When it’s time to transition your little one from a bottle (or the boob) to a regular cup, it’s safe to say that well, things can get a little messy. After all, drinking from a cup is a skill to be learned. Like most skills, it takes the right tools to master. Your best bet? A sippy cup.

Related: Everything you need for starting solids with your baby

Most experts suggest introducing a sippy cup from the time they’re old enough to sit in their high chair at about four months. But if you’ve started shopping around you know this category has a lot to offer. There’s straw sippy cups, hard spout tops, soft spout tops, and most recently, even spoutless designs that more closely resemble a regular cup. How will you know what’s right for your little one? Well, just like bottles and pacifiers, it might take some trial and error to find the right fit. 

Most importantly, remember that a sippy cup is meant as a stepping stone to the real thing, not a comfort object. So just as they wouldn’t walk around with an open cup, it’s probably best to avoid letting them use a sippy cup outside of mealtime and quick thirst quenches. Otherwise, you may end up battling with them to eat (because who’s hungry with a belly full of liquid?) or worse, dealing with cavities down the line. 

Related: Our favorite stainless steel water bottles for toddlers

So what should you look for when your little one is ready? Aside from your child’s preferences, the two most important factors are ease of cleaning and a leak or spill proof design. Nobody’s got time for moldy cups or a lake at the bottom of the diaper bag. And, as a seasoned mom, I’ll tell you right now–only the ones filled with milk get lost under the couch. It’s the Murphy’s Law of Sippy Cups, I believe. 

We’ve rounded up a variety of the best styles of sippy cups for little ones that fit the bill. Happy learning!

Best Sippy Cups

MAM Trainer Cup

MAM

$6.39

Trainer Cup

A great first post-bottle option, the MAM Trainer Cup comes with two different tops–a nipple and a spout–to ease the transition from sucking to drinking. The double, non-slip handles are easy to hold and cleaning is a breeze.

Recommended age: 4+ months

Munchkin Miracle 360 Trainer Cup

Munchkin

$12.44

Miracle 360 Trainer Cup

This dentist-recommended spoutless design from Munchkin comes highly recommended in parent circles. And for good reason! Not only is the clever design totally leak-proof, it also allows little ones to drink from any angle. And without a spout to suck on, it helps promote healthy oral development without soaking your couch, carpet, backseat and everywhere else in the process. Perhaps one Amazon reviewer said it best: “Get these. Use them for everything. Never look back. Be overly dramatic when you tell people how much you love them. Realize you need more interactions with adults. But yeah, get these cups.”

And while they are super easy to clean, be sure to completely disassemble when doing so to prevent mold from growing in the lid.

Price is for a set of two.

Recommended age: 6+ months

OXO Tot 6 Ounce Transitions Straw Cup with Removable Handles

OXO Tot

$11.99

6 Ounce Transitions Straw Cup with Removable Handles

The easy-to-hold straw cups from OXO Tot are great for toddlers making the transition from bottle to cup. Their clever, leak-proof design requires them to bite the straw for liquid to come out–great for your bag, not great for your boob if you’re still nursing and they get confused.😬 Still, parents rave about the fact they’re easy to clean, easy to track liquid intake and comfortable for baby.

Recommended age: 6+ months

Thinkbaby Stainless Steel Sippy Cup

Thinkbaby

$13.99

Stainless Steel Sippy Cup

We love a good stainless steel water bottle, but if you’re looking for something for the youngest in the crowd, we’d choose this instead. It’s lightweight with double handles so it’s easy to hold and keeps drinks (or smoothies!) cold for longer. The durable construction can easily survive the inevitable falls and while it’s not as leak-proof as other models, it’s not necessarily going to flood your diaper bag either.

Recommended age: 9+ months

Replay Recycled Sippy Cup

Re-Play

$21.99

Recycled Sippy Cups

Sustainable and spill-proof? Yes please. The sippy cups from Re-Play are made from recycled milk jugs and can be recycled again once you’re done with them! The standard construction features and easy to remove and clean single piece valve which is completely dishwasher safe. And at just $5.50 each, they’re easy on the wallet as well.

Recommended age: 6+ months

Tommee Tippee Superstar Insulated Sippy Cup

Tommee Tippee

$15.99

Superstar Insulated Sippy Cup

For keeping toddler drinks cool, opt for the Superstar Insulated Sippy Cup from Tommee Tippee. The durable and spill-proof design features a bite-resistent spout that’s made with antimicrobial technology to keep it from becoming a bacteria-fest. When it’s time to clean, just disassemble and pop it in the dishwasher or sterilizer!

Price is for a pack of two.

Recommended age: 12+ months

The First Years Take & Toss Spill Proof Sippy Cups

The First Years

$13.99

Take & Toss Spill Proof Sippy Cups

Pound for pound, these take and toss cups are probably the best kid product I ever bought. Because they’re dirt cheap they’re great for daycare or other places cups go missing and despite their disposable nature, they can last a good long time. In fact, my oldest is 16 and I could probably dig up one or two from our original box. The sippy top isn’t leak-proof, but they go a long way to prevent soaking themselves and can easily just be used as an open cup without the cap. They’re super simple, a cinch to clean and totally indispensible!

Price is for a set of 10.

ezpz tiny cup

ezpz

$11.49

Tiny Cup

Whether in place of or in addition to the above suggestions, the silicone ezpz Tiny Cup is a great way to introduce the skill of drinking from a cup. It’s perfectly sized for little hands and completely indestructible. Just stick with a teensy bit of water and prepare for some wet clothes and floors!