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How to Style a Dress from Summer to Fall

One of my favorite money saving style and fashion hacks is to re-purpose the same clothing items. Why purchase an entire wardrobe for summer, then again for fall, and again for winter, and then spring? That’s madness, I tell you. Let’s get the most out of the clothing items we already have!

Dresses in particular are incredibly versatile. Take a look at a few of my favorite basic dresses. I would bet you have something similar in your closet right now. Then, follow my tips and tricks for taking these dresses from summer into fall.

A maxi dress styled for summer then fall

Take a look through your closet now…Do you have a maxi dress? Great! Solid colors are the most versatile, so if your maxi dress is a solid, then this will be easier. Prints can work too, but be careful. Some prints will work year round, for example: polka dots, chevron, stripes. But some prints will need to stay in one season, for example: certain florals, plaids, and paisley.

For summer, I like to wear lighter jewelry, like these gold coin earrings on the left. I also tie up the hemline of this maxi dress to show a little leg. This maxi dress happens to be sleeveless, so its nice and cool for warm summer weather.

To take this dress into fall, add layers! The darker colors and paisley print of this scarf helps take the bright purple into the cooler season. And this olive green jacket pulls darker color from the scarf. If you like this dress, you can purchase it using the link below…its under $20 and it comes in many different colors!

Get yourself a chambray shirt

Here is another example of the solid color maxi dress from summer to fall. This time, this dress is an infinity dress that can be worn a ton of different ways, depending on how you tie it (hence the name infinity). It is so fun, and looks super glamorous. I have provided the link to this dress as well…see below!

This dress has an open back, so you would think it needs to stay in summer, but just remember the tip: add layers! I recommend adding a chambray shirt to your wardrobe, if you don’t already have one, since they can be styled in so many different ways. I included a link to this exact chambray below. Here, I added the chambray to this dress and threw on a scarf that had the color of the dress and the blue from the chambray to tie it all together. Plaids tend to be fall-inspired, so adding plaid to a dress can also help make it work in the fall.

Bright pink can work in both summer and fall

Now let’s move into sheath dresses. Do you have a sheath dress in your wardrobe? Good! If not, I recommend you get one (or two…or more). Sheath dresses can be dressed up for work, can go into happy hour, or styled for casual weekend events. But that is for another blog post…

I did something radical this time…the scarf is a part of the summer look! Since this scarf is bright pink and white, with a pink flamingo print, it can only be used in summer. I am obsessed with this fun scarf. I got it at the 5 spot at Target for $5! Click the Target link below to see what fun scarves they have available now.

To take this sheath dress into the fall, I added a floral print cardigan as a warmer layer. This bright pink is tricky to take into fall, but it works when paired with darker layers and accessories. Heavier jewelry is another trick for making an outfit work in cooler weather, like I did with this necklace from Noonday. Finally, I chose these amazing Target leopard print flats to further darken the overall color scheme of this outfit. Click the Target link below to see what they have this season!

Change accessories for the changing seasons

My final example is with another solid color sheath dress. In summer, I pair this peach dress with floral kitten heels and sunglasses. These sunnies are from Target. Then for fall, you guessed it, I added layers! I chose this kimono wrap for a layer with a navy, cream, and brown floral print. These colors are very fall inspired. I again went with heavier accessories for hall, like these blue shoes with a chunky heel.

Your turn!

Now, go through your closet and see which dresses you would like to make work as we enter a new, cooler season. Have fun with this! You may create new, exciting outfits from the clothing you already own! Free is the best price for new looks! Leave me a comment with a picture of the looks you put together. I ‘d love to see your creativity!

I hope you found this post helpful! You can enter your email to subscribe to my blog so that you get exclusive emails with fashion tips, style hacks, and access to fashionable, affordable clothing. To get the most out of your existing wardrobe, be sure to check my Fashion page often and Join the 5 Day New Wardrobe Challenge!

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cropped-me flowers Leah Little has a full time job as a social worker, and has managed to travel the world while wearing beautiful clothes by knowing how to score deals in travel and fashion. Learn more about her journey here.  Join the Leah Little Travel and Fashion tribe by entering your email to subscribe to be the first to learn new ways to enjoy the best in travel and fashion for less. Say hi and send her a message! Contact

Related Links:

Summer Fashion 2018

Fall Fashion Trends 2018

Transition Summer Pieces to Fall

DOs and DON’Ts for Transitioning Wardobe

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8 Comments

  1. That is what I always do, wearing summer dresses also on fall and sometimes winter. I just don’t like the idea that when the weather gets colder I should change to less romantic wardrobe. I think japanese mori kei style is a great example of layering ethreal and lacy summer dresses for colder days.

    1. wanderlustleah13 says:

      Absolutely! Good idea!

  2. Alison says:

    This is perfect! As a minimalist I would love to keep my clothes going for multiple seasons 🙂

    1. wanderlustleah13 says:

      Definitely! And i find it fun to make new looks from the same dress!

  3. Thanks for the great tips! I have so many summer dresses but nothing to wear in the fall. I will be trying your tips for sure!

    1. wanderlustleah13 says:

      Yay! Let me know how it turns out!

  4. Christine Mullan says:

    What shoes do you like with maxi dresses for fall? I’m struggling to find something I like that has a closed toe.

    1. wanderlustleah13 says:

      I’d go with booties or flats 🙂

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