Men's Shirt

Menswear-inspired shirting is a key piece in any woman’s wardrobe, and while one in a classic white is a no-brainer, why not go a little more girlie with something silk and brightly hued? This brilliant blouse features a classic gingham pattern in an of-the-moment red and a boyfriend fit, making it the perfect shirt for a pair of dark washed jeans for weekend, or a black or camel pencil skirt for work.
To buy: Madewell Silk Gingham Boyshirt, $110
Long Cardigan

A classic button-front sweater is a wardrobe workhorse, and there’s no reason not to upgrade this essential to one that’s a little unexpected. Keep it weekend casual by wearing with jeans and a T-shirt, and work it 9 to 5 with wide-leg trousers or a pencil skirt.
To buy: Topshop Knitted Split Back Cardigan, $72
Slub-Jersey T-Shirt

A super soft T-shirt is the new standard in casual-cool tops and this V-neck version from Splendid ticks off all the right boxes. Keep things casual by pairing it with colored or patterned denim, or let it lend a laid-back feel to an after-dark look by wearing it with a black maxi skirt, statement necklace, clutch and high-heeled booties.
To buy: Splendid Vintage Whisper Cotton Slub-Jersey T-Shirt, $68
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The Blazer

Nothing pulls together a laid-back look like a structured jacket. It adds a little polish but still keeps the vibe casual. Layer it over tank tops and printed or solid denim, shorts or a bright patterned dress. At night, try it with a long black maxi skirt and a white shirt for a feminine twist on the tuxedo.
To buy: Ponte Rolled Sleeve Blazer, $70
Straight Leg Jeans

While a classic boot cut is universally flattering and the skinny still totally on trend, consider a style that sits in the middle: the straight leg jean. Create an effortlessly cool uniform by wearing these with a boldly colored silk button-up shirt and flats. At night, dress it up with a tuxedo or smoking jacket, a sleek black tank and a pair of heels.
To buy: J Brand Mid-Rise Straight-Leg, $165
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Trench Coat

No closet is complete without a trench, as the staple puts a chic spin on any look. And while a classic khaki version is always in style, consider one that’s a bit more sartorially surprising. It will sit well over everything from jeans, to a work-ready suit, to a maxi skirt.
To buy: Contrast Piping Trench, $80
Studded Ballet Flat

There’s nothing like a sky-high heel to give you a lift, but the reality is 90 percent of the time we need to be more grounded. The perfect combination of refined and rocker, these pretty flats will lend an edgy cool vibe to any look. Play up the punk vibe by pairing them with skinny black jeans and a biker jacket, or let them add a little grit to a girlie printed dress.
To buy: Zara Studded Ballerina, $70
T-Shirt Dress

When the ease of a dress meets the comfort of a T-shirt, the result is a must-have wardrobe essential. Throw it on in the morning with a sandal, sneaker, ballet flat or boot (depending on the season), and you’re stylishly set to take on anything the day has to offer. At night, simply switch the flats for a high-heel bootie, add a statement necklace along with bangles and head out in confidence.
To buy: Rag & Bone Isabel Dress, $195
Low Heel Bootie

There was a time when boots were worn only in fall and winter, but the rise of the low-heel bootie has made the boot a four-season player. As summer wanes, wear this boot with a pair of black shorts and a T-shirt, and come fall, zip it up with all your fall standards—including cords with a sweater and a casual LBD with or without tights.
To buy: Lucky Brand Tablita Boot, $109
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Stylish Sweatpants

We all secretly wish we could spend most of our lives in sweatpants, and now we can thanks to the invention of the street chic sweats. Made from the same comfy knit as the old school versions, these fashion-forward pants are more tailored, more streamlined and flatteringly (read: not baggy) fit, making them as appropriate with T-shirts, crew neck sweaters or a blazer as your tried-and-true blue jeans.
To buy: Mango Knitwear Trousers, $50