growing a minimalist wardrobe: dressing up.

Last week some of very closest friends in the world gathered together to celebrate the wedding of one of our dearests.

More suprising than the fact that all of us are still friends, is the fact that it turns out that you can gather together a group of women who’ve been friends for upwards of twenty-five years and the conversation that is most heated is whether it’s ever appropriate to wear stockings with peep-toe shoes. This isn’t meant to be a sexist slight. And rest assured the conversation also covered deep thoughts on Adnan’s innocence and maternal health in India. But the fact that the lot of us were at once stymied by and impassioned about hosiery begins to suggest that even thirty years in, playing dress up can be cause for consternation.

Without naming any names, here are just a few of the deep thoughts that surfaced in this past week’s conversations about dressing up:

“Is this dressy enough?”
“Can you still see my bra straps?”
“Is this too flashy?”
“I think I went too Kim Kardashian.”
“Do you have those nipple band-aid things?”
“Can I nurse in this?”
“Have you ever worn Spanx?”
“Who the hell named them that anyway?”
“Can you wear Spanx when you’re pregnant?”
“Do my shoes dress this up too much?”
“Do my shoes dress this down too much?”
“My mom suggested that I just wear a black bra and ‘go funky.’”
“I thought you said you were wearing pants.”
I don’t think that this particular group of women is especially dress-up challenged. I think that playing dress up is just hard. For me, a dress for a special occassion feels inherently at odds with my own minimalist wardrobe. While I own a few things that can be dressed up or dressed down, most of what I have allows me to look neat and clean most of the time, but not dressed up per se. By definition, a truly dress-up occasion is something of an outlier. And for a wedding, or any of the other fancy gatherings where I might find myself at this time of year, my dressier take on jeans and a t-shirt approach doesn’t quite work.

When I find myself with somewhere truly fancy to attend, I admit that I tend to lose my nerve. I buy a dress or borrow a dress that doesn’t feel remotely like me. Inevitably I do a last-minute dash to pick up stockings or beg for and borrow a bra that will work. I hem and haw about shoes. I go sans coat rather than worry about finding one that will work. At the end of the night, the biggest relief is just being able to put on my pajamas.

After spending so much time writing about my minimalist wardrobe here, I decided that even if I couldn’t escape every element of the dress-up crisis, this time I would at least choose a dress that felt decidedly like me. After eyeing it for weeks, I decided on this beautifully draped velvet dress made by Elizabeth Suzann. The wide hem and low-v reminded me of my own wedding dress, just made shorter and jauntier and cut from sumptuous velvet instead of cotton. It wasn’t a magical dress—I still had to borrow the right underthings and hem and haw about stockings or no—but it came pretty close. It’s a dress that actually can be dressed up or down. Paired with slim black slacks and a simple necklace, it will be just right for a low-key New Years Eve celebration. Paired with a vintage crystal necklace and a pair of satin heels that I unearthed for the occassion, it was every bit formal enough for a fancy winter wedding. Best of all, it was a dress to feel good in. Comfortable and elegant are two words that don’t get paired often enough, but this dress delivered and then some.

Specifics about the dress that I chose, aside, if there’s a dress-up philosophy that I most want to cultivate it’s that one: choosing dresses that are at once elegant and comfortable and that I won’t hesitate to reach for again and again. Now I just need to finally be a grown up and stop borrowing strapless bras from my mom.

And what about all of you? Am I the only one stymied by dressing up? Tips and tricks you have up your own sleeves warmly welcomed!

Disclosure: I decided to feature this beautiful dress by designer Elizabeth Suzann because it was a true delight to wear and a wonderful addition to my wardrobe. I purchased the dress myself, but I did receive a discounted rate. As always, I’m thrilled to support independent designers doing exceptional work.