Shop With: Sarah Shapiro, fashion buyer, retail insider, almost always in black.
What does she wish all of us knew about the business of shopping?
I / we talk a lot about shopping from gut. From the heart. About how we feel about the things that take our fancy, that pull at our heartstrings, memories and sense of self. But fashion and shopping are also: business.
Sarah Shapiro has spent her career in the business of retail (shopping as we like to call it!). She’s built brands, led merchandising teams, and launched more than a few things of her own. She’s worked internally at both heritage retailers and DTC startups.
Now she’s got a staring role as an expert retail correspondent with Lauren Sherman and the team at Line Sheet, after her industry-famous Retail Diary newsletter was acquired earlier this year by Line Sheet’s publisher Puck News (covered here by
). Her superpower? Tracking the who, what, and why behind what people buy and making you feel like a total insider in the process.Hi! Can you introduce yourself :)
Hi! I’m
, and I’m the retail correspondent on Puck’s Line Sheet.I wanted to be a fashion designer when I was in elementary school and that sent me down a path of being obsessed with fashion and retail. Reading every magazine I could get my hands on (in Virginia Beach there weren’t a lot of stores to channel check.)
I studied fashion design at Syracuse University and they had an amazing retail program, which is where I realized what I really love is merchandising and buying—using the right and left brain. A bit of 7th grade math skills mixed in with creativity around the products. That kicked off many internships and joining the Buying Training Program at Bloomingdale’s.
Since then I’ve been a buyer and led site merchandising for a few companies as well as started my own accessories lines. I moved to the Bay Area in 2011. I started a newsletter, Retail Diary, in 2019 using Mailchimp and then moved it over to
in 2023. It is where I wrote about all the things in the retail and fashion industry that I was thinking about and obsessing over.I needed a space to chat about retail like many people talk about sports.
In late 2024 I had the opportunity to join Puck. Lauren Sherman’s writing (and the whole team at Puck) really impressed me—I jumped at the chance to join Line Sheet.
What does shopping mean to you?
Such an interesting question. I’ve always thought of shopping alongside the work of retail. It’s an industry that I love because of the mix of business and the psychology behind personal choices. Even for myself I think of the consumer psychology behind shopping. What are people, including myself, willing to trade up or trade down in? Why do we want to acquire certain items? How we want to portray ourselves to others?
Has your relationship with shopping changed over time?
Yes. I found that once I was a buyer I became a lot more discerning. I knew what was coming out next and I always wanted the next thing versus what was currently on the floor. I’m also not an impulsive shopper. I usually have been thinking about an item for a long time and then finally take the plunge. I don’t want to buy anything that I think I will only wear for a season or a year. I want items that I will love forever. I don’t think I had that understanding when I was shopping in my 20s.
When/where/how do you shop for yourself?
I “shop” a lot but don’t often buy items. I love shopping with my mom or taking my daughter shopping but I know I frustrate others when I go into stores because I go into my own world. Taking everything in and making mental notes or actual notes on my phone to reference later.
I do go down rabbit holes when I shop online. I love looking at the new landing pages of sites like Mytheresa, NAP, Moda, Shopbop etc. and I know when they are each updated. I also love my “Obsessions” page on TRR and update that regularly. I “heart” a lot of stuff and when I’m ready to actually spend I’ll go back into my “hearts.” For TRR I usually have been hunting something for awhile and then when the right size/quality etc pops up I’ll hit buy now.
What are the last three things you actually bought?
1. I just returned from Mexico City on vacation with my husband. I bought myself two Chava Studio shirts. It’s a purchase I’ve been considering for a long time but since I’m petite (5ft 2) I didn’t know how they would fit me and wanted to try-on in person. Having Olivia fit me in-person was amazing. I could have walked out with three more shirts—I made notes for what I want next.
2. and 3. On the same trip I also bought my daughter a zippered pouch from a local artisan and a Mexico football (soccer) jersey for my son. He styles them so well!
‘Shopping’ has long been part of your professional, and personal, life. You’ve become incredibly well-known for your deep retail knowledge. How does it impact your relationship with shopping?
It’s funny, I’d compare it to that saying that Doctors make the worst patients. To be fair, I don’t think I’m a bad shopper. But I’m super curious and get really excited by new and innovative ideas. If you want to brainstorm retail strategy and concepts come chat with me. I love thinking about how to improve the experience or create special moments that the shopper will love. I also find that I’m really optimistic and get overly excited about retail in general. I think it is the best industry.
