Fall and winter is one of my favorite seasons to dress for, partly because I’m always cold, and layering up with cozy textures and rich colors is simple, comfortable and stylish. I also find it easy to wear only a few pieces and look effortlessly chic while still being comfortable.
Whether you’re dressing for work, visiting a pumpkin patch, dropping your kids at school, heading on a coffee date or just running errands this season I’ve got you covered with some chic outfits that are still comfortable and easy to pull together.
Let’s dive into the world of layering and textures to get you inspired to pull together amazing outfits you feel confident in from your closet. Plus, these fall winter outfits stay warm and chic all season long!
21 Fall Winter Outfit Ideas
Cozy Sweater Outfits
Cozy sweaters are the ultimate staple for fall and winter wardrobes, offering both warmth and versatility. The soft textures and rich colors create a snug and inviting vibe that perfectly complements the seasonal atmosphere. Plus, you just throw them on and go! My sweater collection has grown exponentially since I moved to a cold location and they get so much use.
I also love that sweaters can be effortlessly styled with a variety of bottoms—from baggy wide-leg jeans, flare jeans, corduroys, trousers, skirts and even layered over dresses. This adaptability allows for endless outfit combinations, they key to maximizing their wearability is sticking to classic colors and styles that you can wear over and over again for years to come.
Remember, sweater in different arm lengths can be a fun way to switch it up too! I love this one below and for colder days, just toss on a coat when you’re outside.
Yes, a fun statement sweater like this striped one is also fun, but I wouldn’t make that the majority of your sweaters because they’re simply not as versatile!
Monochromatic Looks
I adore a monochromatic look and fall and winter is the perfect time to pull them out. The neutral tones are perfect for these outfits as they effortlessly blend sophistication with simplicity.
Opt or shades like beige, cream, taupe, black and gray create a minimalist, yet chic outfit that feels cozy, warm and calm—perfect for this season. For holiday parties, try a monochromatic look in all red or green for something fun and festive!
The beauty of a monochromatic outfit is in the details—mix textures and fabrics to create a layered, thoughtful look—think chunky knits with sleek pants or soft cashmere with tailored trousers. These outfits are incredibly easy to wear; simply throw on a coordinating top and bottom, and you’re ready to conquer any occasion with minimal fuss.
You can add another layer with a jacket that either is the same color or contrasts your outfit. Add a pop with some patterned or colored shoes to add some personality to your look.
Trousers Outfits
Trousers and wide-leg pants serve as a great alternative to traditional jeans or corduroys during the winter months. Their flowing silhouettes not only provide comfort but also create an effortlessly chic vibe, making them perfect for both casual outings and more polished occasions.
These wide leg pants can be styled up or down; pair them with a fitted turtleneck for a sleek look, or wear them with a cozy oversized sweater for a laid-back yet fashionable ensemble. With a variety of fabrics and colors to choose from, trousers can easily be adapted to suit your personal style while ensuring you stay warm and stylish all season long.
Statement Coats
Adding a statement coat to your outfit during fall and winter can instantly elevate your look, turning a simple look into a statement. Over the years, I’ve grown quite the coat collection, and after you’ve secured a good camel coat, then you can opt for some bolder ones!
Look for coats with bold colors, cool patterns, or unique textures, these coats bring a playful element to your wardrobe, making even the most casual outfits pop with personality. I love a good check pattern that feels perfect for fall months. Or even a classic colored coat with a unique details like this one below.
Styling Cool Sneakers
Cool sneakers are my go-to addition to any outfit in my fall and winter wardrobe. I love that they effortlessly add a sporty and casual vibe to any outfit.
You can wear them with cropped jeans or long, baggy jeans, trousers, a skirt, a dress—seriously anything!
When paired with a flowy midi dress, tailored trousers, or your favorite denim, sneakers give you a playful contrast that keeps the overall look relaxed yet stylish.
While neutral sneakers and crisp white are so classic, consider adding some bold sneakers in fun colors or interesting patterns to inject some fun into your look to make them a focal point of your outfit. This combination of comfort and flair ensures you stay both chic and cozy and it’s perfect for so many occasions! As a mom, sneakers are usually my go-to!
Styling Ankle Boots
Ankle boots are a quintessential piece for all fall winter outfits and wardrobes, as they can easily transitioning between casual and dressy looks.
For a laid-back day out, pair sleek black leather ankle boots with skinny jeans and a cozy oversized sweater for a chic yet comfortable vibe.
Or, dress them up by opting for a heeled version, which looks stunning when combined with tailored trousers or a midi dress. Whether in classic black, rich browns, or trendy colors, ankle boots provide the perfect finishing touch, making them not only versatile but also a timeless staple for fall winter outfits.
Jeans & Flats Outfits
Pairing jeans with flats is easy and effortless and an outfit I reach for often during the fall and winter seasons. It’s effortless, versatile and comfortable. There are a few different types of flats to consider trying:
Loafers offer a polished, classic vibe, making them ideal for more formal occasions when paired with tailored jeans.
Mules are great for a chic and modern aesthetic and are a great alternative to loafers. For me, loafers don’t always stay on my narrow foot and I love a slide mule that gives a similar look.
Slides offer ultimate comfort for casual outings, and their slip-on design makes them perfect for those on the go.
Lastly, ballet flats add a classic touch to any ensemble, easily complementing skinny jeans. I love a pointed toe with baggy jeans to elongate the leg, or a round or square toe for cropped jeans where you can see your foot. There’s always the regular ballet flat or you can opt for a Mary Jane that stays on your foot a little better!
I hope these outfit ideas give you plenty of inspiration for fall winter outfits over the next few months!
BTW, how to style a brown sweater, and what to wear with flare jeans.
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