40 Cute Everyday Outfits To Wear As The Weather Gets Cold
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If you’re anything like us, you already started creating your fall wardrobe during the summer (Don't worry--we won't tell anyone!) in anticipation of these glorious months. After all, as the leaves begin to turn colors and the cool air creeps in, is there anything better than wrapping yourself up in a warm scarf? Slipping on a pair of boots for the first time in months? We didn't think so!
So, needless to say, we’ve had plenty of time to plan our seasonal wardrobe. But, as the budget-conscious shoppers that we are, we wanted to make sure that these cute fall outfits could also transition from fall directly into winter. (And, let’s face it — into the spring as well. We love versatility.)
So, if you’ve been wanting a bit of a closet refresh but don’t know where to begin, these fall fashion favorites are sure to provide you with inspiration for any activity that you’ll find yourself participating in during the coming months.
For the Gym
An easy outfit idea combining a matching leggings and sports bra set with a lightweight jacket. This is a cute and casual weekend outfit idea that goes straight from the gym to brunch with friends.
Shop: Sports Bra | Flare Leggings | Jacket | Sneakers | Sunglasses
For An Active Day
Athleisure combines the best of both worlds: fashion and fitness. A lightweight long sleeve tee, paired with shorts and matching sneakers is comfortable for all day, with a bright watch for a pop of unexpected color.
Shop: Long Sleeve Tee | Shorts | Sunglasses | Sneakers | Watch | Bralette
For Saturday Errands
A busy weekend means casual outfits that are easy to toss on. This combination of joggers, retro sneakers, and a crop top is a great combination for a post-gym to brunch to whatever-the-afternoon-holds outfit.
Shop: Cropped Tee | Denim Jacket | Joggers | Retro Sneakers | Necklace | Tote Bag | Sunglasses | Gold Bracelet
For Post-Workout
These biker shorts make for the perfect post-workout fall outfit, whether you are heading to a breakfast date or to a coffee shop. The bright and bold neon colors of the cropped sweatshirt and belt bag incorporate a few of the biggest trends of the season.
Shop: Oversized Sweatshirt | Biker Shorts | Hoop Earrings | Sneakers | Belt Bag
For Bedtime
Who says outfit ideas should be limited to outside the home? Matching pajamas and a long robe are always a good pairing any time of year.
Shop: Pajama Set | Robe | Bralette | Slippers
For a Rainy Day
A classic pair of relaxed jeans go easily with a pair of black Chelsea rain boots for a cute fall outfit in any weather. Toss on a trendy shacket over a basic black bodysuit (a wardrobe staple!) and it’s a casual look that makes dressing for fall easy, even if it’s a rainy day.
Shop: Shacket | Wide Leg Jeans | Bodysuit | Gold Ring | Chelsea Boots
For A Netflix Marathon
A long tee paired with these soft, lightweight flared leggings and white sneakers make the best outfit for an all-day movie binge.
Shop: Layer Tee | Flare Leggings | Diamond Studs | Silver Hoops | Sneakers
For the Coffee Shop
A fall outfit full of warm, neutral colors! Combine this V-neck sweater, wide leg jeans, and ankle boots! A few touches of gold add a touch of shine to your fall clothes.
Shop: Pullover Sweater | Ankle Boots | Crop Jeans | Sunglasses | Gold Link Earrings | Tote
For Leaving the Office
Business casual outfits don’t have to be boring or uncomfortable. Wide leg trousers paired with neutral tones are a simple, yet chic look, while loafer mules and sunglasses transition easily to any post-work fall activity.
Shop: Blouse | Trousers | Sunglasses | Baguette Ring | Stacking Rings | Faux Leather Blazer | Loafers
For A Casual Date Night
This pink sweater is a feminine addition to pair over cropped jeans and white booties. Add a few touches of gold with your jewelry and accessories and you have a dressy look for happy hour or casual dinner date.
Shop: Pink Sweater | Wide Leg Jeans | White Boots | Sunglasses | Watch
For Lunch With The Parents
When you’re in the mood for an outfit that is both comfort and classic, you need to reach for an oversized turtleneck sweater and a chic wrap coat. Keep it casual with a pair of slide sandals and light wash jeans.
Shop: Sweater | Wide Leg Jeans | Belted Coat | Sunglasses | Earrings | Sandals
For Visiting An Art Installation
For your own eclectic style, this all black outfit uses trendy outfit pieces—such as the faux leather skirt and platform loafers—combined with wardrobe basics to create a slightly funky, yet elevated look.
