If there’s one season I have endless outfit ideas for, it’s fall. Fall is one of the best seasons to get dressed and the perfect time for a little wardrobe refresh.
I love adding in layers, texture, and prints that are easier to style once the weather is cooler. I love a belt with a print, or pair of shoes in a fun pattern or color that makes your outfit feel a little special. But, year after year, there are also those simple outfits of a button up and jeans that I enjoy wearing just as much. The things you don’t have to stress over styling are the ones you want to keep in your closet every year, and the pieces that add a unique detail fall into place from there! In today’s post, I put together a collection of practical and fun fall outfits that make getting dressed easier.
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Fall Outfit Ideas
I’ve organized everything into categories, but there are definitely outfits that work across different occasions. I always want my most versatile pieces to be used for more than one thing. Even work trousers can be restyled for an elevated casual look, for example.
Early Fall Outfits
This first category is early fall outfits for those days where the calendar says early fall but the weather hasn’t caught up just yet! I also wear these outfits when it’s still technically late summer.
Button Up for Early Fall and Colder Months
This is one of the early fall outfits I’ve been living in recently. A button up with a pair of linen pants is easy, comfortable, and you look put together. I love to carry my straw bag through September before I switch over to leather accessories – if the weather allows!
When it gets colder, I like to wear a mockneck sweater under an oversized button up like the one I’m wearing below. I style it with jeans or trousers, and everything together easily transforms into a true fall outfit.
Fall Colors on Linen
I love to incorporate fall colors into my outfit even when it’s still hot outside. My outfit is all linen, but olive green and black gingham makes it feel like it’s meant for September instead of July. It can stay pretty warm here in DC through September, so this type of outfit is important for me to have.
Click here for my post on how to transition summer dresses into fall.
Casual Fall Outfits
School Pickup Outfit: Jeans and A V-Neck Sweater
School pickup is the perfect example of when you want comfort but you also want to be presentable! In the fall, denim makes getting dressed for this type of occasion easy. It’s the perfect base for fall outfits, so you can style denim with a button up, oversized cardigan, or a classic sweater.
Barrel Jeans With a Simple T-Shirt and Fun Shoes for Errands
I always feel like I’m perfecting my errands’ outfits to be comfortable without using athleisure clothes. In the fall, denim is a staple for these outfits too.
This is perfect for those late summer and early fall nights when you want to wear transitional pieces. My barrel jeans are one of my favorite pairs of jeans, and they come in several different washes. I’m wearing the regular length, but the petite length is also a good fit for anyone 5’4 and under! I tried those on in store and would also purchase them for my height.
Cotton Pants for Coffee Date With Friends
These cotton pants are the perfect piece to add to your wardrobe because they’re unique and practical. They’re a great alternative to jeans! I sized up one size to a size 8, and they fit perfectly even after washing them. I’m excited to style them with a cream or brown sweater this fall. Don’t be afraid to mix and match different shades of the same color in your outfit! These pants pair best with flats.
Family Dinner Night in Chic Wardrobe Staples
You know those nights you just don’t feel like cooking, so you head out to your favorite place? This is the perfect time to rely on wardrobe staples because you don’t have to overthink your outfit. This outfit feels pulled together, and it’s really just a combination of transitional pieces and wardrobe staples.
I carried my straw bag, but this outfit will feel more like it’s made for fall if you carry a leather bag. You could also opt for ballet flats or loafers.
Trousers and Low Profile Sneakers for City Vacation
Okay, I mentioned rewearing work pants, and a city vacation is the perfect time to style trousers in a new way. I love wearing trousers with low profile sneakers for a comfortable and elevated look. It all pulls together nicely with a belt and cozy sweater. I added a short leather jacket and a cashmere scarf in a pop of color to make the outfit feel like it’s more for the weekend than the office. I own this scarf in pink and love how it easily styles on your jackets or as a functional scarf. Click here to see it on me.
Weekend Outfit for Transitional Seasons
A button up and a pair of jeans always works for those days between two seasons. I like to add in pieces that feel like fall – like these fun studded suede flats that I’m wearing below. They were gifted to me without any obligation to share them. I’ve been wearing them a lot now that it’s September, and they’re very comfortable. But, my favorite thing about them is how I can just slip them on!
Fall Work Outfits
Work Skirt Outfit in a Fall Color Palette
This skirt is fun but it’s also professional. The suede jacket makes the outfit feel a little bit cooler than a traditional blazer would. I styled this with transitional pieces like raffia shoes, but it looks so good with brown boots or flats for a true fall feeling.
Corduroy Suit in a Fall Color Palette
When I think of fall outfit ideas for work, this is a favorite for business casual or formal dress codes. I just love how this suit feels unique, chic, and professional. You can easily style it with a layering t-shirt that works well under suits and blazers in general – like this one that I own and love for layering. For a classic and reliably professional look, go for this button up in blue or white. It’s a classic fit!
I also love tonal and monochrome looks, so I styled that type of outfit with this suit below. The pants run long, so if you’re 5’4 or under, plan to have them tailored!
