We go outside in most weather, including a Kitchener winter, because outdoor time is the best part of the day and toddlers need to move. The cold is rarely the problem. Bad gear is. Here is how to dress a toddler so they stay warm and we stay outside.
The layering rule
Think in three layers. A base layer that wicks, like a long-sleeve top and leggings, keeps sweat off the skin. A middle layer like a fleece adds warmth. A waterproof, windproof outer layer keeps the weather out. Cotton against the skin is the one thing to avoid, because once it is wet it stays cold.
The bits that actually fail
Hands, feet, and necks are where a winter day goes wrong. Send waterproof mittens, not gloves, because toddlers cannot manage fingers. Send warm, waterproof boots a size up to fit thick socks. A neck warmer is safer than a scarf. Label every single item, because in a room of fifteen toddlers, identical mittens vanish.
What to leave at home
Skip drawstrings and long scarves, which are safety risks. Skip the fanciest coat, because it will get filthy, and that is the point. Outdoor play is messy by design. Send the gear you do not mind seeing covered in mud and snow by pickup.
Get the gear right and the cold stops being a reason to stay in. Your toddler comes home tired, rosy, and ready for dinner.