summer to fall outfits

8 Essential Ways To Effortlessly Transition Your Summer To Fall Outfits

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We don’t want it to happen, but it’s going to anyway. Summer will end. For a lot of us with kids, school starts next month. This means our schedule will change and bedtimes will get moved up, so the end of summer is in the back of our minds. And though it brings a little bit of sadness, that can quickly be remedied by the excitement of thinking about the transition of your summer to fall outfits! But if you’re feeling confusion instead of excitement, don’t worry. It can be tricky to decide what pieces to keep and what to leave behind as the weather gets cooler. But with these 8 tips, you’ll find the transition from summer to fall to be a smooth, easy, and fashionable process! 

When Should I Transition From Summer To Fall Wardrobe?

Knowing when to transition your wardrobe from summer to fall can be a tricky decision. Generally, the best time to start transitioning is when you begin to feel a slight chill in the air or when the summer heat starts to fade away. Depending on where you live, this could be August or September. 

It’s also helpful to pay attention to daylight hours. As the days become shorter and the nights cooler, it’s a sign that fall is approaching. Additionally, you can keep an eye on fashion retailers and see when stores start displaying their fall collections. (That’s always an exciting time!)

Of course, it’s important to note that every location is different and some places might experience a longer summer or an early start to fall. In the Midwest, fall is in full swing come October, and for others, October may feel like June.

Ultimately, the best time to transition your wardrobe from summer to fall is when you feel comfortable doing so. If you find yourself reaching for a sweater in the evenings or needing an extra layer in the mornings, it’s a clear sign that it’s time to start incorporating fall pieces into your outfits. 

And though you’re probably not transitioning your wardrobe right now, July is a good time to start thinking about it! After all, next month the fashion world is going to shift back to school and retailers are going to start trickling out their new fall arrivals. It’s a good idea to have a plan now so you don’t get swept up in the excitement of a new season. Your wallet will thank you.

1. Invest in Layering

summer to fall outfits


As we transition from summer to fall, layering becomes a key aspect of our wardrobe. It’s not quite cold enough for a heavy coat, but a simple tee and shorts aren’t going to cut it anymore. The best thing about investing in your layering is that you can wear them time and time again. The cardigan you wear now can be worn in December as well as April!

Wondering what’s worth investing in? Start with light jackets. Light jackets are perfect for those in-between days. In the summer months, a denim jacket is a good choice. In October, a leather jacket, utility jacket, or suede jacket all become great options. Come November, you may find yourself needing something a little thicker and longer, like a double-layer trench coat.

Layering doesn’t just mean outerwear either! Long sleeve shirts, lightweight sweaters, and cardigans are perfect for layering under or over a shirt or dress. You can even start wearing them in late August or early September when the temperature starts to drop. Even in the summer, lightweight cardigans come in handy when we get hit with summer rainstorms and it seems as if the weather changes every couple of minutes.

Another layering idea? Try a scarf. A scarf is a great way to add some warmth to your outfit without adding too much bulk. In October, opt for a heavier knit scarf or a cozy blanket scarf.

Don’t forget about what goes under your clothes either, like tights and leggings. These pieces are a great way to extend the life of your summer dresses and skirts.

2. Mix and Match Fall and Summer Pieces

Are you wondering how to transition clothes from summer to fall? The answer lies in the mix and match! Mixing and matching summer and fall styles creates a transitional outfit that will keep you stylish and comfortable during the in-between weather.

One way to do this is by layering your summer pieces with fall essentials such as jackets, scarves, and boots. For example, pair your summer dress with a denim jacket and ankle boots or your shorts with a sweater and tights. This will not only keep you warm but also create a unique look that’s perfect for the fall season.

Another way to mix and match summer and fall styles is by incorporating fall colors into your summer outfits. This can be done by adding pieces like an olive green vest to your floral maxi dress or wearing a pair of medium to dark jeans with your favorite summer top. Incorporate a few pieces from each season for a balanced look!

3. Switch to Darker Hues

summer to fall colors


As the average length of day shortens and you start daydreaming about what you’ll wear to pick apples and pumpkins, it’s time to switch up the color palette of your wardrobe. Say goodbye to the bright and vibrant summer hues and embrace the rich, deep tones of fall. Transitioning to darker hues is one of the key elements in successfully transitioning your wardrobe from summer to fall.

Start by incorporating colors such as burgundy, olive green, navy blue, mustard yellow, or burnt orange into your outfits. These shades not only exude a cozy and warm vibe, but they also effortlessly complement the changing foliage and the overall fall aesthetic. Swap out your pink floral dress for an olive green sleeveless knit sweater dress and your neon shorts for a pair of dark-wash jeans.

