How to Style A Summer Dress for Fall

For Day 25 of 26 Days of Fall Outfits, let’s talk about how to style a summer dress for fall. One great way to get more mileage out of your summer dresses is to wear them into fall with boots and a jacket. This is similar to my LBD with the brown riding boots and jean jacket on Day 15.

How to Style A Summer Dress for Fall

I picked up this black and white jersey knit dress at the CAbi Outlet last spring, and I only wore it once. I know, such a shame! But I don’t wear dresses all that often. Here’s how I wore it last spring.


To bring it into fall, I switched out the pumps for knee-high wedge boots. I suppose ankle boots or booties could work as well, but I’m not a huge fan of dresses with ankle boots on me, so I usually stick to the knee-high variety.

How to Style A Summer Dress for Fall

Instead of the bright pink handbag, I decided to go with a deeper tone for fall. This burgundy clutch is perfect.

How to Style A Summer Dress for Fall

The dark nail polish also helps bring the outfit into fall.

How to Style A Summer Dress for Fall

If the weather is cooler, throw on a jean jacket or a fitted blazer, depending on how dressy the venue is. You know me, I am going to find any excuse to incorporate denim into my outfit!

This is an outfit I’d wear to church or out to dinner. I suppose it might even be appropriate for a professional work environment. Since summer is such a short season here in Pennsylvania, I try to get more mileage out of my summer wardrobe by pairing lighter summer pieces with heavier, cool-weather accessories.

How would you style this dress for fall??

How to Style A Summer Dress for Fall

Outfit Details: black and white dress (similar) | denim jacket (similar) | wedge boots (options here and here) | R Minkoff Mini Crosby Crossbody in Port | Silpada Half Moon Earrings | Tory Burch FitBit Leather Wrap Bracelet

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15 Responses

  1. I absolutely love black and white with a pop of color plus a denim jacket! Perfection! I have an outfit picked out for my husband’s homecoming which includes a black and white swing dress, boots, and burgundy tights. It will be too cold in February for just a denim jacket, but it is still a super cute outfit!

    By the way, I’m sort of sad that your 26 days of Fall Outfits is coming to a end. I look forward to checking them out for daily inspiration! Thanks for the series of posts!



  2. i have that cabi dress as well (I used to sell cabi). Love how you styled it! My favorite way to wear it is to ruche it up to almost a tunic length with leggings and knee high boots.

  3. Great look. I love boots with dresses. I usually pair my summer dresses with a blazer or open front cardigan with heels. Still haven’t found a pair of boots that I love.

  4. Just have to say that these boots look great with the dress! I was the critical one last week when you wore them with pants. They are very flattering with this dress.

    This dress in your spring picture looks great! Love the pop of color with the purse. I think for fall I would probably opt for a cardigan for my pop of color. I always feel weird wearing a jean jacket with dressy clothes and I also feel weird wearing it as part of my outfit. My brain screams “you’re inside!! Take off your coat!!” 🙂 I like the look on other people I just can’t pull it off.

    I hate to see the series end, by the way! 🙂

  5. Thanks for the daily posts! I’m a 5th grade teacher in California and your ideas are perfect for the casual culture of my school. As a matter of fact, any time I wear a dress my students think I’m ‘dressed up’. 😉

  6. Love the dress! And you’ve styled it nicely for fall.

    I recently discovered a CAbi outlet store nearby. Lots of pretty clothes, from previous seasons. And the staff was friendly and helpful.

  7. Totally love that love!! I have a dress that I purchased to wear to an August wedding that I think I can style similar. (The dress is a dark royal blue sheath – knee length, with faux zippered pockets (in the hip bone area) that have a black placket.) If I’m successful, that’s an extra Fall outfit for work. Yay! I may try to incorporate some sheer black tights (maybe patterned?) as it’s cool in my office.

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