Gmail vs. Outlook.com: Which offers the best email in the cloud?

There’s an elephant in the room, and it’s wearing a Microsoft T-shirt.

Of course, when it comes to business-friendly webmail services, Gmail has been the go-to tool for as long as anyone can remember. Outlook? That was purely a desktop mail client. Hotmail? Most business users wouldn’t touch that with a 10-foot spam filter.

But, now, here comes Outlook.com, Microsoft’s new webmail service. And you know what? It’s pretty good. So good, in fact, that it deserves a chance to challenge Gmail head-on. Call it the elephant in the room versus the 800-pound gorilla.

Gmail already has legions of fans and a solid reputation as a versatile, reliable mail service. Outlook.com needs to prove that it’s not just Hotmail with a fresh coat of paint, that it can give business users the tools they need to work quickly, efficiently, and securely. And how does it rate at handling both work and personal email? Can it keep them separate but equal? For that matter, can Gmail?

Before I put these two in the ring, however, keep in mind that Outlook.com isn’t intended to replace Outlook for Windows. Although you can use the former to manage multiple mail accounts (both business and personal), as you can Gmail, it can’t import Outlook PST files—only Outlook contacts exported to a CSV file. If you’re thinking that Outlook.com might just be the tool you need to free yourself from the shackles of its desktop counterpart, think again. (See the comparison chart at the end of this article for details.)

Interface

Proof positive that you can’t judge a book by its cover, Gmail is almost certainly the world’s ugliest webmail service. Anyone new to it would likely be put off by its cluttered and unintuitive layout, its confusing sidebar, and its text-heavy design. Learning your way around Gmail isn’t hard—and there are rewards for doing so—but it isn’t pleasant, either.

Outlook.com, meanwhile, looks warmer and more welcoming, using larger fonts to delineate sidebar sections and message headers. You can quickly switch among a dozen color schemes, all of which accentuate the interface without overwhelming it. Gmail, on the other hand, has lots of themes, but most of them merely add extra distraction to an already cluttered interface.

Even the online Outlook’s ads look nicer, with thumbnail photos that pop up when you mouse over deals that catch your interest. Gmail continues to mix in largely text-based ads, without so much as a shaded background to help separate them from actual inbox matter.

And from a productivity perspective, Outlook.com wins the day with single-click actions for tasks such as deleting messages and marking them as unread—tasks that require two or three clicks in Gmail.

WINNER: Outlook.com

Search

Even if you’re diligent about deleting old or unnecessary email, it’s a good bet that your inbox contains hundreds—if not thousands or even tens of thousands—of messages. So how can you possibly hope to find a single email needle in the haystack that is your inbox? With a robust search engine, of course.

Outlook.com covers the basics fairly well. You can type a keyword into the search field, or click Advanced and add the sender, subject, folders, and/or dates to the mix. Nothing fancy, but it works.

Of course, as you might expect from a Google product, Gmail buries the competition. You get dynamic search parameters that appear as you type in the search field. You can refine your search any number of ways, adding operators for items such as attachments, labels, and even Google+ circles. Best of all, Gmail lets you turn any search into a filter, thus making it simple to run again in the future.

WINNER: Gmail

Mail organization

It’s not uncommon to use your inbox as a filing cabinet, a storage facility for important messages from coworkers, customers, and other business contacts. But Gmail and Outlook.com take decidedly different approaches to organizing all those messages.

Outlook.com relies on a traditional folder system, allowing you to create as many folders as you like and to arrange them hierarchically by dragging and dropping. Likewise, you can drag email messages into those folders. But Outlook also lets you assign messages to categories, which you can then use for Quick Views—filtered lists of messages that make it simple to find mail of a specific type, such as newsletters, notes from the boss, or mail with attachments.

Gmail has long championed its system of labels and filters over folders, and although that system has its merits, some users have a hard time wrapping their brains around it. The arrangement is less intuitive and less familiar. However, Gmail’s superlative search capabilities help to mitigate any such obstacles: Why bother organizing at all when you can so easily search for what you need?

