Building a Work Wardrobe from Scratch | On the Daily EXPRESS


Building a Work Wardrobe from Scratch

Earlier this year, I helped two women build a work wardrobe from scratch. They both work in the front office of a dental practice and their boss (my brother, but I'll just refer to him as The Boss in this post) offered to pay for a few new outfits for them as a thank you gift for their years of dedication. He asked me to help coordinate the process and function as a stylist. They all live in a small town with limited shopping options (no mall, just Wal-Mart), so they hoped my blogging gig and outside perspective could help them find different brands, styles and options to re-build their work wardrobes.

When I mentioned this project awhile back, a few of you were interested in learning more about the process so today I'll walk through the steps we took and give some of my thoughts on what I learned. I did this whole project remotely so we did not take before and after pictures, but I'll give as many other details and visuals as I can. I'll also share some of the exact items that ended up becoming new favorites for each of the ladies involved in case they help any of you build your own wardrobe.

Define Style Objectives
The first step in the process was to define the look we were trying to create. "Work wardrobe" can mean a lot of different things, so before I could shop or make suggestions, I needed to know more specifics about the visual goals for the Boss and Employees and make sure were all on the same page. I created a Workwear Pinterest Board and then had phone conversations with all parties to see which styles spoke to them and what things the women in particular would not be comfortable wearing. While I did want them to try some new things, I also know most women are aware of a few styles that just aren't going to flatter their bodies. I didn't want to waste time suggesting absolute no-go styles, e.g. pencil skirts for someone who already knows that an a-line is their best bet.

The photos in the graphic above are examples of outfits from my Pinterest Board that were fairly well received from all participants. The Boss didn't think it was necessary for them to wear anything as formal as blazers/jackets, but overall he liked pretty traditional work wear pieces (blouses, dress pants, dresses) and didn't have any objections to open-toed shoes. The Employees were open to trying most of these styles, with the exception of shoes. Comfort was a big concern for both of them, and after spending a lot of time looking at workwear outfits on Pinterest, I would estimate that 95% of outfits shown by bloggers feature uncomfortable-looking, impractical shoes. I have no doubt that's because they look the best, but for our purposes we agreed to look for more comfortable options that work beyond a blogger photo shoot.

Shop for Options
And now the fun part - shopping! I browsed a variety of retailers to put together some shopping options for each of the Employees: Express, Ann Taylor, LOFT, Nordstrom, Banana Republic and Zappos. I looked for pants in staple colors (black, charcoal, navy), blouses that could mix and match with the pants, plus two pairs of comfortable pumps in neutrals. For me personally, my nude and black pumps go with almost every "dressy" outfit in my wardrobe, so I started off with those colors.

Employee A
Employee A was interested in trying more skinny, ankle-pant styles, comfortable heels, and colorful pieces (except pink) so here are the first options we discussed. She likes wearing jewelry and was open to lots of options in that department.

Employee A selected 1, 3, 4, 8 and 11. The Banana Republic pants, black pumps, and necklace were a hit for her, but unfortunately both of the tops didn't work out (3 was too long, 4 was too boxy) so we went several more rounds of browse/buy/return until we got some tops that were keepers for her.

Employee B
Employee B wanted to make sure everything gave her a defined waist and helped flatter and balance her pear shape. She normally prefers bootcut pants but was open to trying some straighter leg options as shown below. She also prefers more simple, minimal jewelry

Employee B selected 1, 2, 5 and 6. These pants (#1) and this top (#2) worked out great, but we went back to the drawing board on the other items.

Next we moved on to dresses. I rounded up numerous options for both ladies to review.

Employee A chose #9, but ultimately it didn't fit her well so she returned and we shopped for other options. Employee B chose #7 and loved it, so it was great to get that item right on the first try!

Since several of the tops from the first round didn't work out, I sent over another round options from which both ladies made selections, and again we had some hits and misses. I won't go through all the back-and-forth steps in this post, but since there were a couple of items that worked out well in this batch I'll share those below.

The Portofino shirt (#1) ended up working for both ladies in different colors, and they both really liked this blazer (#6) as well (also in different colors for each person). Employee A loved the wrap top from Banana Republic (#4), and Employee B liked the V Neck blouse (#5) in white for layering under her navy blazer (#6 in Navy).  

Both women also ended up liking the Publicist Pants from Express, even though they had different preferences for the leg/ankle styling. The product description says they're designed "for curvier figures with a smaller waist & fuller hip & thigh." So if that describes you and you haven't had much luck with Editor or Columnist pants from Express, these might be a good option to try.

In case you're curious or using this post to help you build your own work wardrobe and budget, we ended up spending about $750 per person to build four complete outfits (one dress, three tops, two pants, and two pair of shoes that match all four looks). I took full advantage of sales and coupons to get the best prices (shopping as I would for myself!), so almost everything we ordered from Express and Banana Republic was purchased during a 40% off promotion. Part of this process took place over Easter weekend and I took full advantage of those sales. Shoes were the most expensive items since the quality, comfort lines don't tend to be budget friendly, and we spent $100-$150 per pair. 

