3 Ways to Dress a Baby in Winter wikiHow Dressing a winter baby? January 2019 Babies Forums What to Expect When winter rolls in, it's natural to wonder if your baby is warm enough at bedtime. To make those colder nights feel a little simpler, we've put together a handy sleepwear guide 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