanne Damas (founder of Rouje) that is still going strong. This cut is almost universally-flattering, easy to wear (it’s a statement already so you don’t want overthink the accessories), and exudes a laid-back elegance that makes me feel beautiful, feminine, but not too “done.”

My rule of thumb for the fall maxi: look for dresses made of heavier materials and warm neutrals, and style them with minimal accessories in simple shapes.



The accessories I  wear with the dress are the same investment pieces that I featured in my last post, which I incorporated into this outfit because I wanted to show how versatile a few well-made, unique pieces can be!

Shop this look:

  • Paloma Wool Lava Midi Dress (available here, at my fav local shop, Maven!)
  • Faithful Sangria Linen Shirtdress (available on Anthropologie, I love how they style it with a white tee!)
  • at Dawn. Dolman Linen Maxi Dress (available on Garmentory, with a few other similar cuts in different colors)
  • Urban Outfitters Gabrielle Linen Midi Wrap Dress (seen on me in this post, but I’m petite so it fits like a maxi on me! Shop here.)
  • Necklace: Graffiti Beach in San Diego; Bag: Simon Miller; Shoes: Rachel Comey

I hope you are enjoying the fall as much as I am! Be sure to read my next blog post, where I did the photoshoot in one of my favorite spots in my neighborhood of North Park, and I talk about one of my go-to outfits: a recent vintage find paired with shoes by one of my go-to indie designers, Marais USA! Can’t wait to share with you!

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