How Personal Style Builds Workplace Confidence and Career Success

Lindsay Nicholas reconnects with Leigh Ober, global chief people officer for Omnicom Precision Marketing Group and a former colleague from their shared time at RAPP. What follows is a sharp, grounded conversation about workplace confidence, career pivots, and why what you wear still matters more than most people admit.

Leigh's first fashion memory is practical. Her parents dressed her in skirts and dresses, but all she wanted was a pair of jeans. She saved her babysitting money and bought her first pair of Levi's. The stiff kind you had to break in yourself. How they fit and how they made her feel gave her a sense of real confidence. That instinct has stayed with her.

Her career started early. Babysitting, pharmacy work, waiting tables. She credits those service roles with teaching her how to read people, communicate under pressure, and think on her feet. A college internship in journalism saved her from a career she would not have enjoyed, and a handwritten letter to a music PR firm landed her first real job after the recruiter got stuck in a snowstorm and never made it to campus. She wrote to him anyway. Months later, he called.

As a personal style podcast, The Well-Dressed Mind always circles back to how clothing and career identity shape each other. Leigh has lived that evolution firsthand. She started in an era of suits, pantyhose, and heels every day. Now, as an executive woman leading people strategy across multiple agencies, she sees a workplace where anything goes. She is not entirely comfortable with that shift. Not because she wants formality back, but because she believes looking put together signals something important. It tells people you showed up with intention.

Her advice on workplace fashion is balanced. Jeans are fine. Sneakers are fine. But pair them with a jacket, some jewellery, a little structure. The goal is not to dress up. The goal is to look like you thought about it for more than thirty seconds.

Lindsay and Leigh share a moment on the classic "dress for the job you want" principle. Leigh frames it for the people she mentors: do not chase promotions. Chase skills, experiences, and contributions. The title will follow. The same applies to how you present yourself. Your clothes should make people notice you, not the outfit. That distinction matters.

The conversation also touches on identity beyond work. Leigh deliberately leads her bio with who she is as a person, a working mom, a beer yoga enthusiast, a music lover, before any job title. In a world of curated LinkedIn profiles and highlight reels, that kind of honesty stands out.

For anyone looking for podcasts about confidence, career strategy, and executive women's clothing choices that actually reflect real professional life, this episode is worth the listen. Leigh's closing advice: think about the impression you want to leave. Your clothes should complement who you are, not compete with it. Show up comfortable, show up sharp, and let the work speak.

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Leigh Ober

Global Chief People Officer

Omnicom Precision Marketing Group

Leigh Ober is the Global Chief People Officer at Omnicom Precision Marketing Group, where she leads the company's global people strategy, talent development, and organizational culture across its portfolio of agencies. A passionate advocate for inclusive leadership and professional growth, she is dedicated to building high-performing teams and creating opportunities for the next generation of marketing leaders.

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Lindsay Nicholas

President, Creative Director & Founder

Lindsay Nicholas New York

Lindsay Nicholas is the founder of Lindsay Nicholas New York, a luxury womenswear brand, and the host of The Well-Dressed Mind podcast. With a background in advertising and a career spanning New York, Singapore, and Dallas, she has spent over a decade building a brand rooted in the belief that personal style and professional identity are inseparable. Her collections are designed for women who dress with intention.

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How can the way you dress impact your confidence at work?

When you feel good in what you are wearing, you stop thinking about your appearance and focus on your performance. That mental freedom is where workplace confidence begins.

What should women wear to a job interview to make a strong first impression?

Something comfortable that also gives you an edge. A sharp jacket, a clean shirt, polished shoes. Skip the standard black suit and choose something that reflects your personality without distracting.

Why is dressing for the job you want better than dressing only for your current role?

How you present yourself signals how you see your own trajectory. People perceive you partly through what you wear, and dressing ahead tells them you are already thinking bigger.

How can women develop executive presence through personal style?

Wear pieces that make people notice you, not the outfit. Executive presence comes from looking put together without appearing overdone. Structure, fit, and a point of view go further than logos.

Why is authenticity important during job interviews and career growth?

Interviews are the best version of you that a company will ever see. If you are not being yourself, neither side can tell whether the fit is right. Authenticity saves everyone time.

What qualities do hiring managers look for beyond qualifications?

Energy, curiosity, and a willingness to lean in. The ability to ask good questions, admit what you do not know, and show genuine interest in the work matters as much as credentials.

How can women create more opportunities for career advancement?

Do not wait to be tapped on the shoulder. If you overhear a project that interests you, say so. Volunteer before you are asked. Most doors open because someone knocked first.

Why is networking and reaching out to mentors important for career success?

You will be surprised at who responds. Asking for advice is not a burden. Most people see it as a compliment. One letter, one message, or one conversation can redirect an entire career.

What role does confidence play in professional success?

Confidence lets you take risks, ask for help, and recover from failure without losing momentum. It is not about knowing everything. It is about trusting yourself to figure it out.

How can women balance comfort and professionalism in today's workplace?

Start with fit. Jeans and sneakers can look polished if paired with a structured jacket or a considered accessory. The line between comfortable and careless is effort, even a small amount of it.

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