10 Stylish Fall Outfit Ideas for Every Occasion
Does anyone else feel like their schedules are SO crazy during the fall?! I know I can’t be the only one! And with so many plans, comes the stress of figuring out what to wear. I do this for a living and sometimes I even struggle with it. That’s why I’m sharing 10 stylish outfits for 10 different occasions you might have this fall. This way you’ll feel prepared for whatever you have planned this season!
TOP | FOR LESS | PANTS | SIMILAR HEELS | NECKLACE | FOR LESS
Outfit #1) Fun Dinner With Friends
I always talk about how you should take fashion risks and wear things that bring you JOY! So, this first outfit is a really fun option if you’re heading to dinner with friends, going out to dinner with your spouse, heading on a fun girls’ trip, etc. The fun feathery top and boucle pants are both from Karen Millen. You may remember me talking about how pink is a HUGE fashion trend this year. So much so that the trend even has a name…Barbiecore! I love pink so I’m fully embracing it.
This top is really comfortable, zips in the back, and actually stays put. The kick-flare pants are super flattering. I’m 5’4” so they fit like full-length pants, but they are technically cropped pants and will be shorter on taller women. I completed the look with a pair of pink pumps. If you missed it, make sure you check out this post by one of our amazing contributors, Sam Stewart of Sam of Style, about how to wear the Barbiecore trend!
If this first outfit isn’t your cup of tea, don’t worry…the second look is much more practical!
TOP | JEANS | BOOTIES | SIMILAR SUNGLASSES | FOR LESS | BAG | FOR LESS
Outfit #2) Back To School
This is the outfit you’ll wear for all the back-to-school events like parent-teacher conferences, volunteering at the school, etc. It would also be great for running errands, going to lunch or a meeting, or even casual Friday in the office.
I’m wearing a pair of cropped, high-rise black Good American jeans that I can already tell will be a go-to pair of jeans for me this fall. They run really small so I’d size up 1-2 sizes. I’m wearing a 27 (normally a 26) and they’re still a little snug. With the jeans, I have on a Jonathan Simkhai sweater jacket. This is a really cool piece. It has a waist-defining detail that’s very flattering and a small peplum that’s great for hiding a tummy. On my feet, I’m wearing a pair of on-trend, lug-sole booties by Steve Madden. You probably recognize them from the NSale this year. They are a sock bootie style at the top so they’ll go perfectly under any type of jean style. Plus, they’re really comfortable!
LEGGINGS (Limited Sizes) | SIMILAR | SWEATER | FOR LESS | SIMILAR JACKET | FOR LESS | BOOTIES | SIMILAR SUNGLASSES | FOR LESS | EARRINGS
Outfit #3) Gym to Street
You’re busy! A lot of times, when you’re able to squeeze in a workout at the gym, you have something you need to do right after. Whether it’s running errands, meeting a friend for coffee or lunch, or going to pick up your kids from school…you still want to look put together if you’re planning to see anyone, right?? Well, this one is for you!
Let’s say you have on a pair of black leggings and a black sports bra or tank/tee for your workout. I would throw an oversized sweater or sweatshirt over your tank or tee. The sweater will make you look more polished, while the sweatshirt will make your outfit look more casual and sportier, which is up to you! I went with this gorgeous green AllSaints sweater and then added a sporty Blanc Noir jacket. If you’re worried about your hips, butt, and thighs showing, try a longer sweater or an oversized button-down. I finished off the look with the same Steve Madden lug-sole boots and voila! Now you look cool, edgy, sporty, modern, and not like you just came from the gym at all!
TOP | FOR LESS | JEANS | BLAZER | FOR LESS | BOOTIES | SUNGLASSES | FOR LESS | EARRINGS | BAG | FOR LESS
Outfit #4) Travel Day
Maybe I’m old school, but I like to look nice on airplanes! I just feel better when I’m dressed up for the airport…You never know what’s going to happen during travel and getting dressed up makes me feel like I’m prepared for anything! This look is a really chic example of a travel day outfit idea.
I’m wearing a Veronica Beard striped blouse that buttons at the side on the shoulder and has a high neck. It’s a really chic and lovely piece and I absolutely love it. It’s a specialty piece you probably don’t already own, but you could swap it for a nice button-down or blouse. I paired it with a black oversized IRO blazer. Oversized blazers are very on-trend right now and this is a gorgeous option, but there are tons of budget-friendly options out there too. On my bottom half, I’m wearing some of my favorite Mother jeans. They are a cropped flare that is SO flattering and comfortable. Just trust me…multiple Team Busbee members own these jeans and love them! To complete the look, I’m wearing the same Steve Madden booties but you could swap them for sneakers too.
