transition to fall shoes

Step Into Fall: Transition Your Wardrobe with These Stylish Shoe Options

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With fall on the horizon, now is the perfect time to start thinking about how you’ll transition your wardrobe! Don’t worry, it doesn’t have to be complicated. You can easily start small. And one small and easy way to get your wardrobe fall-ready and transition to the new season is to start with your shoes. From ballet flats to clogs, these must-have shoes will help make the transition to fall a ~crisp and cool~ breeze.

1. Woven Ballet Flat

transition to fall shoe outfit woven ballet flat

cardigan | romper | flats | earrings

The woven ballet flat is a perfect and classic shoe to wear as we transition to fall. Thanks to the woven material, it’s light and airy like a summer shoe, but the rich cognac color and texture make it feel more fall-appropriate.

Pair these flats with a denim romper for a casual look that’s perfect for the early days of fall. Throw on a cardigan to not only complete the outfit but also add an extra layer of warmth for cooler days. This outfit is versatile enough to be worn to brunch with friends or a day out shopping.

2. Clogs

clog outfit fall transition

jacket | tee | shorts | clogs | earrings

One style that we absolutely love for this time of year is the classic clog! Though this shoe is trending, it dates back all the way to the 1300s. You know what they say, everything comes back around.

Pair your favorite clogs with some breezy linen shorts, a crisp white t-shirt, and a denim jacket for the ultimate transitional outfit. Not only is this look incredibly stylish, but it’s also practical. The denim jacket provides just enough warmth to combat cooler temperatures without weighing you down, while the linen shorts and white t-shirt keep things airy and breathable.

When it comes to selecting the perfect pair of clogs, choose a pair with an open back. This will give you maximum breathability and comfort for those still-warm summer days. It’s also a good idea to choose a neutral color such as black, brown, or tan to make them versatile enough to pair with a variety of outfits.

3. Mules

fall transitional outfit mules

shirt | skirt | mules

Mules are the ultimate in easy slip-on-and-go footwear, making them a great choice for those days when you need to get out the door in a hurry. (And look good while doing so!)

A striped t-shirt is a wardrobe staple that never goes out of style, and when paired with a cargo midi skirt, it adds a touch of chic to your utilitarian cool look. When it comes to mules, opt for a pair with a slightly chunky heel, which will give your outfit a touch of height and sophistication while still being comfortable enough for all-day wear.

Neutral shades like tan, brown, or black are the perfect choice for transitioning into the cooler months, as they can be easily paired with the other fall pieces in your wardrobe.

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

4. Shearling Slides

shearling slides transitional outfit

top | pants | necklace | slides

These cozy and stylish shoes are perfect for those in-between weather days when you still want to show off a bit of your summer style while embracing the autumn vibes. The soft and fuzzy texture of the shearling instantly adds a cozy feel, making them the perfect footwear choice for wearing into fall!

Pair your shearling slides with a striped tank top for a chic and effortless look. The timeless stripes add a touch of sophistication to your outfit, while the tank top keeps it casual and comfortable. Complete the look with a pair of cargo pants. The utility-inspired design of the cargo pants adds an edgy and trendy fall element to your ensemble whether you’re running errands or meeting up with friends for coffee.

5. Woven Loafer

woven loafer fall transitional outfit

jacket | shorts | earrings | loafers

The woven loafer is a versatile option that can easily take you from the warm summer months to the cooler days of autumn. Pair them with a denim jacket and linen shorts for a chic and effortless look.

The combination of the woven texture of the loafers with the classic denim jacket and comfortable linen shorts creates a perfect balance between casual and polished. The loafers add a touch of sophistication to the outfit, while the denim jacket adds a hint of coolness. The linen shorts keep the outfit light and breezy, making it suitable for both warm and cooler days.

This outfit allows you to embrace the fall season while still enjoying the last remnants of summer!

6. Clog Mules

clog mules transition to fall shoe outfits

dress | necklace | clogs

If you’re not ready to give up on your summer dresses just yet, you don’t have to! A sleeveless sweater dress paired with clog mules can effortlessly take you from summer to fall. The knit dress adds the perfect amount of warmth to combat cooler temperatures while still giving you the comfort of a lightweight dress.

Pairing it with clog mules brings a touch of casual charm to the outfit, making it perfect for daytime outings or weekend brunches. Opt for an autumn-colored dress, such as forest green or camel, and pair it with cognac clogs for a nice contrast. On the flip side, black clogs are cute and versatile too.

7. Sneakers

sneaker transition to fall shoe outfits

jumpsuit | earrings | sneakers

There’s a reason sneakers make it on every capsule wardrobe – they’re so versatile! Sneakers are not only comfortable but also effortlessly chic, making them the perfect choice for pairing with virtually anything – from shorts to dresses and in this case, jumpsuits.

Jumpsuits are a go-to staple for many fashionistas, as they offer a one-and-done outfit that can easily be dressed up or down. To create a stylish fall look, opt for a jumpsuit in a muted or autumnal color such as olive green or burgundy. Pair it with a clean white sneaker for a fresh and modern look.

This combination is perfect for a casual day out or in. With the addition of sneakers, your jumpsuit will take on a more laid-back and cool vibe, allowing you to transition seamlessly from the warmer days of summer to the crisp autumn weather.

Need help figuring out all the wardrobe staples you should have in your wardrobe? Join my list and get a free wardrobe shopping list!

8. Mule Slides

mule slides transition to fall shoe outfits

jacket | shorts | sunglasses | slides

Need a shoe that can handle the changing weather while still looking stylish? Mule slides are the perfect choice for transitional footwear, especially when paired with denim shorts and a cropped utility jacket.

The combination of mule slides and denim shorts gives off a summery vibe while the cropped utility jacket provides just enough warmth for those crisp fall evenings. This outfit is perfect for casual outings, running errands, or even meeting up with friends for coffee.

When choosing mule slides, you can even experiment with different textures such as suede or leather for added depth to your look!

transition to fall shoes

Shoes have the incredible power to transform any outfit, effortlessly taking it from one season to another. And remember, the transition from summer to fall doesn’t have to be complicated or overwhelming!

By investing in a few key pairs of shoes and incorporating them into your existing wardrobe, you can effortlessly create stylish outfits that will carry you through the changing seasons.

Do you know the other fall clothes that are worth investing in? Find your answer in the next post: Classic Fall Capsule Wardrobe (Shopping List, Outfit Ideas, & More!)


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.