Every item on this page was chosen by a Woman's Day editor. We may earn commission on some of the items you choose to buy.
1
these wide-leg pants and heels
Tronjori Wide Leg Palazzo Pants
1
these wide-leg pants and heels
Tronjori Wide Leg Palazzo Pants
Now 15% Off
Credit: Tronjori These super-wide-leg pants have so much personality that you can just pair them with heels and a mock neck bodysuit and call it a day. Add a statement necklace to complete the look, or keep it simple and elegant with your favorite stud earrings.
2
this ribbed skirt and turtleneck
Quince Mongolian Cashmere Midi Skirt
2
this ribbed skirt and turtleneck
Quince Mongolian Cashmere Midi Skirt
Now 60% Off
Credit: QuinceMade with Mongolian cashmere, this calf-length midi skirt is seriously soft, and it looks so chic when paired with a matching turtleneck and cinched with a belt. You can even match your booties to your belt for a totally cohesive ensemble.
3
this corduroy jumper and booties
Gap Corduroy Mini Dress
3
this corduroy jumper and booties
Gap Corduroy Mini Dress
Credit: GapNothing says fall fashion quite like a rich brown corduroy jumper paired with a mock neck long-sleeve shirt. Dress it up with a pair of pointed-toe booties, and if the weather is especially nippy, then you can add a pair of black tights to keep your legs warm.
RELATED: The Most Comfortable Women's Dress Shoes for Standing All Day
Advertisement - Continue Reading Below
4
this button-up cardigan and cargo pants
Universal Standard Blanket Cardigan
4
this button-up cardigan and cargo pants
Universal Standard Blanket Cardigan
Credit: Universal StandardIt may be pricey, but this button-up, rib-stitch cardigan is an investment you surely won't regret. Its pretty cider color just screams fall, and it looks so classy when paired with a bodysuit, a pair of Y2K-inspired twill cargo pants, and slip-on mules.
5
this classic blazer and ripped jeans
Sidefeel Casual Plaid Blazer
5
this classic blazer and ripped jeans
Sidefeel Casual Plaid Blazer
Credit: SidefeelBreathable and comfy, this plaid blazer looks like it means serious business, but you can make it a little more playful with some ripped straight-leg jeans and a pair of suede booties.
6
this cotton turtleneck and pleated trousers
Kotn Fitted Turtleneck
6
this cotton turtleneck and pleated trousers
Kotn Fitted Turtleneck
Credit: KotnKeep it classy and casual with a cotton micro-rib turtleneck, which can easily be tucked into a pair of pleated trousers and paired with a plaid blazer. And to pull it all together, add a pair of chunky loafers.
Advertisement - Continue Reading Below
7
this wool vest and tailored blouse
Gentle Herd V-Neck 100 Percent Wool Sweater Vest
7
this wool vest and tailored blouse
Gentle Herd V-Neck 100 Percent Wool Sweater Vest
Credit: Gentle HerdSweater vests are having a moment, and this boxy wool vest is so easy to style. To give it some shape, wear it over a tailored cotton blouse with slim, ankle-length jeans, and then add some casual sneakers for a playful twist.
8
this belted sweater dress and heels
Good American Belted Body Dress
8
this belted sweater dress and heels
Good American Belted Body Dress
Now 65% Off
Credit: Good AmericanIf you're looking for a one-piece ensemble that really steals the show, then go with this ultra-flattering tie-waist sweater dress. The soft-ribbed knit fabric feels just like cashmere, and it's versatile enough to wear with anything from heels to booties to flats.
9
these cropped overalls and knit sweater
Universal Thread Denim Overalls
9
these cropped overalls and knit sweater
Universal Thread Denim Overalls
Credit: Universal ThreadWho ever said overalls are just for kids? These ankle-length denim overalls are ideal for an indulgent meal, and you can easily dress them up with a brightly-colored cable-knit sweater and chunky heeled clogs.
Advertisement - Continue Reading Below
10
this lightweight flannel and jeans
Old Navy Cropped Plaid Flannel Boyfriend Shirt
10
this lightweight flannel and jeans
Old Navy Cropped Plaid Flannel Boyfriend Shirt
Credit: Old NavyFlannel and fall will always be a perfect pair, and this fun cropped flannel shirt is a great choice if you're looking to layer. Made with 100 percent cotton, it's light enough to wear over a turtleneck, and you can complete the look with classic bootcut jeans and leather booties.
11
this cropped turtleneck and trousers
The Drop Side Button Cropped Turtleneck Sweater
11
this cropped turtleneck and trousers
The Drop Side Button Cropped Turtleneck Sweater
Credit: The DropYes, turtleneck season has definitely arrived, and this cropped one looks Thanksgiving dinner ready when you add some straight leg trousers and heeled booties.
