How to Dress Your Baby for Sleep in the Winter Sleep Wise Consulting How to dress a baby for a winter walk Swipe through for a simple step by step guide. Save this for your next chilly walk winter walk new parents baby How to dress your child for autumn and winter walks? I had a lot of requests to share how I dress my babe for winter. This is an example of how I dressed him for a low 30s high 20s hike., ., My typical layering for a cold day is:, 1. Onesie and wool