two men standing next to each other in front of a building

#88: What should you wear? (Part 2)

Bob Ewing
September 30, 2022
two men standing next to each other in front of a building

Talking Big Ideas.

“People trust their eyes more than their ears.”
~ Herodotus

Everyone is judging you.

Last week we discussed how people take a fraction of a second to form opinions about you based on your appearance. We highlighted three principles to embrace:

  1. BRAND: Dress to build your brand.
  2. CONFIDENCE: Dress to feel good about yourself. 
  3. CONNECTION: Dress to connect with your audience. 

How specifically should you apply these principles? 

Whether you are speaking on stage, interviewing for your dream job, or networking at a big event, I encourage you to follow these suggestions: 

*Use a tailor.* 
Your clothes should fit your body. Very few people find clothes that fit perfect off the rack. Tailors accentuate the good and hide the bad. Better to have a few quality outfits that look amazing on you than a closet full of ill-fitting and mediocre attire. 

Respect basic hygiene. 
George Carlin liked to joke that dentists shouldn’t have blood in their hair. This is good advice for all of us. I’ll add: well groomed hair and fingernails. Nothing stuck in your teeth. And breath and body that smell pleasant. 

Avoid distractions. 
Stay away from dangling jewelry and stubble beards. They are distracting and may mess with a microphone if you wear one. Keep in mind that flashy jewelry creates reflections and extra revealing attire may not be flattering or professional. 

Embrace feedback. 
I used to give talks with holes in my shoes! What are you doing that’s awkward? How can you up your game? Feedback is essential to growth. Seek it out and embrace it. 

Have mentors. 
Who dresses well that you know? Get their advice. For this piece I consulted three friends: Taylor Dawson, Melanie Hildreth, and Deron Lehman. They each have exceptional fashion sense and were happy to help. 

Spark joy. 
Be generous in donating clothes to charity. Give away anything you haven’t worn in a year or so. As well as everything that doesn’t immediately spark joy when you put it on. Fill your closet with clothes that make you feel awesome.

Match the vibe. 
Giving a speech to a toga party in the woods? Wear a toga. Whatever event you’re attending, find out what people typically wear. For a job interview, research the culture. A standard suit could make you seem uptight if everyone dresses casual. 

Adapt to change. 
Here’s a photo of world leaders at the G7 summit in 1979: 

Women wore long dresses. Men had tuxedos. Today these outfits would look weird. Here’s the G7 summit from June: 

Notice the absence of ties. During the first Super Bowl the crowd wore ties and dress shirts (one of the quarterbacks smoked cigarettes). Walking with a severe limp used to signal prestige. Fashion is fickle and times change. 

Travel in style. 
How do you dress during travel? What do you communicate about your brand while you’re en route to your events? 

Clean and press. 
Your clothes should always be wrinkle free. Wrinkles convey low status and indifference. If you’re traveling, use the iron and some wrinkle release spray. Even better, bring a portable steamer (this is the one Maryrose uses and it works wonders). You can also hang your clothes near your hotel shower and run hot water to steam them.  

Look good early. 
Remember that the moment people see you their judgment begins. How do you look walking onto the stage? When you’re mingling earlier in the day? When you first arrive at the event?

Amplify the moment. 
Dress so your attire compliments and amplifies the moment you create. One of General Grant’s biggest regrets was how he dressed for Lee’s surrender at Appomattox. Grant won the war but Lee appeared the victor. Grant wrote, “I must have contrasted very strangely with a man so handsomely dressed . . . and of faultless form.”  

Emulate your role models. 
Which celebrities do you think dress the best? Women the world over used to model themselves after Princess Diana. Today many turn to her daughter-in-law, Kate Middleton. You can ask yourself, “Would Kate wear this?” Or Michelle Obama, Justin Trudeau, Ryan Gosling, etc. 

Kate Middleton, always classy, with her daughter at the 2022 Commonwealth Games.

Know what works for you.
What’s your favorite outfit? Why does it work so well? You don’t have to reinvent the wheel for every event. A mentor of mine says, “I have a million navy sheath dresses and solid-color button down shirt/trouser combos. I know any time I wear them I’m not going to screw up too badly.” 

Personalize your style.
Do you like to make a splash in bright colors like Linda Cliatt-Wayman and her prominent pink dress? Or do you prefer understated attire? Experiment to find out how you look and feel best. Push outside your comfort zone a little. (Just be sure you’re embracing feedback as you do!)

