Hey guys! I have a guest-post today written by my #1 fan - my boyfriend John Maynard! He was inspired by my Great Winter Boot-Off post and wanted to describe his bag shopping experience for y'all. Let me know what you think! ~ Danielle

Satchel. Cross-body Bag. Shoulder Bag. Man Purse. Plain ol’ Purse. Doesn’t matter what you call it, I rarely venture out without slinging my bag over my shoulder. It keeps my pockets from bulging and makes sure that I’ve always got change, a granola bar, and my sunglasses ready to go. Whatever you call it, purses are great and more guys out there should be using them more.

My current bag, and go-to for years now, is on its last legs. The hardware is wearing out, the fabric is wearing through, and I want to replace it before it literally falls apart on me in the middle of the sidewalk.

The style I’m looking for - squarish, 10”-12” long, with a flap - isn’t the most common style out there but I’ve found a few options. I’d prefer leather, I’m looking for strong stitching and reinforced hardware, and if the flap has a clasp that’d be great too. Let’s take a look at some of the options I’ve found that are available in downtown Toronto.

m0851 - Small Vertical Weekend Bag - $475

The first bag I looked at was the m0851 Small Vertical Weekend Bag... and it was one easily of the most expensive. The leather on this bag is soft and supple. The hardware seems sturdier than it looks from the outside, as the loops for the shoulder strap are hidden and protected, instead of being exposed. That said, with the leather being as soft as it is, it made me worry about how sturdy this bag would be in the long run. It is definitely a lovely piece, but how long would it last as my everyday bag? Additionally it had no flap and was a touch larger than what I was looking for, so this bag was a pass. However, the clerk at m0851 was one of the most attentive and helpful out of all of the shops I visited. He was extremely informed about each of the bags and had great insights about what might work for me and what options were available. Shout out to Aaron at their Avenue Rd store for taking care of me!

Roots - Air One Tribe - $368

Now this is the shape and style I’m looking for, but it is on the larger side of the options I was looking at. The Roots Air One Tribe is a leather cross-body bag with a buckle for the front flap. It’s Canadian made, although they also say, “Manufactured with expert Italian craftsmanship” so it’s made by Italian-Canadians or it’s made in an Italian style workshop in Canada? The ubiquitous Roots branding is on the body-side of the bag, not outward facing, which means I get to have what looks to be an unbranded bag, though it also means that the brand label will also be rubbing against your hip forever. The leather is heavier and stiffer than most of the other bags I looked at, but that could be evidence of its thickness and therefore indicate this is a durable piece. It is also full of pockets! The staff at the Roots store on Bloor St were helpful but didn’t seem as knowledgeable about their product as at m0851.

Fossil - Davis Leather City Bag - $238 at The Bay

The Fossil Davis City Bag has a leather variant at The Bay that hit all of my requirements - At first glance this bag was the perfect fit. The size is right, the flap has a buckle, and it has enough pockets to hold everything I need. I’ve also had good experiences with Fossil in the past. My Fossil wallet has served me well and my Fossil briefcase, in Harris Tweed with leather accents, is my statement piece. So why am not just buying the Davis City Bag and ending my hunt now? Because in leather bags, the difference between $200ish and $300+ is a large one. The leather felt both thin and stiff, and the cotton lining was rough to the touch. The quality just isn’t there. If Fossil made the exact same bag, but at $350 with better materials I’d have it over my shoulder right now. How was the staff at The Bay? Couldn’t tell you because I saw this bag at both their Bloor St and Queen St locations and in neither store was I approached by a single salesperson. I did look for this bag or something equivalent at the actual Fossil Store in the Eaton Centre but they didn’t have anything similar on display.

Rudsak - Maddy Large - $295

There is some confusion over the name of this bag. Both the price tag in store and their online store URL say Maddy Large, but the website listing says Maddy Medium. Either way, the Rudsak Maddy is the closest Rudsak could come to meet my bag needs. The Rudsak staff was great, and when we around the entire store looking for the right fit. They put this bag in their women’s collection, but I don’t care. It’s a purse! No shame in that, guys. The leather is soft, the nicest leather I encountered in a bag under $300, but the lack of heavy duty hardware and lack of a buckle mean this one isn’t on the top of my list. On the plus side, this purse is made in Canada.

Tumi - Alpha Bravo Beale Crossbody Bag - $295 at Nordstrom

The Tumi Alpha Bravo Beale is not the bag I’m looking for. It’s not leather and it’s too small. But what’s this zipper around the bottom of the bag? Is this thing expandable? Yes! Fully expanded, the Beale is the same size as my current bag. It is also full of pockets and seems to be an extremely sturdy piece. It also comes in two colours - I’m partial to the navy blue but I need to make sure I’m buying a bag that matches all of my outfits. Brown leather is a look, but brown canvas is just drab. Despite it not being leather, I’m still tempted by this bag. My big concern is the price. If I’m spending $300 anyways, why not get a leather bag? The clerk at Nordstrom was pleasant and helpful as always. No one at any of the stores I visited had an issue with my taking photos of the price tags, but he was the only one who offered to hold the bag for me. In researching this write up I discovered that Tumi has a stand-alone store in the Eaton Centre just below Nordstrom that I’ll have to check out as well.

Online only bags

I’m not comfortable spending this kind of money on a bag sight unseen, but here are a few options I found online.

Brave Leather Faust Leather Crossbody - $253

Brave makes their leather bags in Toronto and sells their bags online. I’d love to take a look at their Faust Leather Crossbody in person, but they don’t seem to have a store or showroom. The price seems right, but I’ve got concerns about the lack of hardware. The strap is stitched to the bag instead of attached with metal rings. That could be a deal-breaker, or the stitching and leather are strong enough to hold up to daily wear. Also, what kind of pockets does it have? Is it open topped or does it have a zipper? Is the magnetic clasp for the flap under the leather, or is the magnet exposed? I have no idea because their site only has one photo of the bag. One photo and no reviews make me nervous about buying this.

Saddleback Leather Co. Leather Satchel - $399USD

Saddleback’s Leather Satchel is the real deal. I’ve got friends who are obsessed with Saddleback bags and their briefcase is an aspirational purchase for me. Their medium sized satchel is the perfect size for my needs. The leather and hardware is top notch and I do not need to worry about this bag wearing out. This is a serious piece of kit. So what are the downsides to this bag? The price for one. It costs over $500 Canadian dollars before shipping and import duties and taxes come into play. There are also trade-offs when getting a bag with such heavy duty leather. The leather is going to be stiff at first and take a while to break in. And because the leather is so thick, Saddleback gives both exterior and interior dimensions, you lose ¼” in all directions due to the thickness of the leather. Finally, the bag weighs over 4 lbs empty, making me less likely to use it as an everyday carryall.

Bag shopping is never easy, especially when it's your every day bag, but what will John choose? It looks to me that all signs point to the Roots bag or will Fossil have a sale and win his money? What would you recommend?