What do I wear when I’m not feeling experimental

let's get dressed.

I sometimes dress for hypothetical lives—many lives, fantasy lives. An artistic exercise I have given myself permission to pursue in this space: wear the heel for the photo knowing full well it won’t work for school drop-off. Or pin on the brooch knowing I’ll probably forget about it on my way to Publix.

Some experiments don’t stick. Which is fine. Others actually trickle into real life, eventually become part of our most intuitive sartorial decisions. One day we wear the heel for school drop-off, and we feel fabulous. The brooch becomes second-nature. And that’s the point of experimenting, whether “it works” or not: to expand our definition of “normal,” challenge our threshold of practicality, enhance our go-to recipes. Recalibrate our taste.

There are spaces that are not conducive to experimentation, though. Partly because experimentation can be distracting as it activates a kind of looping self-awareness. It makes us check in with our bodies multiple times throughout the day to see how the new idea feels, if it holds up, if it was a good idea to begin with. And in certain situations, say a job interview or a public speaking event, we don’t want to be self-scanning, revisiting, analyzing. We just want to rely on what has worked and focus on the task at hand. We want to feel as close as possible to the “true self” that has emerged from previous experiments, the “true self” we have constructed and grown familiar with.

I have such a situation coming up in less than a month. One in which I don’t want to impress anyone but rather show up as myself. Unbothered by what I am wearing so I can actually focus on the task I was assigned.

Unbothered, which is not the same as unintentional.

Which is why I went to my closet and pulled out the pieces that provide absolutely 0 second-guessing, those I have never even thought about selling or donating, those that I lose sleep over when they go missing.

That’s the first step: the closet curation that has happened for years/decades.

The second one is building the outfit. Over the years, I’ve found that the outfits that really work for me—i.e., the ones that seamlessly integrate with my body rather than interfere or distract me from living—tend to abide to the following non-abiding principles and answer the following questions:

1. Non-Negotiables:

Meaning if they are not present, I will probably not wear it:

1. Proportion: Is it playing with negative space? Is it creating fun lines and shapes? Is it cocooned? Is volume in the intended places? Does it wear me? If so, is it intentional?

2. Comfort: Can I breathe? Can I move? Can I walk? How safe does it make me feel? Does it allow me to blend in when I want to blend in? Does it allow me to stand out when I want to stand out?

2. Negotiables

Meaning if they are not present or they are not the main feature of the outfit, I might still wear it:

1. Texture: Unless it really ruins comfort or gestalt

2. Color: Unless it really doesn't work

For instance:

SYA Studio by Sylvia Andrade wool skirt I’ve had for ~10 years, White+Warren merino cashmere blend sweater, old Céline shoes (I love these Alaia), Timex leather strap watch, seashell pendant on a heirloom gold necklace.

The outfit above works for me in terms of proportion and comfort even though the texture and color combination are not groundbreaking (although the skirt details and accessories add texture and the red/black combo feels current thanks to Bottega, The Row, Phoebe Philo, etc.)

Bonus

How the outfit photographs: unless I’m feeling vain or I want the picture for posterity. For instance:

Old Rosie Assoulin dress (linked for reference) I’d wanted for years and finally found on TRR, just in time for my summer of caftans and swim shirts. Tory Burch pierced flats I had also wanted since they launched and finally scored on sale! last week.

This is the kind of outfit I’d wear to a wedding—and one I’d want registered in a photograph as an idealized version of my younger self to revisit in 30 years. It checks all the boxes: proportion, comfort, color (my daughter said it’s giving McDonald’s), texture (that subtle glaze on the Rosie dress is delicious), and how it moves, how it photographs. A 10/10 from me.

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So let’s go through more examples:

Non-Negotiable-based outfits:

Where proportion and comfort are the load-bearing walls of the outfit and color and texture are not the main protagonists but don’t ruin the whole thing either:

The Frankie Shop knit oversized top with Sya Studio skirt, and old Céline pumps (when they fall apart, I’m thinking they can be replaced by these from Le Monde Beryl, or these from Aeyde).

Same but with old Céline pumps in red (here in size 36)

Second-hand Tibi scarf top (there’s this flowy version at Massimo Dutti, this wool one, and I’m waiting for this Mulberry beauty to show-up somewhere), Levi’s 501s, Tory Burch flats

Tibi oversized vest from ~2017, Zara flare pants from ~2018, old Céline pumps but these from The Row and these Chanel have a similar effect.

Look obviously borrowed from you know where

Another borrowed look that always works for me: SYA studio skirt, second-hand Tibi plaid shirt, old Céline pumps.

Remix: with the White+Warren sweater and white old Céline shoes.

Another remix with Tibi’s wool skirt (here’s a size 6 on TRR)

COS wide-leg pants, Unisa ballerina flats (but I love these), White+ Warren sweater, Micah Lexier key tag I’m obviously hyperfixated with. I use my phone to shoot these photos so pretend there’s a phone in that case (mine is from Amazon but here is a second-hand Bottega technology relic)

Vintage Taxco brooch (keep scrolling for links) worn as a pendant, second-hand Tibi skirt I’ve had on my wishlist for years.

Negotiable-based outfits:

by color:

Green/khaki and blue: Jeff’s cashmere v-neck, second-hand Tibi pencil skirt, Tibi boots.

More blue and khaki: Tibi faux nappa boots with a vintage midi trench coat my grand-aunt wore in NY in the 70s and 80s (if you want a very expensive alternative, there’s this)

love an oversized sleeve.

Bright yellow and green/beige/khaki: Tibi circular sweater (here in green) and Tibi wool skirt.

Vintage modernist Taxco brooch worn as a pendant on a DIY necklace. Here is another great spiral Taxco brooch, here for half the price, and here for 95 dollars. Here is another Taxco with a similar spiral design, and OMG look at this one

Green and navy: COS denin shirt, Tibi brancusi jeans, Coach Hamptons bag, vintage Ferragamo pumps (similar here in size 7)

Cerise and Chartreuse and pastel yellow: Miguel Mesa Posada’s handmade vest, second-hand Soeur chartreuse shorts, Tory Burch flats.

Paula Mendoza earrings from ~ 2015.

by texture:

Knit and Satin: Lauren Manoogian pima cotton sweater (here’s a similar one in alpaca), Tibi satin pants, flower brooch (good one from Etsy)

Wool, denim, and satin: Same Tibi pants peeking out, in contrast with the wool material from the Tibi top. Jeans stolen from my dad (but look at these from Citizens of Humanity I ordered the other day), and the Tory Burch flats I won’t take off.

Lace and nylon: my grandmother’s chalina (an experiment that trickled down to real life for me) worn over a Ramosport raincoat (here is a fun orange one also by Ramosport), and COS bermuda.

Wool and denim: Colombian wool ruana and denim

Secured with a vintage 80’s cabochon chain fringe brooch (please admire this preciousness, and this other preciousness)

Speaking of texture: Miguel Mesa Posada’s vest (look at his MoMA entry, and his latest artwork at Casas Riegner), Tibi satin pants, Tory Burch flats.

Top is a sash belt from a Rosie Assoulin dress worn as a top.

Miguel Mesa Posada vest, Chanel rouge 148 but I also love Mac Habanero (discontinued so try Lady Danger)

Hope this helps you, or feels so repulsive you completely rebel against it.

That’s cool too.

Laura🐬