How to Plan for a Speaking Engagement: What Accomplished Women Veteran Leaders Should Wear

You get to decide whether your style is bold, refined, sophisticated, colorful, classic, modern or a combination of all of those things.

I started my speaking career about a year after retiring from the Air Force, but speaking had always been something I enjoyed. I loved sharing what I knew, connecting with people, and helping them see things differently.

Throughout my military career, I was often told that I was a great speaker. In fact, there were times when people joked that they did not want to speak after me because I had set the bar pretty high.

While I was still serving, I became certified as a motivational speaker. After retiring, I continued to build on that foundation and became a certified image consultant.

Those two areas of expertise eventually came together in a way I never expected. I began to see just how much our image influences the experience people have of us, especially when we are standing in front of a room, sharing our expertise and representing what we know.

Over the past few years, one of the biggest lessons I have learned is that speaking is a form of entertainment.

Whether you are a keynote speaker, panelist, or workshop presenter, people want more than information; they want an experience they can remember. I have attended countless conferences, summits, workshops, and fireside chats, and while most speakers are knowledgeable, experienced, and passionate, I have noticed that many forget one important part of the experience...your image is part of the message.

Here is what I've noticed:

• The outfit doesn't fit the level of the opportunity. Someone may be speaking to executives, leaders, or a high-level audience while dressed as though they are attending a casual networking event.

  
  

• The speaker disappears visually. Their clothing may be too casual, too muted, or lack distinction, making it difficult for the audience to immediately register their presence when they walk on stage.

  
  

• They look uncomfortable. You can see it in the constant tugging at a jacket, pulling down a dress, adjusting a skirt, fixing a neckline, or repeatedly checking their appearance.

  
  

• Their personality isn't visible. Sometimes the clothing is so generic that you don't get any sense of who the person is. There is no visual connection between the person and the brand they are building.

  
  

• There is a disconnect between their words and their appearance. They may be talking about confidence, leadership, transformation, influence, or executive presence, but their presentation doesn't visually reinforce those qualities.

  
  

• They look like everyone else. At a conference where dozens of people are competing for attention, a speaker's image can become indistinguishable from the audience.

  
  

• They haven't considered the camera. In today's speaking environment, your audience isn't always just the people sitting in the room. You may be photographed, recorded, livestreamed, or featured on social media afterward. An outfit that works in person may not have the same impact on camera.

I was called to make an impromptu speech at a Women's Empowerment Brunch.

As accomplished women veterans, many of us naturally gravitate toward public speaking after service. We spent years briefing leaders, leading formations, facilitating meetings, representing our organizations, and speaking with authority because it was part of our roles, positions, and ranks.

But something changes after we leave the military.

When you are called to speak in a civilian environment, it can feel surprisingly uncomfortable to figure out what to wear, especially when you are stepping into unfamiliar rooms where you are expected to be the expert, keynote speaker, panelist, or thought leader.

You know how to deliver the message. You may just be figuring out how you want the woman delivering that message to be seen.

Remember, you are NOT in the military anymore.

📍You get to decide what authority looks like for you now.

📍You get to decide how much femininity you want to express.

📍You get to decide whether your style is bold, refined, sophisticated, colorful, classic, modern, or a combination of all of those things.

Here are 3 things accomplished women veteran leaders should consider before the next speaking opportunity presents itself:

1. Start With the Speaking Engagement, Not Your Closet

Before you decide what to wear, understand the assignment.

Where are you being called to speak?

Is it a military leadership event, women's empowerment conference, corporate keynote, nonprofit luncheon, podcast, entrepreneurial summit, virtual presentation, or television interview?

Then consider your role.

Are you:

• The keynote speaker?

• A panelist?

• A workshop facilitator?

• The emcee?

• A guest expert?

• A featured storyteller?

  
  

Your position on the program MATTERS.

The more prominent your role, the more intentional your visual presence should be because your audience is already looking to you for leadership, expertise, and direction. You are not trying to look like everyone else in the room; you are intentionally creating a visual presence that reinforces your role and the value you bring.

The goal is not simply to be seen, but to be remembered for what you want to be known for.

2. Consider the Stage

Presenting a virtual presentation for Airbus, titled "Opportunity Ready: How Professionals Position Themselves to Be Seen, Chosen and Remembered."

A speaking engagement is very different from attending a dinner or networking event because your outfit has to perform as you do. You may be moving across a stage, standing under bright lights, sitting on a panel, speaking behind a podium, interacting with the audience, or being photographed and recorded from multiple angles virtually and in-person. Your clothing needs to support your movement, complement the environment, and translate well both in person and on camera.

You are not simply getting dressed for the event; you are dressing for the experience your audience will have of you.

Think about:

Color. Does it complement your personal brand and help you stand out appropriately?

Fit. Can you move comfortably without constantly adjusting your clothing?

Fabric. Does it photograph well? Does it wrinkle easily? Does it create distracting shine?

Neckline. Does it work with microphones and your movement?

Accessories. Do they enhance your look without competing with your message?

Shoes. Can you comfortably stand and walk in them?

And please, don't forget about your hair, makeup, and nails.

If you are going to be photographed from head to toe, your entire look should be intentional.

3. Plan Your Outfit Before the Week of the Event

One of the biggest mistakes you can make is waiting until the night before a speaking engagement to figure out what you're going to wear. Ideally, select and test your speaking outfit at least a week in advance so you have time to try it on, move in it, sit in it, practice your presentation, take photos from different angles, and make sure your undergarments, jewelry, and shoes all work together. Pay attention to how the outfit performs in motion and on camera, and always have a backup option ready.

The goal is to eliminate unnecessary decisions before you arrive so you can walk into the room focused, confident, and fully prepared to deliver your message.

Your Next Step

If you are an accomplished woman veteran who knows you have more to offer, but your wardrobe no longer feels aligned with the woman you have become, this is exactly the work I love to do.

Your next level does not require you to become someone else. It requires you to become more intentional about how you reveal the woman who is already there. 

This is why I’m inviting you to join me for my next SLAY Your Signature Style, a masterclass on October 26th at 7:00 PM EST👉🏾SLAY Your Signature Style Masterclass

We’ll talk about how to create a signature style that reflects your identity, personality, femininity, authority, and the opportunities you are preparing to step into, so you can stop second-guessing what to wear and start showing up with greater intention.

Keep on SLAYin' until you can't SLAY no more🔥

Rochelle “SLAY Queen” Hemingway is the CEO and Founder of SLAY To Success®️, Transformational Speaker, 5x Author, Image Consultant, and a 30-year retired Air Force Chief Master Sergeant. Her distinguished military career culminated as the Command Chief Master Sergeant at Ellsworth Air Force Base, with a population of over 8,000 people, where she led the wing’s enlisted force and advised senior leadership on morale, welfare, warfighting readiness, and the professional development of nearly 3,200 Airmen supporting the nation’s largest B-1 combat wing. Ellsworth’s new command chief: #SLAY > Ellsworth Air Force Base > Article Display

Today, she brings that same operational clarity, executive presence, and strategic leadership to the work she does with accomplished women leaders whose roles, reputations, and results depend on how they are perceived. Through her speaking, workshops and 1:1 private intensives, she equips them with relevant personal branding tools to align their image, brand and authority for INTENTIONAL impact.