The thing is, I wear the same thing everyday
A few weeks ago, I went out dancing with my friends Claire and Krissy. I was wearing a beige tank top, white jeans, and shoes with a 3-inch stack heel/ankle strap and when Krissy saw me, she was like, “Every time I see you in person you’re wearing a version of this outfit, but when I see you in my inbox, you’re wearing all sorts of other stuff.”
It got me thinking about what I do when I get dressed for this newsletter vs. when I’m dressing for real life.
These (the newsletter) stories are usually born from a pattern I notice within the habits of my own daily rituals (habits such as: I keep wearing this hooded anorak or wow, I have really committed to socks with sandals), or a detail that catches my attention (wearing a headband or red tights actually brightens my mood) but the looks that I build from there are often conjured for the purpose of demonstration — more broad and adventurous stylistic interpretation of the manifold ways you can try a trend or a style than it is a lifelike approximation of what I wear every day.
Some of these demonstrations definitely make it into real life (wore the pink dress/fringe jacket/black knee highs look from last week’s letter on Thursday night) and in that way, the newsletter does serve as a sort of personal catalog of outfit ideas for when I can’t think of what to wear but for the most part, I really do look like this most days:
This denim shirt from Polo is the most tried and true approximation of the ultimate denim shirt if you are looking for something light enough to tuck into jeans easily and to move your arms without resistance. It layers easily under things and looks okay layered over stuff (the one thing I’ll say: if you’re planning to style it over pants as a sort of light jacket, it’s a bit flimsy for that — the hem curls up after a lot of wear). I bought it when I was pregnant as maternity clothes in a size M from the mens store at Macy’s (now there is this womens version, which I am curious about! The wash looks good). You can still find it for $90 here. The jeans are Rouje (the Germain style) and the sandals are from Rene Caovilla. Great sleeper brand to bookmark on TRR.
And the thing that becomes clear to me in demarcating what I wear all the time vs. what I wear when I’m styling is that even though I wear the same thing over and over, there are meaningful insights that inform how I put these looks together and why they seem interesting enough to return to so often.
Jewelry is a reliable sidekick and misunderstood as the main event.
Here you’ll notice two chunky gold chain bracelets: the shiny one is from Paco Rabanne, the other is Paola Sighinolfi (there’s also this one from Paola). On the other arm is a “tennis bracelet” made from crystals or something, by the French brand Daphine. The ring its paired with is from the jewelry company my 3 brothers’ run, which my dad started — Mark Henry Jewelry. I’ll get to how and why this all works below, with alternative recommendations
I use gold jewelry/precious beads (like pearls) or stones (like diamonds/white sapphires/crystals) to make utilitarian fabrics (denim, khaki, cotton twill) feel fancier.
Around my neck are Mikimoto pearls. They were my mom’s, and the string has stretched with age, which I actually like — I think it’s probably taken an 18-inch strand and turned it into one that is like 20 inches.
Rarely will I use these pieces, “precious” by most accounts in the context of an outfit that is already precious (see: silk dress, charmeuse skirt, or even something like this, unless it’s styled with a rigid/very casual and cool feeling t-shirt like this or this, which feels casual and cool because it’s a faded black stiff cotton in a shrunken fit that is also boxy enough to leave be) or too busy — be it by way of colors, patterns or unique textures.
Ever pass by someone on the street talking on the phone and wearing a pinky ring and bracelet? I find nothing shows the pieces off so well as lifting your arm and holding it up to your face, for whatever the reason! This pinky ring is from Retrouvai
If you’re looking to start somewhere, the most confident recommendation I can make is with the gold chain bracelet and pinky ring.
3 good pinky rings of good enough gold quality that you should never have to take them off, produced in 14k gold (as opposed to 18, which is the quality used more commonly with high jewelry). None exceed $1,000.
They inject an instant sense of cool into an outfit and do it insouciantly enough to look like they’ve always been there (as in, on you).
When I’m “occasion” dressing or in things that are more formal — a suit, fancy pants, a fine knit sweater, I’ll often opt for beads/more casual pieces.