It’s hard, then, to answer the question of which system is better. Ultimately the answer depends on what you’re used to and how you like to organize. Both systems are effective; they’re just radically different.

WINNER: Tie

POP/IMAP support

Any good webmail service should be able to send and receive mail from other accounts, thus allowing you to manage multiple email addresses (including work and personal accounts) under one roof. Gmail earns high marks in this area, offering support for both POP and IMAP. But Outlook.com supports only POP, so synchronizing mail accounts among multiple mail clients is much tougher. For example, the mail you read on your laptop won’t sync with the mail you read on your smartphone, and vice versa. (The exception is if you connect via Microsoft’s Exchange ActiveSync; see “Mobile access” below.)

That’s a potential deal-breaker for some users, and arguably it’s the only area where Outlook.com has a fundamental shortcoming compared with Gmail. For the former to compete, Microsoft needs to add IMAP support, stat.

WINNER: Gmail

Attachment handling and storage

When you receive a message containing, say, a Word file or PowerPoint presentation, opening that attachment should be a simple matter. Thankfully, both Gmail and Outlook make the task pretty darn simple.

I emailed a Word document to both my accounts. Outlook made a prominent show of the attachment, complete with a familiar-looking Word icon atop the body of the email. One click, and the document downloaded immediately in its native format (ready for viewing in Word proper), though I also had the choice of downloading it as a .zip file. Or, by clicking View online, I could view the document in Microsoft’s Word Web App, with the option of making quick edits right in my browser.

Gmail operated similarly, with simple View and Download options; the former steered me to a Google Docs viewer and, if I wanted, a full-blown editor.

As for attachment size, Gmail limits you to files no larger than 25MB, while Outlook.com caps them at 100MB—or 300MB if you establish a link to your SkyDrive account. And speaking of storage, Gmail gives you just 10GB, while Microsoft promises an unlimited inbox. Granted, expanding your Gmail storage space doesn’t cost much, but why pay if you don’t have to?

WINNER: Outlook.com

Mobile access

Want to access your Gmail or Outlook.com account on your smartphone or tablet? With Gmail it’s a snap; Android devices have the service built into their DNA, and iOS devices list it prominently when you go to add a mail account.

With Outlook.com, things are a little trickier. iOS still has a button for Hotmail, not Outlook.com, on the list of compatible mail services. You can still use it to sign in to your account, but if you have a different top-level email address associated with your Microsoft account, that’s what will appear when you try to compose a new message.

The better option is to set up Outlook.com via Microsoft Exchange—or “Corporate” if you’re on Android. Setup can be a hassle, though, and Microsoft doesn’t make it easy to find the proper domain- and server-setup instructions. The good news is that once your account is configured, you’ll get IMAP-style syncing.

WINNER: Gmail

The overall winner

As with classic prizefights such as Mac versus PC and Coke versus Pepsi, we have no clear-cut winner; in the end, your choice may merely depend on which features and capabilities you prize the most.

Both Gmail and Outlook.com let you manage work and personal identities with relative ease, funneling various accounts and assigning them their own folders. However, it’s important to note that because Outlook.com doesn’t support IMAP, you may have a harder time working with corporate accounts.

For those keeping score, it’s Gmail by a nose. (See the chart below for more side-by-side comparisons.) But give credit to Outlook.com for being a close second, and for offering a more visually pleasing and intuitive email experience. Can you get your work done using Microsoft’s new service? Absolutely, especially if you deal with a lot of attachments and plan to store massive amounts of email.

On the flipside, Outlook.com could pose a problem for small businesses that need IMAP support and don’t have the tech expertise to deal with Exchange ActiveSync. What’s more, while Gmail can take your inbox to new places thanks to add-ons such as Boomerang for Gmail and SmartrInbox for Gmail, Outlook.com has no add-ons—at least for the moment. It’s no surprise that the desktop Outlook and its corporate, cloud counterpart (Outlook Web Access) offer richer features than the fledgling Outlook.com does.