How to dress with thought.

Of all the things that qualify as overrated, thinking is not one of them. I’m a big fan of it. It’s why I don’t tweet. There’s very little I’ve said spontaneously that wasn’t followed with a pause or a question mark, begging for more context. Think of your thoughts like a ball of dough, they need to be kneaded, and sometimes set aside to sit until they take shape. When they don’t fully rise, you find you were missing a key ingredient, lacking the needed elements to create a fully formed loaf.

Both good and bad sentiments that roll right off the tongue onto the finger tips are given gravitas in black and white. Doubling down on being human means recognizing we can be many things at once, and if you live in the grey like I do, then a wardrobe or outfits that speak in absolutes suffocates your personal style. It’s frustrating that there are two sets of fashion sentiments you find everywhere - from headlines, to Reels: “the last thing I want to think about is getting dressed in the morning” OR it’s opposite “bring joy into your closet, play with your fashion toys.” A thoughtless (albeit stylish) uniform or an unbridled Emily in Paris approach does not describe how I view getting dressed. But to subscribe to neither does not suggest I embrace the opposites of each. There’s a third option, and it’s to be aware of the choices you make, what feelings they conjure, and how they impact the greater whole of your personal style. As you find yourself doing this more and more, pausing, reflecting, thinking - it becomes easier. Not becomes it becomes a rote task, but rather:

• you become better at recognizing when and why something feels off

• you’ve experience in what will fix the problem for you

• you’ll have access to better tools in your closet as your found knowledge helps you buy with more success

In praise of closet thinking, I’m going to take you through my thought process dressing for the U.S. Open. I find my points are always made best with visuals. This isn’t a tutorial on dressing for tennis tournaments, this is about thinking how to think. And that’s good. Let’s go.

The Day Match

The closet components. I’ll show you what was in my closet, what I tried, what worked, what didn’t and importantly why.

What: The Core Pieces

Why: the colors felt right for day, optimistic but interesting. The ring 3 color of the skirt grounded the blue of the tee. While I love all the blues and whites, it felt too preppy. The ring 3 brown let me embrace the moment without the country club cos play. The skirt here is super light weight sporty nylon, it’s going to work for any temperature and I can spill anything on it and it’s balancing out the worn in McEnroe tee with a dose of refinement and femininity. PEOPLE - these sport fabrications are great here, having them in tailored options makes them perfection for these types of events.

What: The Add Ons

Why:

Watch - The accessory I chose to focus on was the watch - the leather felt a little too refined, and I love my white rubbery sporty one but it felt too literal with the vintage tee I found I wanted the contrast and strength my big metal band watch offered.

Sunglasses - I love my Phoebe Philos, but they feel too affected for a day match and too much of a departure from the ease of the tee. And the true sport sunglasses feel to literal - unless I’m waterskiing or actually playing tennis, these tend to take things too far in the sport direction - with the tee so casual I craved something a bit more in between. I’m wearing my Oliver Peoples here because that’s exactly the purpose they serve. Sporty - enough, modern - enough. Refined, no doubt.

Shoes - a flat was my only consideration here, obviously. I started first with the dark brown sandal, but it’s a beautiful day and I wanted something a bit brighter - the color felt like too obvious of a choice with the brown skirt and muted baby blue tee. I tried the white Seth Sneaker, and I was a fan, but it made me crave to change my shirt and level up there a bit but I was committed to the McEnroe tee. The red sandal felt just right - the sporty laces, the ring 4 color pop, refined but not overly so.

Layer Piece - even at a big outdoor event, you’re moving between climates even if it’s just the subway ride to the stadium. The navy Sweater with the brown skirt just made it more of an outfit somehow, and lost the summer fun - if I had on a white shirt I might have felt differently but here, it brought me down. I thought a denim shirt would add interesting texture, but it made me feel a little too collegiate and a bit too bulky for the heat. The white long sleeve cotton sweater did the trick - even just a white long sleeve tee would have worked - anything that could be wrapped at the neck later on and still tied at the waist with drape was what I needed.

Hat - ok, first I am a baseball cap wearer - so this was a no brainer for me. But if I possessed these other hats, I wouldn’t have worn them. Wear that Fedora at the Open and you’ll end up directing guests to the bathroom locales - this is staff uniform. And I think we all know my opinions on big floppy straw hats. Yes, I know they are functional, but it is why I load up on 50 SPF. I’m strongly opinioned here, because this hat conveys a very specific style. AND IF IT IS NOT YOUR STYLE, then you will never feel like yourself in it - and that sucks. If it is your vibe, march on proudly. But if it’s not, grab the sunscreen and move on.

Day Match Option 2:

Ok, I love challenging myself to “do style” but make it “incredibly appropriate.” I’m going to lean in to fashion a bit more here, but it will be a bit of dance getting dressed stepping in and out of looks till the balance is just right. I’ve got this longer men’s vintage BORG FILA shirt. It’s quite masculine in shape - the collar, the colors, the clean lines make it so. If I pair it with the Shirred skirt the balance is just right. The blue and whites feel spot on for the OPEN, but maybe a little TOO spot on, so using green as my layering piece gives good friction. I’m going to wear the sneakers here, coupled with the sporty top and shoe, the Phoebe Philo sunnies are going to be just right. The baseball cap says sport, but the Completed Works earrings tilt the scale and keep everything in check. The rich Watch completes the picture for me.

All the boxes are checked: SPORT, FEMININE, SUPER CLASSIC, SHARP AND MODERN, FRIVOLOUS, HAPPY SUMMER COLOR. Balanced.

The Night Match:

It’s dark out and I’m leaning in to fashion a bit more- but this is a tennis match and I never want to forget that. Showing up ready for a party, even if you’re in the players box, feels off. Not because it’s a bad look - you just literally feel like you’re in the wrong space mentally. I hate that feeling, but I also want to make sure I show up in my personal style.

The black tennis Sweater here may seem obvious, and it is, and I embrace it. We designed this sweater for the collection because I love tennis and love the idea of a traditional tennis sweater, but every option I’ve ever found was always too literal. Not right, not ironic. For this knit, Traci and I worked hard to make sure it had the references we craved without the literalness. Job done. Mixing it with a black sporty nylon Skirt makes it evening, but clearly just right for the moment. The silver Loafer is fun, but hardly ridiculous. For the Watch, leaning to a heavier sport vibe kept the black fit and the silver shoes in check. I topped everything off with gold Hoops - when I tried on the pearls here it felt a bit much with the designed sweater. The simplicity of the gold jewelry in contrast to the silver shoes was all the friction I needed. And it’s night time, so I’m not the asshole in the stands wearing glasses. Ok?

Listen, many of you are at different stages of applying critical thinking in your closet. If you’re just starting out, you may be avidly taking notes here. If you’ve been with me for a while, you’re just nodding and this is reading more like good recipe options that you know how to recreate for yourself with the wholly different ingredients you have at home.

I leave you with one thought. Thinking is good, and sharpening these skills in your closet helps build muscle memory you’ll apply to other facets of your life. Ok?