Seeking Inspirato with Sherry in the Texas Hill Country

A while back, I wrote about my darling aunt, Sheila McKinley. Now, I bring you another McKinley story. This time it’s from my very own mother, Sherry McKinley. Though Sheila and Sherry grew up in the same Houston house with the same parents, their paths to Clothing Confidence are in stark contrast with one another.

Sherry used clothing to communicate her professional persona, while Sheila saw clothing as a form of artistic expression.

In a way, it’s poetic. Sherry became a successful businesswoman who thinks in facts and figures, and my aunt is a phenomenal psychologist and musician.

Without further ado, let me introduce you to my mom, Sherry McKinley.

Photo by Maddison McKinley. Edits by @JessicaWebb.

Who Is She?

Name Sherry
Works as a Part-Time Publishing Executive, Part Time Inn-Keeper in the Texas Hill Country
Age 64
Her style described in three words Texas Bohemian Chic
Which outfit do you feel best in? Tight jeans with cowboy boots and a Johnny Was top

Sherry Dreamt of Success

Sherry, the second child of a family of five, is a snappy, quick-witted force to be reckoned with. Sherry was a persevering child who became a steadfast adult. If there is a resource around her, she presses it into service to achieve success. From a young age, she understood the value of a dollar and planned to put her natural business acumen to use.

And by golly, did she do it. She built a prosperous advertising business in Dallas that she continues to run today, had three children (including yours truly), found her true love late in life in my stepdad, and is now fulfilling a lifelong dream of retiring into a bustling Hill Country life where happy hour marks the end of a busy workday.

Sherry’s Clothing Confidence story is about using clothing as a tool . Dressing well to do well. In combination with her grit and intelligence, clothing became an integral part of her strategy to grasp what she wanted out of life.

When you feel attractive in your clothing, exuding self-confidence and gaining the support of others comes easier. Sherry knew that it was crucial to dress in good taste to impress decision-makers. Clothing is a tool to enhance professional relationships.

For those seeking higher places, know that while Sherry’s experience may be from a different era, her dressing-well-to-do-well strategy will still impress today. Take notes!

McKinley Branded Resourcefulness®

Let me set the stage. It’s the 1960s in a very nice suburb in Houston, Texas. Sherry is attending one of the top schools in the area, Kinkaid. The kids who attend her school are the children of Houston elite—white-collar professionals who have the means to send their children to a top-flight college prep school.

And on the other side of the fence are my frugal, Navy alum, depression-era, grandparents who are busy raising five rambunctious Irish-Catholic children. The house is chaotic. Everyone’s fed, but money certainly isn’t spent frivolously.

By way of her friends, Sherry gets a taste of the good life. Her prep school peers exposed her to gorgeous clothing.

My mom has never been one to be complacent. So what was a girl to do? In a house where the annual back-to-school clothing budget was skimpy, she had to use a dash of innovation to model the latest looks in the hallways of Kinkaid.

She learned to be resourceful. As I’m sure most families do, the McKinleys often point to certain traits in our family that are McKinley® branded elements. We stake out claims to entire words just for ourselves. One of these McKinley-branded words is resourcefulness.

Sherry learned early from her Grandmother Honey, how to sew and create her own clothing.

It wasn't like she could race to Forever 21 to score some cheaply made knock-offs. “Fast fashion” wasn’t even a concept until the 1990s. No, back when Sherry was growing up, it was common practice to sew your own clothing. No wonder people used to have fewer things—they valued and cherished what they had because it was expensive and time-intensive, to replace.

Honing her sewing skills allowed Sherry to create looks that “fit in” with what other people were wearing.

“I made all of my own clothes on that sewing machine growing up. I’d buy the fabric, the pattern, and the zipper and make my own clothes. My dad gave me a small clothing allowance at the beginning of each school year... But he gave me unlimited access to the JCPenney credit card, which is where most people bought their patterns and fabric because JCPenny’s had the nicest fabric.”

College to Clients

Sherry made her own clothing in order to stake out a space of belonging all the way through college, or as I like to call it, the Medieval Period of Clothing.

