Bags in Bags and Bags on Bags

The case for carrying more than one bag at a time...

Does anyone else feel like you can never have too many bags? I know Isaac Mizrahi totally gets me.

I’ve always considered myself a bag-lady. I collect bags of all shapes and sizes, materials, colors, proportions and pricepoints. What I’m drawn to the most about bags are how utilitarian they are by nature, and how they can be a playful element in your wardrobe at the same time. They ultimately have to serve a purpose, and often have a specific end use, but they can be such a great piece to switch up depending on what you’re doing or where you’re going.

So this post is a follow-up to my first newsletter, about bags, totes, and carryalls, that came from a satisfying conversation with Katherine Lewin, of Big Night (who launched her incredible new cookbook last week). She speaks about our bag therapy session on the podcast A Thing or Two and shares some of her favorite things there, which also happen to be some of my favorite things. There’s nothing I enjoy more than being a sounding board for a friend who is on the hunt for something and identifying what functionality is needed, as well as the more fun element of choosing something to express their personal style. In this case, what she decided on came out of some strategizing, as we needed to solve a few end-uses: needing a day-to-day workhorse that needs to carry a laptop among many other practical things, and also needing something that would allow her to go out to dinner or an event at the end of a workday and look chic and elevated.

This time the answer wasn’t a singular bag. It was two bags. It may just be a bag inside of a bag. Or a bag on top of another bag. The biggest question was whether she should invest in a fancy leather tote bag, and if so, which one? Or should she continue to utilize her LL Bean XL Boat Tote? Katherine landed on keeping her beloved Canvas Boat Tote for everything she carries for the day, and investing in the Loewe mini hammock bag that easily fits inside the large tote or she can wear crossbody while still carrying her tote, which adds an elevated element to her look when she wants to leave the big tote behind.

The other option was to choose a fancier leather tote bag to do double-duty. One of the potential issues with this choice is that some of these bags feel too nice to lug a heavy laptop around in. Or that the tote doesn’t feel quite right for taking to an event. On the days you just need to commute a short distance and know you won’t be making too many stops, this can work well. On other days when you know you need to get around, from home to the gym to the office to a nice dinner, two separate bags can be ideal. Plus it’s fun to stack bags to create a layered bag look, or to play with texture or color combinations, but ultimately, it gives you more organizational options. I love to keep my essentials in the smaller bag, ready to take out for a last minute happy hour. Think: phone, keys, lip balm, wallet. And if you’re a mom, maybe add some bandaids and emergency lollipops.

Examples of bags in bags, and bags on bags. Clockwise from top left: Happier Grocery Bag with Casa Ayllon pouch inside. Jess Graves carrying The Row Margaux with the Row Dalia Bag, Jess with the Margaux on top of her Underwater Weaving basket, Jalil Johnson playing Russian dolls with his Chanel pouch inside his Puck News tote courtesy of Lauren Sherman, inside of his Underwater Weaving bag, Leandra Medine double bagging over the years, me triple bagging with my LL Bean Tote, Khaite Osa, and Baggu pouch.

Other bag on bag ideas I’ve saved over the years. Carrying two bags at a time, tying a smaller bag to a larger bag, a small bag inside a big bag, and triple bagging.

Iconic Kate Moss with her Hermès tote on top of her duffle. Here are other favorite canvas or nylon totes that are incredibly durable and timeless. I love to use these for generally larger hauls, day trips, as a carry-on bag. I also collect smaller canvas totes which I use for literally all sorts of things. From top left: LL Bean, Amicalva Pocket Tote, Kule x Bergdorf Goodman, Kule, the bag on my wishlist: this green canvas tote, the classic Longchamp Pliage tote.

Some of my favorite leather totes, that are equally stylish, well-made, and chic. Great for everyday schlepping while still looking elevated. If carrying a laptop, I recommend using a padded laptop sleeve. Clockwise from left: large suede tote, woven leather tote at a great price, elevated suede tote with clip-on pouch, Parker Thatch suede and leather tote, this beautiful oversized leather tote.

Options for smaller bags that fit nicely inside your tote, piggy-backed on top of, or worn separately from your tote. Clockwise from top left: Katherine’s choice, the Loewe mini hammock bag, an asymmetrical design, a mini top-handle / shoulder bag I spotted on my friend Anja Tyson, this mini bucket bag that my chic friend Jacqueline Cameron wears and has made me long for, a timeless shoulder or crossbody bag, easy sling bag that adjusts to a shoulder length.

Pouches are key. I use all shapes and sizes for various things inside my bags. I even have smaller pouches nested inside the larger ones. Clockwise from left: Carven, Lemaire small pouch, leather lipstick case, Lemaire medium pouch, Ilia complexion stick, Loewe pouch, cat eye sunnies, a great option from Madewell, Super Egg hand cream.

What I packed for a 3-day trip to Sonoma County. LL Bean tote, leather drawstring pouch by Casa Ayllon, Clare V rope bag, Brigitte Tanaka organza embroidered bag and pouch, Herve Chapelier mini tote, Baggu pouch set.

I am currently in Sonoma as I write, living through all of my bag choices, and I can say all of the bags I packed have been doing what they need. Doubling up is not only functional, but I love that it gives more of your bags a chance to be used, and for me, it’s also a great way to feed my continued bag obsession.