Fall Wardrobe Staples for Work
Getting dressed for work can be exhausting, but wardrobe staples will make it easier even on the days you’re running late. These trousers come in regular, petite, and tall length so you can find your perfect fit. And, they also come in a great color selection so you can find a color that works with your wardrobe. I personally love the color that looks like khaki and tan, which you can see below, since it goes with so many other neutrals and fun colors. Anyway, pair these with an elevated layering tee, crewneck sweater, and loafers for an instantly professional and comfortable outfit. I also love this belt!
I styled a very similar outfit for the weekend above – I love how you can rewear so many of these pieces for different occasions.
Casual Friday in a Blazer and Jeans
A blazer and pair of straight leg jeans was always my go-to casual Friday outfit when I was in the office five days a week. You can wear a blazer with so many fall outfits, including with a skirt or dress for those days when you need an outfit for a business or business casual dress code.
Plaid Shirt Jacket With Skirt
This plaid shirt jacket is perfect for fall work days or the weekend. You can style this for work with trousers, but I also love how this type of jacket looks with a pleated skirt or a slip skirt. The colors in this particular jacket give you a lot of versatility! Wear it with black, tan, brown, or olive. You can see an older version of this outfit on me below. I’d wear ballet flats, loafers, or boots with a more practical heel! But, you can see how good this type of outfit works with knee high boots!
Dressy Fall Outfits
Flowy Fall Dress for Fall Events or Family Photos
This dress is a good option for date night, school events, family photos, or a fall dinner with your friends. You can style it with flats, sandals, or knee high boots. When it’s early fall, you don’t need to layer over it. But, once the cooler temperatures hit, you can style this with a short brown leather jacket or suede jacket like the one I’m wearing throughout this post.
You can also style it with a leather belt instead of the belt it comes with. I love all the different options this dress brings to your wardrobe!
Fall Wedding Guest Dress in Fall Color Palette
This dress is perfect because it will work across different wedding dress codes! I would style it with simple accessories in other earth tones and let the fun dress be the centerpiece of the outfit. I own this bag in brown leather, and I love it so much. I carried it all over the UK on our trip last fall because it easily transforms from a day bag to a night bag with a hidden magnet. You can see a video of me showing how it works here.
Knit Dress or Sweater Dress With Tall Boots
Sweater weather doesn’t just mean your standard sweater! A knit dress with tall boots or ankle boots is also one of those classic fall outfits that can be styled for different occasions. I loved this type of outfit when I was pregnant because it was comfortable but I still felt like me! Obviously, knit dresses and boots work when you’re not pregnant too. A sweater dress is always a good idea for date night or family photos.
Fall Weekend Outfits
Suede Jacket and Jeans
This suede jacket is my go-to fall jacket because it always makes me look and feel put together. It’s also one of those transitional pieces I look forward to wearing every year because it goes with everything from a summer dress to a silk skirt to denim.
Comfortable and Cute Travel Outfit
Fall is one of the best times of the year to travel. It can be tricky getting everything into your suitcase, but I do love how you can wear things onto the plane that you’ll actually use on your trip to save space – like loafers and your coat.
Click here for more autumn travel outfits.
Matching Set for Weekend Errands or Kid Activities
Matching sets are the solution for busy weekend mornings, whether you’re running errands solo or heading out to activities for your kids. You don’t even have to think about how to style a matching set – you just put it on, add any jewelry you want, and you’re ready! My exact set also comes in other colors.
Click here for more fall mom outfits.
Oversized Cardigan with Stirrup Leggings
I bought a pair of stirrup leggings last year and wore them a lot throughout the winter, but I’m excited to wear them this fall with loafers. They elevate your outfit in a way typical leggings don’t! And, you can wear them with knee high boots when it gets colder. Style these with an oversized cardigan and trench coat.
A Few Tips and Thoughts on How to Style Fall Outfits
Don’t Try to Layer With Thick Sleeves: Choose Sleeveless or Classic Fits for Layering
If you’re wearing a shirt with a lot of material on the sleeves, you should avoid layering with it because it will look and feel bulky. A sleeveless sweater or classic fit sweater will always fit better under jackets and blazers. The one exception is when the bulky part of your sleeve is at your wrist – like a fun and flowy end of your sleeve.
Do Try to Mix Textures
One of the fun parts about getting dressed in the fall is wearing different textures in the same outfit. This is always a good idea, especially when your outfit is tonal or monochrome. For example, denim looks good with suede shoes, a leather belt, and a cashmere sweater.
Do Try to Mix Patterns
Patterns are also a fun way to show your personal style, whether it’s one fun piece or an outfit with different patterns throughout. Maximalist style is a concept I’m adding into my own wardrobe more and more again, and it’s a lot of fun! For example, you can wear an animal print belt with shoes in a fun color on a base outfit of jeans and a neutral sweater.
That’s all from me today! Be sure to sign up for my email list if you’d like to hear more from me on style and travel.
