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It’s time to start thinking about what summer wardrobe staples can easily transition into the fall!

It can’t just be me, right?!? 😉

The beginning of fall here can be very temperamental. So, I’ll be adding some of my favorite summer wardrobe staples into my capsule.

They’ll definitely come in handy when Mother Nature throws in her hot and humid days. But they’ll be great when it gets cooler too. With the right layers of course!

I feel like I’m at a good place with my closet overall. But, one thing that I’d like to eventually do is refine my closet further and have fewer pieces of clothing overall.

That’s why it’s so important to me to buy wardrobe staples that are versatile pieces. Ones that can be worn for most, or all, seasons.

Sure there’ll always be pieces that are only appropriate for one or two seasons where I live. Hello, wool sweaters! But I would ultimately like for most of my pieces to be able to do multiple seasons.

When I thought of doing this post, I had a pretty easy time choosing the summer wardrobe staples that I wanted to include.

They’re the pieces that I really enjoyed wearing this summer. And they’re the ones that I quickly gravitated to when it came time to select items.

This is one of the first steps that I take when I plan a new capsule…I look at the previous capsule to see what ones were the wardrobe staples and which of those will easily transition to the new capsule.

Check out this post if you’re interested in putting together a capsule wardrobe but you’re unsure of where to start.

The Summer Wardrobe Staples

A wooden rack with my 3 summer wardrobe staples hanging from it...a pink slip dress, an olive green jumpsuit and a long floral dress.

For this styling post, the summer wardrobe staples that I chose to style for fall consist of 1 jumpsuit and 2 dresses.

The jumpsuit is made from raw silk and is olive green with spaghetti straps and wide legs. I see myself wearing this with a top layered underneath or a sweater over top for the cooler weather.

The dresses I chose include a tencel/recycled polyester blush pink slip dress and a vintage floral button front rayon dress. I imagine wearing these in a similar way as the jumpsuit, with cozy layers under and/or over top.

Summer Wardrobe Staple No. 1: The Jumpsuit

I bought this jumpsuit back around the beginning of summer. One of my absolute favorite fabrics is raw silk. I love how breathable it is but I also love the nubby texture as well as the fact that it doesn’t feel delicate!

I am wearing my fist wardrobe staple...the olive green jumpsuit with a cream colored silk blouse underneath. The blouse has an equestrian print and I am wearing it with brown boots.

I knew that olive was a color that I wanted to include in my fall capsule so I naturally gravitated to this jumpsuit. The top of the jumpsuit definitely leans towards warmer weather, but with the right layers, it will be perfect for fall too.

Since the top of the jumpsuit is so open, it’s a great piece to layer a top under where a good portion of the top can still be seen. And this vintage silk shirt with an equestrian theme is perfect with it.

The colors go so perfectly with the olive and the details, such as the gold buttons, can really shine (pun intended ;)).

I completed the look with a pair of thrifted brown suede booties and a brown crossbody bag.

Here are some other ways that I have styled this jumpsuit…

Summer Wardrobe Staple No. 2: The Slip Dress

Both of these dresses are items that I bought over the summer, during the month of August.

The second wardrobe staple is the pink slip dress which I am wearing over a silk leopard print dress. I am wearing black combat boots and a black handbag.

I had spent a good portion of the spring trying to find a slip dress that I could use for layering but I didn’t have any luck finding it.

Fast forward a few months, when I had given up on finding one, I came across this blush pink one at a local department store.

The leopard print dress was a late August find. I had been searching online for a piece of leopard print clothing to add to my fall capsule and I came across this dress.

Once I found it, I knew that it would be perfect with so many of my clothes. I think that it adds so much visual interest to this dress and I am really digging the sweet and sassy contrast of the 2 dresses.

To complete the look, I added some black combat boots, which had been a souvenir from a trip that I took back in early summer.

Then I added an old black leather bag with chain detailing. I pulled my hair over to the side and secured it at the base of my head with some pins.

Here are some other ways that I have styled this dress…

Summer Wardrobe Staple No. 3: The Floral Button Down Dress

My third summer to fall transition piece is this vintage floral button down dress that I got from Etsy at the beginning of the summer.

The third wardrobe staple which is floral print button front dress that I have worn with a cream colored mock neck sweater tucked into a tan leather belt. I am also wearing tan boots and holding a tan bag.

I hadn’t even been thinking of all the possible ways that I could wear this dress when I first bought it. But it’s versatility is one of my favorite things about it, third to the buttons and floral print of course ;).

I really love how this dress looks like a skirt with the simple addition of a belt and sweater.

For this look, I folded the front hem of the sweater up and then tucked it into the belt. I think this little styling trick really makes this dress look like a skirt.

I added a pair of tan boots and a cognac tote to complete the look.

Here are some other ways that I’ve worn this dress…


Do you often think of the versatility of your pieces?

I know I never did.

If I bought a piece of clothing during the summer that I wore while it was warm, I pretty much only wore it during that season.

It has only been since I downsized my wardrobe that I have started to think of my clothing as being multi-seasonal pieces.

I encourage you to look at your favorite summer pieces and see how you can style them into fall. And maybe winter!

For more fall styling ideas, check out this and this!

I’d love to hear what your favorite summer to fall look was…1, 2 or 3?

And don’t forget to follow me on Instagram and Pinterest for more style inspiration!

Until next time,


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This Post Has 4 Comments

  1. Jan Marie

    Gillian, you nailed it. These three looks show great versatility in a wardrobe and, my favorite: they aren’t boring colors or fabrics or prints! Dusty Rose, split pea green, buttercream mixed with leopard, tiny 90s floral, and giant galloping horses? That’s a mix, and I appreciate it!

    I hate khaki green but I loved look 1 the best. The shirt’s large scale pattern is so striking against the one-color long dress. This look is really a success.

    Look 3 taught me a new way to do my sweaters up! I know you’ve done it before but this look is particularly successful. Feels very… Montana waking through a field of wheat. I love it.

    Leopard is my fav print and pink is one of my fav mix-ins, so I liked this color/print combo, but I wasn’t a fan of the mixed drapings; with the back interest on the leopard dress I could tell it was a dress (not a shirt) under the jumper, which makes it feel heavy to me. Still a very cool concept though – and love the back on that leopard dress! So sexy.

    All in all I’m LOVING this brave, bold dressing style. Keep it up!!!

    1. Gillian

      Thank you so much for your comment Jan!! I really appreciate you taking the time for such a comprehensive reply! I’m glad that you liked the combinations and that you found a new way to style some of your pieces! I am very much enjoying mixing in some fun prints and colors into my wardrobe! I went through the whole neutral colored everything when I started decluttering my closet, but in the end, it didn’t feel like it was entirely me! I am feeling confident again and not like I’m just following the crowd! Thanks again for your comment!

  2. Krystal

    Gillian, you are 100% the Queen of Layering! I love when you do posts like this – they inspire me to get more creative with my wardrobe (and packing!).

    I think I’m torn between the first and third looks, but that’s a tough call!

    1. Gillian

      Thank you so much Krystal!! I really appreciate your comment!! These are actually my favorite types of posts to do!! If there’s ever an item that you want to see my style different ways, please let me know!

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