It’s the year of transition at Black Sheep. Our new mission has influenced our focus on everything, including other aspects of professional life—particularly our wardrobes. With piles of trendy pieces, staple blazers and thrift store finds, it can be a nightmare figuring out exactly what to wear to the office every day. Thankfully, we have friends like Jenny Schlief Morgan of Settlement Goods and Design to set us straight and help us sort out our closets.


We sat down with Jenny to pick her brain on how to look polished, professional and personal in our work wardrobes. And thank goodness we did, because we’ve got cleaner closets and a whole new LBSD (Little Black Sheep Dress) to show the world. You’ll want to heed her advice so you can make a lasting impression on clients, co-workers and new contacts.

1. We’ve been caught a few times mixing our play clothes with our day clothes. Do we need a separate work wardrobe? Are there essential items we need to flesh out that part of our closet?

It’s totally ok to mix work and play clothes, but you need to understand which outfit is appropriate for which situation. What I recommend for people who have very busy lives is to separate your closet into areas. The best way to describe it is to put work wear closest to where you enter your closet, casual work wear after that and casual weekend/evening wear in the back. The reason for this that when you are struggling to get out of the house each morning, you’ll have the most appropriate things front and center, making it much easier to find them.

2. When we step into our closets, we’re faced with the dilemma of choosing the perfect outfit to transition us from day to night. Do you have some tips on how we can do this flawlessly?

Great ways to take your look from day to night are accessories and footwear. A sparkly necklace, a pair of black patent pumps and a matching clutch thrown in your workbag can easily transition your look from the office to an evening work event. And, luckily, you can stow them in your car or under your desk to put with just about anything.

3. Working in a creative environment, it’s easy to let our imaginations get to the best of us in our fashion decisions. What are some ways we fuse creativity with professional attire?

The easiest way to put creativity into a work wardrobe is to stick to classic silhouettes in interesting colors. You can also show your personality with accessories and footwear—just remember to keep it simple. What I like to do for clients is start Pinterest boards for work-look inspiration and talk about how we can effectively fuse creativity with corporate.

4. Our closets are chock-full of colors and cuts from last season. What can we do to update and stay on trend without breaking the budget?

Buy one piece that represents a current trend. Then, supplement that piece with accessories. Accessories are a great way to update your look without spending a bundle. My shop, Settlement Goods, is a great place to go for jewelry and fashion staples that play well with existing pieces, but there are other great boutiques in town that offer unique options. Myth + Symbol is a great place to find modern dresses and tops, and Saint Cloud is an awesome resource for jewelry and bags. For the boys, Manready Mercantile has great casual staples and The Class Room has great fashion pieces to keep you classy.

Another way to stretch your wardrobe is to have some go-to staples. A good blazer and a black pencil skirt with an updated fashion collar shirt will always be a hit. Boys: invest in a sport coat and get it tailored to you. It will treat you right for many years and you can go crazy with printed collared shirts to your heart’s desire!

5. We’ve had a crazy week of client meetings, after work happy hours and media interviews. What’s the best way for us to do casual Friday—without being too casual?

This is tough, because you do need to be prepared for clients and customers dropping in out of the blue. Things to stick to are skirts, tailored pants and solid colors for casual Friday work wear. Things to avoid are flip-flops, graphic tees and ripped or ill-fitting jeans. Jeans are always tricky in a work environment—better to sub black leggings with a tunic than come off as too casual. What I recommend to my clients is to take a picture of your outfit before heading to the office, if the picture makes you look sloppy, find something with more structure to elevate your look.

As you can see, it’s easy to incorporate your style, creativity and existing clothing into a cohesive work wardrobe. It’s all about feeling confident in what you’re wearing and being conscious of your situation. If you take Jenny’s tips to tame your wardrobe, you’ll be rockin’ the boardroom (or professional happy hour) in no time.