Dress for Success: Elevate Your Executive Confidence With Style

Executive in a stylish suit

You might not equate a sharp appearance with being confident. You might not even care about clothes all that much. The clothes that professionals wear are expensive. When you look in your closet trying to decide what to wear, does it drag you down? Is choosing your outfit for the day one more decision you would rather not make? You know when you head into the office there will be many more decisions to make. Walking out of the house trying to look presentable is so much work that even just thinking about it is exhausting.

There’s a secret reason why you’re avoiding cultivating a sharp appearance, and it might not be what you think. If you had the confidence to dress for success, you would. For individuals who aren’t as confident, this is a bit like putting the cart before the horse, though. If you don’t have the right set of clothes and know how to use them, you will lack self-confidence. And if you don’t know how to assemble a wardrobe that gives you confidence, it’s no wonder you’d avoid trying. It makes perfect sense.

So, if you don’t feel energized by what you wear, you avoid a crucial aspect of confidence. Yes, your appearance can give you that. And it can make a positive and meaningful impression on those around you.

Whether you need a whole new wardrobe or just need to add a few new pieces to yours, here’s an effective 3-step plan to update your wardrobe and develop confidence like an executive. 

Step 1 – Take Stock

To figure out where to go from here, you need to see what got you here in the first place. The best way to do this is to take an inventory of the items in your wardrobe. Try stuff on. Pile up the items that don’t fit and won’t even fit if you take them to a tailor. Pay attention to the items you’ve not worn in at least the last year. Anything the moths got to, let those go. They could be repairable, but it is very expensive to reweave clothing. You could put that towards buying something new and more current for who you are today.

If there are sentimental items you’re holding on to but you’ll never wear again, get a quality canvas bag that keeps critters out but lets air permeate. Preserve those few items in the back of your closet so you have visual space to greet the current you.

With what remains of your original wardrobe, look at the styles and colors. Organize your closet by clothing category. Use this simple game plan to make it look appealing and easy for your eye to follow: 

  • Short to long, left to right.
  • Light to dark, left to right.
  • Hang tops on top and bottoms on bottom.

Interpret this system based on the space your wardrobe offers. This organization method is exactly how the finest retailers merchandise their stores. Your wardrobe can be as easy to organize.

Treat your wardrobe and yourself to a set of good hangers. Use wide cedar hangers for tailored suits and jackets. They are good for the shoulders and to keep critters like moths at bay.

Step 2 – Learn About Your Needs, Style and Taste

Look again at what remains in your existing wardrobe. What do those items say about you? What words would you use to describe your personality based on your clothing style? Do you see those aspects of yourself in your clothes? Personality is a real driver of personal style and confidence.

Next, think about the regular daily needs of your wardrobe. What does a typical head-to-toe outfit consist of that you wear daily? What do you need to wear on an occasional basis for work?

As an example, let’s say that most days you can wear ‘business casual’ to the office. But are there a certain number of days per week or month when you must dress up more? Do you wear a jacket over an existing outfit to dress up? Or do you get more formal and wear a suit for any of those dress-up occasions?

Based on your wardrobe needs, where does your existing wardrobe need more TLC? Look at the colors, fits, fabrics, textures, and patterns in your existing wardrobe. What appeals to you most about all those signifiers?

By paying attention to all these points, you can focus on what to look for based on what you need and on what you like.

Step 3 – Find Your Signature and Stick to It

It’s easy to dismiss clothing as unimportant. After all, Steve Jobs, Mark Zuckerberg, and Jensen Huang developed styles based on one look. Jobs wore an Issey Miyake black mock turtleneck knit with baggy jeans and sneakers. Zuckerberg graduated from hoodies and into custom-fit Brunello Cuccinelli cotton-cashmere T-shirts. Jensen Huang has a collection of black leather jackets that he wears everywhere. It is easy to want to do that for yourself. But beware: wearing another person’s look does not give you any confidence! If you do this, you will parade around trying to emulate someone else rather than being yourself.

Stick to styles, patterns, colors, textures, and fits that make you feel good. What clothing and accessory items do you wear that you receive compliments on? When you stick to what you know, you are bound to build confidence in your style and image. For extra credit, show a little edge of personality missing from your wardrobe. Consider an accessory that reveals some fun, quirky aspect of your personality. This attention to detail can make a subtle difference to your look that sets you apart. And if you plan to use your wardrobe to become a confident executive, you owe it to yourself to stand out.

Confidence is the most invisible thing you can wear. And yet, people see whether you’ve got it or not. Think through what makes you feel self-assured inside and gives off outer confidence. Take care to wear clothes that are appropriate for the people you meet and where and when you meet them. Show up, embodying the outcome you want to have happen. 

Joseph Rosenfeld is an image consultant. He sees people in great detail and with empathy and honesty. He inspires his clients to live up to their full potential. His in-depth approach to building quality presence develops their it-factor and self confidence.