Final Thoughts
This project was equal parts fun and challenging! As much as I enjoy shopping for myself, it's not as easy to make suggestions to strangers and hope it will suit their well as their boss's tastes! It took us over a month from the first planning calls to the final four outfits. We initially discussed doing this in person, but that would involve more complicated scheduling and travel costs.  And in my experience, there's a 90% chance that any given mall will not have the exact items you want in the exact size you need. So even if I had gone for a consult/shopping excursion in person, I think we would have ended up doing a lot online after the fact of the initial trip anyway. If it were a local contact I would probably want to meet once in person and have one in-person shopping trip focused mainly on shoes since that was the toughest piece for us. Then I would do the rest online as we did for this. But overall I don't regret doing it virtually in this long-distance situation.

As for working as a stylist, I shouldn't have been surprised at how time-consuming it was considering I do similar tasks in blogging...but I still was! Lots of browsing selections and creating visual options, plus phone calls and emails back and forth to get everything selected and ordered. Then following up to see what needs to be returned and where we need to go back to the drawing board. According to this article stylists make $25-$120 per hour depending on the ZIP code, and I can see how it's similar to something like an interior designer where you're paying for their time, experience, and guidance on a vision of a particular final result, whether it's for your home or apparel. I thought the rates were interesting to see since it's not your everyday service like a hair salon wash where you can easily make a few phone calls to find the going rate.

I hope this post answers some of your questions about the project and possibly even helps give you some work wardrobe ideas if you're in the market for those!

Linking up with: Rachelle | Carylee | Dawn | JoLynne
Intro graphic photo sources: 1. Source Unknown | 2. Express Stock Photo | 3. DVF Dress



  1. What an incredible experience and you did such a great job. I love how organized and thoughtful you were; it is difficult to style other women. The idea of the Pinterest board was a great one as well as asking them what they would absolutely not wear. I hear from a lot of women I know things like "oh I need you to come shop with me" but honestly when it comes right down to it they like my style on me but they aren't always ready to change up their own style too much.I think the way you handled things was perfect! Your brother sounds like a dream of a boss as well so winners all around! Thank you for sharing this experience!

    1. Thanks so much Kellyann! And's true. Lots of things I like on other people I don't necessarily like on myself! It's no easy task figuring out what someone else will like!

  2. This was a good post to read, so nice to see the process! I used some fun money for a Christmas present to splurge on a personal stylist post-baby once to do a wardrobe detox and it was fun, she had so many outfit ideas for pieces in my wardrobe that I hadn't thought of and while we didn't do the shopping part it was good to get an impartial option on pieces! :)

    Hope that you had a nice weekend :) We went out for dinner on Friday and I caught up with a blogging friend on Saturday so it was a good weekend here! :)

    Away From The Blue Blog

    1. Thanks Mica! How cool to use a stylist post-baby! And that's great that she was able to help you see things in your closet in a new way - sounds like it was worth the cost!

  3. I'm so glad you did a recap on this! I really enjoyed reading it and seeing how you went about it and the final selections!

  4. Trying to shop for other people remotely does sound like such a challenge, but I'm glad you were able to get pieces that will work for both women and help them have a work wardrobe they love wearing!

  5. That sounds like so much fun, but a lot of hard work too. I've gone shopping with good friends before, but never with anyone I didn't know--I think that would make it even harder. (Although maybe it would be easier to stay objective.) How nice of you and your brother both to do that--and I'm sure he loved being called "the boss" in this post :)

    1. Haha, he probably does. I seem to recall saying "you're not the boss of me" a loooot of time as a kid!

  6. Wow Gina, this is incredible! You did a fantastic job! I wouldn’t even know where to begin but your process seems so organized. Styling others is definitely much harder than styling yourself. Kudos to you for helping these women (and the boss!)

  7. What a cool experience and how nice of your brother to treat some of his employees to new outfits! I'm not surprised at how time consuming it was, but I really like the outfits you choose for them! I think it is so much harder to style someone else, but you did a great job!

    Nicole to the Nines

  8. Great post Gina and I'm sure a lot of ladies will find it helpful. You were so thoughtful in your thought process. (ha..a little repetitive) Spending someone else's money would be fun too. That's why I think I'd like being a decorator. LOL

  9. It's so awesome you got to do that, I'm sure it was challenging. Also this post is super helpful to anyone trying to build a work wardrobe.


  10. Nice!!! Glad you shared. Cool recap and behind the scenes look. “The Boss.” 😂


Thank you so much for taking the time to leave a comment! I sincerely appreciate each and every one and always do my best to answer questions promptly!