How to Style a Summer Dress for Fall

berry wrap and yellow eshakti sailboat summer dress styled for fall

Dear Mia,

This is what I get for wearing a fit and flare during a storm– had it hold it down with my hands whenever I went outside. I generally like to have clothing that’s seasonless, but barring that I like to wear things as long into the upcoming season as possible. Especially when it’s summer to fall because I like to layer!

The styling worked out pretty well and I liked this berry color with the yellow. Initially I was thinking blue, but then no, too easy. I ended up picking the berry color because I like it and it’s popular for fall. 

eshakti sailboat dress skirt blowing in the wind

Getting a bit breezy! I like to wear slips under most dresses and skirts. This one’s a Vassarette from Target.

  • Velvet/Anthropologie wrap top (swapped from Lydia)
  • eShakti sailboat dress (c/o, Spring 2013)
  • Arturo Chiang tall suede boots (past season by many seasons)

The last time I photographed these boots for the blog was in 2010! That means they’re going on their fourth winter now… not bad. I also last wore them in a post where styled an out of season piece for the current season, in that case it was a summer dress styled for winter. I hardly ever try to wear summer things when snow’s on the ground any more, but it did make for a fun challenge!

How long into fall do you keep your summer dresses out?


  • Kristin

    Love those boots with it! Such a cute look!

  • Mia

    Ooh, I LOVE the berry+mustard combo. (Not so much food-wise, but color-wise it’s a winner!) For me, it depends on the summer dress. I have a few that are too hard to layer because of sleeve issues, and some other dresses (and skirts) that, due to material or color or what-have-you, just don’t jibe with any of my colder-weather clothing, so I pack them up when it starts to get cooler. There are some that are nice and versatile, though–like my well-worn Aryeh dress–that I can layer up and wear all winter long, though!

    • Alexandra Shook

      I didn’t even think of food until you pointed it out. Yeah… I don’t think I would go for berries and mustard either.

      I think that now this dress has to be put away until next season. I’m not sure about it with tights– woven cotton just seems to stick even with a slip. It just got very cold here… I’m actually wearing pants!

  • megan
  • Shen Dove

    The colors of your top, dress and bag work great together!

  • Eriel

    I just discovered your blog! I adore it! :) I’m definitely going to be reading frequently! Also, I just started a blog and it’d be amazing if you could check it out and give me suggestions? Thanks hun!

  • Veloria in Velvet

    Love this color blocking…mustard and burgundy are 2 of my favorite colors for fall :)

    Veloria in Velvet

    • Alexandra Shook

      Thanks! I was really pleased at how the colors turned out!

  • lyddiegal

    Oh yes, the yellow and berry do look nice and autumnal together!

    I keep my summer dresses out for as long as it pleases me. While I’ve certainly styled some of them with snow on the ground as well, I don’t think I did at all last winter (that was ridiculous).

    Did you do custom sizing with your dress or a normal size? Because I just got a dress from them which I did custom and I’m disappointed.

    • Alexandra Shook

      I got this dress custom made and it is a little large around the lower rib cage. I’ve never had anything normal size from eShakti before… but it could probably work out. Although I don’t have a typical shape, so I think the custom sizing works pretty well for me.

  • Silvergirl

    what a cute idea for this dress
    i love that the wind is kicking up the skirt, looks like your sailboats are sailing away!

  • Nnenna

    Look at you smiling in these pics! :D I love this color combination- I think it’s so pretty.

    • Alexandra Shook

      Yeah I think it’s more of a grimace actually. It was windy.

  • Chrissy (@CrashBeauty)

    I immediately knew that was an eshakti dress haha. I love the berry combo and the dress is the perfect color to work for both seasons.

  • Kelsey

    LOVE THIS!!!! Now I’m wishing I had snapped up that dress when it was available. <3

  • elle sees

    love how you styled this! such pretty colors