3 Non-Boring Work Bags I Always Carry

The below is from editor-in-chief Nikki Ogunnaike's weekly newsletter, Self Checkout. Subscribe here.

With close to 20 years in the fashion industry, I’ve not only seen it all—but also know how to parse through the endless sea of stuff. What’s worth buying? What’s not? In Self Checkout, you’ll find my highly specific recommendations with a few picks from my most knowledgeable, stylish friends.

There’s a lot of chatter on social media right now about which bags people are using for work (or university). I’m focusing on work because that’s what I’ve been doing for the last 20 years of my life, so I know it the best!

No two days are ever the same for me, so I have a multi-prong strategy when it comes to work bags. It all depends on the following: whether or not I’m lugging around my laptop with me, if I’m going to the gym at some point during the day, and what my plans after work entail. Keep in mind that this is coming from a commuter’s perspective—I usually take public transportation or walk everywhere in New York City, so my body is my car. No backseats or trunks to stash stuff over here!

If I’m carrying my laptop…

First and foremost, I look for a bag that has wide, long straps. I find these are less likely to slip and I can wear them over my shoulders (as opposed to shorter straps that you have to carry by hand). I’m currently using the medium LL Bean Boat and Tote with long straps. It fits my 13-inch Mac laptop, Nike Pegasus sneakers, small makeup bag, Nalgene water bottle, a book, and a magazine. I’m also a big fan of the Longchamp Large Le Pliage Tote (I had a red one that lasted almost ten years, and recently replaced it with a baby pink color) that holds about as much as the Boat and Tote. For my luxury lovers, I absolutely love the classic vibes of the Celine Cabas and carried this one for a few years. It fit my laptop quite well, but I was worried about whether the straps would stretch from the weight in it. Now, I reserve this for days when I don’t have my laptop with me.

If I’m going to the gym before or after work…

As any New Yorker knows, you just have to be savvy about how many bags you carry—especially if you’re getting on and off the subway. That’s why I like to employ the small bag, medium bag strategy. I’ll carry a cross-body option that holds essentials (I’m big into the patent finish on this J.Crew bag), plus a gym bag (the one above is a nice Nike option, and I love this Athleta option too) that holds all other necessities (sneakers, change of clothes, makeup bag, and the like).

If I’m going out after work…

Some days, I leave my house at 9 a.m. and don’t return until 9 p.m. (or later). My bag (or bags!) have to hold my laptop and all of the aforementioned things, plus a change of shoes and another small going-out bag. When this is the case, I usually go with a large tote and a small pouch tucked inside that’s sleek enough to double as a clutch. For this, Cuyana cannot be beat: The embossed snake one above and this pebbled leather one are favorites amongst discerning shoppers. As for the large tote, my personal favorites include the bags above, plus this Mansur Gavriel one. They usually have a zip-top so no one can reach in and grab the clutch and run (yes, this is how my Capricorn brain works).

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