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RelaxedFit1 of 16
Cropping Up2 of 16
Tailored yet casual, these cropped pants can be worn on a hike, or paired with a sleek tank for a day with friends.
SHOP NOW: Alternative Apparel Waist Pants, $88
Wake-Up Call3 of 16
This chic asymmetrical dress may have the comfort factor of a nightgown, but it's still sexy enough for date night when paired with platforms and dynamic statement earrings.
SHOP NOW: T by Alexander Wang Dress, $175
Totally '80s4 of 16
We love the "Flashdance" look of this deconstructed sweatshirt, which can replace your cardigan as a lightweight fall cover-up.
SHOP NOW: Aiko Sweatshirt, $128
That's A Wrap5 of 16
Whether snuggling on the couch or meeting friends for after-work cocktails, this ultra-soft wrap is bound to be a wardrobe staple no matter the season.
SHOP NOW: Isabel Marant Scarf, $295
Knit Pick6 of 16
This snuggly cap is a must-have fall accessory for that preppy, back-to-school look.
SHOP NOW: Cacharel Beanie, $150
New Jersey7 of 16
Nothing is more comfortable than jersey fabric, and this top's tie-dye design gives it a trendy edge. Pair with leggings and sneakers for an easy weekend look.
SHOP NOW: L’Agence Jersey Top, $180
Join The Navy8 of 16
A terry one-piece serves as a comfy swim cover-up or, when paired with metallic sandals, a stepped-up casual ensemble.
SHOP NOW: Juicy Couture Playsuit, $150
Hot Pants9 of 16
The ultimate luxury? Skinny sweatpants that are sleek enough to hit the streets when paired with rugged, edgy items like a leather jacket and sky-high booties.
SHOP NOW: J.Crew Sweatpant, $45
Handle It10 of 16
Who says a clutch can't be cozy? Reach for a fabric version when going for a softer look.
SHOP NOW: Lauren Merkin Clutch, $225
Full Suit11 of 16
All you need is a statement clutch and jewels to take this jumpsuit from "just hanging out" to "out all night."
SHOP NOW: T-Bags Jersey Jumpsuit, $195
Not-So-Heavy Metal12 of 16
Make a statement with this hand-beaded chiffon bib necklace.
SHOP NOW: Roarke Bib Necklace, $396
Fancy Feet13 of 16
These color-blocked knee socks are meant to be seen. Wear them pulled up and peeking out of boots, when paired with a skirt for a fall weather look that's comfy and cool.
SHOP NOW: Paul Smith Socks, $38
Magic Slipper14 of 16
Wear a pair of old-school moccasins as slippers when at home or paired with jeans for brunch.
SHOP NOW: Minnetonka Moccasin, $40
Bare Arms15 of 16
This slub-jersey vest adds a stylish edge to even the most dressed-down ensemble. Up the ante and pair with a wide belt for an effortlessly chic look.
SHOP NOW: Splendid Vest, $67
Mrs. Softee16 of 16
Cashmere is the epitome of comfort. Try it a pencil skirt for a little luxe at the office or with leggings when running off-duty errands.
SHOP NOW: J.Crew Cashmere Sweatshirt, $248