Go Old School Style for New School Success

Old School Style

Ruby Thai Restaurant, Christiana Mall

So my younger daughter, Peyton, and I were at the mall after school one day and decided to grab some Thai food to take home. This little restaurant in the food court is good, cheap, and in a prime location, so the queue at rush hour can be 10-15 minutes. It’s worth the wait.

We’d been standing in line for a few minutes when Peyton announced in that whiny teenage girl voice, “I’m bored.”

To which I gave my standard response: “You’re too smart to be bored. Think of something to entertain yourself.”

She thought for a moment. Then, with a mischievous glint in her eye, said, “Three times three.”

“Nine,” I said automatically.

“Nine times four.”

“Thirty six.”

“Eight times seven”

“Fifty six.”

It was a familiar game, one we’d started when the kids were in grade school to help them remember their times tables. Instead of listening to music in the car, we’d do math. Call us nerds. We’re used to it.

The game went on for a few minutes, until I said, “Wait. If you’re bored, why am I entertaining you?”

Peyton laughed as the woman in front of us turned around, eyes wide.

“How did you do that?” she asked me in awe. “I’ve been listening to you and thinking, ‘I’d need my phone to do that!’”

Peyton look at her, confused. “Your phone?”

“It has a calculator,” the woman explained.

We both looked her over. She was in her mid-20’s, fashionably dressed, and hadn’t been out of school long enough to have forgotten basic math.

“But what if you don’t have your phone?” Peyton asked.

“Oh, I always have my phone. It’s practically attached.”

“But what if it runs out of battery?” Peyton persisted.

The woman thought about it for a minute. “Well then, I guess I’m screwed!” she said with a laugh as she stepped up to the counter to give her order.

Peyton looked at me with incredulity. It was all I could do not to laugh out loud.

We were in the car headed home with dinner a few minutes later when she finally let loose.

“She’s ten years older than me and she can’t think without her phone?” Peyton asked, disgusted. “And she’s okay with that?”

Convenience StoreIt was a teaching moment.

Fortunately, I had a lesson ready.

“Your Grandpa Weldon used to have a convenience store just outside of Minden, Louisiana,” I said. “It was on a country road that had a wealthy neighborhood on one side and a poor-as-dirt neighborhood on the other. He made most of his money from the rich people stopping in for coffee and sandwiches.

“But every now and again, some of the really poor people would come in for something. They’d buy one thing. If they had money left over, they’d buy something else. If they still had money left over, they’d buy something else, and so on, until they didn’t have any money left.”

Peyton look confused. “But why didn’t they just take everything to the register at once instead of keep going back and forth?”

“Because they didn’t know how to add. They had to wait and see if they had money left over to see if they could buy something else.”

Slack-jawed, she processed this. “When was this?”

“Late 80s, early 90s.”

She looked at me dubiously. “You’re telling me that there were people in Louisiana as recently as twenty five years ago who were so uneducated that they couldn’t even add up items in a store?”

I smiled. “There was a woman in front of you today who couldn’t add up items without a calculator. The difference between them is that those people in Louisiana probably never went to school, while that woman in front of us went to school but chooses to be ignorant. Either way, having to rely on others for basic day-to-day skills puts you at a distinct disadvantage. You can’t steer a ship if you don’t know anything about boats.”

So you may be wondering…

What in the heck does all of this have to do with you – and clothes?

Well, in a recent survey, I asked my readers to describe their biggest image challenge. Many of them had the same issues:

  • Can’t find clothes that fit
  • Not sure what to wear when
  • Not sure what’s appropriate for their age
  • Not sure what to wear for their particular life stage, like work, motherhood, retirement, etc.

Many said, “I wish there was a clothing app.”

In other words, “I wish someone else would do the thinking for me.”

Now I get that. Sometimes trying to figure it all out can be overwhelming. It’s really tempting to just get someone else to do it for you.

But as I said earlier, relying on others for basic day-to-day things puts you at a distinct disadvantage. First, you have to wait on them to do it, secondly, you have to take what they give you, and finally, you don’t know if they’re doing a good job.

It’s like when I was a kid and my mother first taught me how to scrub a toilet. I told her I didn’t need to know because I was going to be rich and hire a maid.

Her response?

“You still need to know what a good job looks like to make sure you’re getting your money’s worth. So grab that brush and start cleaning. I’ll let you know if it passes inspection.”

When you do something yourself, you know what a good job looks like. Or, if you’re really bad at it, you know what a bad job looks like. Either way, you have a frame of reference to work from.

It’s the same with dressing.

Which styles suit you best?You need to learn how to dress yourself. To determine what styles, colors, and fabrics suit you best. To figure out what to wear for work and what’s appropriate for different occasions.

