By Leigh Anne Jasheway-Bryant, Boomer Humor Associate

In Medford a few weeks ago, a woman came up to me after I’d spoken at a conference and gave me a hug and a compliment. “I love your outfit, especially your shoes. You know what they say, ‘The shoes make the outfit.’

They say that, indeed, although I’m not sure why. I never remember anyone’s footwear unless it is so high and dangerous-looking that I have to keep my finger on my cell phone, ready to dial 911 in case they keel over and stab themselves on their own spiky heels. Personally, I think what makes an outfit is lack of obvious stains and/or dog hair.

I told the woman at the conference “Thank you,” and then we both laughed. At the time, I was wearing an orange blouse (to support Wear Orange for Gun Violence Prevention week), a pair of pants that can best be described as “clown, only more colorful,” and my trusty gray tennis shoes with turquoise stretch lace replacements. Why yes, I am a fashion icon! I keep waiting for Project Runway to invite me to be a guest judge.

Believe me, I wasn’t always such a snazzy dresser – back in the ‘80s, I worked in a bank and wore a navy suit with a navy bowtie (it was the ‘80s and that was a thing), with navy heels. I shudder just thinking about it.

When I first started my life as a humorous motivational speaker and corporate trainer, I attempted to dress professionally. I just couldn’t decide what profession I was in. Sometimes I sported a feminist pantsuit and sometimes I wore a shortish skirt and heels.

But as I’ve gotten older and wiser and more klutzy, I’ve stocked my wardrobe with comfortable clothing and shoes that will probably not kill me. (You try leaping into air on 4” chunky heels or careening off a 3-foot tall stage while dressed as Lucille Ball, and you’d learn your lesson too.)

At this point, I’ve thrown out most of the fashion “wisdom” that has been tossed my way. Advice such as:

  • Black is slimming – I don’t think this is true. If you wear all black, people have nothing to focus on except you and your body. If, on the other hand, you wear, say, a purple and  chartreuse Hawaiian shirt with a pair of pink polka-dot capris pants and a sequined belt, everyone has to immediately look away to protect their eyes. Not only will they not be able to tell if you’ve put on weight, they won’t be able to pick you out of a police line-up.
  • Don’t mix prints – Not mixing fonts makes sense to me because your resume can end up looking like a ransom letter, but why not wear leopard and plaid or paisley and the text to the Declaration of Independence?
  • You don’t want your clothing to speak louder than you do – I say, “Carry a microphone and wear the loudest, most mismatched outfits you can. At least you know they’ll be talking about you behind your back.”
  • Never wear a hat bigger than your stomach – Okay, maybe that’s not it; I don’t really remember. Here’s the thing. The world keeps getting hotter and we all need to make sure to stay in the shade, so find the biggest hat you can and wear it proudly. In fact, get a hat for two and make friends.
  • Speaking of headwear advice… Tiaras are for bachelorette parties and royalty only – Wrong. Tiaras are for days when your only other choice is to drink heavily and never leave the house. Consider a rhinestone-encrusted head piece a form of mental health care.
  • Tube tops don’t look good on anyone – Okay, they may have something here, although I recently put an old tube top of my new dog Katja (that’s right, the Jasheway pack is back up to three!) and she rocked it. Katja is shaped like a tube, so that may be the trick. Also, she insisted on wearing a tiara too.
  • Always match your shoes to your bag – I carry one bag until it literally falls apart. My current purse is a vegan number in bright pink with orange trim and orange polka dots. (Did you expect any less?) I match my shoes to my desire not to be in the chiropractor’s office for a month.

Finally, I believe there are only two pieces of fashion advice anyone needs.

  1. Fake it ‘til you make it. If you believe your outfit works, people will think you’re a trendsetter, not someone who dresses in the dark or can only grab whatever the cat isn’t sleeping on.
  2. Laughter is the best medicine. That goes for life and for what you put on your body. Try it. You may find life a little less stressful if when you look in the mirror, you can’t stifle a giggle.

Leigh Anne Jasheway is a comedy writer, comedian, humorous motivational speaker and wiener dog wrangler. She is the author of 25 published humor books, including Not Guilty by Reason of Menopause and Bedtime Stories for Dogs, and has been included in more than 2 dozen anthologies. In 2003 she won the Erma Bombeck humor award for her true story on how her mammogram caught on fire. When she’s not writing or making people laugh, she’s tossing a ball 7,000 times in a row for her dogs.

Leigh Anne Jasheway is a comedy writer, comedian, humorous motivational speaker and wiener dog wrangler. She is the author of 25 published humor books, including Not Guilty by Reason of Menopause and Bedtime Stories for Dogs, and has been included in more than 2 dozen anthologies. In 2003 she won the Erma Bombeck humor award for her true story on how her mammogram caught on fire. When she’s not writing or making people laugh, she’s tossing a ball 7,000 times in a row for her dogs.