green cable knit sweater and shorts outfit

From Summer to Autumn: 5 Easy Fall Transition Outfit Ideas

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Though it still feels very much like summer weather (hello, humidity), the slightly chilly mornings, cooler breeze, and yellow-tinged leaves have shown us that fall is indeed right around the corner. And whether that makes you feel excited, sad, or a little bit of both, this bittersweet transition gives way to another transition – this time in our wardrobes. If you don’t know where to start when it comes to transitioning your wardrobe, don’t worry! Here I’ll give you 5 simple outfit ideas for fall transition outfits that are easy to put together yet stylish enough to show off the best of the new season.

1. rib knit sleeveless dress + linen blazer + loafers

dress | blazer (similar) | loafers (similar) | bag

Pairing a knit sleeveless dress with a linen blazer and loafers makes for a chic and comfortable ensemble! The rib knit sleeveless dress is a versatile piece that can be worn in any season. Its length and sleeveless design make it perfect for warm weather, but when layered with a linen blazer, it becomes a stylish option for the transition into autumn.

The linen blazer adds a touch of sophistication and provides some long sleeves and extra warmth as the temperatures start to drop. To complete the outfit, slip on a pair of loafers. Loafers are not only comfortable but also add a touch of polish. Whether you’re heading to the office or meeting up with friends for brunch, this outfit is perfect for the occasion(s)!

Let this outfit idea be your reminder not to let the changing seasons stop you from wearing your favorite summer clothes like sleeveless summer dresses. With a jacket and closed-toe shoes, you can easily transition them into the cooler months while still looking chic and stylish.

Need help building your wardrobe with easy-to-style and transition wardrobe pieces? I created a free wardrobe shopping list for you!

2. floral midi dress + denim jacket + clogs

dress | jacket | clogs | bag

One great outfit idea for transitioning from the heat of summer to the crispness of autumn is a floral midi dress paired with a denim jacket and clogs. This combination allows you to still wear your favorite summer outfit (a floral dress) while incorporating some fall fashion styles!

The floral midi dress is a summer staple that can easily be transitioned from summer to autumn, and this outfit is a great example of that. With its mid-length hemline, it’s the perfect piece for cooler weather. And by adding a denim jacket, it not only adds extra warmth, but also creates a casual and stylish look. Denim jackets are versatile and can be worn with so many different outfits, making them a must-have for any fall wardrobe!

To complete the outfit, slip on a pair of clogs. Clogs are a great option because they are trendy yet comfortable, and they add a casual touch to any outfit. It’s a great way to mix your summer wardrobe with some new season pieces, creating a transitional style that’s both fashionable and practical! And when the weather cools down even more, you can break out your knee-high boots and pair them with your dresses.

Related: Classic Fall Capsule Wardrobe (Shopping List, Outfit Ideas, & More!)

3. dress pants + sleeveless polo + ballet flats

pants | shirt (similar) | bag

When it comes to transitioning your wardrobe this time of year, it’s all about finding the right balance between feeling comfortable and looking fall stylish. One outfit idea that checks both of those boxes is pairing dress pants with a sleeveless polo and ballet flats.

The tank top style of the sleeveless polo screams summer, but also has a preppy fall touch in a subtle way. Not all transitional looks have to be olive green and burnt orange! The sleeveless design allows you to showcase your summer tan and adds a summery touch to the overall look.

Pair your sleeveless polo with dress pants. Dress pants are a great versatile staple! For a transitional look, opt for a pair in a neutral color like black, beige, or navy. The sleek and polished silhouette of dress pants adds a touch of sophistication to any outfit, making them perfect for the office or a casual evening out.

Complete the outfit with a pair of ballet flats. Not only are they comfortable for all-day wear, but they also add a touch of femininity to the ensemble. Opt for flats in a complementary color to tie the outfit together. This outfit is perfect for those transitional days when the weather is neither too hot nor too cold. It strikes the perfect balance between a professional and casual look!

4. leopard print slip dress + trench coat + mule slides

dress | coat | shoes

Leopard print is always a statement-making choice, and when it comes to fall transition outfits, it’s no exception. One fabulous combination to try is pairing a leopard print slip dress with a trench coat and mule slides. This look effortlessly blends summer style with autumn sophistication, creating a current yet versatile ensemble.

Start with a leopard print slip dress as the centerpiece of your outfit. The lightweight and breezy material makes it perfect for warmer days, while the iconic leopard print adds a touch of glamour. Layer a trench coat over the dress for a polished and structured look. The trench coat not only adds a layer of warmth for when the weather cools down but also elevates the overall outfit with its timeless appeal.

Complete the look with a pair of mule slides. Mule slides are comfortable and easy to slip on, making them the ideal choice for a busy day or a casual outing. Opt for a neutral color that complements the leopard print and trench coat, or choose a contrasting shade for a bold and fashion-forward statement. As a bonus, this outfit complements other shoes and you could easily throw on a pair of strappy block sandals for date night.

With this combination, you can easily transition your favorite summer outfit into a chic and stylish outfit for fall, while still maintaining a casual look. Whether you’re running errands or going out for a coffee date, this fall transition outfit will have you looking effortlessly put together and ready to embrace the changing seasons!

5. sweater vest + shorts + clog mules

vest | shorts | shoes

As you already know, transitioning from summer to autumn doesn’t mean you have to put away all your favorite summer pieces just yet! In fact, you can and should still incorporate shorts into your fall wardrobe with the right styling. One stylish and cozy outfit idea for the transition is pairing a sweater vest with shorts and clog mules.

The sweater vest is a versatile piece that adds a touch of warmth and texture to any outfit. Opt for a chunky knit or cable knit sweater vest for a cozy and autumnal feel. Pair it with your favorite shorts for a playful and unexpected combination. Whether you prefer denim shorts or tailored shorts, the contrast between the cozy sweater vest and the summery shorts creates a stylish and balanced look.

Complete the outfit with a pair of clog mules. Clog mules are comfortable and on-trend, adding a touch of vintage-inspired flair to your ensemble. Opt for a neutral or earthy tone to complement the colors of the sweater vest and shorts.

This outfit is perfect for those early autumn days when the weather is still mild but starting to cool down. It’s a stylish and comfortable option that allows you to enjoy the last moments of summer while embracing your new favorite season!

Did you find new fall transition outfits to try from this list? It’s time to add them to your outfit rotation. If you need even more help navigating this transitional weather in style, keep reading: 8 Essential Ways To Effortlessly Transition Your Summer To Fall Outfits


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.