What to Wear for 10 Occasions You Have on Your Calendar This Season

10 Fall Outfit Ideas for Occasions

The start of fall usually means a packed schedule and a busy season ahead. Anyone else feel like they have a million things to do and no time to do them?? From social events to shuttling kids around to travel…the list is endless! With so much going on, the last thing you should worry about is what to wear. We’re sharing 10 outfit ideas for 10 different occasions you might have coming up on your calendar, including everything from concerts and tailgating to weddings and wine tastings. We’ve got you covered!

If you haven’t already, make sure you check out our fall capsule wardrobe here.

Fall Outfit Ideas for Occasions

School Drop Off / Coffee Run

If you have younger kids who can’t drive yet, school drop-off is something that you deal with 5 days a week. Maybe you only have to walk the kiddos to the bus stop or maybe you’re a carpooling queen. Whatever your situation, consider ditching your worn-out pajamas for a chic matching loungewear set to look and feel much more pulled together when you’re sending the kids off to school for the day. If you get an elevated matching set like this one, you might even be able to get away with wearing it all day if you work from home 😉 Style it with some cool sneakers, an easy bag, and some sunnies and you’re ready to go! Throw on a chic puffer if you’re walking them to the bus and it’s extra chilly where you live.

Kids Sporting Event fall outfit for Occasions

Kids Sporting Event

Does anyone else have weekends full of sporting events…tournaments, games, practices, etc? If so, this is a simple outfit idea you can recreate again and again! Throw on your comfiest pair of jeans, a cashmere sweater (if you’re outside and it’s going to be cold), and some sneakers. Complete the look with a stylish 3rd layer, sunglasses, your everyday jewelry, and your go-to tote bag.

fall Concert outfit


Depending on the concert you’re attending, this concert outfit might change a little… but the pieces we featured should work for everything from a rock concert to a country concert. All you really need is a cute little black dress! Then, you can change up the accessories based on the concert you’re going to. If you were going to a country concert, you might swap the black boots for some more western-inspired cowboy boots. If you were headed to Beyoncé, you might go with some metallic heels. You get the idea! We also included a super small YSL bag that should fit any stadium bag policies, but it doesn’t have to be this exact bag. Just make sure you always check the venue’s policies before you go.

Tailgate/Football Game

Tailgate/Football Game

Fall means football…and lots of it! So we wanted to give you two tailgating or football game options. Whether you’re headed to the actual game or to a friend’s house for a watch party, one of these options will work. We featured a dress option for those of you in hotter climates and a jeans and sweater option for those of you who are lucky enough to feel the cooler temps. All of these pieces mix and match so you can create your perfect gameday look! We also wanted to point out that there are not very many clear bag options out there that are uber chic…BUT we found this really cool Tory Burch option that’s translucent, very cute, and neutral so it’ll go with any of your team colors!

Fall Date Night outfit ideas

Date Night

You can’t go wrong with all-black, leather, and sheer on date night. We love the black sheer top in this look and if leather pants aren’t your style, it’ll look great with traditional blue jeans too. Throw on some sexy stiletto booties, impactful jewelry, and a jacket, and you’re ready to go!

Brunch Fall Outfit Ideas

Brunch w/ The Girls

This look is perfect for brunch with the girls, a lunch date, or even for dinner. We love the flattering wrap style on this sweater dress…that’s only $100! Lightening up your fall wardrobe with beiges, whites, and tans is so unexpected and chic, but if it’s not your style, each of these pieces come in other color options too.

Wedding Fall Outfit Ideas & Occasions


Wedding dress codes can be tricky. Unless the wedding is black tie, you really can’t go wrong with a midi-length dress in an elevated fabric. It works for cocktail, semi-formal, and formal with the right accessories. This dress is a wonderful, budget-friendly option, a perfect color for fall/winter, and can be dressed up or down! We linked it in two places below in case you don’t see your size at one. You can also find it in more colors here.

Wine Tasting fall outfit

Wine Tasting

This occasion is pretty specific, but the outfit isn’t. You could easily wear this look to lunch or dinner too. We love a flowy, pleated skirt for fall and this one comes in a bunch of colors…although, the chocolate brown is beautiful! To complete the look, throw on a sweater, some booties, jewelry, and a cute handbag (this one is reversible leather and suede!).

Office fall fashion


If you work in an office, sometimes it can be hard to come up with an outfit idea every single day, so here’s a little inspiration and a few pieces that could spruce up your work wardrobe. Instead of a classic blazer, try out a lady jacket. They’re super on-trend right now and this one is classic enough to wear in an office setting. Instead of your basic white button-down shirt, consider something like this fun ruffle button-down. Instead of your classic pumps, loafers, or flats, try a pair of croc-embossed slingbacks for a little extra oomph.

By the way, we have more teacher outfit ideas and office outfits here.

Fall Errands outfit

Running Errands

Straight-leg jeans + casual sweater + sneakers = the perfect fall outfit formula. You can recreate this outfit with pieces you already have in your closet…it’s just so easy! We love these straight-leg jeans by Pistola paired with the oversized striped cashmere pullover. Complete the look with your go-to everyday accessories and jewelry for an effortlessly chic fall look.

If you like this post and want to see more like it, leave a comment below with which occasion you need outfit ideas for!

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6 thoughts on “What to Wear for 10 Occasions You Have on Your Calendar This Season

  1. How about outfits for a weekend gathering with groups of couples? We may go to someone’s house, or meet at a restaurant bar. I want to look nice, but the date night look above is NOT appropriate for this setting. Thanks!

    1. Great question, Laura! For a weekend gathering with other couples, you could take the same concept for the date night outfit and alter it so it’s a little more appropriate. For example, instead of the sexy top…wear a pretty printed blouse with the leather pants. Or you could even swap the leather pants for plain black jeans and pair them with a pretty blouse. Our hope is that these outfit ideas spark inspiration for whatever you have coming up this fall or winter! Let us know if you have any other questions…we’re happy to help! ~Team Busbee

  2. I really like and appreciate this post. I need some “casual wear” ideas…
    As a retired physical educator/ coach, I want to be somewhat stylish when running errands or shopping about town.I think I “dress up” too much, when grocery shopping sometimes. I’m just not into the big printed tshirt, old jeans, old tennies, as most women my age wear. It’s so sad that the rural/suburban women I see in their early/mid 60’s have just “given up.” I want to keep living my best life at this age(64) and continue on!
    Thank you to Erin, and your team, for helping me navigate through this time in life.❤️

    1. Love hearing this, Rachel! Erin just purchased this cozy sweatshirt and matching pants in the toffee color and she LOVES them:, They are perfect for running around town and still looking stylish. And the whole team is wearing the Air Essentials Spanx set which you can read more about in this post So happy to hear you are living your best life and thank you SO much for your sweet compliment! ~ Team Busbee

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