Highlight your strengths. 
Abe Lincoln was the tallest person many people had ever seen. Often tall people hunch over to try to blend in. Lincoln stood straight and wore a stovepipe hat to look even taller. 

Have a thing. 
Adopt a look that people identify with you. Churchill always had a cigar. Johnny Cash was the man in black. I love my cowboy boots. Katherine Mangu-Ward has colored hair


(Men keep scrolling for your own personalized suggestions.)

Elevate yourself.
A shoe with a little height will enhance your pants and skirts. If you avoid high heels, a shorter heel with a pointier toe gives a similar impression of height.

Embrace the capsule wardrobe.
Invest in quality pieces that can pair with anything. It will make traveling for business and quickly getting ready for meetings much easier. 

Be mindful of fabrics. 
Fabric with more weight tends to wear better and be more flattering. Jersey is often too casual. Linen wrinkles easy. Think about how the garment will work in real life, not just a fitting room. If you have to contort even a little to make it work, or if it only looks good when tucked one certain way, don’t wear it. 

Avoid athletic wear.
Don’t show up to important events wearing a football helmet or tennis shoes – or yoga pants. 

Pay attention to your purse. 
Giant totes can easily look sloppy and mess up a silhouette. Empty what you can from the bag and look at how you hold it in a mirror. Find a way that isn’t pulling on your buttons or smashing your collar.

Learn new makeup routines. 
It’s easy to get into a makeup rut. Chat with friends about their best practices. Watch Sephora videos for fresh ideas and twists on new ways to use what you already have. 


Be like Gosling.
Look at the lead photo at the top of this page. Notice how sharp Ryan Gosling looks. He’s wearing classy clothes that fit his body. By contrast, Steve Carell is drowning in his boring baggy outfit. I see way more guys dressed like Carell than Gosling. The bar is low. Jump over it! 

Get good shoes. 
Years ago I asked a mentor to lunch so I could pick his brain on how to up my wardrobe. His first piece of advice: get a pair of Allen Edmonds. Quality shoes bring together your wardrobe. You don’t need dress shoes if you’re wearing business casual, but your shoes should always look good and compliment your outfit. 

Polish dress shoes. 
When you do wear dress shoes make sure they are freshly polished. One time Abe Lincoln was polishing his shoes before an important meeting. A secretary saw him and said in surprise, “Mr. President, are you shining your own shoes!?” Lincoln replied, “whose shoes should I be shining?” 

Know your colors.
What colors look best on you? Most men have no idea. Talk with your mentors or a clothing store you trust. Blues and greens are often good. 

Stay away from khakis.
It’s hard to go wrong with a sports coat, dress shirt, and dress pants. Classy jeans can often replace dress pants. Avoid khakis and anything banal or baggy.  

Have quality accessories.
Men often wear worn out, ratty belts. Don’t do it. Your buckle should be shiny and your belt should coordinate with your outfit and shoes. Watches, rings, and other jewelry all have an impact on the rest of your attire. If you wear eyeglasses they don’t need to be fancy, but realize they are part of your brand.  


Give friends money. 
I don’t naturally have good taste in clothes. So every few years I give friends with fashion sense some money. We go out together and they buy me stuff. It’s a blast and I’m always grateful afterwards. 

Rehearse in dress clothes. 
When you have a big talk coming up, do a few of your run throughs in the clothes you plan to wear. Mimic the event as best you can – including the stage and microphone. 

Watch the shift. 
Right now the world is going through a civilizational shift. Remote work and new technologies will blend with post-pandemic norms to create untold impacts on culture and etiquette. 

But principles are timeless

Follow the suggestions above while working to build your brand, confidence, and connection. 



Dress with intention.

Take a look at your closet. Give yourself an honest self-assessment. Do your clothes fit? Are they decent quality with no stains, holes, or visible wear? 

What’s one easy way you can take your wardrobe to the next level? Consider donating old clothes or adding one new piece. Check Amazon Essentials to build your foundation of basic pieces.

BONUS: Start your journey to a better wardrobe by paying it forward: Make a foster child’s dream come true! Go to and click on ESSENTIALS. You’ll have several options like this: 


HEADSHOTS: Getting a headshot anytime soon? Taylor Dawson made a style guide just for you. Thanks Taylor! 

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