The old rules of fashion are a thing of the past. Today, the chicest looks are often the most comfortable, born from a clever mix of relaxed staples and polished pieces. Fall is the perfect season to master this high-low art form. It’s about pairing your coziest sweater with tailored trousers, or throwing a sharp blazer over your favorite hoodie. This guide celebrates that perfect blend, offering 32 fall outfit ideas that effortlessly combine comfort and chic. These ensembles are designed for real life, proving that you don’t have to sacrifice one for the other to achieve the ultimate autumn look.
1. Blazer over a Hoodie
The ultimate high-low combination. This look perfectly mixes a sharp, tailored blazer with a soft, casual pullover hoodie. The key is to let the hood of the hoodie drape over the blazer’s lapels. It creates an instantly cool, street-style-approved look. This unexpected pairing is perfect for a creative workplace or a stylish weekend outing. Pair with straight-leg jeans and sneakers or loafers to complete this chic yet comfortable outfit.
2. Sweatshirt with a Satin Skirt
This outfit is all about textural contrast. Take a cozy, oversized crewneck sweatshirt—a ultimate comfort piece—and pair it with a luxurious, slinky satin slip skirt. The juxtaposition of the casual, athletic sweatshirt with the elegant, feminine skirt is what makes this look so fashionable. It’s unexpected and incredibly chic. Do a loose front-tuck with the sweatshirt to give your waist some definition. Pair with sneakers or heeled boots.
3. Trench Coat and Joggers
Elevate your favorite loungewear. A pair of simple, comfortable joggers in a classic color like black or grey can be made instantly chic with the right outerwear. Layer a classic, timeless trench coat over your joggers and a simple t-shirt or sweater. The tailored, polished structure of the trench coat provides a beautiful contrast to the relaxed joggers. It’s a perfect look for a travel day or running errands in style. Add stylish sneakers and a great handbag.
4. Oversized Sweater & Leather Pants
A perfect balance of cozy and edgy. A pair of sleek, straight-leg leather or faux-leather pants provides a chic, tough base. To bring in the comfort, pair them with a very oversized, chunky knit sweater. The softness and volume of the sweater is a perfect contrast to the smooth, edgy leather. This is a great outfit for a date night or a weekend outing where you want to be both comfortable and cool. Finish the look with heeled ankle boots.
5. Knit Dress & Combat Boots
Another fantastic high-low combination. A soft, comfortable knit sweater dress, particularly in a midi length, is a cozy fall staple. On its own with heels, it can feel very dressy. To give it a cool, comfortable, and practical edge for daytime, pair it with a pair of chunky, durable combat boots. The toughness of the boots provides a great contrast to the soft femininity of the dress. Throw a leather jacket over the top to complete the look.
6. A Knit Set with a Wool Coat
The chicest way to wear a “sweatsuit” out of the house. A matching two-piece set of knit pants and a sweater is the epitome of comfort. To make it chic, layer a long, tailored wool coat over the top. The structure of the coat instantly elevates the relaxed knit set. This is a perfect travel outfit. Complete the look with a pair of clean, minimalist sneakers and a structured leather handbag.
7. A Shacket Over Leggings
The “shacket” (shirt jacket) is a versatile fall layer. A thick, oversized plaid shacket is a great casual piece. For an easy weekend look, throw it on over a simple base of a comfortable t-shirt and your favorite black leggings. The look is comfortable and has a cool, rustic vibe. It’s perfect for a casual coffee run or a walk in the park. Pair with your favorite casual sneakers or boots.
8. A Turtleneck & Slip Dress
Extend the life of your favorite summer slip dresses. Layer a thin, fitted turtleneck sweater underneath a simple, midi-length satin or silk slip dress. This not only adds a layer of warmth but also creates a chic, ’90s-inspired look that is very on-trend. A black turtleneck under a champagne slip dress is a classic combination. Pair with ankle boots or loafers.
9. A Denim Jacket & Knit Dress
A classic casual pairing. A simple, comfortable knit dress, perhaps in a midi length, is a great fall staple. To give it a more casual, daytime feel, layer a classic, medium-wash denim jacket over the top. The sturdy denim provides a nice textural contrast to the soft knit. It’s a foolproof combination for a relaxed weekend. Finish with a pair of white sneakers.
10. A Tailored Vest Over a T-Shirt
A tailored vest is a great layering piece that adds a touch of polish. For a modern, casual look, wear a simple, tailored waistcoat or vest open over a classic, high-quality white t-shirt. Paired with a pair of relaxed, straight-leg jeans, it’s a look that is both smart and effortlessly cool. It’s a great way to add a layer without the bulk of a jacket.
