Because it has a pull-on design, this satiny slip is covertly comfortable. Wear a chunky knit with sparkly kitten heels for a formal fête.
In terms of easy wear, you can't beat a jumpsuit. This one is made from a soft fabric that won't dig in or pull, and is ideal for layering over turtlenecks or long sleeves.
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You might not have thought you needed another button-up, but that's before you saw this candy cane-esque striped one in the perfect oversized fit.
This customer-favorite has over 28,000 reviews and 32 colors to pick from. Grab it in a festive mulled wine hue when you have a low-key dinner to dress for.
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With its plaid printing and touch of leather, this blazer is peak fall. Throw it on over a slip dress if you need a bit of warmth or want to break up an all-neutral look with a hint of pattern.
If you're all about pumpkin-colored everything this time of year, keep the theme going with your wardrobe.
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For any winter weddings (or just really, really fancy affairs) this floor-length gown is definitely black tie-appropriate.
Wear it with jeans, with side seam-split leggings, or even with an elastic-waist mini skirt—any way you style this smocked shirt, you'll look put-together.
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An LBD that's actually comfortable is always a win in our book. This one has a drop waist that makes it pregnancy-friendly and a crinkled texture that helps it stand out.
Credit: amazon essentials It's called sweater weather for a reason. Add this long cardigan to the mix when you want to reach for something softer than a blazer to head to brunch.
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This bright red dress is great because it can be worn two ways: buttoned up as a preppy midi over knee-high boots or fully open as a festive layer over jeans and a tee.
One step above your fave sweatsuit but just as cozy, this sweater set comes in tons of colors and is the ideal uniform for holiday movie marathons.
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Think of this black jumpsuit as a blank canvas—there's so much to do with it! You can re-wear it for every holiday party in your calendar. Switch up the jewels, shoes, and layers to keep it feeling fresh each time.
With its furry shearling trim, this purple piece screams muppet-chic (in the best way). It's outerwear eye candy guaranteed to spice up the simplest of outfits.
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If traditional red and green is too on-the-nose for you, opt for a lighter sage shade to keep the color palette alive in a more elevated way. This silky dress is effortlessly elegant.
Elastic waistbands are the name of the game, and it doesn't get more autumnal than a splashy orange pair of sweater pants you can wear to Thanksgiving.
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Complete with gauzy fabric and puffy sleeves, this ethereal dress is one you'll want to wear year-round. It also comes in a pretty persimmon color, if you want something more saturated.
Paired with a leather blazer or suede trench, this stretchy sweater midi is office-appropriate and just dressy enough to wear to any post-5 p.m. get-togethers.
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These jet-black bootcut jeans look every bit as dressed-up as trousers, making them the perfect thing to put on when it's time to graduate from leggings.
Meet the one true shapeless-yet-stylish piece of clothing: the poncho. It's the closest you'll get to a socially acceptable form of wearing a blanket outside the house (and this one has a hood, too!).

Elly Leavitt is a fashion and luxury commerce editor with over seven years of experience covering fashion and design. Her writing can be found in Harper’s BAZAAR, ELLE, Town & Country, Esquire, ELLE Decor, and more. Previously, she was an editor at Domino magazine. You can probably find her in line at Trader Joe's. You will never find her at SoulCycle.
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