Fashion and the (Real) Working World

I started binge-watching Suits recently. Working in the legal world, I was immediately drawn into the intrigue, the back-room deals, the manic world of Pearson Specter. The thousand-dollar suits on the men, the Manolos and pencil skirts on the women. Gorgeous.

But let’s talk about real clothes for real working women.

First of all: if you’re a working mother and you can look even 20% like any of the women on Suits, you are my hero. Truly. I can’t come close. Most days I’m pleased to have made it out of the house dressed at all, and I don’t even have young children.

If you’re anything like me, deciding what to wear to the office is a confusing, frustrating, mind-numbing exercise.

The pencil skirt

What are the chances you have a clean, neatly laundered and pressed skirt hanging in your closet right now?

I thought so.

A skirt requires maintenance. Have you shaved your legs recently? That determines whether you’re going bare-legged, in sheer tights, or in the thickest pair you can find. Which leads to digging through the drawer for a pair without a “how on earth did that get there” hole in it.

The shirt

I don’t know about your office, but mine maintains exactly one temperature: two degrees below meat locker.

Which means every lovely short-sleeved or sleeveless top must be covered with whatever sweater is hanging on your chair, or worse, the office sweater. You know the one. So ugly the person who retired five years ago wouldn’t take it with them. A shade of orange-puce-brown that goes with everything.

The shoes

I love shoes. All kinds. But anything over a half-inch heel makes my knees and feet complain, and three or four inches makes my back join in. I genuinely don’t know how I used to wear those.

How do the heels look? Do they need cleaning? Have you picked the one pair that makes that clip-clop-thump sound as you walk past the boss’s office? And for those of us in colder places — did you leave a pair at the office to change into, or is this another bag to carry?

The accessories

There’s a woman I work with who has the most extraordinary necklaces and somehow pairs them with exactly the right earrings, then adds a bracelet for fun.

Me? I try very hard every morning to remember earrings that match each other.

The only accessory I can guarantee I’m wearing is a step tracker. It’s hot pink, goes with nothing, counts my steps and lets me eat more. I’m at peace with it.

The part that isn’t funny

All of that is a joke, and it’s also a fairly precise accounting of unpaid labour.

Add it up. The laundering and pressing. The tights. The shaving. The second pair of shoes carried in a bag. The matching earrings. The mental energy spent each morning solving a puzzle that has no correct answer — too casual and you’re not serious, too done and you’re trying too hard, too plain and you don’t look like you’re going anywhere.

None of it is on anyone’s timesheet. Most of it has no male equivalent. And it is largely mandatory, in the sense that the cost of getting it visibly wrong is real.

Which is why the Suits version grates slightly beneath the enjoyment. Those women aren’t aspirational so much as impossible — they’re dressed by a costume department, they have no commute in the snow, and nobody’s office is that temperature.

Comparing yourself to them is like comparing your business to a competitor’s website. You’re measuring your inside against their production budget.

What I’d actually suggest

Not a capsule wardrobe lecture. Three practical things.

Decide once. A small number of outfits that work, that you know are fine, that you repeat without anxiety. The decision-making is the expensive part, not the clothes. Most men have been doing this unremarked for decades.

Optimise for the meeting that matters, ignore the rest. If there’s a day when how you’re read matters — a pitch, a board meeting, a difficult conversation — put the effort there. Tuesday at your desk is not that day.

Notice whether the standard you’re holding is actually anyone’s. A great deal of the pressure here is internal, inherited from television, and enforced by nobody. Worth checking who exactly would object, because sometimes the honest answer is no one.

So the next time you look out the office window and see her — the perfect pencil skirt, the sleeveless shirt, the gorgeous heels, the pearls — remember: she has either just stepped off a film set, or she’s on holiday.

If this resonates, you don’t have to figure it out alone.
We host small, thoughtful Round Table conversations inside Women’s Entrepreneur Network where women leaders talk through exactly this kind of challenge.
You’re welcome to join us.

Related Posts

5 Working Mom Career Tips

5 Working Mom Career Tips

Getting through B-School was one of the toughest things I’ve ever done. It ranks right up there with having four children, and having a full time career. I’ve had to learn a few survival skills over the years, so I thought I would share some working mom career tips that I’ve learned.

You Can’t Have It All. Choose the Trade-Offs Deliberately.

You Can’t Have It All. Choose the Trade-Offs Deliberately.

~by Haley Lynn Gray~ It's true: you cannot have it all. There really are only 24 hours in a day, I do not possess a time machine, and I am not crazy. So the honest version of running a business with children isn't balance. It's trade-offs — choosing deliberately what...

Running a Business With Children: What Actually Helps

Running a Business With Children: What Actually Helps

~by Haley Lynn Gray~ I am not Wonder Woman. I say this repeatedly, mostly to myself. I am one person, bound by the space-time continuum, and I do not do time travel — the risks are considerable. What I do have is four children, a business, and a set of things that...

Parenting is a Full-time Job. Is it Time for Help?

Parenting is a Full-time Job. Is it Time for Help?

Have you ever felt that you needed another “you” to get it all done? Parenting these days is a full time job. If you are a mother and have ever felt that you just couldn’t get it all done, you are not alone.

Working Mom Interview – Angie Carter

Working Mom Interview – Angie Carter

Angie Carter is a mom of 3 and business owner. She made the transition from working for others to running her own business designing her own line of personalized totes in the wedding related space.

Working Mom Interview – Nicole Bruno

Working Mom Interview – Nicole Bruno

Working Mom Nicole Bruno has 3 children. She is the co-founder of a non-profit organization called Guiding Lights, which provides support to family and professional caregivers.

Find what you need

Lead Your Team

Delegation, hiring, difficult conversations, and becoming the boss you'd want to work for.

Build the Business

Pricing, launching, systems, and building something that doesn't depend on you.

Women in Leadership

Negotiation, the pay gap, and what the research actually says about women who lead.

Get Seen

Being visible without the cringe — podcasts, content, and being remembered.

Lead Yourself

Courage, your inner critic, time, and protecting what matters most.

You're Not Alone

The loneliness of leading, and why the best owners don't solve everything alone.