Shop: Faux Leather Skirt | Bodysuit | Loafers | Tote Bag | Earrings
For An Afternoon with Friends
A striped sweater can be worn over a pair of raw hem jeans with a pair of vintage inspired clogs. Just the right amount of casual for a cool weekend look that is perfect for lunch or dinner, too. (Try adding faux leather leggings for a dressed up variation!)
Shop: Striped Sweater | Wide Leg Jeans | Black Bag | Clogs | Sunglasses
For the Farmer’s Market
Dressing for fall means lots of layers and slow, easy Saturday mornings means comfortable sweaters and jeans. Tan combat boots and a quilted vest finish out the simple fall outfit.
Shop: Cotton Polo | Jeans | Quilted Vest | Gold Bracelet | Crossbody Bag | Boots
For A Pumpkin Patch Date
The color combination of this sherpa jacket and orange jeans scream fall fashion, so pair it with a classic white tee for the quintessential fall outfit that is right at home for a date to the pumpkin patch or into the country.
Shop: Sherpa Jacket | Ankle Pants | White Tee | Belt | Stacking Rings | Sunglasses
For Brunch With Friends
Clogs have been a popular trend throughout the year and it looks to be continuing into the fall. Combine other comeback trends of the year—such as the denim maxi skirt that harkens from the 2000s—with a cropped sweater and gold jewelry. This is a cool outfit that you can rock just about anywhere.
Shop: Cropped Cardigan | Denim Maxi Skirt | Clogs | Gold Earrings | Sunglasses
For Happy Hour
A cropped blazer and square toe heels give business casual vibes while destroyed wide leg jeans make the entire look into a casual fall outfit.
Shop: Cropped Blazer | Jeans | Heels | Sunglasses | Pink Wallet
For a Concert
All black inspires an outfit that is easy to put together, while still providing layers for warmth during the cool fall months. But to make it something unique, add a bright splash of color! If your concert is outside, the tall Chelsea boots ensure that your feet stay dry while you listen to your favorite music.
Shop: Sweater | Faux Leather Leggings | Moto Jacket | Mini Bag | Tall Boots
For Open Mic Night
Many ‘90s trends have made a big resurgence in the past year, but none that is closer to our hearts than the grunge look of denim and plaid shirts. This cute fall fit feels right at home just about anywhere.
Shop: Plaid Shirt | Black Jeans | Tank | High Top Sneaker | Black Tote
For A Trip To The Apple Orchard
First day of fall outfits don’t get any easier than this. A plush Pendleton jacket paired with your favorite denim and short rain boots is a cute outfit to sit and sip apple cider in.
Shop: Fleece Jacket | Vintage Jeans | Rain Boots | Sunglasses | Zip Tote
For An Afternoon of Thrifting
Not only is thrifting an excellent way to create a sustainable wardrobe, we love finding mix and match clothes to make cheap fall outfits. Plus, slip-on sandals make it easy to walk around to your favorite thrift stores all day.
Shop: Cardigan | Straight Leg Jeans | Round Sunglasses | Crossbody Bag | Slip-on Sandals
For The Movies
Comfy clothes are essential to our weekend outfits in the fall. But, we want to be even more comfortable if we’re headed to a movie. Leggings and a sweatshirt are casual outfit must-haves, but we’re making it modern with this year’s big trend — flared leggings.
Shop: Sweatshirt | Flare Leggings | Watch | Stud Earrings | Sneakers
For An Afternoon In A Bookstore
Spending the afternoon curled up with a good book calls for a great fall outfit. This casual look pairs a sweater vest and flared jeans for a cozy outfit idea perfect for a day spent reading.
Shop: Sweater Vest | Jeans | Transport Tote | Pearl Earrings | Sneakers
For Dinner with Friends
If you want a dressy fall outfit (that still keeps it casual), try wearing this faux leather blazer and buckle sandals with your favorite turtleneck and boyfriend jeans.
Shop: Faux Leather Blazer | Jeans | Turtleneck | Round Sunglasses | Gold Bracelet | Slide Sandals
For A Casual Friday
When you don’t know what to wear this fall, remember that you can never go wrong with a black and white color combination. The overall jumpsuit is extra-soft (not to mention easy to put on), and a pair of funky sneakers gives the outfit some personality on an otherwise average afternoon.
For A Fall Wedding
If you’re attending a fall wedding this season, you’ll need a fancy outfit! This fit and flare dress is simple (we love a look we can wear on repeat!), with just a bit of added sparkle from silver jewelry and strappy heels.
Shop: Dress | Stud Earrings | Hoop Ring | Strappy Heels
For A Big Presentation
Let’s face it — presentations are stressful enough as it is, there’s no reason to stress about what to wear, too. This chic black and white look is not only flattering, but it feels like a power suit, only in dress form!
