Confessions from the Worst Dressed List


On Saturday night we went out for a birthday dinner where Jas ordered a dessert that was almost as big as she is.

For context, we had her put her hand up so you could see how big this chocolate cake really was.

What you don’t see in this photo is the rest of her outfit comprised of:

+ the black sparkly top + black leggings + knee high faux patent leather boots + AND a pair of denim shorts. Yes, denim shorts.

I told her that proper girls don’t dress like that in public to which she responded, “Well I do.”

Oh, and she also wore a crossover purse to complete the outfit.

The next day I recounted her outfit to her mother (who didn't go to dinner with us):


For only being seven years old she definitely has her own sense of style. And yes, I’m jealous of it.

There was a time when I had my own sense of style. My closet is full of printed skirts, colorful dresses, and high heels that haven’t been worn since…

...well since I started running. You know, because running and high heels don’t really go together.

After years of running before work, then hurrying to shower and get dressed to get to work on time I adopted a uniform of T-shirts, jeans and sneakers. And not even cute sneakers - old running shoes sneakers.

And now that I work from home, where I wear sweats all day, the jeans/T-shirt/sneakers look has become my version of getting “dressed up.”

I didn’t realize how bad it had gotten until last month when I was packing for two consecutive weeks of work travel. Shockingly I realized that I did not even have enough outfits to make it through one, let alone two weeks!

I knew that it was time to invest in some new “work clothes.” I started paying more attention to the style and fashion blogs that I follow, making mental notes of current trends.

I used this photo (that I absolutely adore) as a source of inspiration…


{Photo source}

I spent the past two weekends “school shopping” and I must say, it was an eye opening experience.

I learned that:

+ Digging through mushed together items in the Sale section is like a workout in and of itself...

+ Dressing rooms have blazing lights and no air circulation which makes you sweat and feel really gross especially when trying on silk tops, which seem to be all the rage right now...

+ Along with leather - bits and pieces of leather everywhere…

+ And I’m not really a leather person…

+ Nor am I built to wear skinny jeans…

After many stores and countless dressing rooms where I asked strangers, “how does this look on me?” (and wondered if I should really trust their opinions), I settled on a handful of core items (mostly from J Crew where I never shopped before) that I can build a decent wardrobe around.

Now to accessorize...