Tell me three items that are currently on your list to buy in the next 3 months?
1. I am taking tennis lessons again and I’d love a new tennis fit.
Shop Girl finds: OMG this dress, this tennis dress and Nike over here. But if you’re into a short combo, these are a winner.
I know it’s summer but I’m already excited for “back to school” shopping. Fall shopping is my favorite. It’s the best season to shop for items I love to wear (especially in the Bay Area) and I’m always so nostalgic for shopping at that time of year.
Item wise I could use a new blazer, a dress for a few events coming up and hopefully I’ll find something fun to obsess over – like a pair of shoes or a handbag.
What's the most unexpected item you've ever bought?
I’m not that unexpected!
Many of us are looking for more ‘intentional’ shopping moments these days. How does this sit with you?
Absolutely here for it! I equate this to being more thoughtful about what we are buying, what we need and how to go about it. It is one of the reasons why I love resale. If I don’t have an explicit desire to have an item fresh/brand new, then I’d rather buy resale.
I’ll debate myself and add that I also love shopping for entertainment and window shopping for pure enjoyment and exploration. It doesn’t mean we always have to buy something but we can also have fun, spontaneous moments with shopping.
Do you ever have any guilt around shopping?
Sure. Especially around spending money, but I tend to wear my pieces a lot. So after I’ve worn an item many times and see how much I enjoy it and how much use I get out of it, that guilt goes away.
What's the one item in your closet/home you can't live without?
Ballet flats. My favorite style of shoe, clothing, etc
And probably a black cashmere sweater—I wear one almost every day.
What’s the best shopping experience you’ve ever had?
Shopping with my mom and having fun days in NYC exploring our favorite stores and brands together.
What does it look like inside Sarah Shapiro’s closet?
98% black clothing. Items that look identical to my husband and kids. But I can tell the difference between each pair of black pants in detail. Organized like you would find in a store. What can I say, I like to merchandise.
Can you tell us about the product hunt? What’s involved when you’re hunting down something you really want to buy? Do you have a memorable story?
I’m Type A and a little OCD. So lots of lists, Pinterest, saving on Instagram—all the places (Hi Carted!) I’ll visit items online or in person multiple times before I purchase and start dreaming about how I will mix them in with what I already have.
The memorable finds are the ones I’ve been thinking about for awhile and then either a reason/event comes up to make the purchase, I find a good deal via resale or an in person opportunity—and I finally buy.
What makes you fall in love with a brand/product/item?
It feels both special and like something that fits in with everything else I have, but makes my older pieces feel all new and fresh.
What do you think the future of shopping looks like?
Omnichannel, tech enabled but with personal qualities. I think the tech side can improve the back-end but shopping should still be fun, personal and provide those moments of “wow” and passion.
Shopping will still be everything from shopping a single, small 400 square foot store that is appointment only, to in person to online shopping late at night.
What’s the #1 thing you wish shoppers (consumers) knew about the business of retail?
The the most important thing is understanding how pricing works and why products cost what they do. There is such a push and pull between shoppers saying they want quality, products made by people who are paid a fair wage (by brands who treat people ethically) but then seeing a lot of shopping behaviors don’t align with that.
Not knowing who they are, can you write a question for the next person I interview?
What do you wish you could change about the retail industry?
Rapid Five
1. What city do you call home?
Lafayette, CA but I also still consider NYC my home even though I haven’t lived there for a bit.
2. Favorite place to eat?
Not a specific place, but with friends or family —good company where the food is delicious and the conversation is flowing.
3. Favorite place to shop?
Walking the streets of NYC.
4. Favorite place to run/hike/pilates/yoga/dance/tennis
Locally I like to run or walk the Lafayette Reservoir. NYC I love running in Central Park. But you can usually find me in my garage using my Peloton treadmill or bike.
5. Favorite coffee (tea/matcha/milkshake)?
Diet Coke (I don’t drink coffee).
Honestly, I just saw Sarah's face and hit the heart before reading. Loved this so much, a huge congrats to Sarah and her retail greatness and a big yes to Diet Coke and the Bay Area.
Omggggg reading this made me realize just HOW MUCH I miss Sarah here on SS!! 💙😘