Gwen's Wardrobe Tweak: Part One (Shopping the Closet)

My dear friend Gwen recently finished graduate school and got a brand new teaching job at a local middle school. She is a very passionate teacher and has been working in schools as an assistant for three years already.

But as head of the classroom, she felt like her wardrobe needed a little tweaking. She needed a look that was comfortable (teachers do a lot of squatting to be at eye level with students seated at desks) and unpretentious (Hawaii is the land of anything goes Aloha wear). But she also wanted clothes that would help her own her authority so that her students and co-workers would take her seriously.

When she asked for my ideas, I couldn't wait to get started. Gwen is gorgeous and always looks super cute- remember how she inspired my hunt for boat shoes? This was a great project because it was just about aligning her clothes and appearance with her new situation and her evolving self. No overhauling going on here. Just tweaking.

The first thing we did was go through her closet. Gwen didn't have a ton of stuff- she is diligent about sending things out the door when they no longer work for her. However, she did have a lot of shirts hiding folded in drawers, and the shoe situation needed to be addressed. If you can't see what you have, you won't wear it. She also tended towards jeans and a tee when she wasn't sure what to put on.

First, we went through the closet and pulled out all her favorite pieces so she could show me what she loved and the sort of look she wanted to create. We discovered that she is drawn to cheerful, feminine prints, vintage inspired looks and color.

Then we went through all the rest. We pulled pieces that she liked but wasn't sure how to wear and put them in a "to figure out" pile. She got rid of things that didn't fit with her new vision for her wardrobe, felt dated or were damaged.

Getting rid of what doesn't work right now is the most important step in being well dressed. It keeps frumpy, ill fitting things from even being an option. Instead, you have a closet full of things you look and feel great in. It's much harder to go wrong that way. Gwen is ruthless about this. Here is the pile to prove it:

Then we began experimenting with creating looks. This is the part that I think many people just don't do. They throw something on in five minutes and decide that's as good as it can get.

If you want to be well dressed, you have to take the time to do it well. I completely understand that mornings are often rushed and frantic. It's not the time to be pulling things on and off because they don't work. Gwen told me she often dresses in the dark to avoid disturbing her husband. This is exactly why we took the time to create looks ahead of time, so the mornings will be smoother and she'll know she's leaving the house looking smashing.

Here we paired a plain white tank, a ruffled top and a pair of cargo pants with her famous boat shoes. I think the result is polished but casual and fun.

Gwen also segregated her clothes into "work" and "play". We discovered that many of the things she thought of as play clothes could go to work and vice versa. Here we put a pair of flamingo printed Vans with a striped polo. I love how the dark green cargos work as a neutral but add a little flare. Don't forget that the secret to mixing pattern is to vary the scale of the pattern.

This top is a favorite of Gwen's that she didn't wear as much as she wanted to. We paired it with some cropped white trousers and a stacked wedge shoe. I love this look!

Then we added a pretty printed tank and a brown structured jacket. Flip the cuffs and voila- she's a teacher! Don't forget to be open minded. Gwen said "I never would have put this together, but I never would have thought I could look this good in my own clothes!" Remember, we hadn't even bought one garment yet! These were all great things she already had.

The brown jacket works with almost everything Gwen owns- and adds a dash of professionalism. Here, she added a pretty rhinestone pin that had been hidden in her jewelery box for ages. The dark wash denim is also very grown up.

Here is her closet after day one. We got the shoes sorted into pairs, put her accessories into cubbies she can reach easily and hung her tops all in one place. Swimsuits were put in a bin so they are easy to grab from the top shelf when she needs them.

We also made sure to hang her scarves and belts on the wall at eye level so she can see them and will be encouraged to wear them more often. Next, we made a shopping list and hit the racks! I can't wait to share Day Two with you!

What are your suggestions for keeping your look fresh and fun? How do you organize your closet?