11. A Half-Zip Sweater & Jeans
A sporty and comfortable choice that is very stylish right now. A chunky, knit sweater with a half-zip or quarter-zip collar is a cozy and versatile piece. Pair it with your favorite, comfortable, straight-leg or relaxed-fit jeans. You can wear the collar zipped up for a turtleneck feel or open to show off a necklace. It’s a perfect, easy outfit for a casual fall day. Add sneakers or casual boots.
12. A Sweatshirt & Tailored Trousers
A perfect mix of casual and formal. Take a classic, comfortable crewneck sweatshirt and pair it with a pair of sharp, tailored trousers. The key is the juxtaposition of the casual, athletic top with the polished, formal pants. This high-low mix is very modern and chic. Give the sweatshirt a little front-tuck to define your waist. Add loafers or clean sneakers.
13. A Puffer Vest & a Sweater
A great layering combination for a crisp, sunny fall day. A lightweight puffer vest provides excellent core warmth. For a chic and textural look, layer it over a cozy, chunky knit sweater. The combination of the sleek, quilted vest and the soft, chunky knit is a beautiful contrast. It’s a stylish and practical look for any outdoor fall activity. Pair with jeans and boots.
14. A Hoodie & Leather Pants
Another great way to mix edgy and comfortable. A simple, soft pullover hoodie is the ultimate comfort piece. To give it a chic, evening-ready edge, pair it with a pair of sleek, straight-leg leather or faux-leather pants. The contrast between the casual hoodie and the luxe, edgy pants is a favorite of street style stars. Add a pair of heeled boots to dress it up even more.
15. A Cropped Sweater & a Button-Down
A clever way to play with layers and proportions. Layer a cropped sweater over a longer, oversized button-down shirt. Let the collar and the long hem of the button-down peek out from under the sweater. This creates a very cool, preppy, and layered look. This combination works perfectly with a pair of slim-fit jeans or leggings. Add a pair of classic loafers to finish the look.
16. A Long Coat & a Baseball Cap
The ultimate model-off-duty look. This outfit is all about mixing formal and casual accessories. Take a long, elegant wool coat, the kind you would normally wear for a formal occasion. For a cool, street-style look, pair it with a simple, casual baseball cap. The juxtaposition of the sophisticated coat and the sporty hat is unexpected and very chic. Wear it with a simple base of a sweater and jeans underneath.
17. A Knit Skirt Set
A matching knit set is the epitome of comfortable chic. A set consisting of a midi-length knit skirt and a matching sweater is a sophisticated take on the trend. In a fine-gauge, ribbed knit, it skims the body beautifully. It’s as comfortable as a sweatsuit but looks incredibly polished and put-together. It’s a perfect outfit for a smart-casual event. You can style it with heeled boots for a dressier look or sneakers for a more casual vibe.
18. A Cardigan as a Top
Wear your favorite cardigan in a new way. Instead of layering it, wear a classic, button-front cardigan as a top. A style in a soft, fine-gauge knit like cashmere or merino wool looks particularly chic. Button it up and tuck it into a pair of high-waisted jeans or tailored trousers. It’s a simple styling trick that makes a classic piece feel fresh and modern. It’s a perfect, easy look for a coffee date or a casual day at the office.
19. A Half-Zip & Leather Pants
A sporty and edgy combination. A cozy, slightly oversized half-zip or quarter-zip sweater has a relaxed, athletic feel. To give it a chic, evening-appropriate edge, pair it with a pair of sleek, straight-leg leather or faux-leather pants. The mix of the casual, sporty sweater with the edgy, luxe pants is a perfect example of modern high-low dressing. Add a pair of heeled boots or chunky loafers.
20. A Plaid Skirt & Combat Boots
A preppy classic with a tough edge. A classic, pleated mini skirt in a traditional plaid pattern has a smart, academic feel. To give it a modern, street-style twist, pair it with a pair of chunky, heavy-duty combat boots. The juxtaposition of the preppy skirt and the tough boots is what makes this look so cool. On top, a simple, fitted black sweater or a cozy hoodie works perfectly.
21. A Denim Shirt & Knit Pants
A comfortable and stylish weekend look. A pair of soft, comfortable, wide-leg knit pants feels like wearing sweatpants but looks much more elevated. Pair them with a classic, blue denim or chambray shirt. You can wear the shirt tucked in, or wear it open like a jacket over a simple tank top. The combination of the soft knit and the structured denim is a great textural mix. Add your favorite comfortable sneakers.
22. A Long Coat & a Baseball Cap
The ultimate model-off-duty look. This outfit is all about mixing formal and casual accessories. Take a long, elegant wool coat, the kind you would normally wear for a formal occasion. For a cool, street-style look, pair it with a simple, casual baseball cap. The juxtaposition of the sophisticated coat and the sporty hat is unexpected and very chic. Wear it with a simple base of a sweater and jeans underneath.
