Let’s talk about bags!
So this latest pod is all about bags and menswear. Obviously it’s an important thing, because bags are a bit like an extension of the style (both life and clothing) that you have. Suit wearing lawyers have leather briefcases, milsurp guys have satchels, and casual students tend to have back packs. It’s just a fact of life that if you have a pretty significant EDC (especially in the age of the freelancer), you’re gonna need a bag.
Listen to the Podcast Episode
Obviously this topic has been discussed to death many times before (we prefer the ones by PTO and Die Workwear), so don’t expect this to be any new information. In fact, Spencer and I only made this as a supplement to our discussion on the podcast, where we focus more on our personal views on bags and history with them. Like I mentioned in the “dressed-down” pod, the podcast is just an avenue for us to rant talk about things in an even more candid way that doesn’t always come across in this blog (which is already basically my personal voice through writing).
Give the podcast a listen and follow along with this post!
Update 3/6/2021: We did a follow-up stream on this topic! Most of our ideals haven’t changed (especially since we’re still inside due to quarantine), but it was an interesting conversation. Take a watch!
The Rundown
So this is a basic rundown of the bags we talked about in the podcast. Remember that we don’t necessarily recommend you buy any of these; just think of this as inspiration!
Backpacks
- Super basic, probably the best one if you’re young and got books and a laptop.
- Don’t wear it with suits.
- Backpacks are practical for students, and certain kinds (vintage military rucksacks in canvas) can work well with more rugged casual looks.
- Jansport is cool if you’ve got a punk vibe. Add in patches and stickers as necessary.
- Current “trend” is the minimalistic, leather ones. Skip it; it seems too fashion-y for us.
- I hear the kids are two strapping it now.
Tote Bags
- History of the tote via Racked.
- Tote means “to carry”.
- This is our favorite one.
- LL Bean introduced their tote bag in the 1940s as an ice carrying bag.
- Colors were first offered in the 1960s.
- Canvas totes give off preppy, whimsical vibes. It’s currently the favorite for a lot of people in classic menswear, specifically the Drake’s crew.
- Bonus points for using the “merch” ones you’d get from your favorite bookstores or from fundraisers.
- Good for carrying everything from laptops to books and writing tools. The downside is that they don’t really “close” or have cushioning.
- I put an indigo blanket in all of mine to keep things from jostling.
- Leather or suede totes are a dressier alternative and tend to break in better. They are popular within the workwear/milsurp styles but can be done with tailoring.
- We recommend LL Bean (vintage/custom), Brycelands, Clark and Barba.
Messenger Bags and Satchels
- Good alternative to backpacks. A bit more mature and has more character.
- Perfect for college students or young professionals.
- Most people in general recommend this.
- Go full leather for dressier looks, waxed cotton/canvas for more casual.
- Some will have sleeves and pockets for laptops.
- We recommend the Amazon Kattee for cheap, vintage for character, and Filson for you rich boys.
Briefcases
- Only advisable for business attire, looks very try hard with casual looks.
- Not much space for laptops, if you go for the classic versions.
- Leather is certainly the coolest version. I wouldn’t get a canvas briefcase.
- Niles Cane got bullied for it, so maybe skip this.
- Get an Ortus if you got the monies for it.
Folios
- A more streamlined version of a briefcase. Holds documents and maybe a thin laptop, but not much else. If you don’t have a lot EDC, maybe this is for you?
- Popular at Pitti.
- PTO article.
Crossbags
- Basically a fanny pack worn across your body like Chewbacca’s bandolier.
- It’s small and should carry things like a wallet and phone, but not much else.
- More for street/tech wear crowd. I can’t see it with tailoring.

These aren’t bad.
Our Bags
Here’s the bags we owned that we mention on the pod.

Hard to see, but this is that canvas rucksack/back pack thing I got from Urban Outfitters.

A random briefcase thing, that would hold notebooks and my laptop/chargers.

A canvas zip one from H&M.
This Kattee bag (bought on Amazon shortly before my London and Paris trips of 2017) was the main bag of choice for a long time. it’s made of a sturdy canvas with leather detailing, but the main reason I got it was because it came with a removeable camera compartment! It basically has space for everything I need, from my laptop (in a sleeve) to multiple chargers, batteries, back up glasses, cables, and so on.
It’s definitely a very cheap bag, but it got the work done for me on multiple trips, even the travel-heavy NYC one. I also don’t think it’s particularly stylish and doesn’t fit in with my regular style, being more suitable for a college student.

Spencer’s GIANT tote bag from J. Crew.

My tumblr tote bag.
I finally went on the tote bag trend after seeing so many of my Drake’s pals have them. This one is a custom boat and tote from L.L Bean, and is miles ahead in quality than the Kattee bag (yes, I realize they are different styles).
It’s definitely more of a carry-all, so I just put random shit in it from whatever I’m doing. I have brought along my laptop and camera to do work at a boba cafe, but I’m always hesitant on truly making it my everyday bag as there isn’t special compartments for electronics. I’m afraid things will jostle around and get damaged. Like I said earlier, I do put in a folded indigo blanket for cushioning and it does help a bit.
The good thing is that the canvas is pretty hefty and a bit thick, so it does offer some protection; the top also has a zipper closure. For these reasons, it is my travel tote of choice.
The real winner is the leather tote that we designed with Clark & Barba, a local Los Angeles leather maker. I literally bring it with me everyday, carrying my lunch, gym clothes, and other electronics to work. My laptop/camera remain in my Kattee messenger bag, but if I’m attending an event (where I just need a camera, water, and batteries), I’ll only have this leather bag.
It’s really fantastic and perfect, basically to the extent where I seldom use my L.L Bean tote! The main reason for differentiation is basically the vibe and what I’m doing. In most cases, I’ll stick with the leather tote. If I don’t need too much or if I want to lean hard into prep (or if I know Spencer is bringing his bag), then I’ll go with the L.L Bean.
As I stated on the original article, there are two models, the Spencer and Ethan; the former is larger.
Conclusion
Listen to the podcast episode on bags!
I hope you enjoyed these brief notes on the bags in menswear! If you listened to the podcast, you’ll know that we definitely prefer the tote bag. Like a soft shoulder or a bucket hat, it just seems so easy and slouchy to wear, instantly making an outfit more approachable and grounded in everyday life. I know that sounds weird, as I wouldn’t normally think of a bag as “part of an outfit”, but as you can see in the article, bags have different vibes. Choose accordingly!
But yes, the tote goes with everything.
You can buy the Ethan and Spencer Tote bags if you are so inclined! You can use code SPREZZA for a little discount (limited time only)
Always a pleasure,
Ethan W.
Street x Sprezza
Enjoyed your article. I use a small, dark brown messenger bag. I attend classes at a boxing gym three times a week and the clothes I wear don’t have pockets, so the bag is a good solution for me.
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