What Does Casey Wear to Work?

Last week, Bridget shared some insight into her day job as a high school teacher. Today, it’s my turn to dish the scoop on my “real job” outside of the blog and the clothing I choose to wear to work each day.

Casey's work wear is professional yet versatile.But in order to explain my work wear and current day job, we should dive a little into the history of my career. Ever since I was a little girl I always dreamed of being a TV journalist. I absolutely loved reading, writing, and English classes and idolized the newscasters I saw on TV. After studying broadcast journalism in college, I graduated and moved to small town in Wisconsin to become a news reporter.

I loved it, but eventually, I was ready for a bigger city and more experience. At that time, Finn & I moved to St. Louis where I worked for Anheuser-Busch (yep…the beer company!) producing and hosting all of their internal videos. It was an awesome job! I was on-camera, writing scripts, and traveling all over the country to produce fun & entertaining videos. But my real goal was to find a TV job in Chicago to be closer to our families.

Add a pop of color to a basic color palette to liven up your work wear.We moved back here in 2013 and I ended up working for a local channel producing a DIY show here in Chicago. Combining my love for DIY with my skills in TV was a match made in heaven,  and I ended up producing 3 seasons of the show Weekend Workbench.  But all good things must come to an end, and I was ready for a new challenge so I accepted a new job last fall.

Today, I work for a large startup in the healthcare industry producing lifestyle content that airs nationwide (think cooking shows, exercise videos, patient stories, doctor interviews, etc.) My office is located in the heart of Chicago, and I absolutely love what I do!

My office has a definite startup feel, and is very casual. The rules are no pajamas and you shouldn’t ever be able to go from work to the gym without changing. So yes…it’s incredibly laid back.

Casey's business casual office gives her a lot of flexibility with her looks.I typically dress for my day. So if I am out interviewing a doctor, I’ll dress up a bit more than I would if I’m just reviewing footage and writing scripts.  But just because I can dress fairly casually, doesn’t mean that it comes easy for me! It can be hard getting dressed everyday and I’m still working on finding my work wear style.

My Go-To Work Wear

Here are a few of Casey's "go to" favorite pieces for the office.
Overall, I aim to look pulled together and also comfortable when I head out to work each day. And like Bridget, I don’t want to spend a ton of money on a huge wardrobe so I look for quality pieces that I can wear during the week and on the weekends. Here are some of my staples…


A simple blazer can transform almost any outfit, and dress you up in one quick step.I love a good blazer and own at least a half-dozen. I think my love for these jackets stems back to my news anchor days when I literally wore one on-air every.single.day. Today my blazer arsenal is much smaller, but I still love the feeling of putting on a blazer and feeling put together.

This structured blazer is modern and professional, and updates any look in a flash.This structured blazer is my current favorite. It’s dressy, but has a bit of an edge to it so it certainly isn’t boring. I actually got this one on sale at an outlet store, but I’ve seen a lot of great structured blazers in-store recently (like this one). I also have a rotating collection of blouses (like this one from LOFT) that I wear underneath, mostly in blues, grays, and blacks.

Skinny Work Pants

Finding the perfect work pants can be a challenge- my go to favorites are skinny leg- and I found these amazing ones at Ann Taylor!I feel like we need to do an entire post about finding the perfect work pants because it is HARD! Some of the ones out there are a bit too frumpy, or if they’re the slim kind then they’re often cropped at the ankle (which isn’t great when the temp is in the single digits in Chicago). I recently picked up these work pants from Ann Taylor on sale for $25 and they’re amazing! Thick, appropriate for work, and they are skinny at the ankle. Yes, yes, yes!

Comfy Shoes

Comfortable and cute shoes are key- I avoid heels because of my walk on my commute, and opt for wedges instead.I never wear heels to work and instead opt for boots or wedges. I have these TOMS in both black and gray and wear them constantly. They’re so comfortable and I have no problem on my commute to work (where I walk over a mile).

These Toms wedges are a favorite- I own them in several colors- because of their comfort and look.I have yet to find the perfect pair of flats that are both chic & comfortable. I find that I’ll often wear some and the soles break down or the backs give me blisters. But once winter is over, my goal is to find a great pair that I can wear to work and on the weekends! Any advice for finding good flats? Any brands you love?

Structured Bag

A large, structured bag is the a must have accessory. Hold all your key items in a chic looking piece.Finally, my work wear look wouldn’t be complete without a big ass bag. I’ve always been a working girl with a big tote because I like to always be prepared and have things on-hand. This black bag was a steal from TJ Maxx and it holds everything from file folders, to my laptop, to my yoga clothes. They’ve got a good collection of work bags at good prices (like this one).

Head to toe- Casey's work wear for your inspiration. A great blazer, skinny work pants, cute and comfy shoes, and a structured bag.
Now I want to hear…what is your office dress code like? Are you more casual like my office or are you super dressy? Hopefully, we can all learn some fashion tips from one another as we try to look polished for work each day!


The Year of Casey

Hey there!

I’m Casey Finn, the voice behind The DIY Playbook. I’m a Chicago gal teaching you how to design, DIY, and maintain your home…by yourself! Learn more about me right here.