What Not to Wear: One Speaker’s Struggle for Style

I need to go shopping.

This is a dilemma.

I don’t like to shop for anything.

Well, maybe books. Also wine. And chocolate.

Back to my dilemma: I’m shopping for something very specific – a dress appropriate for an upcoming presentation.

It’s a task that fills me with dread, especially this time of year. My winter weight has not yet sprung ahead to spring.

I blame the crockpot meatballs.

So, I’m not quite where I want to be – internally, externally, literally, figuratively, physically, mindfully, fashionably…

Given the difficulty of this assignment, I consult an expert. A store-assigned professional stylist who will take my information, select outfits, and generally ensure success in this venture.

I will call her Edwina, even though that’s not her name, so as to protect her identity.

She seems like an Edwina.

I’m not an easy client. I admitted as much when Edwina sent an email requesting sizing, preferred colors and budget.

I explained why selecting something to wear on stage is so challenging.

You have to look good, dressed at least as nicely as your audience, and also look like yourself. The clothing needs to be polished and professional, yet functional and comfortable.

I’m seeking a simple dress.

Sounds like a simple assignment but it’s not.

The dress can’t have too many details or embellishments. Nothing that could rub against a lapel microphone or otherwise rattle, flash or distract.

Edwina, we must find a quiet dress.

It can’t be too heavy, like a knit, or I’ll sweat under the lights. It can’t be too sheer or the lights will show my form underneath.

Edwina, we must find a temperature-appropriate dress.

It needs to have a pop of non-distracting color. White is no good, nor is black. No busy patterns and ideally something that complements my skin tone. I’m a fall or winter.

Edwina, we must find a properly-hued dress.

I prefer blues and violets, like this one:

This is the Olympic gold-medal dress. No other dress will compare. Besides being entirely simple and comfortable in that familiar A-line kind of way, this dress has POCKETS, something I realized moments before I stepped on stage.

POCKETS! Such an exciting discovery, I wrote about its greater symbolism in The Remarkable Discovery of a Dress with Pockets.

The problem is, I’ve been photographed in this dress (as you can see, above).

So I feel I need another (half-dozen) options.

That’s where Edwina comes in. Literally into my dressing room with her arms full of… stuff.

I survey her selection in dismay. Lots of reds, pinks, some blush, even a tangerine. Not my requested color palette.

But… things can look different in person than on a hanger so I promise Edwina I’ll keep an open mind.

“Be honest with me and tell me what you truly think!” she chirps. “I won’t take offense!”

I agree to do so.

This is my first mistake.

You’d think I’d have learned from all my years in the corporate world that when someone says “Tell me what you think. I won’t take offense,” what they actually mean is, “Tell me what I want to hear. Otherwise, I will take offense.”

It’s why so many meeting attendees disagree with the person running it, outwardly nodding like bobbleheads and inwardly wondering when some poor soul is going to question why we’re wasting our time in a meeting for what could have been decided in an email.

That poor soul was generally me.

I have opinions and I’m not afraid to share them. Honestly.

Beware, Edwina.

I consider the first dress. It’s a heavy-knit red and black St. John frock that looks like a cross between a Star Trek costume and something a 65-year-old Grandma might wear while walking her poodle down Park Avenue. I point out the price tag to Edwina – $1,150. That’s my budget plus a small mortgage payment!

“It’s on sale!” she replies chirpily. Edwina speaks Chirp.

Even if this poodle-walking Star Trek get-up is 95% off, I’m not buying it.

The knit is terrible, as expected. So bad, I can’t even show it to you. Beam me up, Scotty.

Edwina points out that shapewear undergarments will smooth out the lumps and bumps and make me appear 10 lbs. lighter. But if I take the stage in too-tight Spanx for the sake of scale trickery, I’ll be unable to secure the oxygen necessary to talk through my 90-minute presentation and will pass out on stage. That’s not a good look.

I dismiss a handful of other dresses that appear meant for a party.

And two others that look like Delta flight-attendant throw-aways.

“This is a great dress!” Edwina says, pointing to a hot pink number with bell-bottom sleeves.

I try it on to make her happy.

No, the mirror says. No, it’s not. At this point, I feel I must visually document what words cannot truly bring to life.

