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15 Stylish Fall Outfit Ideas for Every Occasion
Does anyone else feel like their schedules are SO crazy during the fall and winter season?! 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 15 different occasions you might have this fall and winter. This way you’ll feel prepared for whatever you have planned this season!
By the way, we just launched a NEW resource with 45 outfit ideas for even MORE occasions you probably have on your calendar this fall/winter. All you have to do is sign up for Busbee emails & texts to get the password! Get all the info and sign up here.
Outfit #1) Holiday Party
The first event or occasion you might have coming up soon is a holiday party! In this look, I’m wearing a gorgeous green Farm Rio top with the most beautiful details…dotted fabric, ruffles, smocking…it’s SO pretty! I styled it with a pair of classic straight-leg jeans by L’Agence that are high-rise, have the perfect fit, and go with any shoe style. I completed the look with some embellished shoes and a pair of crystal chandelier earrings to make this look even more holiday party-ready!
Outfit #2) Casual Lunch Date
If you’re headed on a casual coffee or lunch date with your girlfriends or partner, this is the look for you. I’m wearing a cool whipstitch polo sweater by En Saison that’s super cozy and so versatile. Then I threw on this super chic faux fur and nylon puffer jacket by SAM. If you don’t have a black puffer already, this is a wonderful option. On my bottom half, I’m wearing a pair of cropped jogger pants that are the perfect way to stay comfy and casual but still feel elevated. On my feet, I’m wearing a pair of booties by La Canadienne that are so chic and warm. This brand is known for its high-quality, warm shoes for those of you who live in colder climates like me!
Outfit #3) Date Night
Next up is a fun, sexy date night option! I’m wearing a mixed-media Staud sweater dress that’s such a stunner! It has this corset-like fit at the bust, a thigh-high slit on the side, and is form fitting…I mean this dress is sexy! But in contrast, you get this soft and comfortable ribbed material for the bodice, and a cotton poplin collar, and long sleeves. Such a unique combination that is both sexy and sophisticated. I’m wearing it with a pair of brown suede Schutz boots and I LOVE this monochromatic combination. I have these boots in multiple colors and they’re SO good…just trust me!
Outfit #4) Back In Office
Keep scrolling if you’re in the work-from-home grind because we have another WFH outfit below. But if you’re headed back into the office and looking to add some pizzazz to your work wardrobe, this look is for you! I’m wearing an affordable pinstripe blazer by Steve Madden that’s a must-have if you work in an office…it’s such a good basic! Underneath, I’m wearing a cool white button-down shirt with a dramatic collar that’s just SO fun and different. On my bottom half, I’m wearing a pair of Veronica Beard denim pants that are elevated enough to wear to the office even though they do have that denim look. To complete the look I’m wearing my favorite Stuart Weitzman sock booties I’ve owned for years and wear all. the. time!
Outfit #5) Brunch
If you’re headed to lunch or brunch, you want to look chic and stylish but also feel comfortable and on-trend. In this look, I’m wearing a fabulous faux fur jacket by Frame that’s so luxe-looking, on-trend, and chic. This jacket has an oversized fit, zip-up front, slant hip pockets, large lapels, and a cropped silhouette. You can wear it with everything from jeans to dresses. I styled it with a classic beige sweater, jeans, and knee-high boots. This sweater is by Brochu Walker and is such a good basic to have in your closet…it’s pricey but I’ve been wearing it for years and it washes and wears so well that I know I’ll wear it for even more years to come. These jeans are a pair of skinnies by Mother that are perfect for tucking into knee-high boots. On my feet are the same pair of Schutz boots I styled with the brown dress in look #3…so you can already see just have versatile they are!
Outfit #6) Fun Dinner With Friends
I always talk about how you should take fashion risks and wear things that bring you JOY! So, this 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 and for fall 2023. So much so that the trend even has a name…Barbiecore! I love pink and adding pops of color 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 #7) Back To School / School Event
This is the outfit you’ll wear for all the school events like parent-teacher conferences, pickup/drop off, 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 are a go-to pair of jeans for me each 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. I love this sweater jacket so much that I have it in two colors. On my feet, I’m wearing a pair of on-trend, lug-sole booties by Steve Madden. You probably recognize them from the NSale. 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 #8) 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 #9) 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. This looks is perfect if you would describe your personal style as being more classic. But if classic style isn’t your thing, you could also add one fo your favorite leather jackets to edge this look up a bit. 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 #10) 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 and winter is taken up by sporting events this year…I know it was coming as the kids got older, but I was not prepared for every winter and fall day to be spent this way!
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 #11) 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 #12) 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 of 2022. 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?!
Outfit #13) 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 it 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 #14) 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 dress 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 last year 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 is a more casual option. It’s 100% cotton but the material is thick and heavy, so it doesn’t wrinkle at all. I wore it all last 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!
Note: all of these dresses are older so they are sold out, but I linked some more options below. Hopefully, these looks will provide inspiration!
If you’re looking for more wedding guest dresses, make sure you check out this post with even more options!
Outfit #15) Beach Side
Some of you lovely ladies are lucky enough to get to spend time by the beach in the fall and winter. I LOVE the beach and wish I could be there all the time…but especially in the fall and winter! If I was beachside, I’d wear something like this! It’s a mint green sweater by Free People that you probably remember from the NSale last year. This exact sweater is sold out so I linked another light-colored sweater option below. I paired it with some white Mother jeans that are actually the same style as the sideline sporty jeans I shared in look #10. 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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