How Your Wardrobe Should Evolve With Your Career

At some point, you may realize that you're still getting dressed for a job you had five years ago.

The suits are there. The shirts still fit. You've taken care of everything. But now you're running your own business, meeting clients over dinner, or spending half your week traveling, and those clothes aren't quite as useful as they used to be.

Or perhaps it's gone the other way. Your days used to be fairly casual. Now you're giving presentations and attending meetings where your usual clothes leave you feeling a little underdressed.

When I look at a wardrobe in this situation, I want to understand what's changed in your day. That tells me far more than your new job title.

What Does Your Week Look Like Now?

Think about the appointments that have become more frequent. Maybe you used to spend most days at your desk, and now you're in front of clients several times a week. Maybe the meetings haven't changed much, but the dinners afterward have.

Those details matter. You can have a perfectly good office wardrobe and still struggle every time you need to go somewhere after work.

If you're regularly changing out of your entire outfit before dinner, I'd want to look at why. Perhaps the shirt feels too corporate. The trousers only seem to work with dress shoes. Or you don't have a jacket you like wearing outside the office.

That's something we can work with. “I need to dress better for my new role” is a much bigger, less useful shopping brief.

A New Role Doesn't Always Mean a Suit

It's easy to assume that moving forward in your career means dressing more formally.

Sometimes it does. You may need a suit you feel good wearing for a board meeting or an important presentation. But if you've left a traditional firm to run a business with a relaxed office, another suit might spend most of its time beside the ones you already own.

I'd be more interested in what you're wearing on an ordinary Tuesday. Can you put together something that feels appropriate for a meeting, comfortable at your desk, and right for wherever you're going afterward?

A good pair of trousers, a knit polo, and a jacket with a softer shape may do quite a bit for that kind of week. The right choice depends on your setting and what feels natural on you.

Some of Your Clothes May Just Need a Different Outfit

I wouldn't assume that everything from your previous role needs to go.

Take the navy jacket you always wore with a dress shirt. Try it with a fine knit and different trousers. You may find it has more life in it than you thought. The same goes for dress trousers that you've only ever considered part of a formal outfit.

Of course, the fit still has to work. If the jacket pulls across your chest or the trousers feel tight every time you sit down, changing the shirt won't solve that. This guide to fit will help you see what needs attention.

Think About the Whole Day

Say you're flying in the morning, meeting a client in the afternoon, and going to dinner that evening. It's worth figuring out what you'll wear before you're standing beside an open suitcase.

Try the outfit with the shoes you'll actually bring. Check how the trousers feel when you sit. See whether you still like the shirt when the jacket comes off.

Small decisions like those make a wardrobe much easier to live with. You know what to pack, and you aren't relying on a last-minute change to make the outfit work.

Start With the Part That Keeps Catching You Out

You probably already know where your wardrobe is falling behind. It's the dinner you always shop for, the presentation that sends you back to the same suit, or the business trip that takes far too long to pack for.

Start there. If you want to look more closely at what you already own, use the professional wardrobe audit to work through your current options.

Your clothes should feel at home in the work you're doing now. And you should be able to get dressed without wondering whether you've brought your old job along with you.