Edwina removes the first round of dresses from the room along with the $300 flowered shirt I refused to try on because, as I explained, it resembles an overpriced lampshade.

I think she has taken offense.

The second round proves no better. Edwina’s chirp is less chirpy. She tells me she’s already brought me half the dresses in the store.

“The ugly half?” I joke.

Now I know she’s offended. I must remember to not speak so honestly.

But we have a job to do and Edwina regroups to ask if I’d consider separates – a skirt and a top? I nod.

She brings me this:

I’m not sure what it is. Like a tube sock skirt and a satin pajama top.

Edwina points out the tangerine top I’ve been avoiding. It’s St. John, her favorite overpriced brand, and is essentially a drape of a square knit tablecloth top for $595 paired with $395 ill-fitting white pants (never wear white pants on stage!)

For that kind of money, I’d want an outfit that not only looks fabulous but also washes and irons itself and earns a small income on the side.

Edwina then tries to chirp me into a “terrific” two-piece Theory get-up in bold red, a great color for a speaker!

On the hanger, it’s got promise.

On my body, it looks like I’m the person relegated to the back row of a 1983 Jane Fonda workout class.

Are elastic high-waisted pants a thing now? Who wears these?

Even Edwina is horrified and rushes me out of the outfit.

We’re clearly getting nowhere and I feel Edwina’s spirits sagging. So I ask if she can find me a structured blazer. Something I can pair with slim black pants.

“This is a great blazer!” she’s back to her chirpy self, handing me a pin-striped jacket with thick shoulder pads, clearly a leftover from a 1996 community production of Guys and Dolls.

There’s no luck for this lady tonight.

I dismiss the $300 Vince shirt that’s not only the wrong color (how many times can I say “no white!”) but also something I could wear while eight months pregnant. Looking at this picture, I already appear to be eight months pregnant.

It’s at this point that I sense Edwina might be punking me. Except she’s lost her chirp and I feel kinda bad for her.

I leave the store with one item, a simple black and white polka dot shell I can put under a blazer when I eventually find one. It’s not a wardrobe-changer, but it’s inexpensive and I felt I had to buy something. It’s going to take Edwina hours to put back all of the (awful/ugly) clothing choices I discarded and get over the hurt my honesty has caused.

I thank Edwina for her time, embarrassed for both of us. She’s glad to be rid of me, I can tell, and will probably write on her own blog about her difficult customer who didn’t like any of the gorgeous outfits she selected.

I head to Marshall’s where I find a fabulous pair of discounted Tory Burch printed pants and a plain navy top. I summon my inner Edwina and pair the outfit with a surprising splash of pink in a structured Talbot’s blazer. Bonus points: the blazer is a size up but it’s petite which makes me feel delicate and tiny and like my meatball-filled winter doesn’t matter.

The entire outfit comes to under $200.

My kids are aghast when I pack my suitcase. The pants are ugly, they say, the jacket too bright. I can’t wear that.

My kids are jerks.

I stand by my choice. J-Lo says hot pink is the color this season. People will be able to track me down at the conference – I’m the lady in the bright pink blazer! The pants are comfortable.

I feel good in this outfit. It feels like me.

If I’m going to ignore the advice of a “professional” stylist, I’m also going to ignore the advice of my teens who are embarrassed by everything I do anyway.

I fly across country and take the stage in my printed pants and too-bright blazer.

I’ve skipped the shapewear, am still 10 lbs. too heavy and have ignored the advice of a professional stylist.

But it’s all good. I trust my content and my ability to deliver it. The rest is just clothing.

As the 100+ attendees complete one of the interactive exercises, I survey the room. A woman looks up from her workbook and points at me, smiling.

“Those are great pants!” she whispers.

She’s the Edwina I need.

I strut the stage in my printed pants and rock the rest of the presentation.

I would wear the outfit again but now that it’s been photographed and you all know I got it at a discount, that means one thing… I have to head back to the stores to find something new to wear…

Valerie Gordon is a keynote presenter and workshop facilitator who helps high-achievers lead with impact and influence through the power of storytelling. The author of “Fire Your Narrator! A Storyteller’s Guide to Getting Out of Your Head and Into Your Life,” she blogs often and shops infrequently. She has lots of ideas but nothing to wear…