These necklaces are Roxanne Assoulin (shorter one) and Blooming Dreamer. The little diamond earrings are actually a key component that creates a micro-contrast of fancy vs casual, playing into the broader contrast of the formal wool suit against the summer beads. I also just saw this necklace and am like, you know what? If you want your jewelry to be the whole outfit, by all means, wear this.
What also works: a pendant on a leather cord (like this from Deszo, or this from a new collab between Lingua Franca and John Hardy — or you can make your own with cord from a trimming store [make sure its rounded cord!] and a pendant you already have), opals, something that could wrap 100 times around your wrist (I think it’s time to bring back the Hermes leather bracelet).
This kind of add is great if you are trying to toughen up or make more casual the outfit you’re wearing.
If I’m wearing something acutely simple and dark in color, I will add a strand of something light in color: coral (color is tricky, you want something soft and light as opposed to burnt; use this as a reference. As far as shape, I like a thick-ish disc like this) or as mentioned opals/something like them.
I’ve taken to Dorsey’s lab-grown necklaces too, which to me are best with a casual crew neck (sweater, sweatshirt, grey tee, etc.)
Those necklaces are good with a tank top too, which is actually its whole own science and opportunity for adventurous medley (bead pairings!). Will break down when high summer’s closer.
The last thing I’d say re: necklace is that if you wear more button-downs than crew necks or tanks, you’ll want the necklace to be something like ~16-18 inches long. This way the exposed neck/chest inside of the shirt won’t get cut off and shorten your decolletage in too high a spot.
So that’s where I’m at on a basic outfit and how to keep it refreshingly rewearable. Use your jewelry as a contrast, not a complement.
The center will hold if it is a belt
Meanwhile, here’s the outfit I described at the top per my convo with Krissy, the friend:
Your task order here is to think of the belt not as a contrast or complement but as the center of the look.
As mentioned, I wore this to go dancing and now that we’re here it seems clear to me that 10/10 this outfit was not my original idea…
You would be surprised at how much you can do with the right kind of belt. It eliminates the need to spruce up your basics with jewelry, gives more leeway to your footwear choices (you go for the thing that’s simpler/has less hardware which is often also the more comfortable pair) and you can wear it (the belt) the traditional way as shown above or get weird with it within the same or a similar outfit by, for example, styling it over your shirt and jeans.
Though this belt is much simpler, the shade of red is a daring enough pop of something unexpected to carry the rest of the looks’ weight. The other shoes are better for the purpose of dancing though.
Because they have an ankle strap. These in partic are from resort 2015. It took me until last Fall to find them
I have a clear preference for this belt from Khaite which has so much going on it seems like it’s almost too much but I think that’s exactly the balance you want to strike — it feels like almost too much, so the rest of your look doesn’t have to do much.
Shoes, bags and jackets: an interchangeable feast
The last thing I do to accommodate my wearing the same thing over and over is treat my shoes/bag/jacket like an interchangeable feast. Example:
Here’s a pass at a simple outfit that doesn’t employ any denim: a plain white skirt and black t-shirt. You could wear it with flip flops during the day or with socks and brogues to go to work or with heels to spruce yourself up or:
Ready to rock! Let’s examine the difference in a scroll-by-scroll:
Exhibit A: young Jewish professional ready to give a presentation.
Exhibit B: mom on the loose! But like, only 2 blocks away from home.
The key ways they’re different is in that the first look is for an environment where social convention rules, so the same conventions are applied within the outfit: wear a light wool blazer with pointed toe slingbacks and you will look more professional.
You agree as opposed to contradict.
In the second variation, a personality jacket dripping with fringe in a rugged weighted suede contradicts the delicate satin mules, which are thrillingly exacerbated by the inclusion of sheer ankle socks and pulled together with one more satin item in the form of a pop-of-color-adding pouch.
And that’s it! That is the whole science. So there you have it: when you’re trying to figure out how to wear the same thing but feel different everyday, ask not what you can do for your accessories but they can do for you.