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13 Ways To Transition Your Wardrobe From Summer To Fall (Hint: It's All About The Layering!)

As much as I love the summer, I always get excited at the thought of wrapping up in chunky knits and oversized sweaters when fall finally arrives. I love the summer to fall transition; and now that we have moved into our forever home in Texas, I have full access to my whole closet, so the layering possibilities are virtually endless!

Summer To Fall Transition Outfits 2021 

Layering is the key word here, as I think layers are the best way to transition your outfits from summer to fall without falling into the trap of wearing too much too soon. How many times have we woken up to a frosty morning and wrapped up in our heavy wintry clothes, only to break out into a huge sweat by lunchtime when the temperature soars? Dressing for fall can actually be quite complicated in places with unpredictable weather, so starting off small with subtle layers can be easily taken off and put back on is the best way to do it.

How Do You Transition To Autumn?

Although Texas weather isn’t unpredictable, per se, it definitely doesn’t match up to the monthly calendar expectations temperature wise. I've waited a while to write this post because Texas has been giving us lots of sun and warmth this month, which I'm definitely not complaining about because we all need that extra Vitamin D, but it does mean I have to wait a while to fully get into the fall spirit.

With this in mind, I want to show you how I am tackling the transition from summer to fall. Expect to see lots of layering (the key to nailing any transitional look!) as well as some pieces you might not expect to see from a fall wardrobe. You know I love to mix things up with my fashion and play by my own rules! And of course, lots of warm and cozy fall favorites that are going to transition wonderfully into winter too!

Look 1

I thought I'd start strong with one of my most treasured pieces – I am of course talking about this gorgeous long floral Kimono that quite a few of you have been complimenting me on. This is one of my favorite purchases of the year! I watched – nay, stalked – it online for months until it went on sale, and then I snapped it up straight away. You may recognize it from my Instagram account, as I recently created a reel about six different ways to style a kimono for all occasions and temperatures. Although it can be worn for all seasons, I'm going to get a lot of wear out of it this fall – something about the floral mixed print and the super-long length makes it so unique and perfect for working into my start-of-fall outfits.

This look is all about the kimono, which has the starring role, but it’s nothing without its supporting castmates – my high waisted wide leg jeans, ribbed layering tank, and Chanel espadrilles. All of the colors seem to work together so seamlessly to complement each other, and I am so obsessed with this whole ensemble! Do you love this look as much as I do?


Look 2

There are so many easy fall outfits to put together using brand new fall-ready pieces, but you absolutely can wear summer pieces like summer maxi dresses and summer jumpsuits too – and the secret is layering! Ps, you don’t have to opt for strictly autumnal color palettes either, as you can still wear light summer colors such as whites and pastels or even brighter pieces if you accessorize the layers accordingly. That's exactly what I've done with my floral summer jumpsuit, as I've teamed it with a layering top underneath in a complementary color, and added my Chanel platform lace-ups to give the look some edge. Summer to fall in an instant thanks to one simple top!


Look 3

How To Wear Summer Pieces In The Fall

Speaking of summer maxi dresses…

I wasn’t quite ready to put this maxi dress away yet, so I wanted to find a few fun and innovative ways to transition it into my fall wardrobe. Luckily it didn't take much to make this summer dress work for fall, as I simply teamed this dress with my oversized French terry sweatshirt. I’ve heard the question so many times how to wear dresses in autumn, and I think this is the perfect example. Layers work both ways – the previous look was all about layering underneath your hero piece, whereas this look is about layering on top. Super casual I know, but I love it!

Summer To Fall Transition Shoes

On this occasion, I finished the look off with my Hermès Oran sandals as it's still sandal weather here in Texas, especially in the daytime, but I will be wearing close toed shoes when the weather gets a little chillier. Retiring my summer dress is not an option though!