In short, you need to go old school and sort this all out for yourself. To know, once and for all, what looks good on you and what doesn’t.

Only after you’ve done that should you go looking for apps and stylists and personal shoppers to go find the clothes that suit you best, so you can tell them what to look for. You’ll know from their results whether you’ve gotten your money’s worth or not.

Now you may be thinking, “But doesn’t it make more sense to just hire people to do stuff you’re not good at?


And no.

If you’re “all thumbs” when it comes to clothes, hire an image consultant to go through your closet and teach you what’s right for you. Have her explain which styles suit you best and what’s appropriate for work and different occasions. By the time she leaves, you should know exactly what to wear and what to look for when shopping.

But to not know what suits you and just hire people to go buy clothes? Bad move. You’re flying blind. You’re relying on others for basic day-to-day stuff, and chances are – especially in the world of fashion styling where there is no licensing and anyone can put out a shingle – they’re going to get it wrong. This Buzzfeed writer’s story of working with 5 different personal shoppers is typical, because most fashion stylists have no clue what to do with petite, plus, or tall size women, let alone any combination thereof.

So why is dressing so complicated?

Because women’s bodies are complicated.

Men’s clothes go by measurements. Their pants are waist by inseam. Their dress shirts are neck circumference by back of neck to wrist length. Their jackets are fullest part of the chest by height. It’s by the numbers, simple and straightforward.

But women have breasts and waists. We bloat one week a month. We don’t like to measure our body parts unless they’re in good shape. The list goes on and on.

It’s for all these reasons that men’s ready-to-wear became widely available in the early 1800s while women’s ready-to-wear didn’t become widespread until the 1920s – over a century later – and only then when loose, chemise-style dresses were in fashion.

So having trouble finding clothes that fit is not a new problem. It’s been an issue for centuries. The only way you can get exact fit is to either have clothes custom made for you or have them tailored to your body.

If you DO find clothes off the rack that fit, consider it a blessing. Because usually it’s like a treasure hunt that ends in frustration. Be loyal to brands that fit you – they understand your needs.

Which brings me back to point of this article: don’t look for shortcuts when seeking your best looks. Go old school, bite the bullet, and learn what’s right for you once and for all.

Which clothes suit you best?Because learning how to dress is a lot like learning how to type or how to drive: it takes a little time up front, but once you master it, you have that skill for the rest of your life. You really don’t have to think about it anymore. Then, like switching to a smaller keyboard or changing cars, you can easily re-calibrate your clothing needs if you change shape, jobs, or lifestyle.

So educate yourself. Do your homework. Don’t farm this out to someone else.

Learn how to dress old school style and enjoy all the success that comes with it.

Diana Pemberton-SikesDiana Pemberton-Sikes is an image consultant and author of Signature Style Blueprint. Need some help learning which styles suit you best?  Signature Style Blueprint can help.


  • Mary

    Reply Reply January 17, 2016

    Great article!

    • Diana

      Reply Reply January 17, 2016

      Thanks, Mary! Glad you enjoyed it!

  • Malebo

    Reply Reply January 17, 2016

    I missed you and glad that all is back to normal at home!

    This is a great article as usual. In a few years time I am sure I’ll be a good Image Consultant just like you, that gives honest advice. Thank you!

    • Diana

      Reply Reply January 20, 2016

      Hi Malebo, Glad you enjoyed the article! Thanks! I wish you much success in your career. You’re going to have a blast!

  • Valeria Martin

    Reply Reply January 20, 2016

    Hello Diana, Great to see you again! Wishing your family healing! This is a great article! Over the years I’ve learned through trial and error what styles look best on me. It’s still a work in progress now that I just turned 55 as I don’t want to look frumpy or be a throwback from the 80’s. It’s important to be informed about what you know about yourself. It can help you develop your signature look! Last summer I was in Macy’s looking for a dress. I usually don’t rely on sales help but, a sales associate pointed out a beautiful dress, but it was orange-red. Years ago I had my colors done and I learned I am a winter. Therefore, that shade of red will make me look washed out. Knowing that information about myself, I did not consider that dress. I would have considered if it was violet-red. I tried to explained this to the sales associate, but she wasn’t listening to me. She was actually dismissing what I said as if I didn’t know what I was talking about. I felt patronized and anger welled up inside me. So, I didn’t buy a dress that day. It’s having the self-confidence to know what works and what doesn’t.

    • Diana

      Reply Reply January 29, 2016

      Hi Valeria – glad you enjoyed the article! Thanks for your note.

      Yes, it’s very frustrating to shop when the sales clerk doesn’t know what she’s doing. Unfortunately, that happens all the time because retailers have largely forsaken proper training in the last 20-25 years. Good for you for standing up for yourself! 🙂

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