Welcome back to Retail Therapist. There are many modalities when it comes to counseling—this one is shop therapy. Every session, GQ’s Gerald Ortiz answers a real shopping conundrum from the fashion anxious.
“I’m looking to buy my first “nice” bag. I’ve been a canvas tote bag guy for years and it’s served me well through a certain coming-of-age era of my style journey, but I’m ready to move on to something a little more mature. I don’t really know what I like, though. There are so many options, which is equally exciting and daunting. How do I find the right bag for me?”
—Bagging For Help
You should be proud of yourself for taking the initiative to better your personal style through an accessory, especially when it’s so easy to default to something like shoes or pants. There’s nothing wrong with a canvas tote, of course. But the fact that you’re seeing your style grow beyond the basic bag shows real improvement.
Now, the door you’ve opened leads to many different kinds of bags, and it’s easy to get overwhelmed, but let’s take it in digestible bites. Your homework is to go through this list, where I’ll break down the four types of bag attachment styles with examples for each. Take some time and assess your own practical needs as well as how you want your bag to speak to your growing sense of style. Keep in mind, personal bag attachment styles can change over time, so don’t get too hung up on whether you get it “right”. That’s what return policies and TheRealReal are for.
Upmarket Tote
You like security and the familiar, but know you deserve better. Upmarket Totes share many features with your faithful canvas tote bag, but are better in every other aspect, from the materials to the construction to the overall aesthetic. You’re also very practical and want a bag that feels a bit more elevated, which is distinct from the overwrought, utilitarian bag styles that result in briefcases or technical backpacks. Practicality in the Upmarket Tote sense means that your bag is still fairly simple, with enough space for your daily carry and perhaps includes a few compartments to segment your personal effects.

