"Buy Less, Choose Well” has been a tenant of my business model from the beginning. If you aspire to simplify your life, clothing is a critical place to keep edited. While there are a wide variety of ways to maintain law and order in the closet, there is an important question I want to ask you…

How do you feel about repeat performers in the specialty dress category?

At the beginning of the year, I had an urge to celebrate dresses this summer. Although I didn’t wallow 2020 in sweatpants, I missed the balance and feel of putting on a great fitting dress. Treating my own closet as I would a client’s, I methodically covered my needs and identified the following criteria for what I planned on wearing in the upcoming months.

• • A black sundress (I ended up with two!)

• • Two “throw & go” styles in color

• • One lifestyle appropriate showstopper

Mind you, I had no idea what the summer was going to look like, but I imagined myself out and about in the ease of an effortless dress. With COVID restrictions lifting, I have a couple of opportunities that require something special. My edited list helped me determine a reasonable and diverse selection of dresses that can cover my needs and desires this season. It’s easy to get caught up in the moment and justify any number of reasons to keep adding dresses as invites fall into your calendar. But, a dress for each event does not necessarily bring value to your wardrobe nor leave you with having a better time. I’ve committed to one great dress to wear to any and all events this year. So far, the first is my son’s 2020 graduation, and the second is a good friend’s 50 birthday party in Connecticut, where I’ll be attending my first polo match. These are back-to-back weekends, and I plan on doing what many might find the unthinkable, depending on what side of the Millennium you were born. Seriously, when did it become taboo to double down on an outfit? Is it truly the curse of social media?

Tiffany Haddish is one of my style heroes. Not only is she side-splittingly hilarious, but she took an expensive Alexander McQueen dress and created more than a red carpet statement. In my opinion, she’s defined CPW and proved how it could work. Change the hair, change the audience, and value the investment of an amazing garment. If you are unfamiliar with Tiffany’s McQueen gown, take a look at the moments she amortized the layout and turned a taboo into what she likens to a brand.

“I wear it to the DMV. That’s how I get recognized. It’s how I get to the front of the line.” – Tiffany Haddish

Photo Credit: Brightside 

As the story goes, Tiffany Haddish bought this gown herself - it wasn’t borrowed or a contractual obligation - and equated the cost to more than a mortgage payment. After wearing it the first time to the premiere of “Girl’s Trip,” she decided to get some CPW and wore it when she hosted SNL. This is when I first became aware of her doubling down with McQueen (nice choice!).

“I feel like I should be able to wear what I want, when I want, however many times I want, as long as I Febreze it!” – Tiffany Haddish

Tiffany explained how much the McQueen gown cost in her monologue and how her team urged her not to wear it again in public… because it was taboo. This left an impression on me about our value system. Somewhere along the way, we became addicted to what’s next and new. We have been conditioned to not wear things on repeat - that doing so can be perceived as a sign of failure in that we don’t have the means to acquire more. But in reality, the value of a quality item should be appreciated because of the way it makes us feel every time we wear it. Ms. Haddish has now recounted that many major moments of recognition in her career were celebrated in that gown. The dress was eventually retired after her appearance on “My Next Guest Needs No Introduction with David Letterman.” She explained that as her career has become big, her body has become even bigger. Revisit her SNL monologue as she aspires to take this dress to her grave in a comedic riff that is quintessential Tiffany Haddish.

So, I challenge how we’ve been conditioned to imagine a “repeat” as taboo. If Tiffany Haddish can take one dress to five major moments, odds are you can too. Change your hair, your shoes, your bag, and your company, and I’m quite certain you can feel as special the second time around. I’ll be posting my “double down” dress on Instagram.

Other notable “wear it again” moments.

Anna Wintour via The Daily Mail

Helen Mirren via Brightside

Naomi Campbell via Brightside