Today, I’m so thrilled to kick off a new series here on Memorandum, one that has been requested daily by many of you for YEARS—a dive into career advice from my early days working on Wall Street to my experiences today running both a fashion tech startup and a fashion blog in New York City.  To kick things off, I wanted to start by discussing a challenge that every working woman faces at some point in her career—how to tell if something is office-appropriate.  Given Memorandum’s roots in workwear, we thought this would be the perfect place to start!


Did she say “we?”


Yes, yes she did.


In addition to sharing my own career tips and anecdotes, I thought it would be even better to have my friend Lauren McGoodwin join the conversation as well.  If you don’t know Lauren, she is the founder of the incredible site Career Contessa where she and her team offer invaluable career tips and resources for working women.  Lauren and I became fast friends after meeting over a year ago when we did a webinar together for her site and I’ve been dying to find a way to bring her amazing advice to Memorandum readers ever since.


In this Career Memo series, Lauren and I will be discussing all sorts of job-related challenges that working women face.  Since no two work environments are exactly the same and there’s no one formula for the perfect career path, I wanted this series to be collaborative and conversational with someone whose opinions I truly respect.


When it comes to today’s topic—figuring out what’s appropriate to wear to work—there’s definitely no one-size-fits-all uniform.  Nevertheless, as you’ll read below, Lauren and I agree that there’s a universal approach that everyone can take regardless of whether you’re a grade school teacher in Albuquerque, an an accountant in Chicago or an attorney in NYC.





MARY:  Lauren, I’m so excited to collaborate on these posts!  When thinking about sharing career advice and discussing job-related challenges, I knew there would be no better wing-woman than YOU, the queen of career advice!  For readers who don’t know you already (shame on them) can you tell us a little bit about your professional background and how you came to start Career Contessa?


LAUREN:  I live in Los Angeles, and before beginning Career Contessa in 2013, I worked for many years as a corporate recruiter for Hulu. And before that I was working as an assistant, desperate to try something else. So, I’ve been on both sides of the hiring table and I’m obsessed with helping women build successful careers on their terms. My career advice has been featured in Forbes, Fast Company, Huffington Post, Business Insider, Entrepreneur, etc. and I’m thrilled to have the opportunity to talk about my favorite topic with Memorandum readers!




M:  Ok, so needless to say, when it comes to career advice, you’ve got #ExpertStatus.  So let’s dive into today’s topic, shall we? The perpetual workwear quandary of how to determine what’s appropriate for your office.  I think this question is particularly scary and stressful when you’re just starting your career or just beginning a new job and you haven’t yet had the chance to scope out what your colleagues are wearing every day.  Where does one start?


L:  Starting a new job can be scary—what will it be like!?—and an added stressor is the inevitable question of what to wear on your first day of work. Nowadays, workplaces vary more than ever, which means it’s not always the norm that corporate attire is the way to go. However, there are universal ways to approach this challenge to alleviate your first-day jitters and narrow down your sartorial selection.





M:  I absolutely agree. While there is definitely no dress code across industries, there’s a lot you can do to identify what’s appropriate.  Most frequently, I get asked about what to wear to an interview, and I always advise people to (1) do as much research online as possible; (2) ask friends who work in similar industries about what they wear to work; and (3) when in doubt, OVERDRESS.  


L: I completely agree with your ideas! When I worked in tech where we had a very casual dress code, I loved to see interviewees dress up a bit more. You don’t have the job yet so make sure you’re still in that “dress to impress” stage. If you’re interviewing in a more creative field like fashion, they’ll often want to see that you fit their “vibe” or culture. For example, I had a friend recruit at Tory Burch back in the day and they totally expected the interviewees to dress similar to the Tory Burch style. For those more creative fields it’s another way of saying “I’m truly a brand ambassador of this company.”



M:  I completely agree.  If you’re working in fashion or any creative field, your appearance should reflect that you have a demonstrable interest in fashion and creativity!  But let’s shift gears here. Let’s say you’ve aced the interview and landed the dream job. How do you suggest people approach dressing for the first days of a new job?  It’s so important to make a good first impression!


L:  Long before your first day,  there are a few tricks that you can use to help figure out the dress code. The key is to be observant.  If you have an in-office interview, take note of what the interviewer is wearing. Is she super dressed up on a Friday? If so, it’s probably safe to assume that the company expects traditional corporate attire. Before your interview, when you’re walking into the building itself, make mental notes of what other employees are wearing, too. That being said, if everyone is wearing jeans, it might still be best to wait until after your first few days to follow suit (pun intended!).


It’s also a good idea to check the company’s social media accounts for outfit inspiration. Does the company post pictures of events on Facebook or Instagram? What about photos on Glassdoor or oncompany profile sites? Scroll through those feeds to see if you can find any photos with employees, and take note of their clothing.


Finally, if you are still in doubt, check with HR or recruiting. Call or email your hiring contact and ask if there is a specific dress code for the company or if she can give you an overview of the typical attire.


M:  I couldn’t agree more.  I think it’s always a good idea to be a little more dressy during those critical first days when you’re meeting people for the first time.  I have to say, I love your recommendation about stalking those company social media accounts! Ahhhh technology. I would also absolutely not be shy about emailing HR or one of your female interviewers asking what people wear to the office.  When I worked on Wall Street I had several new hires email me before they started to ask for advice on what women typically wore in our office and I thought it was a great question! It showed me that the new hires were excited about their first day and taking it seriously.





M:  Now, many people think that once you’ve landed the job, the tough part is over, but I think your first week or two on the job requires special attention.  How do you think this period should be approached?


L:  It has been said time and again, but it is always best to err on the side of being overdressed. This is true even if you are working in a more casual environment.  Studies actually prove that it is better to overdress, as your attire can affect your confidence level and the way others perceive you. Since your first week is all about setting great impressions, you want to feel your best!


During those first few days, watch how top people in the office dress, taking cues from women in management, and err on the side of “dress for the job you want.”  If you feel overdressed on your first day, no worries—just adjust your outfit for the next day.


M:  Amen!  I think it’s important to note that at this point in your job, you have limited ways to send strong, positive messages to your boss and your colleagues.  Since it’s your first few days, you haven’t had the chance yet to prove how brilliant you are or how amazing you are at the actual job. Instead, you have to send those messages in other ways and presenting yourself well is a huge part of that. Set a great first impression by showing up early, reaching out to introduce yourself to colleagues, asking thoughtful questions and dressing your best.

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