The Office Outfit Formulas of 3 Successful Women

Updated 05/01/19
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The best office outifts

Dressing for the office doesn’t mean you have to lose your sense of style. In fact, we’d argue wearing outfits that communicate your taste and personal style is not only important within a professional setting (self-confidence, people), but actually achievable no matter what office environment you’re dealing with. If you work in a corporate setting, make small tweaks to your looks, like hiring a tailor to create a perfect fit or wearing colors that feel of-the-moment. Or, if you work in a more creative industry, try out more trend-forward pieces that work within the confines or professional attire.

So, what, exactly, are the office outfits successful women wear to work? I turned to three successful women in the fashion e-commerce, talent management, and digital publishing spaces to share their best office outfit formulas. Whether they’re drawing on some of the biggest fall trends (hello, ’80s), layering on a tailored blazer, or gravitating toward structured shapes, these are all outfits that make them feel professional and, most importantly, confident. Scroll down to see the work outfits these successful swear by and shop pieces to replicate their looks.

Office outfit formulas of successful women: Caroline Huang Maguire

Caroline Huang Maguire, Fashion Director, Shopbop

"I am obsessing over the '80s movement and plaid. A strong statement blazer in a bold color or print screams power."

Wool Oversized Blazer
Natasha Zinko Wool Oversized Blazer $1295

"There's something really classic and timeless about a plaid blazer, but you can also make a statement with mixing two classic plaid pieces together or pairing with a neon accessory."

Classic Striped Blazer
Scotch & Soda/Maison Scotch Classic Striped Blazer $225

"This two-piece tailored suit paired with a graphic T-shirt and sandals is the perfect balance of professional and stylish."

Tailored Drop Trousers
R13 Tailored Drop Trousers $495

"I love that these pants are a heritage print but updated in a drop crotch harem style—très chic!"

Office outfit formulas of successful women: Vanessa Flay

Vanessa Flay, Partner and EVP of Talent, Digital Brand Architects

"I have two approaches to office dressing, and they are mainly determined by whether I have in-person meetings, lunches, or client events that day. If I do, I like to feel as polished and effortless as possible, and I do that by putting on an easy one-piece, like a jumpsuit or dress, along with heels. If I don't and I'm just returning emails, taking calls, and plugging away with my team, I go for comfort, and that usually entails jeans, a blazer, and either flats or sandals."

Chriselle Lim Collection Jane Stripe Portrait Jumpsuit $119

"You don't have to think much with one-piece dressing, so this jumpsuit is a great solution. The pinstripes are classic, and the slight off-the-shoulder cut makes it feel current."

Chriselle Lim Collection Bianca Piped Houndstooth Blazer $119

"Perfect for fall, this houndstooth blazer is easy enough to throw on with jeans on a down day."

Office outfit formulas of successful women: Sacha Strebe

Sacha Strebe, Editorial Director, MyDomaine

"I wear black every day, so dressing for the office is all about layering and bringing interesting shapes together in the one outfit. I love to have fun with silhouettes, such as a pairing a structured blazer with a silk slip dress or wearing a sheer tulle top under a T-shirt, that's worn over the top of a fitted dress and finished off with leather leggings and heels or boots. Whether I'm dressing for the office or the grocery store, I love to wear clothing that makes me feel strong and beautiful.

It's my daily confidence boost."

Camilla and Marc Etienne Jacket $720

"I am obsessed with Camilla and Marc's blazers. They are so well cut and always make a statement. I love how this can look professional in an office setting but be paired with jeans for a casual weekend dinner or coffee date. It is a little on the expensive side, but the cost per wear is affordable thanks to its versatility. I always receive compliments when I'm wearing it."

Ellery Flared Midi Skirt $225

"I am a huge fan of Australian designers, and Ellery is at the top of my list. She has really grown into herself since moving to Paris and showing at fashion week. I love seeing how she has evolved her designs, and there's always something each season that I want to invest in. This Olympia skirt is from a few seasons ago, but it's still one of my favorites. I love wearing it to work with a structured blazer, but it can easily transform into a cocktail outfit if I need to attend a work event after hours."

Kaia High Heel Sandals
Alexander Wang Kaia High Heel Sandals $595 $417

"I like simple heels for the office, or flats. I'm wearing sold-out WWW collection shoes in this photo, but I also love the simple look of these Kaia shoes by Alexander Wang. I've had my eye on them for months. It might be time to bite the bullet and get them. I do love that these have a low heel for the office, which also transfers nicely to the weekend or going out. I can't do the killer stilettos of my youth anymore."

Shop Editor-Approved Office Outfit Picks

Oversized Tartan Gabardine Trench Coat
Rokh Oversized Tartan Gabardine Trench Coat $1790

Pile on the checks.

Bourgeoise Leather Knee Boots
The Row Bourgeoise Leather Knee Boots $1895

The boots I've had my eye on for months.

Wrap-effect Checked Wool-blend Canvas Wide-leg Pants
Monse Wrap-Effect Checked Wool-Blend Canvas Wide-Leg Pants $1190

A cool take on traditional pants.

H&M Jersey Jacket $35

Blazers are always a cool way to tie together an office outfit.

Intarsia Fishnet Tights
Gucci Intarsia Fishnet Tights $85

Layer these under skirts and dresses—or even jeans.

Knife Logo-embellished Houndstooth Wool Mules
Balenciaga Knife Logo-Embellished Houndstooth Wool Mules $1190

Low heels are my preferred shoes for the office.

Coleen Cutout Stretch-crepe Midi Dress
Khaite Coleen Cutout Stretch-Crepe Midi Dress $1260

To wear with over-the-knee boots.

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