Five Winter Boot Options for Men

March 13th, 2011

Blizzards are no time for boat shoes, drivers, canvas sneakers, loafers, etc. From late December to early March, I probably wear boots about 75% of the time.

A boot is not just a boot, there are different styles for different occasions and it’s important to have the right pairs in your winter rotation.

Here, five different styles, with five different aesthetics.

1. Rugged/Alpine


For those unexpected blizards that can bring 13 inches of snow overnight, you need at least one pair of trudging-through-the-sh-t boots. I lace these things up and don’t have to think twice about what I’m steeping in or on – they’re insulated, completely waterproof and have a virtually indestructible beefy rubber sole.

Where I wore this: Class – “History of Menswear”

Bonus Tip: Red laces? Why not? Winter outfits are generally darker and more muted, allowing an unepected dash of red to be the sole “pop” (no pun intended). Matching stripe on gloves was a coincidence.

Bonus Tip II: Looking for a timeless but inexpensive outerwear piece? Official Navy-issued peacoats are abundant in vintage stores. Try-on a handful of them until you find a proper fit (or at least one that needs minimal alterations). For $50-$100 these classic built-to-last  jackets are a no-brainer.

Bonus Tip III: An accesorry, particularly a lapel pin, can be made of just about anything. It’s a great place to be innovative and add a personal touch. More on unique/unusual acceorries (including the anticapated lapel acceorries) coming soon. (We can only work so fast! We are juggling several projects at once).

  • Brown leather alpine boots by Alife ·
  • Navy peacoat Vintage naval issue ·
  • Grey micro-check washed cotton shirt by Steven Alan ·
  • White striped cardigan by Rag&Bone ·
  • “New Standard” Raw denim jeans by APC ·
  • Grey suede gloves by Thom Browne ·
  • “Roman Coin” brooge Vintage

2. Wingtip Brogue


A leather brogue wingtip is very versatile because it looks both dressy and casual at the same time. These are one of my favorite pairs of boots. They can be dressed up (see here) or down (see here).

Where I wore this: A meeting with potential buyers (samples in duffle bag).

Bonus Tip: When it’s wet out sometimes I tuck my pant hems into my boots to keep them dry. Once you walk inside, simply pull them out and let them fall over the laces.

Midnight Wool Coat

Wool Flannel Trouser in Mid Gray

3. Boat Boot


The comfort and casual aesthetic of boat shoes but for off-summer  months. Genius. Just remember these are casual shoes, not meant to be dressed up.

Also keep in mind they are unlined leather – so if there’s snow on the ground, you might want to think about thick wool socks.

Where I wore this: A friend’s apartment, then college basketball game at Madison Square Garden

Bonus Tip: Burgundy, or it’s deeper brother “oxblood”, is a versatile and style-forward footwear color that doesn’t stray too far from traditional.

  • Burgundy boat boots by Sperry ·
  • Tan moleskin peacoat by Filippa K ·
  • Navy washed cotton shirt by Steven Alan ·
  • Olive cargo pants from Army/Navy surplus store

4. Suede Chukka


A chukka is another boot that can easily be dressed up or down. The simple and clean silhouette works as great with slim flannel trousers as it does with straight raw denim.

Where I wore this: Art show in upper manhattan

Bonus Tip: Everybody has suede chukkas in tan, brown and black. Try a more unexpected (but still neutral) color like forest green, burgundy or navy blue.

Bonus Tip II: Leather soles are generally stiffer and slimmer – which makes shoes dressier and sharper in shape. Rubber or crepe soles (like Clark’s famous “desert boots”, for example) are unmistakably more casual in nature – and thus work better with jeans than suits.

Bonus Tip III: A suede boot is a little counter-intuitive. They’re boots that you can’t wear in the rain or snow. This makes them a “luxury” type of item. With that said, a suede chukka should be well-made and sharp, not casual and sloppy.

Wool Flannel Trouser in Mid Gray

White USA Oxford Shirt

5. Captoe Lace-Up


What do you do when someone steals your favorite pair of Ralph Lauren leather captoe boots (see way back, here)? You upgrade them with a bad-ass pair of handmade Italian oxbloods.

These, in my opinion, are close to the “perfect” boot. Oxblood leather, 8″ lace-up, brogue captoe, rubber sole, perfect last shape (notice the toe box – not square but not round).

Where I wore this: Vintage shopping.

Bonus Tip: Colors are starting to lighten up as Spring approaches and we begin seeing sunny days again.

Bonus Tip II: Transitional times are coming – soon it will be time to start mixing fabrics and colors (light blue unlined cotton trench over wide-wale corduroy vest and oxford shirt, for example).

  • Oxblood boots by Scarpe di Bianco ·
  • Light blue cotton trench by Burberry Prorsum ·
  • Grey cotton shirt by Onassis ·
  • Navy corduroy vest ·
  • Slim washed denim jeans by Polo Ralph Lauren

Thanks for reading.

Yours in style,

Dan Trepanier


Photography by Alex Crawford.