As we’ve mentioned approximately 8,329 (but who’s counting?) around these parts since mid-November, it’s that time of year. Doesn’t that sound ominous to you? It’s like when you were a child and your parents used to spell out words that would upset you when they were talking to each other and you were in the room – maybe if no one says the name of the impending holiday, we’ll all stay calm and the stress and airport lines and eating of feelings just won’t happen this year.

To the casual observer, men’s bags might be a tad boring, particularly for those who are used to the multitude and variation of women’s bags. How many messengers and carry-ons and briefcases can one person need, exactly? Well, that’s precisely what nonbelievers say about women’s bags, and they’re wrong. Just because mainstream men’s bags tend to have a more limited color palette and set of shapes than women’s doesn’t mean that there aren’t important differences, even between bags made for the same purpose.

By this site’s very nature, we spend a decent amount of time talking about things that are very expensive. Expensive handbags, expensive accessories, expensive shoes over at TalkShoes. Back in the real world, though, we like things that feel like a good value for our money – the biggest luxury bang for the buck, if you will. Lucky for the dudes out there, men’s bags often provide that in spades.

Selecting a briefcase for a working man, particularly a young, reasonably stylish working man, can present some issues. Traditional, super-structured options are stylish in their Don Draper, retro-cool way, but they’re not an everyday solution for a man who doesn’t commit to the midcentury look with his full enthusiasm. (And trust me, it takes a lot of enthusiasm to make those hairdos happen on the regular.)

On the other end of the spectrum, many pieces that are intended as work bags have ventured too far into “casual messenger” territory to be appropriate for an office with anything more than a business casual dress code.

Usually for Man Bag Monday, we talk about the bags you (or your man) should buy. We’ve seen some beautiful choices recently – Valextra, Lanvin, Givenchy. They’ve been so beautiful, in fact, that an unsuspecting first-time man bag shopper might get the impression that choosing a good bag is idiot-proof. Sadly, that’s not the case. There are still plenty of bad choices out there, and because we like to think of ourselves as service providers, we thought it might be helpful to discuss a few types of things that you (or the man in your life) shouldn’t buy.

As most of you guys know, I love examining how a brand takes a successful women’s bag and translates it to the men’s market. When it’s done carefully, it’s instructive of the differences between what male and female customers want in their luxury accessories. In the past, we’ve looked at dude versions of the Yves Saint Laurent Cabas ChYc and Mulberry Bayswater.

In the months (years? How long have we been doing this?) we’ve been bringing you Man Bag Monday, we’ve looked at tons and tons of solid-color leather holdalls. They’re masculine, they’re functional, they form a great foundation to a man’s bag wardrobe. Take ‘em to the gym, take ‘em on a road trip, use ‘em as a carry-on for a flight.

Menswear, as an industry, is in an interesting position right now. More men than ever are interested in personal style and upping their aesthetic game, but because of the traditional cultural views on men and fashion in the US, so few of them have any idea where to start. Of course, we have a novel (or not so novel, to our loyal readers) idea: Start with a great bag, like the AllSaints Stonewall Laptop Bag and go from there.

For a long time, I wondered why Alexander Wang didn’t do men’s bags. Wang’s dark, industrial, ultra-cool aesthetic is patently unisex, and bags have always been a great success for the brand. Many of Wang’s larger women’s bags have been favorites of fashionable dudes for a long time, and when there’s a clear market, a smart company tries to fill it.

As we often note, men’s bags tend to be more subdued, more neutral and more cleanly designed than women’s bags; the men’s market just isn’t into as much look as female luxury consumers are. That’s the traditional view, anyway. The menswear industry is in a period of rapid modernization at the moment, and suddenly a much wider variety of aesthetics and ideas are considered within the mainstream.