October is here, can you believe it? Just like that, we are on the tail-end of 2023. And with that, one of my favorite seasons is here as well – fall! Fall is only the beginning of all that comes towards the end of the year. Holidays galore, family time, football season, and so much more. Because there is so much going on at this time of the year, that also means that there is so much to dress up for! Occasions such as family photos, heading to events like the pumpkin patch, or even apple picking. And of course, so many life events continue to happen in the fall as well. Events such as fall weddings, date nights, and even heading off to work. Because there is so much to celebrate and to dress up for this month, I’ve curated 30+ outfit ideas for the fall season that are included in this month’s lookbook. These outfit ideas include timeless, classic, and elevated looks for all the different events and occasions that will fill your calendar this October.

The pieces in this lookbook were selected because they can be styled in many different ways. Including pieces that can be styled time and time again was intentional because my hope is that even if you just add one new item to your wardrobe, that item will become a go-to in your closet. So, let’s get to styling!

30+ Outfit Ideas for the Fall Season

fall family photos

Are you planning to take family photos this October? If you answered yes, this outfit is for you. Try a fall-colored floral maxi dress like this one as your main piece, and add a felted wool hat for warmth and style. Pair your maxi dress with light leather knee-high pointed-toe boots to bring in a contemporary touch. Complete the look with gold twisted hoop earrings and a lipstick shade perfect for fall. This look strikes a balance between comfort and style, making it the perfect choice for capturing October’s memorable moments, and possibly chasing around some small children while doing so!

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lunch with friends

October is the month for cozy yet stylish outfits, and when it comes to meeting up with friends for lunch, here’s a look that checks all the boxes. Start with a soft cashmere cable knit cardigan sweater that’ll keep you warm without sacrificing style. Pair it with high-rise straight-leg jeans for a timeless and flattering silhouette. Slip into comfortable yet chic loafer mules that effortlessly bridge the gap between casual and put-together. Don’t forget to accessorize with small gold hoop earrings for a touch of elegance. A brown leather shoulder bag adds a classic element while offering practicality. Finish off the look with a lip glow oil to keep your lips hydrated and radiant throughout the day.

Sunday brunch

When it’s a crisp October Sunday morning and you’re headed out for a delightful brunch, this outfit is your go-to choice for a perfect blend of comfort and style. Start with a cable-knit ruffle neck sweater lady jacket, an ideal piece to keep you cozy while adding a touch of sophistication. Pair it with a faux leather mini skirt for a trendy twist. Slip into leather ankle boots to complete the look with an edge, while a white leather mini bag offers a clean and chic contrast. Add a timeless gold watch for a touch of elegance and top it off with pearl and gold drop earrings for a hint of glamour.

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fall date night

When October calls for a romantic date night, this look has you covered in style. Slip into a side-slit midi sweater dress that’s both cozy and chic, keeping you comfortable as the temperatures drop. Paired with bone leather knee-high boots, this look exudes confidence and sophistication. Add a white belt to cinch the waist and create a flattering silhouette, and don’t forget the gold twisted hoop earrings for a touch of glamour. Complete the outfit with a white leather shoulder bag, practical and sleek. Finish it off with lipstick in a deep, fall shade to make a statement.

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fall look

October is all about embracing the changing leaves and cooler temperatures with style, and this outfit perfectly embodies the essence of fall. Start with a luxurious cashmere mock neck sweater top, providing both comfort and a touch of sophistication. Pair it with a flowing satin maxi skirt for a blend of elegance and ease. Slip into leather almond-toe heeled ankle boots and accessorize with gold teardrop earrings and a felted wool hat to elevate the look. Complete your outfit with a brown leather shoulder bag, offering both practicality and a classic touch. Don’t forget to finish off the look with a lipstick shade that mirrors the season.

Apple picking

October brings the charm of apple picking season, and you’ll want an outfit that combines comfort and style for the occasion. Begin with a cozy white wrap sweater, perfect for those crisp autumn mornings. Pair it with a wool a-line skirt that brings a touch of warmth and sophistication to your look. Leather knee-high boots not only keep you snug but also add a timeless flair to the ensemble. Add a touch of elegance with small gold hoop earrings and a brown leather shoulder bag. Shield your eyes from the sun with brown tortoise sunglasses, and finish the look with a shade of tinted lip oil that captures the essence of the fall season.

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country outfit

As October rolls in, it’s time to embrace the country vibes and get ready for that fall country concert you’ve been looking forward to. Picture this: a charming long-sleeved floral ruffled mini dress that effortlessly combines feminine flair with a touch of rustic charm. Slide into knee-high faux leather western boots, offering both style and comfort for a night of dancing. Top it off with a felted wool hat, the perfect accessory for those cool autumn evenings. To complete the look, keep your lips hydrated and subtly tinted with a lip balm.

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casual outfit

As October ushers in cooler temperatures and a vibrant display of autumn colors, it’s the perfect time to curate your fall wardrobe staples. This outfit is full of timeless pieces, such as this tan chevron topcoat that exudes elegance and warmth. Layer it over an ivory turtleneck sweater for cozy comfort and a classic look. Pair it with high-waisted straight-leg jeans, offering both style and versatility. Step into leather almond-toe ankle boots for a dash of sophistication. Complete the look with a white leather shoulder bag for a clean and modern touch. Add a subtle touch of glamour with a pair of pearl and crystal cluster stud earrings.

lunch with friends

October calls for chic and cozy outfits, and when it’s time for a leisurely lunch with friends, here’s a look that strikes the perfect balance. Slip into a cable knit mock neck long-sleeve sweater dress, combining warmth and style effortlessly. Pair it with knee-high leather boots for a timeless touch. Accessorize with gold twisted hoop earrings to add a hint of elegance. Tote your essentials in a brown leather shoulder bag for practicality and sophistication. And of course, don’t forget to complete your look with a lipstick shade that embodies the hues of fall.

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For even more fall outfit ideas, see this post!

With these 30+ fall outfit ideas, you’ll be prepared for the season as you style your wardrobe with confidence. These curated outfits offer countless options no matter where you’re headed.

Curious for more? Be sure to enter your email above to receive the entire downloadable shoppable lookbook. Sharing this monthly lookbook with you is one of my favorite things – you don’t want to miss it!

Which of these outfits for fall is your favorite from the lookbook preview? Let me know in the comments below!



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