Look 4

I wanted to sneak another sweater over dress look into this edit because I don’t think we give enough credit to the power of layers. I'm really into living a more sustainable life and doing away with fast fashion, which is why I like to get the most out of every single piece in my closet. As a lot of you already know, I’ve been on this journey of creating my own clothing line and I’m just amazed at how much time and energy goes into every single garment on the market. So let's give each treasured piece in our wardrobe as much time in the sun as it deserves; that means wearing them when they're not traditionally supposed to be worn. Not everyone would wear a midi slip dress in the fall, but when teamed with an oversized sweater and some fall-appropriate footwear, it becomes a whole new outfit! I've teamed this bronze colored midi slip dress which definitely didn’t get as many outings as I wanted it to this year with my patriotic mix fabric sweater (another fave!) as well as crew socks and statement sneakers.

Look 5

I could write a whole post dedicated to overalls. (Does anyone dare me to? I'm happy to accept the challenge, just like I did for the now infamous baseball caps post!) But for now, I just want to talk about how much I love overalls because of their versatility and their ability to work for every single season without even trying that hard. In the summer, overalls can be worn with cropped tops and tank tops, and in the colder months, they can be worn with long sleeved tops and even sweaters, as well as with added layers such as biker jackets and scarves. There are no wrong ways to wear overalls, and they're one of the easiest pieces, in my opinion, to transition from summer to fall with just a click.

How To Style Overalls 2021

As overalls can sometimes be quite androgynous, or something you wear when you want to have a dressed-down day, I decided to dress these ones up and make my look more feminine by teaming them with a floral peasant blouse, a velvet hair bow and my black Chanel boots.


Look 6

After everything I said about my love affair with overalls, it shouldn't surprise anyone to see that I have included one more overalls look into this edit. This look goes in a whole different direction, which I think proves just how versatile and hard-working the humble overall can be. I think I've proven how to wear overalls fashionably over the years, but if you want to know how to style overalls for fall specifically, please read on. I have paired another pair of overalls (you didn’t think I had just one, did you?) with a simple Henley, silk neck scarf and plaid shirt around the waist for some added dimension, as well as to bring in the waistline which can sometimes disappear when wearing overalls, and some brogues

Cute Fall Outfits


Look 7

Miranda Priestly was famously unimpressed with florals for spring, so I think she would be pleasantly surprised with florals for all – it's all about breaking with tradition and expecting the unexpected, right? You may remember this outfit from my social media last month, when I asked my tribe to help me choose an outfit for a double date to my favorite sushi restaurant in town.

This outfit – which consists of a long floral blouse, a layering brami, barrel jeans, and my Chanel platform lace-ups – is the one I decided on, and I'm so glad that I did because it was such a fun outfit that made me feel happy and confident – what more could you want from a date night outfit? I will be wearing this outfit all year long – when it's warmer, I will swap the shoes out for sandals, and when it gets even colder, I’ll probably throw on some of my go-to winter staples such as a long trench coat to complement the length of the blouse. It's safe to say I have a lot of coat options to choose from, so I can mix and match and create new outfits each and every time!


Look 8

This is one of my favorite casual fall outfits that I think pretty much sums up the cozy fall season. My straight leg jeans can be worn all year long, but I love them for the start of fall as they're the perfect length for teaming with my Chloe brogues, which I think is such a great footwear choice when making that summer to fall style transition. I.e., it's too chilly for open toed shoes, but not quite boots-weather yet!

On this occasion, I've teamed the outfit with a cute layering top, a cream drop sleeve cardigan, and a Chanel beanie hat. All that's missing from this autumnal outfit is a pumpkin spiced latte or a hot chocolate with marshmallows! – yum!


Look 9

Adding a pop of color to a fall outfit always puts a smile on my face. Don't get me wrong, I love the seasonal orange and brown hues too, but I will never stop wearing colors! This green fitted shirt dress is one of my dearest pieces in my closet right now, and I love how easy it is to quickly adapt and rework so it can be worn in all four seasons. I didn't want anything to cover the beauty of this dress, so I chose not to hide it with a chunky cardigan or a winter coat. Instead, the mild fall weather allows me to team it with a simple layering top underneath, and my Stuart Weitzman Lowland boots.


