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.teacher-fashion-sweater-skirt-bridget-standing

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


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.


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.teacher-fashion-sweater-skirt-bridget-7

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!


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!teacher-fashion-sweater-skirt-bridget-4

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

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.


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!teacher-fashion-sweater-skirt-bridget-laughing

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!


  • Casaundra Donahoe

    OMG! Thank you for starting this series. Deciding what to wear to work is a daily struggle and when I google for ideas all that comes up are high fashion options which are not realistic. Business casual attire can be so hard!

    • We feel the same way, Cassandra! Hopefully we can all learn from each other and at least get the conversation started!! Thanks for support!

  • Katy

    I am a manager of a group of engineers — all male besides me. Our dress code policy is “Dress for your Day”, which means that jeans are acceptable as long as you are not meeting with external clients. I really struggle with this dress code, as I sometimes find myself going too casual, but I also don’t want to dress up too much and appear stuffy to my employees. Additionally, I am the only female engineering manager, so there isn’t anyone to look to for guidance. I’m thinking about getting some blazers, but I’m not sure how to incorporate them. I wear a lot of button-up shirts with cardigans in the winter, but summertime is tough as I don’t want to wear layers but my outfits seems to always feel unfinished without them. Obviously, I could use some help!

    • what about a wrap dress? I work in IT also with a lot of men and am all about the neutral colored wrap dresses when it’s hot out!

    • Katy,
      This is exactly how my workplace operates (dress for your day!) I’ll be chatting more about it next week when I share more about my workwear, but I totally agree with your sentiment. I either feel too casual or too fancy…it’s hard to find a good middle ground.

      Excited to tackle this more here on the blog!

      And Morgan…love the idea for a wrap dress!


    • Katy

      I look forward seeing your post and hopefully getting some suggestions!

    • Thanks Katy!

  • Kara D

    Love this series too! I don’t feel comfortable in skirts/dresses at work, so I’m always wearing pants. Lately, my staple outfits have either been:
    1) Solid dark leggings/skinny pants with long loose tunic tops and tall flat boots
    2) Express Portofino shirts, layered over either a tank top or thin long sleeved top, with trousers. Sometimes a sweater/cardigan layered on over it.

    The tops I will wear over the weekends too, but the bottoms will change to jeans or athleisure pants, etc. Plus the accessories and hairstyles help change up the “fanciness” level.

    • Love this plan Kara! Casey is also obsessed with the Portofino shirts from Express. She’ll be sharing more about her work wear next week, but it sounds very similar to yours!

  • Erin

    my department dress code has changed drastically because we merged with a team that is based in florida, and their dress code is SUPER casual. While our office had always been business casual because we are headquarters. My usual work uniform is heels/wedges with ankle pants & a portofino blouse (and it’s always bright colors).

    However, our dress code has gotten a lot more casual because one, my old boss had broken her foot a couple years ago and since then she’s always worn sneakers. Secondly, the florida team dresses very casual as in they do wear shorts to work! That is a bit much for me! I don’t go that far down the casual road. but i do wear jeans a bit more often. I try to keep it mixed up where I’ll wear dark colored jeans with a dressy top. but i still try to stick with wearing my vans on fridays only!

    Though come summer time, I can’t even bear to think about wearing jeans because it is way too hot to even think about pulling those on — that’s when i default to my work uniform, it’s a lot cooler, and i mix it up between my portofino blouses & sleeveless blouses. I cringe every time i see someone come in the building wearing jeans when it’s 90 degrees outside!

    • Aren’t those portofino shirts the best?! So easy to throw on and feel pulled together. Love it!

  • The glasses are coach, I got them at my eye doctor a few years ago. If you’re looking for new glasses, check out Warby Parker — seriously amazing (and SO many options!)

  • I am super excited for this series! I work in an office setting that sometimes sees clients we fund coming around (and sometimes without warning), so its pretty formal around here. However, we recently relocated our office and we went from having lawyers and accountants on all the other floors to being the most professional organization in the building and the attire has slowly veered more and more casual since. It’s interesting to see how the others companies and organizations around you affect things such as clothing standards!

    Sweet Spontaneity

    • Sounds like you’re having the same struggles we are, Sarah. Hard to find a good balance between super dressy & super casual! Hopefully we can all figure it out together.

  • kates

    YES YES YES!!! Love this idea. I work for a small arch/eng firm and our dress code is part “wear for your day” part “business professional” and part “business casual”. It is really hard to dress for that some days! Not to mention living in the midwest (Iowa) we don’t always follow the latest fashions and we don’t have a lot of the stores most fashion bloggers use. So love to see your outfits.

    Also big fan of my sperry’s for daily wear. I have a pair of black and tan ones that i have lived in for like 2 years now.

    • I’m glad you’re on board!! And yes, I completely agree when it comes to a comfy pair of shoes… once I find a pair I love, I wear them on repeat to work!

  • Thanks Sheila, it’s TRULIO from TJ Maxx!

  • Pia

    I love this! I too struggle with work clothes – I end up wearing the same “blah” items over and over again because I’m never able to find anything work-appropriate that I actually want to buy or wear!

    I would love to see a post on what you consider your work essentials – like 5-10 awesome (affordable!) items that can be mixed and matched to actually look put together without spending a ton of money or time each morning deliberating!

    • I know exactly how you feel! Thanks for the feedback, I will definitely start working on something like that!! Thanks Pia =)

  • PAM

    I am lucky..I work in an insurance office(crop insurance only) so I pretty much wear what I want. So it’s jeans and tops..tennis shoes(in summer, shorts and tank tops)..hair up in a ponytail if I want..I usually don’t wear makeup either..we rarely see any farmers..it’s all done over the phone or through the mail or online.

    • Jeans? Ponytail? AND Gymshoes? That sounds amazing, Pam!!

  • Meghan Kearney

    What a great topic! I am currently struggling with upping my professional wardrobe. My road blocks seem to be “ease of corralling toddler in the AM and surviving drop off” to “construction site appropriate” since 2-3 days a week I’ll transition from office client meetings to muddy construction sites… I’m always interested in others road blocks and how they overcome them.

    • Wow, those are some very real “road blocks”! From corralling a toddler to the construction site then to the office, talk about super woman!! You go girl!

  • Trang

    Man, I wish I could wear workout clothes (aka athleisure) to work daily! It is the most comfortable style for me. Monday-Thursday, I wear mostly skinny pants and a cotton shirt or sweater; very simple looking. Fridays are jeans and t-shirt day! I don’t even sport makeup anymore either because I come straight from the gym and shower there. I can’t be bothered to provide myself time to put on makeup. I work in a very small office and hardly anyone is there most days. I’m also the only woman in the office so it makes it much easier not to have to put on my ‘show’ face. The men I work with definitely don’t care about that sort of thing. I sit mostly throughout the day taking phone calls and working on the computer, but I also want to be comfortable. I was actually telling my husband that I needed new work pants (aka, approval to spend $ on more clothes) because the ones I have are a few years old and they are either stretched or have stains on them. I can’t wait for your new series on this topic!

    • The struggle is real, isn’t it Trang!! So happy to hear we’re not the only ones having a hard time!!