STYLE

How To Style: C-Suite

November 14, 2025

Let’s get to work! Discover sophisticated sets, structured blazers, pencil skirts, and T-strap heels that mean business, picked by Tuckernuck co-founder Maddy Grayson.

Meet Our Expert:

Maddy Grayson

As a co-founder of Tuckernuck, Maddy wears many hats and works closely with members of the c-suite—like her sister and Tuckernuck CEO Jocelyn as well as many team directors. With more than a decade of professional leadership experience, Maddy's thoughtful ideas and creativity radiate through her personal style.

What Is C-Suite Style?

They say “dress for the job you want,” but what about romanticizing the job you have? Channel a confident power woman with sophisticated sets, tailored blazers, pencil skirts, and T-strap heels that (mostly) mean business. The look: understated yet commanding, with all the polish of a power move.

1. The Structured Blazer

Top layers that add instant polish. From our iconic Diana blazer to heritage plaids, any style feels timeless and sharp.

2. The Power Skirt

Sleek, chic, and even better in a matching set. We especially love pencil skirts.

3. The Classic Shirting

From pinstripe oxfords to feminine puff sleeves or wrap styles, these put-together picks are meant to pair with your best bottoms— from work to weekend.

4. The Next-Level Heel

From a classic t-strap to a playful point, shoes (mostly) mean business. Choose a lower heel to easily go from commute to conference room.

5. The Boss Lady Bag

Sleek shapes, from ladylike top handles to neutral, carryall totes, are essential for holding everything you need.

6. The Work Pant

Whether you choose relaxed trousers, our signature Ashford or Watson, or a leg-lengthening flare style—a power pant is key to nailing c-suite style.

7. The Staple Sweater

Luxe cashmere, ladylike cardigans, and fitted turtlenecks—these flattering knits are pieces to count on in and out of the office.

8. The Dressy Denim

For an office appropriate look—choose dark washes and current shapes. You’ll reach for them on those days when you need a desk-to-dinner outfit in a pinch.

See You in the Office!