If You’re A City Schlepper, Read This


I’ll be the first to admit, I’m a bag lady. A city schlepper, if you will. It started in college. I distinctly remember begging my mom and dad to buy me the Free People vegan leather tote (this is exactly what it looked like). When they finally got tired of me asking, I became a bag lady. I remember stuffing it to max capacity and beyond just because I could. It felt so right. And since then, I’m constantly searching for the best work bag as I evolve in my career and my personal style.

If you’re anything like me, you don’t want just a functional bag. Of course, that’s the most important thing, but you also want a bag that feels like it matches where you’re at in life (in this case, it’s career-focused). And it needs to carry a lot. At the end of the day, we need our work essentials that’ll help us conquer the 9-to-5 life. Much like nailing down the perfect wardrobe along with your most comfortable shoes for work, a good work bag is also crucial for those in-office days…or days we’re just running around.

In a pre-pandemic world when I was still living at my parent’s and commuting into the city every day, I had 2-3 bags with me at all time. Why? Well, I needed my regular every day bag that carried my wallet, ID, chapstick, etc. So yeah, this was a smaller crossbody bag usually. Then, I would have, what was at the time, my best work bag. This bag was essentially for any work I was bringing home with me (actually I didn’t get a work laptop until 2018). I also went to SoulCyle 3-4 times a week, so my clothes needed to be in that bag too.

As I got older, my version of the best work bag changed. I wanted cooler bags that still were able to fit anything and everything – I needed to up my game. The idea of letting go of that “function first” was a little tough, but I was up for the challenge of finding the best work bag that ALSO fit my design preferences.

“Must Haves” For The Best Work Bag

While on the hunt for the best work bag, I look for designers and brands that I can not only proudly rock at the office, but that I can also say I did not sacrifice comfort or personal style. In a weird way, “success mindset” can arguably start with the right work bag.  When it comes to finding a new bag to schlep around, there are a few “must haves” that I’m looking for.

  • Does it sling over my shoulder easily with AND without a coat?
  • How many interior pockets are there? Bonus points if there are multiple.
  • Cost per wear
  • Where does the value come from – the design or the functionality?

At the end of the day, it’s a personal choice. For me, I need the best work bag that can carry my literal AND emotional baggage to work each day. Ya feel me?

The Best Work Bags

Best Work Bag: Montauk Tote

J.Crew Montauk Tote

Honestly, this is the bag I’m carrying to and from work now. It’s quintessential J.Crew to me, and it’s a VERY practical bag. I have the Medium, and the interior is large enough to fit my 14″ laptop. There is also a pretty large interior pocket, which is a nice plus. I also love the convenient front pocket – I slip my cardholder in there for easy access when I’m all over different floors in our office.

Bonus: You can monogram it;)

Freja: Paloma Tote

I think I was served an Instagram ad for this brand, and I’m not mad about it. Or maybe I am, because now I feel like this bag is at the top of my list. I’m OBSESSED with the separated interior pockets. The website says it can fit up to a 16″ laptop, and has a ton of interior pockets. The sleek exterior alone is enough to make me want to purchase!

LL Bean Tote

I’ll preface this with this probably will not be your actual work bag. But I did bring this to work with me every single day when I worked at Free People. I was commuting back and forth, and my boss always had her L.L Bean tote. And then I wanted the L.L Bean tote. I got the large and it is….LARGE. It’s a really good weekender bag, but if you’re a commuter with places to go in the city, this is also a great option. (Side note: helloooo, have you seen the “ironic tote”?)

Cuyana System Tote

The Cuyana System Tote is definitely the number one recommendation I’ve seen for the best work bag. I’m pretty much a sucker for anything that is insanely customizable (even if it ends up costing me an additional arm and leg). This collection of bags and matching accessories gives you the space to tailor your purchase to your needs. Think thick attachable strap, a tech carryall, a flap bag that can be used in your bag OR on its own, and a zip pouch insert to create a separated interior.

Oh…these pieces can ALSO be monogrammed!

Everlane Studio Bag

This bag reminds me of my Celine Sangle bag (pictured above). This is definitely a bag that you bring to and from work if you DON’T need your laptop. BUT you can still definitely fit a 13″ laptop vertically if it was a necessity. This bag comes in a lot of color options, seems to be made out of durable leather, and the strap is adjustable. I also like how the exterior pocket is large.

Dagne Dover Daily Tote

My sister has this bag, and I’m going to start this by saying IT IS LARGE AND IN CHARGE. It is a VERY stiff/durable bag. It comes in two sizes, and the large fits up to a 16″ laptop. There are A TON of compartments – my sister makes use of every single one. The one con I’d say is that the strap isn’t adjustable. My sister and I are shorties (my sister is even shorter than I am), and that’s definitely an annoying non-feature. I think this would be a great carry on option as well if you travel a lot (especially for work).


Leave a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.

1 Comments

  1. 5.22.24
    Gigi said:

    Hi Dana,

    We love your style and would love to be our bags to be featured in your blog! We think you’ll love our Transform Tote Air Edition that is perfect for work and travel.

    https://pondla.com/products/transform-tote-air-edition-navy

    Please let us know your thoughts!

    POND Los Angeles is a small, AAPI female-owned business dedicated to creating functional yet beautiful handbags and clothing. Founder and Creative Director Daphne Chen previously designed at Ralph Lauren, Giorgio Armani, and Paige. We would love to be considered for The Strategist shopping guides and are happy to send a bag for you to experience firsthand. 

    Thank you for your consideration,
    Gigi