Fall Transition: Sleeveless Dresses

I’m a big advocate of sleeveless dresses. I often gravitate towards sleeveless so I don’t have to worry about the fit across my shoulders. I’ve found I have wider than average shoulders, so any dresses that are more structured and have sleeves can be hit or miss for me.  I also love that you can wear sleeveless year round with just some slight modifications.


Today I’m joining in on a blog hop from The Blended Blog! Three of us will be featuring ways to transition your wardrobe into fall, so be sure to visit Leslie and Sarah.

On to transitioning sleeveless dresses. There are three different ways to do so; cover, over and under. I’ll go over each way with an example.


Cover is likely the easiest way to transition sleeveless dresses. You can use a cardigan, blazer or even a vest if your weather is still warm. I say this is the easiest way because all you need to do is throw on and go. Plus it is nice if you might get warm once afternoon hits and need to remove a layer.


Over is a great way to get a skirt look using a dress. Throw on your favorite sweater or even a long sleeve shirt. This look takes a bit more planning. Be sure to take into account how your dress lays on top. The best bet is to go with a dress that is a bit more fitted, at least above the waist. If the dress you want to wear is bit more flowy, try a sweater that is slouchy. Also be aware of where your sweater hits at your waist/hips. You don’t want to completely lose your waist with a sweater that hits too low. Best best is to play dress up in your closet to figure out what combinations work best.


Under is the one style I struggle with. The biggest component for this is the type of shirt you wear underneath. My big find last year was a tissue tank from Old Navy (try this one from J Crew) and it was a game changer. A tissue tank is thin enough to lay nicely under your dress. Wearing something under your dress is a great way to change up a look. You can try a monochrome look like I have in this example (people actually thought the dress had long sleeves!) or you can go with more contrast like this look. I recently got a heavy t-shirt type tunic and can’t wait to try a plaid shirt underneath it. When picking out items to try, go with lightweight items for under and more structured, heavy dresses on top. This will help the layers lay nicely and you won’t get those dreaded funny bumps from your undershirt!


What is your favorite way to transition sleeveless dresses; cover, over or under?


Now, be sure to go visit Leslie at Once Upon a Time and Happily Ever After on how to transition lace tops and then Sarah at Foxy’s Domestic Side with booties for week two of The Blended Blog blog hop.

Shop Cover, Over, Under options



25 thoughts on “Fall Transition: Sleeveless Dresses

  1. Chelsea @ That's So Chelish

    Here from TBB hop. I totally feel you on the man shoulders issue – finding things that fit my shoulders well is always a struggle. Your ideas of layering with a sleeveless dress are so smart! Thanks for the tips!


  2. Sarah @ Foxy's Domestic Side

    Those knee high boots, love them! And I’ve always tried to get the shirt over my dress thing to work, but it never quite works out for me, you did it great, and putting the t-shirt under the dress, awesome! That one you styled is perfect!

    1. Alison C

      I’ve found fit and flare dresses work the best for sweaters over and then a sweater that isn’t really long. Ha, I just realized all three outfits had the same boots, guess I wear them a few times 🙂

  3. Leslie Clingan

    Hey, love! Great, great ideas here. I have a couple of sleeveless dresses that I hesitate to wear, no matter the weather, because I no longer love my arms. I have used a cardi with them but love the idea of over! That over business transformed your dress into a cute skirt-look. Genius! XO

  4. Carrie

    My fave is the first look! That blue is gorgeous and you chose the perfect jacket to go with it. The boots are to die for too. Thanks for linking up with Whitney, Casey & Carrie.

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