• Meaghan

How to Dress AT Your Dream Job feat. Gwynnie Bee

Updated: Oct 9, 2018




Maybe it's because I was always destined to work in fashion, but I vividly remember what I wore to my first internship interview at JANE Magazine. I was a sophomore in college, and while I had a job since I was old enough to hustle my babysitting club idea or haul chairs on the beach (yes, really), this internship was the ticket I needed to get in the door and climb straight to the corner office (or so I thought). An internship at a major fashion magazine in 2003 was BIG, and in my eyes it would be my first introduction into the "real world". I remember being anxious, but not really nervous and that , I know, had everything to do with my outfit. Even back then, I knew the power of the perfect look. And so, as I put on my navy blue suit, shadow stripe button down, tortoise patent leather Jimmy Choo's stilettos and the perfect (borrowed from mom) diamond earrings I had not only secured my buttons, but I had secured my confidence.


In 03' I had NO CLUE what a fashion stylist was, and blogging wasn't even a thing. The world we live in now didn't exist - but I knew in my gut that I was meant to be in fashion. I was so enthralled with the power of dressing that I somehow managed to make a career out of it. 15 years later, I am still focused on the "look". Only now, it isn't just for my own appearance, it's also for my clients'! My career path had some {very} windy roads... but the twists and turns were all worth it because they brought me here....

As Meaghan O'Connor, fashion stylist & blogger.



I have my dream job, and I am so incredibly grateful. Part of that gratitude comes from knowing that not everyone is there yet! This month, Gwynnie Bee partnered with Year Up , an organization that helps students 18-24 from low income homes prepare for and land internships at some of their dream companies! SO, When Gwynnie Bee reached out to see if I’d be interested in partnering together to share some of my “wear to work” tips, tricks and advice - I immediately hopped on board! 


Not only because I love Gwynnie Bee for being a size inclusive (0-32) clothing subscription service (wear, return, repeat), but because I'll jump on any opportunity where I get to to encourage others to live their best life, follow their path and dress their best for whatever dream job they're looking to land! While all of our paths are different, and all our timelines unique- the one common thread is fashion. With each interview, internship and job comes a new look! The beauty of fashion is being able to enhance your own story with clothing, using them to better express who you are!

It's all about letting your look tell the story.


So today, I'm sharing what I wear on the job and some tips/tricks I use in my day to day......






I put together this simple, functional, chic look for a day of returns (read: hauling boxes and bags back to showrooms etc) and meetings. My days always have a bit of rough / tough grit mixed in with meetings so my look typically needs to be comfortable enough for me to hit the pavement with bags, boxes and what have you but also chic enough to meet someone for a coffee to chat about a collab or a new gig! Here are my top three tips for looking your best and making your look work overtime without overworking yourself!


1. Polished. Not Perfect.

You always want to look polished, but stop striving for perfection. Fashion is meant to be FUN, so have fun! Use your look to show your personality, who you are and what you like. If you're always worried about a crease or a wrinkle, you'll only be adding to the stress of your work week!


A LBD is the perfect go-to for me. Mostly because its so easy to look polished in a simple black dress, but also because if I do happen to spill my coffee while running to the UPS truck, you can't see it! (Speaking from experience, of course!)

2. Functionality.

Not every gig is going to require a functional wardrobe - and certainly not at the level that job as a stylist requires, but I do find it important to consider functionality of wardrobe when it comes to dressing for your work environment.

My job requires me to be moving around, picking things up, getting down on the floor, dressing models, dragging bags and suitcases etc etc. It's a lot of manual labor, so while I do need to look put together and polished (hello, I work in fashion), I also need to be able to move freely and comfortable throughout the day. This usually means an oversized tee or dress, sneakers and a lightweight layer for cold studios and days that turn into nights!

3. Keep it simple, then add something.

Remember that accessories are a great way to bring out your personal style and aesthetic whilst keeping a polished and professional look. My grandma always said, "all you need is some lipstick and a pair of sunglasses". That completes whatever look I have on - be it workout clothes or a full length gown.


So, for me, its adding lipstick (typically red or pink) and a pair of sunnies. That signature add-on, has not only become part of my style personality, but it always rounds out whatever look I have on that day!









Year Up’s mission, Gwynnie Bee's mission and my own personal mission as a fashion stylist is one in the same.....


Providing women access to options that allow them to feel confident and stylish!

Something I think we can all get behind!!


Remember y'all...


When you look good, you feel good.




**Thank you GWYNNIE BEE for sponsoring this post.

All opinions are 100% my own. Because, duh!


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