JACKET | TEE | JEANS | SIMILAR SNEAKERS | FOR LESS | HAT
Outfit #5) Sideline Sporty
Where are my sideline moms?? Anyone else feel like they’re either in the car driving to the sporting events or sitting on the sideline watching the games 24/7? It’s like our entire fall is taken up by sporting events this year…I know it was coming as the kids got older, but I was not prepared!
While you’re on the sidelines, you want to feel cute, comfortable, a little sporty, and be protected from the sun or weather. It’s a tall order but I’ve found a great outfit formula for that sideline sporty look. In this look, I’m wearing a sherpa jacket by Alo Yoga. It’s super cozy and warm but also looks chic. Underneath, you can wear a lightweight sweater or tee…go with a cotton tee if it’s warmer and a cashmere sweater if it’s cold.
To add sun protection, keep my head warm, and add a stylish accessory, I’m wearing a faux suede baseball cap. Baseball caps are having a moment right now so there are SO many cool options out there! On my bottom half, I’m wearing the same Mother jeans from #4, but in white! On my feet are a pair of Golden Goose sneakers that have a removable shearling sole. I love this pair SO much because of the cool color combo.
I know Golden Goose sneakers are expensive so I’ve done an entire review answering questions about quality, sizing, and more in this post.
JACKET | FOR LESS | SWEATER | SIMILAR JEANS | SIMILAR SNEAKERS | FOR LESS | HAT | FOR LESS
Outfit #6) Sideline Chic
This is the same concept as #5 but it’s just a little more polished. If you want to have a little more sophistication at the game, bust out something like this! I’m wearing a pair of old Mother distressed jeans but I’ll link something similar. To stay warm, I’m wearing a Herno high-neck puffer. If you live in a cold climate, Herno puffers are SO good, and I love the neutral color of this one. Underneath (and unfortunately not pictured) I’m wearing a super cute Rails sweater that has stars on it.
On my feet, I’m wearing the same Golden Goose sneakers but if you’re not ready to invest that money, there are some other great options out there by P448, Steve Madden, Veja, and Rag & Bone. On my head, I’m wearing a Rag & bone hat that’s chic, provides sun protection, is warm, and really elevates the whole look.
Outfit #7) Cozy Day
One of my favorite “occasions” is…a cozy day at home with absolutely nothing on the calendar! Even though you’re not doing much, you still want to feel put together, comfortable, and like you can comfortably answer the door if you need to. This set is by Jenni Kayne and you may remember it from this post where I feature some of the best loungewear trends. I love the combo of these two pieces together, but you could wear them as separates too. They are both comfy, cozy, and SO luxurious-feeling.
The pants are the perfect length for me (I’m 5’4”) but if you’re taller, they’ll be more cropped. I also have to talk about these fuzzy mules! They feel and fit like slippers but they have a sole, so they have traction and you could technically run errands in them! Real shoes with the look and comfort of slippers, what more could you ask for?!
TOP | JEANS | SIMILAR BOOTIES
Outfit #8) Work From Home
I work from home so I’d wear something like this every day for zoom calls. The goal is to look good at least from the waist up. To do that, pick a beautiful colored top like this jewel-toned blouse by Paige. It’ll brighten your face and looks beautiful on camera. Then pick a pair of comfy jeans like these super flattering dark wash wide-leg jeans by Paige. I paired the look with booties, but if you’re walking around your house you could do no shoes or something comfortable like slippers or sneakers.
PURPLE DRESS | HEELS | CUFF | EARRINGS
BLACK/BROWN/WHITE DRESS (Limited Sizes) | MORE SIZES | BLACK HEELS
SIMILAR PAISLEY DRESS | ANOTHER OPTION | BOOTS
SIMILAR DRESS | SIMILAR DRESS | BLAZER | FOR LESS | BELT | BOOTS
Outfit #9) Fall Weddings
This is one of the biggest occasions I get requests for! The looks above would be perfect for weddings and any special occasions you have on your calendar like showers, parties, and other celebrations.
The first dress is a Zimmerman maxi in a regal royal purple color. It has a high neck, puff sleeves, voluminous skirt, flattering tie waist, and it’s a linen blend so you won’t get hot. When I put this dress on, I feel like a princess!
I wore the second dress to my niece’s wedding and it’s a really gorgeous dress. I love the puff sleeve, strategic cutout, full skirt, black, brown, and white color combo, and the longer length.
The third option is one I’d wear to a Texas or country-esque wedding. It’s a paisley Misa dress with a high neck, sleeves, and longer length. Pair it with boots and a belt and you’re good to go! Since it’s sheer, you might want to get a full-length slip.
