Transitions can be a bitch. I’ve just traded in my big black Sony Vaio tower for a slim silver MacBook Pro not-laptop (because it runs so hot). On the one hand, I’ve said good-bye to a 750Gb RAID drive and a dual-monitor video card capable of running two 30-inch Cinema Displays. On the other hand, I’ve also said good-bye to daily virus updates and the constant fear that my entire system is going to become unstable and turn into a Russian Zombieputer overnight and start to spam myself about how small my penis is.

Now, I can carry my digital world around with me. Convenient, sure, but also it presents a quandary to a homosexualist like myself. Pardon me if I seem cliched and stereotypical, but it’s important for me to try to look good no matter what I’m doing, and that goes for my computer, too. If I’m going to be hauling my notebook into the latest trendy coffee shop and stare at my 15” glossy LED-lit screen as I sip a latte and nosh a bagel, I need it to look good not just sitting there glowing softly, but also look great coming and going.

If you’ve just dropped two-and-a-half large on a little folding computing wonder, doesn’t it make sense to spend a goodly amount on a bag that can contain that investment in style, and allow you to cram your other digital toys in as well? And how do you balance style and practicality? Sure, a fat backpack with a cable-out for your earpods is serviceable, but what does it say about you? Do you want to look like you’re off to day camp, or do you want your bag to say “look at me! I’m sexxay! I’m stylish! I’m capable of dressing myself without looking like a pile of rags in the corner!”

If you don’t want to look like everyone else in the coffee boutique, here’s my short list of laptop bags that will cost you plenty of hard-earned disposable income, and make you look good doing it.

1. The Isaburo City123 Rucksack $699.00 - $799.00

Let’s start at the top, shall we? Let’s shall! Pretend you’re a globe-hopper and fashion victim. (I said “pretend.”) and you regularly visit Herzog & de Meuron’s Prada store in Tokyo. You’re not entirely satisfied with this season’s shoe choices and now you have $700 burning a hole in your pocket. Poor you, what are you going to do?

Well if you’re me, you take a short walk around the corner to Isaburo, the 120-year-old leather goods manufacturer that insists on using only the best materials and workmanship and you plunk down your AmEx black card and ask for a one-of-a-kind, made-to-order City123 Rucksack. The shape is the same for everyone, a kind of smooth turtle built from a hard PVC shell, then coated in luxurious buttery leather in your choice of color and texture. Every City123 is made to order for you and takes a month to manufacture.

Now let’s say you don’t think you’ll be ending up in Tokyo any time soon, but you’re already salivating about getting your mitts on one of these gorgeous and slightly weird-looking oddities. Now you can! What you can’t get is any color you want — the online version only comes in “signature” dark red. For $100 more, you can get a premium skin like “silver snake” or “black crocodile.” But dollars to donuts, you’ll be the only one in your coffee klatch with one.

2. Takumi Shimamura’s Monacca Bag $280 - $325

When you want to talk drool-worthy, you’re talking this green-friendly wooden briefcase, available in the U.S. at the Museum of Modern Art store. I must confess that I personally own the original version of this bag, made of Japanese cedar that’s hand-molded into its soft-corner shape, then lined with canvas. Its leather handles are smooth and creamy and the new version has been improved with a shoulder strap.

It’s sized to fit laptops up to 17”, so even those of you who think size matters can fit your big-ass notebooks inside. What it doesn’t have is a secure way of making sure your laptop doesn’t bang around inside it — not that you’re apt to be throwing this in the overhead, anyway, perchance to mar its beautiful surface. Still, I suggest accompanying your purchase with a Foofbag from our Australian friends at Foof. In keeping with the Japanese flavor of the Monacca, order the Origami Kuro model, made with Japanese cotton and resembling a kimono. Take it from me, you don’t want to pull a fluffy pink computer out of this sleek case.

3. Jack Spade Nylon Canvas Tech Field Bag $185.00

Let’s take a trip away from Japan and see what’s available on our own shores. Jack Spade doesn’t really exist, did you know that? Kate totally made him up. I used to think it was her husband or something, but no — just another marketing figment. But so what? Does the fact that Tony the Tiger is a faux kitty make Frosted Flakes any less awesome?

The Nylon Canvas Tech Field Bag has a name that’s far too long. Basically, it’s a messenger bag, but it’s built for “today’s modern man,” and that’s you, believe it or not! Our first two candidates may scream style, but this bag screams “Substance!” It’s a basic messenger bag, to be sure, but it adds a few nice perks to the mix, namely an exterior zippered pocket for your cell- or iPhone, ample interior pockets for books, magazines, hair extensions and the like, plus a removable padded laptop sleeve with its own Velcro fastener, so if you need to travel light but protect your data, just take the sleeve and leave the bag! I promise, no one will laugh at you.

4. Mandarina Duck ‘File’ Briefcase $375.00 - $695.00

If you’re a label whore, as well as a bag slut, it’s hard to better impress your fellow label-bag whore-sluts than to whip out a piece of lux Mandarina Duck. Basically, if you want those who pay attention to such things to be salivating over your shoulder holder, buy some Duck. A Mandarina Duck bag of any sort is 100% guaranteed, so if anything ever happens to your beauty just bring it back and they’ll get it fixed, repairing zippers and reattaching handles at no cost. Sure, they may have to send it back to Italy, where the Duck makes its home, but aren’t you worth the extra effort?

The File series is new to MD, and as usual you can kit yourself out completely in an entire line of matching File gear, from carry-ons to trolleys to wallets and dopp bags. One thing that this bag has over almost every other bag here is that you can get a 17” bag to fit those extra-large, extra-heavy, extra-impressive ginormous notebooks that some of you think you need, even though you only discover you don’t when you plug an external monitor into it and make that extra-big screen kind of superfluous.

Lest you think this is a bag about beauty over brawn, let it be known that practicality has not been cast aside. File briefcases come with removable cable pockets and separate document compartments in addition to the necessary padded laptop area. And you can pick from black or brown — or, in a select few cases, a high-tech orange (a hue which they call “Brandy”) that’ll make you really stand out in a crowd.

5. Oakley S.I. Computer Bag $175.00

“But what about me?” I hear you saying. “I’m not some mamby-pamby girly-man looking for fashion. I need to look tough! I need to look rugged! And, dammit, I need pockets!” Oakley hears you, even if I scoff and roll me eyes. This Oakley bag defines “overcompensate” by attaching three little “removable pouch pockets” to its exterior, in addition to myriad internal storage pockets, a padded computer pouch, daisy chain webbing (yeah, me neither), side compression straps and a custom D-ring from which, one assumes, one may hang a length of chain attached to one’s wallet.

As if all that ain’t macho enough for you, listen to the name of its color: New Kalki! Why settle for old kalki when New Kalki awaits, all soldierrific? I know I’m erect.

Oh, I kid because I love. Having seen one of these in person in my trendy fashion-conscious ‘hood, I can attest that it is something to behold. Nobody but nobody will be accusing you of being unprepared if you’re bearing one of these babies around, and think of the fun toys you can stash in those side pockets! It’s a party on your shoulder!

And there you have it! Five guaranteed stylish, selective and unique solutions to your… er… my laptop dilemma. Look for me in your corner coffee shop. I’ll be the guy getting my case luggage felt up.