Summer to Fall Transition Outfits – Cute Fall Fashion

With fall weather almost upon us, this is the perfect time to get the most out of the last days of sunshine while putting together the best summer to fall transition outfits checklist. You see, there is something refreshing about shifting your focus from trendy warm-weather fashion styles to fall-appropriate assemblies. Sure, sometimes the thought of kissing our cute floral dresses goodbye can be a bit disheartening. However, that doesn’t mean that we can’t have fun hunting down cute fall transition outfits. Now is the time for early fall outfit ideas!

Luckily for us, the top trends have graciously offered us a slew of fashionable yet practical ideas for this season and beyond. But, before you start dusting off your chunky sweaters and trusted puffer jackets, let’s take a moment to appreciate those summer to fall transition outfits that help us battle the unpredictable weather changes.

Let’s be honest. There is nothing more frustrating than feeling extra cute in your lightweight knit in the morning. But, as soon as the afternoon comes, you find yourself sweating profusely. Yes, we’ve all been there. It seems like you can never win with these temperatures, right? Well, you will be happy to hear that I have been on a mission to trick the frustratingly contrasting fall weather with outfits that match both the temperature and my obsession with the #fallvibesaesthetic.

Fashion blogger, Bella Bucchiotti of xoxoBella, shares some summer to fall transition outfit ideas.

Cute Summer to Fall Transition Outfits: Tips & Ideas

Let’s get started with the biggest seasonal clothing swap out of the year. Spoiler alert: There is a lot to discuss.

Lightweight Outerwear is the Key to an Easy Summer-To-Fall Wardrobe Swap

Yes, I know. You have been dreaming of chunky sweaters and snuggle-worthy cardigans since July. We all prefer to sit next to the fireplace with our cozy blanket and a cup of hot cocoa in hand. However, during the first months of fall, this type of layering is simply not allowed. Instead of splurging on the top knitwear trends, try investing in some easy-to-wear, everyday layering pieces. Why? Simply because lightweight jackets for fall are ridiculously easy to throw on and off as soon as the weather changes during the day. They are a great addition to your fall capsule wardrobe.

Fashion blogger, Bella Bucchiotti of xoxoBella, shares some summer to fall transition outfit ideas.

Opt for a slightly-oversized denim jacket for all your future streetstyle-approved outings. That way you will have a key, staple piece ready for grabs to complement each and every ensemble while still keeping you warm and comfy. Once the weather decides to start getting warmer again, you can shed the layer.

Just in case you aren’t a fan of denim jackets, there is an array of lightweight outerwear for all at your disposal. Think button-up fleeces and military-inspired neutral-coloured jackets.

Fashion blogger, Bella Bucchiotti of xoxoBella, shares some summer to fall transition outfit ideas.

Maxi Dresses for Fall Layering

Maxi dresses are equal parts cute and layer-able. Amongst all options, these beauties certainly reign supreme. Summer-to-fall dressing requires breathable, thin fabrics that offer enough coverage to protect you from the sudden wind blows. Maxi dresses for fall aren’t only ultra-comfortable, but also double as the perfect layering pieces. The best part? Even your floral dresses count! Toss them on before you leave the house in the morning under a denim jacket. If you really want to stay on top of the 2021 fashion trends, choose a vibrant colour maxi dress for your summer to fall transition outfits.

Fashion blogger, Bella Bucchiotti of xoxoBella, shares some summer to fall transition outfit ideas.

Fall Outfit Ideas with Interesting Tops

It’s no secret that I love statement-making tops. Whether its sleeves adorned with ruffles or the classic bell-sleeves pattern, anything goes really. Arguably, you can’t talk about the cute fall transition outfits without listing at least 5 cool-weather-appropriate tops for women. Nowadays, tops with statement sleeves are certainly the most sought-after fashion piece. Even if you are putting together a lazy girl outfit, these beauties can instantly add an effortlessly chic vibe.

Pair them up with your favourite maxi denim skirt when the weather is a bit too chilly, tack them inside your tailored trousers or rock them with a pair of figure-flattering jeans. The styling possibilities are endless. Plus, no one is stopping you from using your new staple piece, the slightly oversized denim jacket, for the ultimate denim-on-denim look.

