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Fit – Fit is a bit subjective by nature; however, for those riding in temperatures that require layering, it’s worth thinking about. A tighter fit is recommended for layers meant to be closer to your skin, like a long sleeve jersey or baselayer. For jackets that should go over a mid-layer, it can sometimes be helpful to size up. This is particularly true with insulated jackets, where a skin-tight fit might compress the insulation too much and render it ineffective at holding in warmth.
Humidity – It’s often easiest to talk about winter layering pieces in terms of temperature range, but humidity can be a big factor in winter kit selection. If you ride somewhere that is cool and dry, such as Colorado, where it might be in the 30s with humidity around 20-30 percent, you likely will be able to use lighter layers. A highly breathable garment can do a much better job of keeping you warm in these conditions due to its more effective moisture transfer. The same garment would be far less effective in New England, where the temperature might also be in the 30s, but humidity can hover around 50-60 percent. In these conditions, you’ll want something with better windproofing at the expense of breathability.