Spring Wardrobe Challenge Outfit #2 – Taking Fashion Risk

This series is part of the10X10 Spring Challenge. For more information on what it is and how it works, click here.

I’m not the biggest fan of dresses or skirts. I wear them in the summer, but pretty much steer clear of them in the colder months. I have a handful of reasons for not loving them but the three reasons that stand out the most are:

1. Finding a comfortable shoe that is stylish. I seriously don’t have a single pair of shoes that don’t bother my feet! I primarily stick to comfort shoes since I have tendonitis in my big toe. I wear something cute for photo shoots, but in real life it’s riding boots and Hunters.
2. I don’t like stuff around my waist. My stomach is the widest part of my body, so wearing a skirt or a structured dress is not very comfortable. I only wear them when it’s an absolute must or in the summer when it’s warm. I usually have to talk myself up quite a bit to wear a dress. Once I do, I enjoy them, and by the end of summer it does start to feel like second nature.
3. I hate looking stuffy like I’m going to church or a desk job. I feel like everyone else looks so cool and stylish when they wear dresses and skirts, but not me! See my attempts HERE HERE and HERE. These turned out pretty good, but I feel like the black tights might have made me look a little too dressy. It also helps that all of these dresses are from J. Jill and are knit so they are very forgiving! A knit dress is also more casual, which is more me.

Taking Fashion Risk

Let’s get to the point of today’s post – trying something new and taking a fashion risk! Even though it was outside of my comfort zone, I styled this dress as a skirt and look how good it turned out. 🙂

What I like about this look:

1. The dress is super comfortable and stretchy, a great length, and non-constricting. You probably wouldn’t have guessed that it is color-blocked?! Visit the link to see the entire dress. It’s ideal for a capsule wardrobe, as it’s extremely versatile. I know I’ll wear this dress through summer and again in the fall with tights.
2. The sweater is adorable! I am obsessed with the ruffle collar. Isn’t it the sweetest?! It also comes in three colors so I would suggest adding at least one of them to your wishlist. I know the pink color is going to be super popular.
3. It’s versatile as mentioned previously. I’m able to go bare leg or wear tights and still be comfortable. I love how I was able to make this spring dress more transitional and wear it with my winter booties.

Other notables…

The kitty bag, keeps things fresh and care-free. While the necklace is the perfect final touch. I’m also wearing a new lip color, Urban Decay 1993, which I would categorize as a nude brown. I really like the color for everyday; it’s a little dark in photoshoots, but otherwise has great staying power.

I will definitely be wearing this look for as long as the season lets me, and will try my best to continue to take fashion risks, even small ones!

Have any tips for dressing down a skirt or dress? Share in the comments.

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Dress: J. Jill c/o | Sweater: J.Crew | Necklace: Lace & Pearls Jewelry | Purse: Ted Baker (similar) | Lipstick: Urban Decay 1993 c/o

*c/o: courtesy of or gifted.

📷: Genelyn Jaye Photography