Fashion blogger, Bella Bucchiotti of xoxoBella, shares cute fall transition outfits.

| Top | Jeans | Shoes |

A special thank you to Allison Kuhl for the most amazing photos. ❤ 

Put Your Trust in Athleisure

The athleisure trend has taken over the entire fashion world by storm – and, honestly, who is complaining? For years, the simple idea of rocking your workout leggings anywhere outside the gym was frowned upon. Fast-forward to 2021, hoodies, bicycle shorts, windbreakers and everything in between are flooding the streets. Luckily for us, Athleisure is yet another clever way to style the ultimate summer to fall transition outfits.

Fashion blogger, Bella Bucchiotti of xoxoBella, shares cute fall transition outfits.

No matter if you are planning on meeting your friends in the city, going to the movies, or have just started roller skating, comfortable yet utterly stylish athleticwear is the key.

We’ve seen cropped hoodies with leggings, skirts, sweats, and even tailored trousers. Are you a fan of the varsity outfit trend? Layer your favourite varsity-inspired jacket with a comfy sports bra and a pair of vintage jeans and you are good to go.

Time to Upgrade Your Fall Denim Game

Everyone and I mean everyone, loves a great quality pair of jeans. They are classic, versatile, and will never go out of style. We are talking about the best all-year-round option that can take you from day to night. Plus, the process of styling these trousers is a breeze.

Now, even though there are many rotating trends, you need to consider many factors before splurging on the latest “it” style. Pick the one that fits your silhouette the best. Moreover, it’s a matter of personal preference as well. Not everyone loves a super slouchy pair of 90s inspired jeans. At the same time, many might want to avoid skinny jeans like the plague. Some adore mum jeans, while others prefer patchwork and multi-coloured options.

Fashion blogger, Bella Bucchiotti of xoxoBella, shares cute fall transition outfits.

It’s not all about denim trousers though. There is a plethora of cute fall transition outfits that revolve around denim dresses as well. These figure-flattering styles look fantastic with sneakers and fall boots, what more can we ask for? The material offers enough protection from the chilly weather, while also keeping you cool.

Let me know if you have any other fall outfit ideas that I should add to this list of summer to fall transition outfits. For many, autumn is a favourite season, so let’s embrace it!

Bella Bucchiotti

Bella Bucchiotti is a storyteller, food lover, dog mom and adventure seeker living on the Pacific coast. She shares her passion for food, dogs, fitness, adventures, travel and philanthropy, in hopes of encouraging followers to run the extra mile, try new recipes, visit unfamiliar places and stand for a cause. Bella lives with Type 1 Diabetes and Celiac Disease.


Welcome to xoxoBella! You will find delicious recipes, travel inspiration and all the things that Bella loves.

Leave a Comment

  1. Deborah wrote:

    This is such a pretty top – bell sleeves are lovely!

    Posted 9.4.20 Reply
  2. sophia lu wrote:

    ohhh they look gorgeous! i also love the texture of the ones you’re wearing <3

    Posted 9.4.20 Reply
  3. your top is SO cute!!! I love the shade and cut! and this spot is gorgeous!

    Posted 9.4.20 Reply
  4. Jenny wrote:

    I love that top on you! Plus this bridge is so cool and makes for a fab photo backdrop.

    Posted 9.4.20 Reply
  5. You always have pics in the most amazing places– this is so cool!

    Posted 9.4.20 Reply
  6. Anna Hubbard wrote:

    This sweater looks so cute and comfy!

    Posted 9.4.20 Reply
  7. Love the bell sleeved look! I’m currently wearing a top like that right now!

    Posted 9.4.20 Reply
  8. Alix Maza wrote:

    I’m not the biggest fan of bell sleeves, but this top is so cute!

    Posted 9.4.20 Reply
  9. Obsessed with that Thermal Bella!



    Posted 9.4.20 Reply
  10. My Converse are in desperate need of a wash, I’ll have to try out your tip!

    Posted 9.4.20 Reply
  11. Ash Neverson wrote:

    I love this location shoot! You’re sweater looks so good!

    Posted 9.4.20 Reply
  12. Karoline J. wrote:

    I am in love with bell sleeves! Gorgeous outfit

    Posted 9.4.20 Reply