preppy fall outfit idea

7 Fashionably Cute Fall Outfit Ideas Using Staple Items In Your Wardrobe

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As soon as the weather cools down and you can finally get away with wearing a sweater, I’m running to my closet faster than you can say pumpkin spice latte. Point is, I love fall fashion and putting together fall outfits. But you want to know what I love even more? Putting together fall outfits using staple items that are already in my wardrobe! In this post, you’ll find 7 looks to inspire your fall dressing this season using items you may already have…or ones that are at least easy to get your hands on! None are too “overly fall-y”, because here at MCO, we love that classic element. Now keep scrolling for these fashionably cute fall outfit ideas!

1. striped shirt + blazer + shorts + loafers + socks

Fall is perhaps the only appropriate time where you can channel preppy back-to-school fashion even if you’re erm, way past back-to-school age. Even if school days are behind you, break out the loafers, socks, and collegiate-inspired blazers with gold buttons. Pair it with stripes and a classic bag to update this look!

shirt | blazer | shorts (similar) | socks | shoes (similar)

Shorts add a unique twist to this outfit and are a good option if your weather hasn’t cooled down yet, but if cut-offs aren’t your thing, switch them out for a denim skirt instead. For my over 50 crowd, I’d recommend cropped jeans, because you may feel more comfortable in this denim style and it still allows you to show off your loafers!

Related: How To Master Fall Fashion for Women Over 50

2. cropped boxy sweater + straight leg jeans + sneakers + layered necklaces + hobo bag

Need a cute and casual outfit to wear on the weekend or out and about? This is it. Easy yet stylish fall dressing is the name of the game this season! A boxy fit cardigan is a nice twist on this everyday staple while a stack of gold necklaces dresses it up.

You can experiment by front tucking in your cardigan, wearing it over a top, or wearing it as the top itself. Embrace the loose fit as that’s what makes it perfect for the weekend! If the weather is getting colder, you can easily add a scarf to this outfit to cover up your neck as well.

cardigan | jeans | bag | necklaces | sneakers

This fall, it’s time to try some new denim styles. Push your skinny jeans to the side and break out of your comfort zone to try out straight leg, slim leg, or my favorite, cropped flares! A new jean style can instantly update your whole look and make it feel like you have a new outfit, even if everything else is 5 years old. Pair this look with sneakers for some easy stylin’ and don’t forget your tote bag to be your weekend carryall!

3. graphic sweater + blazer + straight leg jeans + loafers + fedora

Yes, even a graphic sweatshirt can look chic and classic. Just pair it with loafers and you instantly elevated this casual item! A sweatshirt with embroidered lettering is all too reminiscent of a college sweater, making this a perfect fall option.

blazer | sweatshirt | jeans | hat | loafers (similar)

Straw hats are an excellent choice for spring and summer fashion, but to add that touch of fall to your look, complete this outfit with a fedora instead. The mix of casual and chic, sweatshirt and blazer, is an outfit that rivals J.Crew’s lookbook catalog and shows off your styling ability!

4. houndstooth dress + blazer + tights + knee-high boots

Channel your inner Blair Waldorf for this outfit that screams preppy chic! Fall and winter are the ideal times to break out the classic houndstooth print and you can never go wrong with a houndstooth dress. To be fair, a houndstooth dress may be the only thing not already in your wardrobe, so feel free to swap this out for a plaid dress or a sweater dress instead.

dress | blazer | tights | boots (similar)

For dresses that are on the shorter side (or for just a fun style tip in general), consider adding tights to your dress or skirt ensemble. Not only are tights practical, but it’s a great area to add some extra interest to your look and there’s a tight style that suits every personality! My picks would be sheer black tights or these designer ones if I was in the mood to splurge. Do you like colors or patterns? You can easily have fun mixing and matching with the rest of your look.

What’s fall without boots? A pair of cognac leather boots with a slight heel are the perfect classic addition to this look. Not only does it make it feel like a fall outfit, but the color is a nice pop and pairs really well with black, white, and gold.

5. white button-down + oversized blazer + leather leggings + mule slides

Whether you’re a stay-at-home mom, a gym rat, or just a lover of athleisure style and comfort, everyone loves leggings. Myself included! And since leggings aren’t leaving our closets anytime soon, I think it’s best to just embrace them and find ways to incorporate them into chic looks. There are 2 main ways to do this.

blazer | leggings | slides (similar) | button-down (similar)

First, let the gym leggings be gym leggings. Meaning, leggings made out of spandex material that have a slot for your phone are the leggings that scream working out. Save those for when you’re working up a sweat and look for leggings that are more on the stylish side, such as having a moto detailing or being made out of faux leather fabric. Plain black is good too.

The second main way to make your leggings look chic is to pair them with chic items! An oversized blazer and button-down are just the things you need. The key to pulling this look off is using an oversized blazer. Not only does it cover the bum, but the long length contrasted with the shorter button-down adds instant visual interest. Mule slides are one of my top choices for fall. Pair with a classic handbag and you’re all set!

6. white button-down + striped sweater layered + button mini skirt + knee-high boots

If you can’t break out the preppy looks for fall then when can you? A tweed (or tweed-inspired) skirt is a perfect fall pick and as you can see, gold buttons are just the thing you need to elevate an outfit. Half tuck the white button-down for a more relaxed feel to this otherwise dressier outfit.

button-down (similar) | striped sweater (similar) | skirt | boots (similar)

Pull out your classic leather boots (brown preferably, for a pop of “color”) and a classic bag. The finishing touch is a sweater casually draped and tied across your shoulders. Striped, of course!

7. striped sweater + cropped flared jeans + mule slides

Is it truly fall if you don’t wear at least one sweater? And tell me, what is more classic than a striped sweater? This 3 piece outfit (4 if you count the bag), is an outfit to break out for grabbing lunch with friends or heading to HomeGoods to stock up on all the neutral-colored pumpkins.

sweater | jeans (similar) | slides (similar)

Dark washed jeans are a great option for the cooler months and slip-on shoes make this outfit easy to wear. You don’t really need a necklace with a turtleneck like this, so consider adding some gold hoops instead. Simple and classic!

With these fall outfit ideas, you now have an outfit for every day this week. If you found that you’re missing some staples, like a blazer or a sweater, then check out this next post to help you get your shopping list together!

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

Fashionable Fall Outfit Ideas
fashionably cute fall outfit ideas


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.