The last dress is by Jenni Kayne and a more casual option. It’s 100% cotton but the material is thick and heavy, so it doesn’t wrinkle at all. I’ve worn it all summer and loved it. But to transition it to fall, I’ll wear a blazer over it like this cool cropped Kimberly Goldson blazer. I’m obsessed with this blazer! Everything from the color, fabric, peaked lapels, shoulder pads, cropped length…it’s SO good!
If you’re looking for more wedding guest dresses, make sure you check out this post with even more options!
SWEATER | JEANS | HEELS | NECKLACE | PRE-LAYERED NECKLACE
Outfit #10) Beach Side
Some of you lovely ladies are lucky enough to get to spend time by the beach in the fall. I LOVE the beach and wish I could be there all the time…but especially in the fall! If I was beachside this fall, I’d wear something like this! It’s a mint green sweater by Free People that you probably remember from the NSale this July. I paired it with some white Mother jeans that are actually the same style as the sideline sporty jeans I shared in look #5. If you find a pair of jeans you love, I suggest buying them in multiple colors/washes.
What events do you have coming up this fall? Let us know in the comments below and we can help you come out with an outfit idea!
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I left a comment about a site using Erin’s photo for their own purposes.
I saw it used in a site called: Daily Drip – Sneakertoast.com
Two photos of Erin with the text: Pay attention to pockets
I love the wedding dress ideas. How about a business/ black tie affair in November?
Great idea, Melinda! We’ll add it to the list for our next post… If you’re looking for more wedding guest dress options, make sure you check out this post too: https://busbeestyle.com/wear-wedding-guest/ ~Team Busbee
I purchased the pink pants! They ARE very retro flattering. How else would you style these Karen Millen kick flares? Can you post a couple of additional looks? Thanks! Love the chunky gold necklace and the cropped jacket too…so much to love.
So glad you liked this post, Rachel! You could wear the pants with a fun printed blouse that has a little bit of the same pink color in it, with a simple solid blouse and blazer, or even with a tee and leather jacket to edge them up and make it more casual. Hope that helps and thank you SO much for being here! ~Team Busbee
Love your most recent post! Your creativity and sass comes through! I love the Herno puffer. What size and color are you wearing? I’m a similar size to you. Thank you!
Glad you liked this one! 😀 I am wearing a size small. ~Erin xo
Thank you!
You work really hard at your messaging! So when I saw a Facebook article showing how pockets should look and they used a pic of YOU to demonstrate – to me it was a ripoff of your brand! Be aware! Next time I will note the Facebook site. You do a great job of fashion for all body types! I am 78 years old and still love to dress! My tombstone will read: she was always coordinated!
You are so sweet, Gloria! Thanks for being on the lookout…Unfortunately, sites do use our content without permission pretty frequently. But we just stay focused on bringing you quality posts! Thank you so much for being here! ~Team Busbee
Ideas for 5 days in Sante Fe first weekend in November.
Great idea, Julie! We’ll add it to the list for our next post… ~Erin xo
Hello… love the blog but also wish you’d show style that flatters those of us who aren’t a size S or XS….
Thoughts?
Wanna come to Colorado and model for me?? 😉 I think most of what I feature can be worn by women of all shapes and sizes. The wardrobe basics apply to everyone.
The style ideas are applicable to all. There are probably a few wild cards, but not many. I can see a curvy woman rocking the jeans/tee and duster look. Or all black with a statement coat. Sweater and boots works for all too! Are there specific occasions you need outfit ideas for?? Erin xo
Hi Erin, I recently subscribed to your blog and I’ve found it incredibly helpful. Have you done a video or blog on over the knee boots? As you’ve said in this video, they have a very sexy vibe, but I’m also interested in how to make them work in a more subtle or elegant way? Can they ever be worn in an office setting – like an ad agency or tech company – if so, how to make that work? Perhaps even some suggestions on brands and styles that stay up (less tugging), or options for someone like me who has skinny runners’ legs. Always a problem for me to find narrow calf styles. Thank you so much for all you do and for helping me stay engaged and in love with fashion. – Laura
The Stuart Weitzman 50/50 boots are ideal for narrow calves: http://rstyle.me/n/csjyg558an I think a flat pair of OTK boots would be easy for the office, with black leggings and a longer tunic or sweater.
Flats would tone down the sexy. I think if you go monochromatic, that will help too.
Love, love, love the plaid coat. Almost makes me wish I still lived in snow country…………….almost! In Scottsdale I would have no use for that gorgeous coat, unfortunately. Looks great on you.
LOL… thanks, Kathy! How long have you been in Scottsdale?? I was pretty ready to leave Texas after 8 years. Looking forward to the snow, believe it or not! Got my car starter ready!! Erin xo