For A Fall Festival
With the weather cooling off, the fall festival season will soon begin. If you’re headed to an outdoor concert, backyard music festival, or any other event with tracks to dance to, this bold print dress will give you all of the bohemian vibes. Style it with a pair of short boots with a chunky heel for a little bit of height and a little bit of added comfort for walking on grass and uneven surfaces.
Shop: Dress | Earrings | Sunglasses | Boots
For A First Date
A sweater dress can be the perfect first date outfit. Not only is it figure flattering, but it works perfectly for a wide variety of dates and could easily go from afternoon to evening— casual dinner, coffee shop chats, or even anything outdoors!
Shop: Dress | Tote | Gold Hoops | Boots | Sunglasses
For A Hay Ride
Hay rides or a trip to the fair in the fall months can be tricky due to unpredictable weather. Combining a lighter weight top, such as this wrap sweater, with a pair of jeans and boots is the perfect outfit pairing. While we love a pair of plush socks for added comfort in our boots, they also provide warmth if the weather turns cooler. As the sun sets, toss on your favorite jacket to cozy up even more!
Shop: Sweater | Jeans | Gold Bracelet | Boots | Sunglasses | Socks
For A Taylor Swift Concert
Is anyone else’s favorite Taylor Swift album, Evermore? While the typical outfit to the Eras Tour might be bright and full of sparkles, this dress is an ode to the exact one that she wears on stage—can’t get any more perfect than that!
For A Trip To The Local Flea Market
Flea markets are full of vintage finds and long lost treasures. With its warm color palette and flower earrings, this outfit feels reminiscent of the ‘70s, so you’ll fit right in as you comb through the booths looking for hidden gems.
Shop: Cardigan | Blouse | Faux Leather Pants | Sunglasses | Loafers | Earrings
For A Day Spent At The Library
We don’t know about you, but there’s something great about a sweater dress that gives us modern librarian vibes. Paired with brown knee high boots, it also feels like nature is calling us back into the forest before the leaves turn colors in the fall.
Shop: Dress | Earrings | Sunglasses | Boots
For A Trip To The Museum
Whether it’s a museum filled with classical artwork or a science museum, pairing a turtleneck with trousers is a classic silhouette that is simultaneously grown-up and sophisticated. The bold pop of color in these trousers stands out against an all-black color palette for just the right amount of interest (that doesn’t pull attention away from the exhibits, that is!).
Shop: Turtleneck | Trousers | Handbag | Bracelet | Mules
For A Trip To The Arcade
If you’re not ready to grow up just yet, this ultra-casual look styles one of the biggest trends of the year—cargo pants. Yes, the 2000s have made a big fashion comeback, and while the baggy pants with pockets might not be your first choice, you can’t deny that they provide a handy place to store all of your game tokens!
Shop: Tank | Necklace | Cargo Pants | Sneakers
For A Day Spent Volunteering
It doesn’t have to be Earth Day to spend a few hours working to make our planet a better place! Regardless, the greens and browns in this look do bring out our inner environmentalist—a perfect outfit whether you’re spending your time volunteering at a food bank or raising money for your favorite charity.
Shop: Tee | Trench Coat | Pants | Belt | Flats
For An Afternoon Spent Outdoors
The workout dress is another activewear trend that has made its way from the tennis courts and into everyday looks. As comfortable and versatile as it looks, when paired with sneakers, this is an outfit that you can spend all day outside in and never break a sweat!
Shop: Workout Dress | Sunglasses | Duffel Bag | Sneakers
For The Boardroom
The blazer dress is another look that has all the command of a power suit, but in a more feminine package. It’s an elevated business casual outfit that can be styled with opaque black tights and loafers or with a pair of your favorite sky-high heels when you’re ready to make an impression.
Shop: Blazer Dress | Bracelet | Pumps | Sunglasses
For Dinner At A Sushi Restaurant
Pulling our inspiration from Harry Styles’ newest album, let’s style an outfit perfect for a sushi restaurant! The sweater and trousers are office appropriate, but when you’re ready to close your laptop for the day and head out to dinner, the faux leather jacket adds some edge. (And yes, you really can wear black and brown together!)
For Making An Impression When You Walk Into A Room
This red trench coat makes a statement! The can’t-miss color is the star of any outfit that it’s included in and perfect for that attention-grabbing moment. We suggest styling it with a simple pair of grey trousers and white blouse for an outfit that is all sophisticated fashionista—and not Carmen Sandiego!