College was an important time for Sherry because it allowed her to (1) gain a ticket into the workforce, and (2) motivate her to trade her down-to-earth/granola lifestyle for something a little more polished. Turns out too much of a good thing can get old, and this applies to hippie clothing as well. Hey, it was the ‘70s!

“When I went to college [at the University of Texas at Austin] I had long hair down to the middle of my back. I just wore stuff that was comfortable like cowboy boots and blue jeans and went to school. Everyone was a hippie.”

Sherry’s Medieval Period quickly changed to a Renaissance once she had her degree in hand—proof that she was ready for the workforce. Now, she just needed her clothing to reflect how serious she was about taking over the business world.

Working 9-5+: 1978 Dallas, Texas

Sherry’s favorite song during this era: “Mammas, Don't Let Your Babies Grow Up To Be Cowboys”.

“I got a job at an ad agency and needed to dress for the clients. I was still making my own clothes, but I learned to make things that were attractive and professional to our clientele, which of course was mostly men.”

Sherry learned quickly to dress for men, both personally and professionally.

Why? Well, let’s take a step back. It’s 1978 and Sherry has just graduated college. She’s entering the workforce with big goals. Think snapping necks and cashing checks.

The thing is that men dominated the workforce, every decision-maker was a man. For Sherry, it was critical to her success that she had a seat at the business roundtable, and her clothing aided her in making the statements of (1) notice me, and (2) take me seriously.

“Women were just entering the workforce en masse. I was on that front line. I was an outlier. I wanted to become a female executive who owned a big ad agency. I was willing to dress whatever part was going to propel me the fastest.”

Men were dominant in representation in the workforce, and women were just entering the white-collar job market. Check out this study by the U.S. Bureau of Labor Statistics.Not to mention, Sherry was entering the workforce in Dallas, Texas. Texas being the important word here. At that time, women were meant to be in the home room, not the board room.

The dress code for women was just that, dresses. No one could wear jeans, and the particular client Sherry was tasked with servicing in her first job out of college didn't allow women to wear pants. Yes, you read that right.

In reference to this particular client, Sherry remarked:

“He was a total sexist [laughs].”

When you can’t cry, laugh? I can’t help but laugh, too. This is almost like a fantasy world from where I sit. We’ve come a long way, people.

“So, I was pretty smart and would make my clothing professional, but sexy. I figured out pretty quickly that the cuter you are, the easier things went for you. The better you look, the easier your life is. It’s true. People treated women based on how they looked. We had yet to prove how competent we were!”

My question for her at this point was: did you feel good about how you were showing up in the world?

“Yes! I was so sick of being a college hippie in worn-out jeans that by the time I graduated, I wanted to get into the business world and be a business person.”

Sherry looked good in clothing. She felt powerful because she was doing what she had always wanted to do. But her Clothing Confidence was more external than internal. She relied on reactions from those around her to curate her wardrobe and forever pieces.

Leave it to my mom, but this is the first time I’ve spoken with someone who has been so candid about the fact that external affirmation heavily dictated what stayed and what went from her closet.

Reflecting on this, I have to admit that when someone I love compliments a piece, I may be biased to keep it for longer and wear it more frequently than I would have otherwise. If I like it and someone else likes it, then I tend to like it a little more.

My generation may scoff at this because frankly, it’s cooler to admit that you dress entirely for yourself and that you’re not looking to impress a soul. It sounds much more independent and confident.

But I don’t think it’s 100% true. I think the truth lies somewhere between Sherry’s POV and the hyper self-reliant.

Frankly, most of the time we’re dressing with an audience in mind. We wonder if the recipient or group will approve of our look, and this is particularly true in high-pressure situations. Don’t take my word for it, look at the top Google searches for “how to dress for a…” below.

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It’s important that our clothing is appropriate for the setting because one of the worst imaginable feelings is the impression of being shunned from the group.

For Sherry, it was all about how others reacted to her clothing, including negative feedback. This was her own high-pressure situation.