Look 10

The previous look was very feminine and romantic, so time for something a little different now. I love mixing my silhouettes up, and this look shows how you can be wrapped up for fall, casual, but still show off your figure. This form-fitting outfit consists of a white button down – a staple in everyone's wardrobes, am I right? – which I've teamed with a sweater vest, plaid patterned leggings and Jimmy Choo Cruz ankle boots. Got to have some sparkle in there!

I adore the juxtaposition of the sharp blouse and the casual leggings – it's all about mixing and matching not only in terms of price points but also in terms of smart and casual vibes. This outfit is so easy to add even more layers to, so I wouldn’t hesitate to add a scarf, beanie, and long coat when the weather gets a little colder.


Look 11

Another look that incorporates both smart and super casual elements to create what I think is the ultimate summer to fall outfit. I am obsessed with these patterned harem pants – I think the colors are so autumnal and the pattern is just so fun! I've dressed the harem pants up on this occasion by teaming them with a classic white button down – although I am not opposed to wearing them with a white tank top in the summer – and my Chanel platform lace-ups.

This look can be changed up by adding a waist-cinching belt, instead of tucking one side in, to add an added touch of glamour to the outfit. Tucking one side of the button down into the pants is an effortless way to show off my figure and not drown in all of the fabric of the oversized pants and shirt – I love simple yet effective styling hacks!

Look 12

Plaid always reminds me of the fall/winter season, and this oversized plaid shacket is one of my favorite pieces to break out at the end of summer. I love effortlessly throwing it over my outfits as it goes with so much; but it's also great to create brand new outfits with and make it the star of the show. I've teamed it with my black acid wash skinny jeans and camo statement sneakers, but I think the silk hair scarf really makes the outfit as it complements the plaid shirt beautifully and makes the whole look seem well-informed and style savvy.

You know how much I adore adding scarves to everything, and scarves can be added to hairstyles during all four seasons – I love this one for this time of year because the colors scream fall to me!


Look 13

This is my best-loved outfit of the entire post, so I've actually saved the best 'til last! Let's do things unconventionally and start from the bottom and work our way up, just to keep things interesting. These Chanel boots are among my most cherished pieces of footwear for the fall season – not only is their low heel comfortable and understated enough to wear for all occasions, including super casual ones when I know I'll be on my feet all day or running after the kids – but the attention to detail just blows my mind every time. If you look really closely, you can see the super fun gold eyelets where the laces run through, which I think is such a nice touch!

I'm also wearing my ripped mom jeans – no need to explain why I love them because I'm sure you're all bored of hearing me rave about my love for mom jeans, and jeans in general – and this graphic tee, which is another fave when transitioning from summer to fall, as the bright sunshine yellow color complete with the retro design keeps things interesting. It's not what everyone would expect from a fall outfit, which is why I always try to reach for it on cloudy days to cheer myself up. And it always works! The lace layering top is another unexpected piece which elevates the look and takes it from casual to polished – at least in my opinion. Oh and the Chloe sunglasses and Bottega Veneta Jodie bag are casual but sophisticated, and tie up this whole look wonderfully. I hope I've justified my love for this whole look!

What do you think about my summer to fall transition pieces? I love planning my looks and putting outfits together in advance, but I also love unexpectedly throwing outfits together at the last-minute, because you never know what surprising looks you’ll come up with. I know I will find even more fun ways to wear my favorite pieces over the next few months. Next year's summer to fall style post will probably look a whole lot different, which fills me with excitement!

Thank you for reading, and stay tuned for my next post which is all about the hottest trends of the new season, and how I will be slotting them into my current fall/winter closet. I love a challenge!

Lots of love,

Lily x x