1
Year-Round Essential
Lioness Trencherous Coat
What makes a trench such a worthwhile investment piece is that it’s multi-seasonal: Wear it during autumn, spring, and even warmer winter days. Because this one has a roomier menswear cut, it’s ideal for layering.
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2
Bold Minimalism
GUESS Amalia Maxi Rib Skirt
The epitome of an elevated staple, this creamy ribbed sweater skirt has an elastic waistband for comfort and a high slit for pizzazz.
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3
Zhuzhed-Up Basic
The Drop Renata Rib Midi Dress
Now 34% Off
Credit: The Drop
The qualifications for a perfect sweater dress are a longer, looser silhouette that can be worn to the office, paired with a small detail that makes it fun enough for after-work happy hour as well. This caramel-colored design has a side slit that fits the bill.
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4
Detailed Trousers
English Factory Front Slit Pants
If you find a good pair of cigarette pants, they’ll be in rotation as often as your go-to denim. This version has slits at the ankles to distinguish it from the many (many) options that are out there.
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5
Sophisticated & Versatile
WAYF Olive Vest
You don’t need to abandon the cropped vest—simply get creative with it. Swap the matching shorts for straight-leg jeans, and when it starts to get really chilly, pop a button-down underneath.
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6
Slim-Fit Sweater
ASTR the label Aldari Sweater
For proof that not all knitwear need be of the chunky, sack-adjacent variety, look no further than this off-the-shoulder option. It’s all about asymmetry, from the sleeves to the shoulder.
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7
Collarbone Cut-Out
Line & Dot Sweater Dress
The dipped neckline on this slim-fitting sweater dress makes it date night-appropriate; add some glitzy earrings to complete the look.
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8
Airy Outerwear
Lioness La Quinta Blazer
An ever-so-slightly baggy linen blazer will come in handy when you need a light layer to throw on over jeans and a tee. Pick out this earthy green one for when you need something neutral-adjacent to break up a monochromatic outfit.
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9
Clever Layering
English Factory Pleated Mini Dress
A sartorial optical illusion, this mini dress is designed to look like separates but has all the convenience of one piece.
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10
Alternative Classic
Levi’s Ribcage Wide Leg Jeans
When you’re tired of blue jeans and want something that’s just as comfortable with a little more edge, add this pair to your denim collection and thank us later.
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11
Wardrobe Hero
AYR Deep End Button Down
This blue oxford is about to become a closet mainstay—if only because your white button-down is bound for laundry day eventually. Play into the slightly more casual look by leaving a few buttons undone in either direction.
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12
Autumnal Florals
o.p.t Smocked Maxi Dress
Come chillier weather, swap your pastel florals for moodier botanical prints. This smocked frock can be dressed up with block heels or kept simple with slides.
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13
Artful Design
Vince Marble Crew
Gossamer-thin fabric and watercolor-like swirls conspire to create one of the coolest crewnecks you’ll find this season.
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14
Minimalist-Friendly Pattern
PAIGE Jia Trousers
Micro-houndstooth and cuffed hems make these pleated pants a mod alternative to your go-to black work trousers.
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15
Lightweight & Luxurious
State Cashmere V-Neck Sweater
Cashmere for under $150 is always a good idea, particularly when it comes in the shape of a pistachio green v-neck with just the right amount of slouch.
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16
Jigsaw Cut-Outs
Amanda Uprichard Puzzle Dress
You likely already have one (or several) little black dresses in your closet but add this one to the mix for when you feel like spicing up a perennial favorite.
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17
Bohemian Twist
Ulla Johnson Maggia Blouse
Riff on a classic with Ulla Johnson’s take on a crisp white button-down, which includes pintuck balloon sleeves and a peter pan collar.
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18
Puffy & Printed
SEA Arlita Puff Top
If you’re in need of more workwear, this 3/4-sleeve top fits most dress codes and looks just as good with white jeans as it does more tailored pants.
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19
Earthy Hue
ANINE BING Leanne Mini Dress
Now 47% Off
Credit: Anine Bing
Your summer silk mini just got a cool-weather upgrade in the form of khaki green. This autumnal color works well for any fancier events you have on your calendar.
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20
Statement Shoulders
Norma Kamali Shoulder Pad Crew Top
For a night-out look that’s more stylish than shabby, we love this Norma Kamali crew top. It’s ultra-fitted for a sleek line that can be worn with a mini skirt or cigarette pants, keeping all the focus on the star of the show: those massive shoulder pads.
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