I am writing from the North Eastern United States and I have to say, this year the cold weather has been slim to none over the past couple of months.  This is great as I have been able to get my longer rides in outdoors and keep group riding later than usual.  With that being said though, Winter starts December 22nd (2015) and the colder air and snow will inevitably be here before you know it.  The following are the ways that I dress myself when the mercury starts to dip to stay comfortable when exercising outdoors and are backed by years of mistakes, frozen toes, and soaked base layers.  However, what works for me may not work for you, please keep that in mind…

65+ degrees fahrenheit

• Head – Nothing unless it is really bright out and I want a casquette to keep the sun out of my eyes.
• Torso – Summer weight jersey >75+ F.  Regular weight jersey + wicking sleeveless base-layer otherwise.
• Hands – Nothing, unless I am racing then I will put a regular pair of bike gloves (fingerless) on to prevent road rash on my palms in the event of a crash.
• Legs – Summer weight bib-shorts >75+F.  Regular weight bib-shorts otherwise.
• Feet – Nothing

55-65 degrees fahrenheit

• Head – Casquette.
• Torso – Regular weight jersey + sleeveless wicking base-layer.  I keep arm warmers in my jersey pocket in case it gets cloudy/windy, or for descents.
• Hands – Nothing, unless I am racing then I will put a regular pair of bike gloves (fingerless) on to prevent road rash on my palms in the event of a crash.
• Legs – Regular weight bib-shorts.
• Feet – Nothing.

45-55 degrees fahrenheit

• Head – Wool casquette that covers the ears.
• Torso – Regular weight jersey + sleeveless wicking base-layer + wind-resistant/proof vest + arm warmers.
• Hands – Full length wind-resistant/proof lightweight gloves.
• Legs – Regular weight bib-shorts + mild/medium embrocation, or knee/leg warmers.
• Feet – Wool socks + toe covers.

35-45 degrees fahrenheit

• Head – Wool casquette + plastic covering over helmet/aero helmet with minimal venting.
• Torso – Thermal long-sleeve jersey + long-sleeve wicking base-layer + wind proof vest/jacket.
• Hands – Full length wind-proof heavyweight gloves.
• Legs – Regular weight bib-shorts + medium/hot embrocation, or leg warmers.
• Feet – Wool socks + overshoes.

25-35 degrees fahrenheit

• Head – Balaclava + plastic covering over helmet/aero helmet with minimal venting.
• Torso – Thermal long-sleeve wicking base-layer + Thermal long-sleeve jersey + wind-proof heavy jacket.
• Hands – Full length wind-proof heavy weight gloves + hand warmers, or lobster-claw mittens.
• Legs – Thermal bib-tights.
• Feet – Heavy wool socks + overshoes + toe warmers, or winter cycling shoes.

<25 degrees fahrenheit (you are braver than me!)

• Head – Wool casquette + balaclava + plastic covering over helmet/aero helmet with minimal venting.
• Torso – Long-sleeve wicking base layer + thermal long-sleeve wicking base-layer + Thermal long-sleeve jersey + wind-proof heavy jacket.
• Hands – Glove liners + lobster-claw mittens + hand warmers.
• Legs – Regular weight bib-shorts + thermal bib-tights.
• Feet – Wicking lightweight socks + heavy wool socks + overshoes + toe warmers, or winter cycling shoes.

Other considerations

I will dress 1 temperature range higher when I am performing high intensity intervals, riding steadily at SST or LT, riding in the woods, or racing.

I will dress 1 temperature range lower and add a waterproof shell layer when it is raining/snowing.  I will also dress 1 temperature range lower in a group ride as there tends to be long bouts when you are just chilling (pun intended 😉 ) in the paceline as others are working on the front.