Welcome to Rules To Live By, where CULTURED asks sartorial voices—renegades, visionaries, and annotators—to unpack their style DNA and share the edicts they follow (and break) in the absurd game of life.

In 10th grade, Rachel Tashjian wrote a short story about a woman going on a blind date. When her protagonist showed up, the guy was wearing Tevas, so she left. Looking back, the New York-based writer and fashion critic stands by her work, but concedes that there are people out there who can pull off just about anything.

The voice behind the beloved—and exclusive—"Opulent Tips" newsletter credits her parents with her opinionated yet good-natured approach to dressing. Die-hard clotheshorses with an affection for Ralph Lauren, they taught her that shopping doesn’t have to mean buying, and that bold experimentation is rewarded—even when it borders on ludicrous. Tashjian describes her present style era as “luxury bizarro,” citing brands like Loewe, the Row, and Alaïa, which, she says, produce strange and exquisite garments that have “a sense of connoisseurship to them.”

Tashjian joined the Washington Post as a fashion writer in April, and five months later, the paper has announced the relaunch and expansion of its Style section, where the writer will be contributing tentpole features and content for the new Style Memo newsletter. As her work life has shifted, so too have Tashjian's vestimentary needs. She’s been working remotely, and mostly mulls over what to wear on walks with her dog, Ritz. You can find her in an assemblage of loose linens, silks, cottons, and, more often than not, an outré hat, hitting the New York streets with her canine companion.

Rachel Tashjian’s Rules to Live By:

1. Always have a cocktail dress in taffeta or nylon (think windbreaker material!) or a wool and silk blend, in the crispest and most dangerous black you can find. You can ball it up like dirty laundry in your suitcase or closet and shake it out for emergencies and languorous events alike. 

2. Never wear a logo or words on your T-shirt or sweatshirt, unless you are friends with the person who made it. 

3. Always ask more questions than you answer. A curious and gracious person is a chic person! Bonus: You’ll have all the best gossip, which will make you powerful and, more importantly, a desirable guest. 

4. Always watch at least four movies, read at least three books, and go to at least two museum shows a month. Your outfits will be better, your accessorizing more attentive, and your weekends more visually extravagant.

5. Never hesitate to ignore mediocrity. 

6. Never forget to develop an unhealthy obsession with a single designer, refuse to wear anything but their clothes for several years, enmesh your entire identity with the symbolism and semantics of their runway output, and then abruptly change your mind and move onto something else.

7. Always dress your table, living room, and bedroom as meticulously as you attire yourself. Create the You Extended Universe—insist on personalizing your mentally sprawling domain. 

For other fashionable people's rules to live by, check out our interviews with Kimberly Drew, Gia Kuan, and Emmanuel Olunkwa.