Please welcome our super cool guest, Anthony Mastracci, master of the hip men’s lifestyle guide, The Next Gentleman. Ladies, wondering how to keep your men in fashion during these colder months? Anthony has some tips for you and for our gentleman readers to stay “hot” in both meanings of the word!

“Winter is coming,” Jon Snow muttered into the frozen night from underneath his full body fur cape. Most of us know the famous line from Game of Thrones but what many don’t know is that he’s actually talking specifically about New England.


If you’ve ever lived in Boston, you know all about the struggle of walking around the city and commuting in the frigid weather while still trying to look somewhat put together. I’ve even gone as far to say “screw it, just survive any way you can,” keeping in mind that monstrosity from 2015-16.


Fortunately, there is a way around this, and it starts from the bottom up. The key to putting together a great cold-weather outfit is hearty, reliable boots, and then working the rest of your outfit around that.


Here are four looks I’ve recently put together that have me cold-weather ready:

  • Ribbed Sweater: H&M
  • Overcoat: Frank + Oak
  • Jeans: Jack Wills “Kirkham”
  • Chukka Boots: Ugg “Freamon”
  • Sunglasses: Ray-Ban

  • Leather Military Jacket: – Urban Outfitters
  • Jeans: 7 For All Mankind “Paxtyn”
  • Lug-soled Boots: Olukai “Kohala”
  • T-Shirt: Commune
  • Hoodie: H&M
  • Beanie: Nordstrom Rack

  • Shirt: Jack Wills
  • Jeans: 7 For All Mankind “Rhigby”
  • Down Puffer Jacket: Wellensteyn
  • Shearling Lined Boots: Sperry
  • Trapper Hat: Target
  • Shearling Lined Suede Gloves: Stolen from My Father
  • Sunglasses: Ray-Ban

Clothing ℅ Wrentham Village Premium Outlets

  • Flannel: J Crew Factory
  • Down Puffer Jacket: Wellensteyn
  • Jeans: 7 For All Mankin “Rhigby”
  • Lug-soled Boots: Olukai “Kohala”
  • Undershirt: Express Outlet