“I remember having a white linen suit, with a long skirt that had a slit down the front. It was a splurge from Neiman Marcus. It was so well made, and I loved it, but I never got a lot of good reactions when I wore it, so I weaned it out of my wardrobe. Whereas, I had a red suit that was two pieces with a belt and an A-Line skirt and every time I wore that people perked up and were like ‘Come into my meeting!’ ... I figured [I’d] wear it next time I was negotiating something. It was pure and simple feedback.”

This was a critical time in Sherry’s life. It was make-it it or break-it, baby. She had goals and dreams of money and success—clothing was a tool to help her get it.

In contrast, many of Sherry’s female colleagues didn’t make it. They got married and left the workforce. For Sherry, this simply meant less competition.

It’s the trailblazing women like Sherry that allowed the rest of us to integrate into the workforce with ease. Her story reminds me that there were women before her that propelled us forward, and there will be women after us that do the same.

The “Aha” Moment: the 4C’s

Sherry never stopped looking for ways to improve her wardrobe.

“I remember having an epiphany moment when I was about 28. A couple of friends came out to my house and we decided to clean out my closet together. I started holding up different outfits to my face, and my friend said, ‘Do you realize that all of your necklines are jewel necklines?’ and I said, ‘I don’t know what that means,’ and she said, ‘it’s like a necklace is going around your neck… that’s a neckline for people with round faces and you have a heart-shaped face. I bet your mother wore that.’”

Her friend was right, that had been the neckline her mother had worn. From this point on, her awareness of Cut, one of the 4C’s, allowed her to take ownership of her looks and feel confident in the pieces she chose. She still used the feedback loop of others, but began to notice how the pieces looked on her unique figure as well, including which colors worked best for her skin tone.

“I started taking fabric swatches and putting them up to my face and noticing what made me look good, and what made [me] not look good. That was pivotal.”

As she was putting the pieces together herself of what looked good versus what didn’t, she decided to hire a personal stylist who understood the craft of dressing well, Leah Garmon. Leah was a local stylist and fashion expert who worked 1-1 with Sherry to help her understand her ideal Cut, Color and Cloth because while Sherry had an awareness of these elements, Leah deeply understood how to work them into her wardrobe.

The relationship with Leah catapulted my mom’s closet. She got rid of stuff that wasn’t working and noticed that her clothing was able to breathe. She was able to put together looks from clothing she wasn’t even able to see before.

Sherry had a new-found confidence in herself because she understood the fundamental cuts, colors, and textiles that worked best for her. Leah also provided accessories and how to style them, which Sherry never invested the time to curate. A few, simple necklace and earring combinations brought outfits to a whole new level.

Accessories are beyond powerful. They add “personal” to Dynamic Personal Style. They make an outfit go from basic to fantastic.

Coco Chanel once said “Before you leave the house, look in the mirror and take one thing off.”

But she also said, “Dress like you are going to meet your worst enemy today,” which I take to mean wear all the diamonds you have... I suppose it’s all in the interpretation...

Texas Bohemian Chic

The Sherry today is nearly retired from publishing, but she will never stop working. She’s building another empire in hospitality through her Cottages at Canyon Peaks. I’m not sure she got the memo that retirement means that you get to relax. It’s too late now. She and my stepdad have guests practically every day of the week and the reviews are touching. Mom can’t fail.

One area of life she’s completely softened is her style. She has embraced this Hill Country Chic vibe and it works for her. Some may say she’s revisited her U.T. days with some elevation and class? Hippie with a side of Hustle?

She does have some parting words for the women seeking Clothing Confidence, and spoiler alert, it’s well-aligned with my message. Like mother, like daughter!

From Her Lips to Your Ears

Sherry’s advice for women in search of Clothing Confidence is to (1) figure out what you want to emphasize, and (2) understand how to put pieces together that work for your 4Cs.

“Stand naked in front of a 3-way mirror to figure out what your best asset is—arms, shoulders, legs? What do you want to pump up and feature, and what do you want to not emphasize?”

If you don’t have a 3-way mirror, a floor mirror and a hand mirror will do, or make your own!

We all have elements of our bodies worth showing off! It’s a matter of identifying them and supporting them well.