10 Stylish Fall Outfit Ideas for Every Occasion Your Have Coming Up

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Fall Outfit Ideas

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!

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!

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!

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!

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.

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.

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.

PANTS | SWEATER |MULES

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.

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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