23. A Classic Hoodie & a Mini Skirt
A fun, youthful way to mix sporty and preppy. Take a classic, comfortable pullover hoodie and pair it with a short, pleated mini skirt, perhaps in a classic plaid or a solid color. The look is a playful mix of aesthetics that is very popular in street style. To keep it from looking too much like a costume, add a great pair of chunky loafers or cool sneakers and a pair of visible crew socks.
24. A Button-Down & a Bralette
A chic and slightly alluring layering technique. Wear a crisp, oversized button-down shirt and wear it open, or with only one or two buttons done up. Underneath, let a beautiful, delicate lace bralette peek out. It’s a look that is both relaxed and intentional. It works perfectly with a pair of high-waisted, relaxed-fit jeans. It’s a great look for a casual evening out with friends.
25. A Fleece Jacket & Tailored Trousers
Another great example of high-low dressing. A cozy, plush fleece jacket, a piece usually reserved for outdoor activities, can look incredibly chic when paired with sharp, tailored trousers. The contrast between the rugged, comfortable fleece and the polished, formal trousers is very modern and unexpected. Keep the colors classic—a cream fleece with black trousers is a great combination. Add clean sneakers or loafers.
26. Leggings & an Elegant Coat
The key to making leggings look chic is what you pair them with. A simple pair of classic black leggings can be instantly elevated by a beautiful piece of outerwear. Throw a long, elegant, tailored wool coat in a classic color like camel or grey over your leggings and a simple top. The structure and luxury of the coat completely transforms the casual leggings. Add a pair of stylish sneakers and a great handbag to complete the look.
27. A Knit Skirt Set
A matching knit set is the epitome of comfortable chic. A set consisting of a midi-length knit skirt and a matching sweater is a sophisticated take on the trend. In a fine-gauge, ribbed knit, it skims the body beautifully. It’s as comfortable as a sweatsuit but looks incredibly polished and put-together. It’s a perfect outfit for a smart-casual event. You can style it with heeled boots for a dressier look or sneakers for a more casual vibe.
28. A Cardigan as a Top
Wear your favorite cardigan in a new way. Instead of layering it, wear a classic, button-front cardigan as a top. A style in a soft, fine-gauge knit like cashmere or merino wool looks particularly chic. Button it up and tuck it into a pair of high-waisted jeans or tailored trousers. It’s a simple styling trick that makes a classic piece feel fresh and modern. It’s a perfect, easy look for a coffee date or a casual day at the office.
29. A Half-Zip & Leather Pants
A sporty and edgy combination. A cozy, slightly oversized half-zip or quarter-zip sweater has a relaxed, athletic feel. To give it a chic, evening-appropriate edge, pair it with a pair of sleek, straight-leg leather or faux-leather pants. The mix of the casual, sporty sweater with the edgy, luxe pants is a perfect example of modern high-low dressing. Add a pair of heeled boots or chunky loafers.
30. A Plaid Skirt & Combat Boots
A preppy classic with a tough edge. A classic, pleated mini skirt in a traditional plaid pattern has a smart, academic feel. To give it a modern, street-style twist, pair it with a pair of chunky, heavy-duty combat boots. The juxtaposition of the preppy skirt and the tough boots is what makes this look so cool. On top, a simple, fitted black sweater or a cozy hoodie works perfectly.
31. A Denim Shirt & Knit Pants
A comfortable and stylish weekend look. A pair of soft, comfortable, wide-leg knit pants feels like wearing sweatpants but looks much more elevated. Pair them with a classic, blue denim or chambray shirt. You can wear the shirt tucked in, or wear it open like a jacket over a simple tank top. The combination of the soft knit and the structured denim is a great textural mix. Add your favorite comfortable sneakers.
32. A Long Coat & a Baseball Cap
The ultimate model-off-duty look. This outfit is all about mixing formal and casual accessories. Take a long, elegant wool coat, the kind you would normally wear for a formal occasion. For a cool, street-style look, pair it with a simple, casual baseball cap. The juxtaposition of the sophisticated coat and the sporty hat is unexpected and very chic. Wear it with a simple base of a sweater and jeans underneath.
The modern wardrobe is built on the beautiful idea that you should never have to choose between feeling good and looking good. These 32 fall outfit ideas prove that mixing comfort and chic is the true secret to great personal style. By pairing your coziest, most-loved basics with polished, timeless staples, you can create a wardrobe that is versatile, stylish, and perfect for every occasion on your autumn calendar. So go ahead, throw that blazer over your hoodie—you’ll look fantastic.
