Would that it were easy for women to dress professionally without being critiqued on every aspect of their ensemble. If that were the case, then we wouldn’t have so much to write about when it comes to the intersection of fashion and women’s issues. From hairstyle to hemline to heel height, women are constantly bombarded with differing opinions as to what’s acceptable to wear in the workplace.

With on-campus interviewing season right around the corner, you’ll need to look and act the part. The hour has drawn nigh for some tips that will allow our female readers to maintain a stylish appearance from a day in the office to a night out, all at the click of a button. Because fashion should be a piece of cake, even for lawyerly ladies who are too busy to shop….

For the advice presented in this post, we’ve consulted with Millie Tadewaldt and Cecelia Myers of CakeStyle, an online service that pairs women with personal stylists. Not long after filling out a short questionnaire on their website, you’ll receive a box overflowing with clothes and accessories, as well as a video link explaining how to use all of the items that were handpicked just for you. Any law student living off government monopoly money will be able to appreciate this part: you only have to pay for what you like. You can send back the rest without being charged a dime. What’s not to love about risk-free fashion?

Perhaps the best part of CakeStyle — aside from the home-delivered box of fabulosity — is the fact that one of its founders, Millie Tadewaldt, is a recent graduate of Harvard Law. After all, she knew that female attorneys would truly appreciate the ability to quickly access stylish looks, all from the comfort of their homes or offices.

Before we get into their expert fashion advice on how to rock a look that can last from interview to bar review (which you can see on the following page), let’s get to know CakeStyle’s founders.


How did you come up with the idea for CakeStyle?

CM: We knew so many women who were busy, and wanted to look stylish, but they didn’t always have the time to spend in stores making that happen, and didn’t always have the know-how or confidence to rock a new trend right away. We started brainstorming ways to fix that, and saw enormous opportunity in the online retail space for women — only 9% of apparel sales are currently occurring online. Out of those brainstorms came CakeStyle, which was a great way to offer customized style choices to women in their own homes, on their own time.

What inspired you to create a personal styling service?

CM: Style is hard! Most women face a lot of constraints on what they can wear to work, on the weekends, and out with friends. Figuring out a way to build a versatile wardrobe that can be mixed and matched takes a lot of effort. Our stylists live and breathe fashion so that our clients don’t have to (but still look amazing).

MT: I’ll be honest, I was not the most stylish girl growing up. So when I got my first job after law school and had my first grown-up salary, I was really looking forward to becoming a stylish career woman. I was surprised to find that even with a decent paycheck, I wasn’t always comfortable navigating higher-end brands and stores, and didn’t always know the right way to try out new trends.

Millie Tadewaldt and Cecelia Myers

What is your background? How did you end up in fashion?

MT: I’ve always been into technology and business, so when I finished up my design degree at UC Davis, I opened my own web application development company and built applications and websites for small businesses, IT shops, and ad agencies. A few years later, I found my way to Harvard Law School, where I was drawn to the business strategy side of problems, rather than the legal strategy. Following law school, I worked at BCG as a management consultant, and simultaneously launched my first web startup, DashMob. After that, I had officially caught the startup bug, and so when my friend introduced me to Sandbox Industries, the Chicago-based venture capital firm and startup foundry, it was a natural fit.

CM: I started out in startups and venture capital. I’ve watched many consumer tech companies succeed and fail and learned a lot about how to create a strong business. Fashion has always been a great love of mine, so the opportunity to create a startup fashion company was the perfect match for me. I love that reading Elle, Vogue, W, Lucky, and many other style magazines is my homework alongside building financial models and marketing plans.

Have you always had an interest in business law?

MT: Yes, and my JD comes in handy every day, whether it’s giving me added credibility in a negotiation, or giving me the confidence to read legal documents and formulate an opinion about them.

We assume that you’ve made a foray into the world of fashion law with this venture. Tell us the part you like the most.

MT: I’ve always been interested in IP law in general, and its application to fashion is no exception. In the last 10 years, enforcement of and support for copyright law in the fashion industry has been increasing. “Fast fashion” retailers like Forever 21 and Zara have built their businesses on copying the styles of big name designers. It will be interesting to see how high-end designers continue to respond, what will happen to these discount retailers, and how the law will take shape, given the grey areas this begins to touch upon.

Do you have any advice for lawyers looking to get out of the legal profession to start their own business?

MT: Don’t be intimidated and have confidence. Most lawyers I know are extremely bright and would fit in well on the business side of things. Take advantage of your strengths: law school teaches a rigorous, systematic way of thinking that is helpful in financial modeling, product management, computer programming, marketing analysis, and more. Try to identify a real problem that you’ve encountered in your personal or professional life to which (here’s a key point) someone would pay for a solution. Don’t be too discouraged by competition (lawyers are notoriously risk averse) — if others are out there already trying to solve your problem, that can merely mean that you’re trying to solve a popular problem. And finally, find someone whose skillset complements yours (Cecelia and I are a great example). Lawyers can often be solitary thinkers, but startups work best when multiple smart people are getting to the answer together.

What’s your favorite trend right now for professional women?

CM: The renaissance of patterns has been great for professional women. This season, we are seeing a lot of 70s mod-graphic prints, which is fun under a classic suit. Patterns can add personality and flavor to a basic outfit like nothing else. The key to mastering patterns is picking something you love, then balancing it with a simple top or bottom for the workplace.

Is there anything that you consider to be a major fashion “don’t” when it comes to professional dress?

CM: Fit is it. You’re better off in something that is a little dull that fits well — you can always add a fabulous necklace or scarf to kick things up. If something doesn’t fit you properly, though, that’s the only thing people notice. Also, make sure your shoes are neat and well cared for. I’ve interviewed a lot of women in great outfits with heels that looked like they lived at the bars. It really created a disconnect in how they presented themselves.

We’ve received some rather controversial advice in the past on the great “skirt v. pants” debate. What’s your take?

CM: Honestly, you should go with what suits your figure and makes you confident. Clothes work best when you own them. If a knee-length pencil skirt makes you feel sharp, then it’s your best bet. Conversely, well-tailored cigarette pants, or slimming wide leg trousers can be just as chic. As long as you follow the basic conventions of appropriateness (not too short, not too tight — no one wants to know what type of underwear you’re sporting), then people will notice you (in the right way), and your clothes will enhance that.


We here at Above the Law wish Millie and Cecelia the best of luck with CakeStyle. If you’re interested in receiving a box of clothing and accessories, simply click here to get started. If you’re in the Chicago area, you can stop by the CakeStyle boutique at Ohio and State in the River North neighborhood for a consultation.

On the following page, we’ve got some photo collages from CakeStyle for their interview to bar review looks, as well as a sample video that was used for one of the company’s clients who happened to be an attorney….


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