A Week of Fall Transitional Outfits for Every Occasion

As fall approaches, we often find ourselves stuck in that awkward in between stage between summer and fall. We want to wear comfy fall clothes, but the temperatures are still feeling like it’s summertime! Because of this, finding the perfect outfit can be a bit of a challenge. But don’t worry, I’ve got you covered! Today, I’m excited to share a week’s worth of stylish transitional outfits that will have you covered for various occasions. Whether it’s dropping the kids off at school, dressing for work, planning a date night, or just looking effortlessly chic as you transition from summer to fall, there is something for everyone. So stay tuned for some chic summer to fall outfit inspiration that will hopefully inspire your transitional wardrobe and make getting dressed this season a little easier.

A Week of Fall Transitional Outfits for Every Occasion

Sharing a week of fall transitional outfit ideas for every occasion. From dropping off the kids to school, workwear looks, date night, and more, there is something for everyone!

Fall Transitional Mom Outfit | White Tee, Jeans & Samba Sneaker Outfit

Wide Leg Blue Jean | Skims Boyfriend Tee | Demiellier Suede Bag | Adidas Sambas

For moms on the go during the transitional fall season, a comfy yet stylish outfit is key. I personally love wearing a pair of wide-leg jeans for that extra comfort and style. If you love a comfy pair of mom jeans, check out my post here for some of my favorites! Then, pair your jeans with some effortlessly cool sneakers like these Sambas for ease when running errands or dropping the kids off at school. Check out my Adidas Samba review for info on sizing, outfit ideas, and more. After that, add a comfy tee, a chic bag and some accessories. You’ll be ready to tackle the day in style! Also, if it’s hot out, be sure to swap the long sleeve tee for a short sleeve and you’ll be good to go!

Fall Transitional Workwear Outfit | Striped Cotton Dress & Suede Boots Outfit

Banana Republic Suede Boot | Striped Midi Dress | Demellier Suede Bag | Gold Earrings

Heading to the office during the transitional fall season calls for a chic and comfortable workwear outfit. I adore this stri p ed midi dress, because it’s sure to keep your feeling comfortable in the in-between weather. To add a touch of sophistication, pair it with some heeled boots. Suede ones like these are ideal for the autumn season. Be sure to check out my business professional and fall workwear outfits ideas if you are needing more workwear outfit inspiration as well. To match your suede boots and to go with the fall vibe, add a suede bag like this one from Demellier. Additionally, for more on why I love Demellier bags, check out my review here.

Fall Transitional Business Causal Outfit | Trench Coat, Jeans, & Flats

Trench Coat | Wide Leg Blue Jean | Skims Boyfriend Tee | Brown Flats | Demellier Suede Bag

For a versatile and chic business casual look during the transitional fall period, pair a classic trench coat with wide leg jeans and comfy flats. This outfit is not only sophisticated, but also offers flexibility for changing weather. You can easily layer the trench coat for cooler mornings and remove it if it warms up during the day. For more trench coat outfit ideas check out my post here. Additionally, you can swap the long sleeve tee for a short sleeve option to stay comfortable and stylish regardless of the temperatures.

Fall Transitional Date Night Outfit | Silk Top & Pant Outfit

Favorite Daughter Brown Silk Pant | Brown Silk Halter Top | YSL Suede Shoulder Bag | Gold Earrings

When planning a fall transitional outfit for a date night, I love embracing rich autumnal colors like a gorgeous chocolate brown. To balance the outfit for transitional summer to fall feel, opt for lightweight fabrics such as a silk top and matching pants. I love this set from Favorite Daughter. Favorite Daughter has a lot of other amazing transitional pieces as well, check out my review of them here. Finally, pair your outfit with elegant heels and a chic handbag, and you are set to go for a chic date night.

Fall Transitional Lunch Date Outfit | Linen Shorts & Lady Jacket Outfit

Mango Lady Jacket | Brown Turtleneck | Zimmermann Floral Shorts | Cult Gaia Tan Suede Bag

For a fall transitional outfit that’s perfect for a casual lunch date, I love combining summer and autumn elements. Start with a pair of dressy shorts, such as these stylish ones from Zimmerman, and pair them with a chic jacket or cardigan to add warmth and style. If you love lady jackets, but need some help styling them, check out my post here. Then, finish off the look with comfortable flats, and chic fall makeup, and you’re set for a gorgeous lunch date outfit.

Fall Transitional Wedding Reception Outfit | Pleated Mini Dress & Heels

Cult Gaia Pleated Mini Dress | YSL Suede Shoulder Bag | Gold Earrings

When it comes to a fall transitional outfit for a wedding reception, I love choosing a mini dress in a fall-color, like this pleated one from Cult Gaia. Then, to elevate the outfit, I pair it with stylish heels and a matching shoulder bag. A suede bag, such as this Saint Laurent one, adds a touch of fall vibes to the overall look, making it perfect transitional look for celebrating the special occasion in style. For more fall wedding guest outfit inspiration, be sure to check out my post h ere.

Fall Transitional Brunch Outfit | Brown Maxi Dress

YSL Suede Tribute Sandals | Smocked Brown Maxi Dress | Demellier Suede Bag

For a stylish fall transitional brunch outfit, I love incorporating fall colors, while keeping comfort in mind. This chocolate brown smocked dress is a perfect choice. Its cotton fabric and off the shoulder design are perfect for the transitional season as well. To complete the look, I opt for a pair of chic sandals, like these suede Tribute sandals from Saint Laurent and a matching suede bag. This look will keep you feeling comfortable in the transitional weather, while having you look stylish and ready for fall.

For more style inspiration, check out my latest posts!

Please feel free to email me at thegraydetails@gmail.com if you have any questions! I’m always happy to help with styling or picking out a specific outfit for an event! Have an amazing day!!

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A Week of Fall Transitional Outfits for Every Occassion