12
this eyelet crewneck and cargo slacks
Thakoon Embroidered Balloon Sleeve Sweatshirt
12
this eyelet crewneck and cargo slacks
Thakoon Embroidered Balloon Sleeve Sweatshirt
Credit: ThakoonFor the comfort of a sweatshirt and the style of a sweater, go with a fun hybrid, like this pretty eyelet-sleeve, drop-shoulder crewneck. It looks just as great with jeans as it does with a pair of straight-leg cargo trousers, and for a pop of color, add some eye-catching pointed-toe mules.
Advertisement - Continue Reading Below
13
this extra-long cardigan and paperbag pants
A New Day Long Sleeve Button-Front Cardigan
13
this extra-long cardigan and paperbag pants
A New Day Long Sleeve Button-Front Cardigan
Credit: A New DayWearing a knee-length cardigan to Thanksgiving dinner will make you feel like you're swathed in a cozy hug all night — and you can keep it looking stylish with a bodysuit tucked into paperbag pants and a pair of suede booties.
14
this square-neck midi dress and tall boots
Madewell Tiered Midi Dress
14
this square-neck midi dress and tall boots
Madewell Tiered Midi Dress
Credit: MadewellThis puffy-sleeved tiered midi dress becomes the perfect fall staple when you add a pair of tall heeled boots. You can also bring along a casual striped cardigan to keep your arms covered if you're worried about feeling chilly.
15
this oversized sweater vest and ripped jeans
Viottiset Oversized Houndstooth Sweater Vest
15
this oversized sweater vest and ripped jeans
Viottiset Oversized Houndstooth Sweater Vest
Now 26% Off
Credit: Viottiset This oversized houndstooth sweater vest is a favorite on Amazon for a reason: It's so, so versatile. However, if you're looking to wear it to Thanksgiving dinner, then try layering it over a crisp white button-up with cropped, ripped jeans and some edgy heeled booties.
Advertisement - Continue Reading Below
16
these elastic waist pants and ribbed bodysuit
Everlane The Dream Pant
16
these elastic waist pants and ribbed bodysuit
Everlane The Dream Pant
Credit: EverlaneWhy are these called "The Dream Pant," you ask? Because they feature an elastic waist, sleek tapered leg, and wrinkle-resistant knit fabric that provides all the comfort of your favorite sweatpants. Dress 'em up for the night with a cute ribbed bodysuit and brightly-colored ballet flats.
17
this fitted sweater dress and trench coat
Old Navy Fitted Sleeveless Rib-Knit Midi Sweater Dress
17
this fitted sweater dress and trench coat
Old Navy Fitted Sleeveless Rib-Knit Midi Sweater Dress
Credit: Old NavyYou simply can't go wrong with a form-fitting rib-knit sweater dress the color of pumpkin pie. To accessorize, keep it simple with a lightweight trench, suede booties, and a delicate gold chain.
18
this tailored blazer and leggings
Eloquii Long Tailored Blazer
18
this tailored blazer and leggings
Eloquii Long Tailored Blazer
Credit: EloquiiYes, you can get away with wearing your stretchy black leggings to Thanksgiving dinner — just as long as you pair them with a tailored blazer that hits below your hip and some stylish penny loafers.
Advertisement - Continue Reading Below
19
these pull-on pants and plaid button-up
Madewell Jacquard Pull-On Pants
19
these pull-on pants and plaid button-up
Madewell Jacquard Pull-On Pants
Now 52% Off
Credit: MadewellIf comfort is your main priority on Thanksgving, then these jacquard pull-on pants (which can be adjusted at the hem for a more tapered look) are a must. You can even make them look a bit more formal with a fitted plaid button-up and a pair of chunky loafers.
20
this voluminous plaid skirt and ribbed sweater
Tanming Wool Plaid Skirt
20
this voluminous plaid skirt and ribbed sweater
Tanming Wool Plaid Skirt
Now 13% Off
Credit: TanmingWith a skirt this gorgeous, you don't have to overdo it with accessories. A simple ribbed sweater tucked into the skirt and a pair of tall heeled boots will round it out nicely.
Editor
Corinne Sullivan is an Editor at Cosmopolitan, where she covers a variety of beats, including lifestyle, entertainment, relationships, shopping, and more. She can tell you everything you need to know about the love lives of A-listers, the coziest bedsheets, and the sex toys actually worth your $$$. She is also the author of the 2018 novel Indecent. Follow her on Instagram for cute pics of her pup and bébé.
Advertisement - Continue Reading Below
Advertisement - Continue Reading Below