Archive - What Should I Wear?

The Summer Fun Issue

Anny Choi, Emily Sundberg, Colu Henry and Tammie Teclemariam on how to have the best summer

Jun 22 •

What Should I Wear?

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Talking shop with Melissa Ventosa Martin

The founder of Old Stone Trade on shopping IRL, Bob Dylan's closet and her quest for the perfect jeans.

Jun 10 •

What Should I Wear?

May 2025

To Mom, With Love

Our annual ode to mothers and their infinite wisdom, starting with Tory's mom, Reva

May 11 •

What Should I Wear?

April 2025

The Mother's Day Gift Guide

Sunday, May 11 is coming. Here, 49 gift ideas, organized by moms and their obsessions.

Apr 23 •

What Should I Wear?

Women at Work: Rose Chalailai Singh

Our final food entrepreneur is the ultra-chic Parisian chef who is a favorite of the art and fashion worlds.

Apr 6 •

What Should I Wear?

March 2025

Women at Work: Atef Boulaabi

Next in the series: the founder of SOS Chefs, the in-the-know source for spices and compelling ingredients beloved by New York City chefs and foodies.

Mar 30 •

What Should I Wear?

Women at Work: Paris Starn

The 'Playing with Food' writer is carving a singular path with projects that weave together her love of baking, art history and fashion.

Mar 23

Women at Work: Kerry Diamond

Introducing the Women at Work: Food Issue. First in the series, the woman at the center of of it all, the founder of Cherry Bombe.

Mar 9 •

What Should I Wear?

February 2025

11 Things We Loved from FW25

A magical Monday night at MoMA. Tory's twisted American sportswear had it all, must-have pants, skirt suits we want to wear now, plus Martha in the…

Feb 16 •

What Should I Wear?

January 2025

Story time with Sarah Hoover

The art-world insider on the benefits of complaining, the eternal chic of the Delia's catalog and her new memoir 'The Motherload.'

Jan 26 •

What Should I Wear?

December 2024

Giving. Receiving. Wearing.

Some of our favorite Substack writers, stylish friends and Tory share their holiday plans.

Dec 8, 2024

What should I gift?

Our 2024 gift guide, organized by the characters who may be in your life or whom you might simply find inspiring.

Dec 1, 2024 •

What Should I Wear?

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