Remember, incorporating darker hues into your wardrobe doesn’t mean you have to completely abandon your summer wardrobe! You can still (in fact, you’re encouraged to) mix and match pieces from both seasons to create a seamless and stylish transition.

4. Pick Fall-Friendly Bottoms

Start by picking fall-friendly bottoms such as jeans, trousers, and leggings. Dark-wash denim is always a great option for fall and can easily be dressed up or down. Trousers, or pants, in a heavier fabric like wool, are perfect for colder weather and add a touch of sophistication to any outfit. Leggings are also great for fall and can be worn with long sweaters, tunic tops, and even under dresses.

Don’t forget about skirts! Opt for longer lengths in heavier fabrics like suede or leather. Midi and maxi skirts in autumnal hues like burgundy, mustard, and forest green are also great choices. These can be paired with tights and ankle boots for a chic and cozy look.

Related: Your Guide on How To Wear Ankle Boots (and More) With Jeans, Plus Tips for Always Getting It Right

5. Incorporate a Few Statement Prints

summer to fall prints and patterns


Prints can add interest and personality to any outfit, and they are a great way to transition from the lighter, brighter colors of summer to the richer, deeper hues of fall.

When choosing statement prints for the fall, consider opting for prints that are reminiscent of the season. Animal prints, such as leopard or snakeskin, are always a classic choice and can add a touch of fierceness to any look. Floral prints, although typically associated with spring, can also work well in the fall when paired with darker, more autumnal colors.

Plaid is a fall go-to that is a great indicator that this new season has begun. To incorporate statement prints into your fall wardrobe, start by choosing one printed piece to be the focal point of your outfit. For example, you could wear animal print shoes with jeans and a neutral top. If you’re feeling bold, you can even try mixing different prints together for a more daring look.

6. Update Your Footwear

During the summer months, sandals and flip-flops are the norm. But when it comes to fall, it’s time to bring out your mules, slides, boots, and other closed-toe shoes.

Start by storing away your summer footwear and then, invest in some key fall pieces. Ankle boots are perfect for the fall season and can be worn with almost anything. They’re great for pairing with jeans and a sweater or even with a dress and tights. A classic pair of black or brown boots will serve you well for years to come.

If you’re looking for a more comfortable option, opt for some stylish loafers or flats. They can easily add a touch of sophistication to any outfit. And don’t forget about sneakers! White sneakers are a year-round staple, but in the fall, it’s not a bad idea to look for a pair with fall accents, like these for example.

Some shoe styles that blend summer and fall well are raffia clogs, sandals in a dark suede color, and slip-on clogs.

7. Choose Transitional Pieces

summer to fall outfits


There are just some clothing pieces out there that have nailed the perfect balance between summer and fall. Whether it’s the silhouette, style, or color, incorporating a few pieces like these into your wardrobe will make the transition feel effortless.

So what are some of these pieces? Take fall-colored shorts as an example. Shorts are a go-to summer style and help you beat the heat, while shorts in a fall color like olive green add that fall touch, making it a perfect piece to wear in-between seasons.

A camel rib-knit sweater tank is another great example. The sleeveless tank silhouette means you can wear it when it’s still sunny and warm, but the color and material scream fall.

8. Consider Adding a Fall Trend

Though a wardrobe shouldn’t be made up entirely of trends, it’s always exciting to experiment with new trends as the seasons change. Plus, adding a trend to your transitional wardrobe can instantly freshen up your look and make it more current.

The secret is to pick a trend that won’t overwhelm, overpower, or date your outfit! The key to finding the perfect trend is to find a piece or style that’s been around for a while and just gets more popular in the fall.

For the 2023 season, a “ready to wear” style is in. (I mean, it always is!) This means real-life looks, such as wardrobe basics, tailoring, and a model-off-duty look. Other trendy ideas include western ankle boots, clogs, and animal prints.

Need help building the right wardrobe? I have a free shopping checklist that you can get by signing up here!

With fall on the horizon, now is a good time to assess your wardrobe. Do you want your money to be well-spent? Of course you do! To ensure that your fall pieces can be worn well into January and February, the key is in a capsule wardrobe. Up Next: Minimalist French Capsule Wardrobe for Fall/Winter


Founder and editor of My Chic Obsession, Carolyn is your trusted fashion maven. Carolyn's drive to help others achieve a classic and timeless wardrobe fuels her posts, making a go-to resource for style seekers worldwide. Beyond the wardrobe, she resides in the heartland of the Midwest, dreaming up new ideas and raising her two lively boys - her biggest fashion critics.