What does Bridget Wear to Work?

As you guys know, both Casey and I have jobs outside of the DIY Playbook. I am a high school special education teacher and really love what I do. My class schedule looks slightly different from two years ago when I wrote this day in the life post but overall my days are still just as hectic from 7:00am-4:00pm.

I teach workplace skills in the morning and finish my afternoon co-teaching government and economics at the same high school where Casey and I attended just over ten years ago. I work at a high school of almost 4,000 students, so the campus is pretty big. I don’t teach in the same classroom two periods in a row, which means I’m always on the move… literally.One Teacher's Look: Work to Weekend Wear | DIY Playbook

I share this information with you not to tell you all about my day job, but to show you that I can relate to a lot of you when it comes to buying “work clothes” because that’s what you’ll find me wearing Monday through Friday. I wish I could rock holey jeans, a tee. and converse everyday but that is far from my reality. And I don’t know if you guys feel the same way about finding work wear but as far as I’m concerned… the STRUGGLE IS REAL!

Work to Weekend Wear

Bridget works hard for the money at a high school, and she sometimes struggles to find versitile, professional clothes like this cream sweater and black skirt.

I have a small closet and limited storage space at home so I really try to purchase work wear that I can wear on the weekends too. I know that’s not always the reality for every single piece of clothing, but I really try my best to only choose items that are versatile… and affordable.

At her high school, teachers dress professioanlly Mon through Thursday and wear jeans on Friday!Casey and I were recently chatting about this strategy and realized that we’re probably not alone in the pursuit to find clothing that can double as work wear and weekend wear, all on a budget. So we decided that we are going to start to weave in some “Work to Weekend” posts on Wednesdays so we can highlight pieces in our closets that do double duty for us.Do you have signature pieces you can wear at work and on the weekends? Would you wear Bridget's pencil skirt for more than just work?

Plus when we turn to Pinterest or even the blogosphere, we don’t see a ton of realistic work fashion finds (not everyone wears heels & a power suit everyday!) so we figured, maybe starting the conversation will teach us all something together! <— we can use all the tips we can get from the amazing community of working women tuning in!

But before we dive into Work to Weekend gear, we figured we should each share a little information about our current work routines so that you can learn what factors go into each our of work wardrobe choices.

Comfy Shoes are a Must!

When it comes to work wear, comfy shoes are a must. But they have to look good too! We love these low heeled black booties.

Like I said before, I work in a high school Monday through Friday. There isn’t necessarily a strict dress code for teachers but looking professional, dressing modestly, and being comfortable are all important factors. I dress professionally Monday through Thursday and love Fridays because we can wear nice jeans and school spirit gear… with gym shoes!Be comfortable but professional and save money with Work to Weekend Wear | DIY Playbook

From Monday through Thursday I try to look professional and feel comfortable. I work in a large school and do not have my own classroom but instead walk to a new room all 8 hours of the day. I recently tracked my steps and figured that I walk almost three miles within the building each day, which means comfy shoes are a must!

The first 3-4 years of teaching I wore heels every single day (ouch!) but have changed my ways a bit since then. I still wear heels on extra special days but usually wear wedges or flats in honor of comfort… and making it to my next class on time!

My Color Scheme
When it comes to choosing versitile work to weekend wear, we like neutral colors like black, cream and taupe.

Sometimes I’ll wear skirts or dresses but in the winter I always pair these staples with tights because it’s just too darn cold without them. In the warmer months, I don’t mind wearing dresses or skirts without the tights but that usually means that the skirt/dress must be knee-length so I feel comfortable and professional.

I mostly wear neutral colors because I feel most “me” in them and they are far more versatile. I’ve found that I can pair neutrals with a ton of different outfits for work or the weekend, which has been key in keeping my small closet contained.


And last but finally not least, I usually accessorize very simply. You know I love my statement necklaces so I will wear those quite a bit. I’ll wear stud earrings and a watch too but that’s about the extent of my jewelry at work.

Simple Accessories like this large purse are an important part of Work to Weekend Wear | DIY Playbook

But even on days I don’t wear any jewelry, you’ll always find me with a bag. Since I travel from classroom to classroom, I need to carry around a bag with me. I keep my lunch in there, my laptop, graded student work, and a whole slew of supplies. <— I can never have enough pens or pencils in my bag. If I had a dollar for every time a student asked for a pen, I’d probably be rich by now!Pull it off with a smile: Work to Weekend Wear | DIY Playbook

Those are pretty much the basics when it comes to choosing my work week wardrobe! I can’t wait to dive into more detail as we roll out the work to weekend series (not every Wednesday, just as we see fit). I feel like a lot of us are in the same boat and could use each other as we all try to build versatile closets that don’t break the bank.

What are your tips?

What do you guys think? Are there certain work to weekend topics or wardrobe items you want us to tackle first? Next Wednesday Casey will dive into her work wardrobe guidelines to give us all a little background on her work environment. Then you guys will have a better idea of each our workplaces so that we can kick-off our first work to weekend post soon!

In the meantime, what factors go into choosing your work wardrobe? We’d love to hear what you do for a living (#GIRLBOSS) and what wardrobe challenges you face!


The Year of Casey

Hey there!

I’m Casey Finn, the voice behind The DIY Playbook. I’m married to Finn & mom to Rory and Ellis. Together we’re creating our dream home in Chicago, one DIY project at a time.