Menswear-Inspired Outfits That Give Major CEO Energy

From pinstripe pants to oversized blazers and tailored trousers, these pieces mean business.

By Alexa Vazquez Oct 16, 2026 3:18 PMTags
rainmaker hero image.jpgGetty Images

It's official: Power dressing is back in session. With the season two premiere of The Rainmaker, we're taking inspo from courtroom style and giving our wardrobes a seriously chic promotion.

Menswear-inspired fashion is all about borrowing traditionally masculine silhouettes and making them feel effortless and modern. Think tailored trousers, oversized blazers, and sophisticated accessories that say we mean business—even when our biggest decision of the day is what to order for lunch.

An oversized blazer instantly elevates your favorite jeans or leggings, while high-waisted trousers paired with a crisp button-down deliver a polished, put-together energy with minimal effort. For extra attitude, add a sleek pair of slingback heels or a structured satchel tote to take any outfit from the office to happy hour.

Whether you're dressing for an important meeting, refreshing your workwear wardrobe, or simply channeling your inner girl boss, you don't need a corner office (or a CEO salary) to nail the look thanks to these affordable Amazon pieces.

Mutitop Button Down Shirt

A simple white button-down is a classic that every working woman needs in her wardrobe. This one is made from 100% cotton with a crisp construction that always feels put together.

PRETTYGARDEN Tailored Wide-Leg Dress Pants

Available in 19 neutral and bold colorways, these affordable trousers have a high waist, flowy fit, and subtle pleating. 

Grlasen Oversized Blazer

To make a blazer feel modern and trendy, opt for an oversized silhouette. It looks chic layered over a mini dress or tights and instantly elevates a plain t-shirt and denim.

JW PEI Ziva Metal Lock Decoration Tote Bag

With its timeless turnlock design, this structured tote looks so much better than a backpack. Choose from black or brown.

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ZESICA Summer Business Casual Strapless Blazer Vest

Add a little drama to your office-ready look with this blazer-inspired strapless top featuring button and pocket detailing.

NIMIN Wide-Leg Work Pants

These wide-leg trousers with pleated accents are a versatile piece that you can wear a million different ways, whether with a blouse or cozy sweater.

VOLEECE Slingback Heels

Putting on heels is an instant confidence boost, especially when they're these pointed-toe slingback stilettos with a glossy patent leather finish.

Gleeivy Striped Button Down

Looking for a twist on a button-down? This breezy option features smocked cuffs with a ruffle accent. Choose from 21 colors.

Refresh your black jeans for fall—Old Navy has denim under $20.

How We Choose

The E! Insider Shop editors and writers search the internet to find the best products out there. We interview expert sources, comb through customer reviews, and use our own personal experiences to make shopping easier for our readers.

As an editorial team, we independently create content and determine coverage based on research, reporting and what we think our readers would like to read about. The goal of our content is to provide a service and inform readers who are on the hunt for the latest products to help make their life better. Items are sold by retailer, not E!. Pricing and availability are accurate as of publish time.