One dress, three looks

I was at the gym recently talking to a friend who had just cleaned out her closet and was frustrated by how many dresses she had. She said she wished that she had some more practical clothes for her daily life. Since I almost always try to dress for the day no matter what my plans are, I encouraged her to wear them anyway!

I’m not sure she was convinced. And to be honest, when I got home, I took a good hard look at my closet and realized I have been neglecting many of my own dresses that I normally consider too dressy for day to day wear. I have so many cute things that I pass over for jeans and leggings. I was actually kind of sad when I thought about it because truly, I am a dress girl. I much prefer them and while I do have several knit versions I keep in rotation, I just haven’t considered some of the dressier ones as practical for my “lately” kind of life.

I think this is a common wardrobe challenge, particularly for stay at home moms. But in the last few years, I’ve challenged myself to wear my “dressy” clothes for the average day. It’s easy enough to take what you might normally consider a going out top or dress and make it work for your day time activities.

To prove this I’m using a very basic, but cocktail approved dress that I bought recently for a wedding and styling it three different ways. Below you can see how I originally wore it, with simple jewelry and some open toe heels.


Living in Maine, I knew that I wanted to show a layered look and my first thought was to grab a long, draped cardigan. And while that is definitely a great option, how fun is it when I add this cute pink vest and navy over the knee boots? I would totally wear this look to run errands. I love the pink and navy combo, but a cream or tan vest would work great too. This was definitely my favorite look of the day.


Finally, the most casual version involved a blanket scarf with a bold pop of color and matching hat. I wore booties but I think it would have looked great with my brown Frye boots too. Super simple and easy to throw together.


A few things to remember. Make sure the base (the dress) is a simple shape, with clean lines. Use your accessories and/or makeup to make the statement! I’ve attached a few different dresses for inspiration below but chances are you have at least one basic dress in black or another neutral that you could easily rework to give that dress a little more life. I know when I looked in my closet I was excited to see several dresses that haven’t gotten much attention lately that would definitely work with a more casual vibe. Shop your closet – you might be surprised that by what you find!


cowl neck dress // swing sweater dress // pleated ponte dress // crepe shift dress

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