My mom thought I was sartorially unprepared for my entré into the professional world—and her doubts were well-founded. Three weeks after graduating from college in Kansas, I’d managed to land a job as a magazine editor in New York. I celebrated this feat like any reasonable 22-year-old would, and got matching tattoos with my best friend.

I’d kept the tattoo on my left foot carefully hidden, but mom was on high-alert after she found my “To-Do Before New York” list, on which I’d written “get tattoo” because that was just the kind of responsible person that I was. One morning, mom’s suspicions proved true, when I got out of bed and sleepily forgot to put socks on.  She was irate, and I got a strong lecture about living and working in the real world—aka, being an adult—and also a new wardrobe, which was a strange punishment. But the new wardrobe was dressy officewear—black, boot-cut dress pants (this was the early ‘00s), stretch cotton button down shirts, and pointy black kitten heels—all the kind of clothing that I would never buy for my self, and all the kind of stuff that my mom was convinced I’d need in my newfound life as a fledgling career woman. I packed it all into my suitcase, got myself a one-way plane ticket, and once in New York, never wore a single piece of it.

My mom was far from the only parent I knew who tried to equip their offspring’s closet for grown-up cubicle life. My roommate’s dad insisted she get a suit custom-made. “You’ll need it for interviews!” he said, even though she had just spent four years studying sculpture and had no intention of going on interviews, much less any that required a suit. Her dad was involved enough to take her to the tailor, but not involved enough to stick around for the process. With no parental supervision, she designed and had made the suit of her dreams: billowing, wide-legged pants, topped off with a sleeveless button down suit vest that came complete with a detachable hood and had a bright pink lining. The result—though made with care and by no means cheap—was too hideous, even for an art major.

For our parents’ generation, dress for success meant somber, conservative clothes that made the wearer blend in and look responsible. For our generation, especially those of us who aspired to creative careers, the rules for dressing for success were much more vague and open to interpretation. And in a sense, also much harder to follow.

When I got to New York, I wasn’t rebelling against anything by not donning a button-down and dress pants that my mom had bought me. I would have worn them had they seemed appropriate, but they actually didn't. No one I worked with dressed like that, at all. I worked with beauty and fashion editors, who wore distressed jeans and platform heels, vintage dresses, boutique bags and handmade jewelry. They didn’t dress like they were trying to look responsible, they dressed like they were cool. If that was success, then dressing for it was as hard to grab onto as a chiffon scarf billowing in the breeze of a passing L train. The other adage we always hear is 'dress for the job you want, not the job you have.' That's a good point, but when the job you want seems to involve a Céline bag and a Saint Laurent jacket, that's hard to accomplish on a Forever 21 budget.

Fortunately, I had a savoir: fast fashion. I couldn’t afford what my coworkers were wearing (and in retrospect, I’m pretty sure a lot of them couldn’t afford it either), but I could at least keep up with the trends. Every paycheck, I'd treat myself to a high-street shopping trip, where I'd scrutinize the sale rack at Zara as if it were the new arrivals at Barneys. I still remember one of the best, possibly back-handed, compliments I’ve ever received, from a senior beauty editor I worked with. “I don’t know how you always look so cute,” she said to me one day as we were walking out of the building, “When I know you don’t make any money.”

As my career progressed, my jobs got more ‘creative’ and my outfits followed suit. Since I now had the job I wanted and no longer had to just dress for it, the lines blurred between what I'd wear out on a Saturday night and what I'd wear to work on a Tuesday morning. Was it always appropriate? Probably not. I once showed up to work a holey T-shirt that I’d bought off eBay (I was in a vintage Americana phase), which said ‘Maui High Life’ and was illustrated with weed leafs arranged to look like a beer can logo. “Nice shirt,” my boss said. “Thanks!” I said, “It only cost $4.” Once again, hindsight is 20/20, and he was probably being a bit sarcastic.

It wasn’t until I quit my full-time job to go freelance that I really started to think about how I dressed again.

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It wasn’t until I quit my full-time job to go freelance that I really started to think about how I dressed again. When I was working for a brand or a company, I had that pedigree behind me. I could go to meetings in a weird hat and astrological nail, and know that the business card I threw down on the table was my calling card of professionalism and know-how. But representing myself, I didn’t have that luxury.  Instead, everything about me had to look professional and like I knew what I was doing. When I'd quit my full-time job, I’d initially told myself that things like shopping and manicures were luxuries that would stop when my steady paycheck stopped. Instead I came to see them as, if not actual business expenses, at least justified purchases. I had to dress for the jobs I hoped people would hire me to do. Since I work from home, I still don’t get dressed every day (and I’m actually sitting here in leggings as I type), but you can bet that when I have a meeting, I put on something appropriate, wear a little makeup (to show that I didn’t just roll out of bed), and leave the weed T-shirt at home.

How to dress for your own version of success:

1.     Know what looks good on you. Even if everyone around you looks killer in a trend, skip it if it doesn’t work on you. I love the look of a sophisticated one-piece jumpsuit, but since I’m short, I just look like I’m the janitor who’s come to take out the trash.

2.     If you don’t know what to wear, ask. Every place I’ve ever worked has been non-traditional, and it was always painful to see people show up to interviews in a suit (le sigh, they probably listened to their parents or a well-meaning career counselor). You can always ask the person setting up your interview if there’s a dress code, and they’ll probably give you some hints.

3.     If you’re going to a meeting, think about your potential client. You wouldn’t show up to a meeting with Coke drinking Pepsi, would you? If you’re meeting with a fashion company, you don’t have to wear their brand, but dress on a level that’s on par with their products, and be aware of obvious brand conflicts. People want to know that you can understand their brand and think like they do, and what you wear is just one way you demonstrate this.

4.     It really is all about the investment pieces. I still shop high-street brands like Zara and Topshop for most of my clothes, but have learned to splurge on shoes and bags. A nice bag will make the most casual outfit look more polished. Have your eye on a few investment pieces, and set up sale alerts (ShopStyle is great for this) so that you can snag them as soon as the price drops.

5.     Avoid impulse buys. Give yourself a monetary limit, and if something costs more than that, impose a waiting period where you have to think about it. Usually, practicality will win out, but if you really did fall in love, and can’t stop thinking about those red patent leather pants, then by all means. Eventually, by buying thoughtfully, you’ll end up with a wardrobe as opposed to a closet crammed full of things that don’t go together. That's the kind of closet that induces those "I have nothing to wear!" mornings.

6.     When in doubt, keep it simple. Your outfit doesn’t always have to make a statement, especially when it comes to job interviews or meeting new contacts. Coco Chanel herself is quoted as saying it is always better to be slightly underdressed, and when you leave, you want people to be talking about you, not what you were wearing.

Kate Williams is a freelance writer and editor in Los Angeles. Previously, she was editorial director at Nasty Gal and at Urban Outfitters, and a senior editor at NYLON magazine. Her work is a mix of editorial, ghostwriting, branded content and fiction.