How To Dress Like You’re In Charge: The Lady Boss Edition

August 20, 2020

As workplaces become more casual, getting dressed when you’re the boss and you’re a lady is getting trickier. Many of my clients are the only woman in a leadership position within their organization. Being the only woman in charge is challenging because it means you’re without examples of how to dress for your role or a sense of what’s appropriate in different professional contexts.

If you’re sick of getting lost in the shuffle of pantsuits and sensible separates or, out of fear of not being taken seriously, you’ve veered towards styles that are overly masculine or stuffy, here are four tips to help you reclaim your personal style and maintain your authority at work.

Assess The Unspoken Sartorial Culture

When you’re the only lady boss in the building, trying to figure out the appropriate female equivalent of a button down and jeans isn’t always clear. Wearing the exact same outfit as the guys can give off a less feminine feel than many women want. Plus, it’s boring.

One trick to gauge the general level of workwear formality in a male dominated office is to look at the shoes of several men in similar leadership positions as you. Are they wearing Ferragamo, running sneakers or some generic shoe you couldn’t pick out in a line up?

This will give you a sense of the wardrobe culture of the office and is indicative of the expectations around investing in your wardrobe. If they are wearing expensive shoes with jeans, invest in accessories and shoes and add one structured piece (a shoe, a bag, a blazer) to your look with dark denim. If they’re more of the running shoes and jeans crowd, go with a boot or flat (or a fun sneaker), skip the blazer and add a vest or a cardigan.

Use The +1/-1 Rule To Find Your Workwear Comfort Zone

Next, play around with wearing one level of formality up or down from your office’s baseline until you get a feel for what works for you and your work context. If you want to dress down more, play with heel height, proportion (wear a boxy top with a very fitted bottom or a wide leg pant with a fitted top) and pick pieces with less structure like a boyfriend cardigan instead of a blazer.

If you want to dress up one level add a structured piece to a casual look. Throw on a well cut blazer or a heel to stand out as the leader in an otherwise casual work environment. If you’re in a creative or more laid back environment, try one of these in a print or bold color to take the formality level down a notch.

Use the Third-Piece Rule To Look Polished

And by “rule” I mean something women’s magazines made up but it’s actually pretty smart so we’re gonna roll with it.

The Third-Piece Rule states that in order to make a boring outfit stand out you should add a third item like a blazer, vest, cardigan, cape or statement accessory (hat, scarf, belt, necklace, cuff, etc) to your top (first piece) and bottom (second piece). It’s a super easy trick and consistently adding a third piece when you’re planning your outfits can have a real impact on how polished and “together” you look and feel.

Here are some examples to give you an idea:

Third piece: Leather Jacket
Image Source: Fashion Me Now

Third Piece: Blazer
WhoWhatWear via

Third Piece: Scarf + Fourth Piece: Statement Earrings
Image Source: WhoWhatWear

Invest Like It Matters

While not every promotion comes with a big pay increase,  investing in your work wardrobe should be a priority because it contributes to building your personal brand and increases your confidence. Many clients I work with consider upgrading their wardrobe a business expense when they get a promotion. That doesn’t mean you have to go crazy and spend a lot of money at once. Simply identify what pieces you can add to your existing wardrobe to elevate it and budget for them.

Comments +

Leave a Reply

Your email address will not be published. Required fields are marked *


Download My Ultimate Guide To Dressing For The Camera

Get The Guide