A Great Dress for Summer into Fall

I wanted to share this outfit with you guys today because it’s affordable, super cute and perfect for transition from summer and fall. Really in general, a lot of the dresses you have been wearing this summer can transition into fall by adding certain accessories.

Boots are the most obvious addition. It’s so simple to throw on a pair of knee-high or over-the-knee boots to take a dress from summer to fall. The exact boots I’m wearing in these photos aren’t available anymore so I linked similar ones from Sole Society that are great quality. I don’t own these particular boots, but I own over a dozen pairs from Sole Society and I can tell you with certainty that they are some of the best quality shoes I’ve ever had.


The color of your accessories can also make something feel more appropriate for fall in my opinion. For instance, my backpack is a rich neutral color that reminds me of the leaves changing color. I love this backpack so much and have been carrying everywhere lately. Backpacks are a great way to free up your hands so you’re not lugging a big purse around all the time. Don’t get me wrong, I love my purses and still use them regularly, but this backpack has been so convenient. Especially while chasing my two kids around. Well, chasing Molly and holding Riley. I need my hands free as much as possible to do those things!

I also think a fun wide brim hat feels very fallish to me. I have a huge head so I prefer a hat with a wider brim because they look better on me. And really, I think they just look better on everybody.


I bought the dress I’m wearing because it was affordable at under $60 and easy for me to breastfeed in. I kind of just figured it would be a summer dress while Riley was young, but the other day when I went out in the morning it was kind of chilly so I threw on boots and realized it was absolutely perfect to transition into fall. Plus this dress will be flattering on most body types, which is so great.

I just love this entire look and wanted to share all the details with you guys! Let me know if you have any questions in the comments below. My plan is to respond to EVERY comment on this post today!

P.S. Some of the below photos are what it is usually like these days when I try to take photos with Molly. Ha! It’s always eventful 🙂


21 Thoughts

21 thoughts on “A Great Dress for Summer into Fall

  1. Sweet dress! Such an easy-breezy look. Ali, I love how you include flowers in a lot of your photos – today’s flowers in your post are especially cute – love the wild flowers look! Reminds me of myself – whenever I am out and about on my travels I try to make it a point to pick up some flowers to either bring back with me, stop and smell, or put in my hair! Such a simple thing but it can brighten up your day : )


    1. I love flowers! Though I have been really loving faux greenery to use to decorate my house. It gives me that feel and doesn’t die on me after a few days 🙂

  2. I love knee high boots, but as of now, I don’t have any because it is soooo difficult for me to find a pair that fits my calf! Ughhh

  3. You look adorable, Ali! Molly appears to acting point on for a 2 yr. old!😊 I like the dress in the blue floral pattern, too.

  4. Ali can you tell me where the top is from on your IG photo with Molly the other day? I absolutely loved it!

    P.s it’s definitely getting to be fall in the Berkshire’s 😀

  5. Love this outfit! I am decent at picking out cute pieces, but terrible at putting outfits together. I always reference your blog for inspiration! Looking forward to more fall fashion posts! 💕

  6. This gives me all the fall feels! You are so pretty.

    Would you consider blogging about your family planning and how you and Kevin arrived at the decision to stop at 2 kids? I know it’s very personal, but you’re usually so open, and I’d love a dedicated post on all the factors you weighed as you determined family size.

  7. Ali, I’m old enough to be your mother (!) but I’ve been following you since your Bachelorette days. You are so refreshingly “normal”, down-to-earth and genuine. It’s fun to get clothing ideas from you and I’ve ordered so many of the things you’ve posted over the years and have loved them all. Thank you! You and your family are darling. 💗

  8. Love the dress? How do you think this dress would look with leggings and a cardigan? Would it ‘work’? Thanks for always sharing!

  9. Ali,

    I’ve been reading your blog for quite some time now, but I’ve never left a comment before. I’ve never considered myself to be very good at fashion, but your outfits and ideas have been really inspiring me. I have actually been having a lot of fun lately by looking through tons of your posts and using that inspiration to reinvent my own wardrobe (which is something I never thought that I’d enjoy doing!). Thanks for helping me feel like I can do it too! I especially love all your fall and holiday posts over the years – I can’t wait to read more of them throughout this coming season!

    ♥ Kassie

  10. Oh man I can’t WAIT for fall!! I’m dying over here- I have a feeling fall weather won’t show up until mid October here (I’m in Ontario, Canada) love this outfit. I love wearing dresses in the fall usually I have to wear tights under them because it can be quite cold!

    I had to laugh at your photos with Molly. I’m going through the same thing with my daughter Rylie. She’s only a few months older than Molly and man can she be a handful. She is so photogenic but getting her to take a photo or listen these days is a real challenge! Haha oh 2 year olds…

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