The time my mother picked out my outfit

Seven winters ago my husband asked me to marry him on a cold, snowy Chicago afternoon.  We were standing on the DuSable bridge, freezing, watching the heavy snowflakes fall into the Chicago River.

It was magical, I said yes, and now we are living happily ever after.  

There’s one part of my engagement that stands out almost as much as the magical proposal.

Karl had planned a weekend of activities with family and asked my mother to pack for the weekend, as everything was a surprise to me.  

At the time I was in graduate school in Colorado so we were only home for a short time. In an attempt to make the most of this trip, our families planned to end the weekend with a huge surprise engagement party.  

I’m getting to the part that still haunts me…

When I got back to the hotel to change out of my snowy clothes and get ready for the post engagement dinner I got a glimpse at what my mother had packed me.  

First I saw pants. I have a strong disdain for pants. I much prefer dresses. I don’t like things tight on my belly and I have an extremely short waist (Which anyone who saw me pregnant and thought I was having triplets can attest to.)

Next, I saw a halter blouse and no strapless bra- hmmm?

Lastly, I saw a cropped Tory Burch sweater that I typically wore when I taught math to a bunch of students who “wanted a job in fashion” and hated my very existence for making them problem solve. Basically, the sweater didn’t hold good vibes for me.  

First, I naturally got angry at Karl (poor husbands) and then my mom. I sent her a text that said “what were you thinking?!”

I put my coat back on, grabbed my purse and headed to Bloomingdales on a mission to not hate what I wearing on my engagement night.  

Bloomingdales had NOTHING and we were already running late for our dinner reservations. I pouted and cried and I tried on a bunch of dresses in a rush.

Long, painful story short I ended up wearing the heinous outfit my mother sent with me.  

At dinner a woman overheard that we had just gotten engaged and she turned to me and said “you don’t look very happy” to which I replied “Thank you.”  In my head I said “would you look happy if you were wearing pants at your engagement dinner?”

The same exact scenario happened when we arrived at my parent’s house for our surprise party. I walked into a room full of guests and went right upstairs to change my clothes with shaking hands and tears streaming down my face.  

As ridiculous that it is, and I understand that it’s ridiculous, this situation scarred me. I started shopping for event outfits months in advance, making sure I had multiple options for fear that I would have the same terrible experience. However, this solution didn’t help because I was making all of my purchases out of fear. I ended up with a closet full of crap that I didn’t really love but that acted as an insurance policy against embarrassment and event anxiety.  

Here’s what I know now and that I didn’t know then.

Even if I would have packed my clothes myself that same situation would have happened. It wasn’t my mother’s fault or Karl’s.  

I didn’t know what I wanted to wear or what I wanted to feel like in my clothing.

That is why searching at Bloomies didn’t do any good. I was in a store full of amazing dresses with stress pretty much erasing my price sensitivity and I still couldn’t find anything to wear.  

Nothing made me feel good because I had never tapped into what that would even feel like. Clothing had become so painful for me that it was a lose lose situation.  

The fix was actually incredibly simple.

I figured out what I need to feel like in my clothing to be excited for events.  I figured out what I need to look like to feel like myself so I’m open, receptive, social and loving.

It’s not a tangible discovery, but rather an emotional relief.  

This month as you partake in your most favorite activities take note of how good they make you feel. This is gold. This is how you want your clothing to make you feel.  

It’s possible and it’s life changing.


With love,