Do Your Clothes Match Your Job?

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What happens when you leave behind one career, and its style tribe, for another?

The idea of  “dressing for success”, certainly for women, is one complicated by the invisible but lethal tripwires of fashion faux pas. Come for a job interview, in NYC media, wearing sheer, flesh-toned pantyhose, let alone plain black pumps, and you might as well go home. But show up for work in the boys’ clubs of banking, law or finance in peep-toe pumps and you’ve marked yourself as Stupid.

A dress code of any sort is something of a risible notion for most freelance writers, for whom switching from PJs to sweats is a typical fashion decision as we start the workday, commuting from bed to desk. Of course we dress up for meetings and media events; last year I was on CNN and BBC television, and now have my go-to outfit ready, a cashmere turtleneck and black blazer.

I hate summer because it’s so much easier to look really, really bad.

In my three newspaper staff jobs, it was clear from the start what the style was — “Fashion? Feh! I’m too busy seeking Truth.” Or some equally tedious variation.

It was like high school all over agan, the peer pressure to look like the cool kids. At the Globe and Mail, Canada’s respected and prestigious national daily (then the only one), one woman reporter wore knee socks, sandals and a skirt. Um, seriously? But the larger message was a good one — get the story first and best, and who cares what you’re wearing?

At the Montreal Gazette, to my horror and disappointment, it was all about the low-cut sweaters and short skirts. Ugh. One young woman wore long dresses cut so tightly you could practically read the label on her panties. At the Daily News, it was back to whatever-world. Your best pick was anything you could run fast in or do a ten-hour stakeout in 80 degree heat.

I’ve never, thank God, worked in a place where Manolos or Choos or Chanel were de rigueur. I love to dress up and to dress well, but not as a daily, I’m-paying-for-it uniform, the rules unspokenly enforced by chilly gazes.

From yesterday’s Wall Street Journal:

For most people, it isn’t easy to purge a closet, especially when it’s full of items that were once meaningful. Christos Garkinos, co-owner of high-end Los Angeles consignment shop DecadesTwo, says he often has to coach people as they work up the gumption to relinquish items from their former selves to his boutique. And he often gets calls days later, when a client regrets having let go of an item.

One client, he says, sat on her bed and shivered with emotion as he sorted through her wardrobe. “I actually would have to stop and give her reassuring hugs and have her give ‘permission’ to let her clothes go,” he says.

People often feel the need to reinvent themselves when they reach midlife or the years before retirement, says Dr. Barbara Becker Holstein, a psychologist in West Allenhurst, N.J. It’s common for people like Ms. Kan to feel that they’ve compromised too much of themselves for their job or their marriage, and to want to rectify that by starting afresh.

I suspect that the pace of change in technology and business also contributes to people’s sense that it’s time to change skins. Our jobs and industries keep moving, morphing, and disappearing, creating opportunities for image changes—and the fear that we’ll need to change, whether we like it or not.

Despite the lure of letting go, Dr. Holstein suggests avoiding hasty decisions to leave a job or home or even to toss out significant portions of your closet. And she warns against purging photos and mementos—items that can never be replaced if your feelings change later. “The average person has a natural pull to stay connected to who they were,” she says.

Have you changed how you dress as your work or career has changed? How?

5 thoughts on “Do Your Clothes Match Your Job?

  1. Letting go of certain clothing that has been through a bad day with me is certainly something I do. If a day went all wrong, I feel the clothing has lost some of its appeal and I don’t feel good in it anymore.

    I think the notion of ‘fashion’ and how we show ourselves to the world and to ourselves is so important a topic. Also how we feel in our clothes! There are many other nuances than those I was able to discuss in the article in which I was quoted by Christina Bickley in the WSJ.

  2. I used to work in an office in a large city. My wardrobe consisted of the same type of nice pants suits, dresses, suits, skirts with tops, sweaters and blouses that most of the office staff wore. Then, I moved and changed lifestyles, I garden and walk and haven’t worn a dress in years.

    It didn’t bother me because living one day at a time, I didn’t know that time was passing so fast that everything about style was changing as well. I went to put on one of my former favorites not too long ago and it fit me no where at all.

    Sweats, jeans and tops have been my wardrobe for nearly a decade and I say long live casual dress as an option.

  3. aurora

    “Come for a job interview, in NYC media, wearing sheer, flesh-toned pantyhose, let alone plain black pumps, and you might as well go home.”

    Ouch – good thing I don’t work in NCY media. That plus a skirt suit is basically my non-Friday work outfit. While rare these days, especially with younger women like me, I do think it’s the best look for almost any white-collar workplace. It’s attractive and feminine (unlike pantsuits), but also matching the formality and authoritativeness of the standard male business suit.

  4. April Peveteaux

    When I graduated from college my mother took me shopping for a suit. I never wore it. The idea was every college grad needs an interview suit but my first job was in the music business and everything after has been just as casual (or more, as you point out – I’m freelancing in pjs quite often).

    Being in a creative field has meant never having to dress conservatively. But I did step it up when my office was in Soho – just so I didn’t completely feel like a slob when standing in line next to models at Dean and Deluca.

  5. Caitlin Kelly

    Chris, casual clothing is always more comfortable, but the problem with sweats and leggings is you can gain all sorts of weight and not notice it. My mom keeps reminding me to wear clothing with a waistband and it’s good advice.
    I also find it a little sad to never dress up as I do enjoy it.

    aurora, styles differ quite a bit — even within NYC and certainly between industries. For some women, sheer hose and black pumps is considered a great look; for others, it signals (to the fussy) a lack of style or creativity and/or confidence — all considered fairly crucial within “creative” fields like design, advertising, etc. What looks great in one office can be considered hopelessly dowdy (or casual) in another, which is why men in suit are fortunate! I have to disagree with you about a woman in trousers; it doesn’t have to be (as it often is) a sad, dull copy of a man’s look, but can be in a beautiful color or texture with neutral trousers and an interesting shoe. Having lived and worked in Canada and Europe, I’ve seen women stay both feminine and authoritative — some American workplaces seem pretty humorless on that point.

    April, I find conservative dress dull — but classic dress my easiest and usually default choice. Give me a black suit and a light wool or cashmere turtleneck and some great accessories and I feel totally at ease. I almost never wear skirts but love to wear dresses and, sometimes, heels. The challenge of working alone at home is finding or creating places to step up your game a bit.

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