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).
Boots by Alife. Navy peacoat vintage (size 36). Shirt by Steven Alan (size M). Cardigan by Rag&Bone (size M). Jeans by APC (size 32). Gloves by Thom Browne (size 9). Vintage ”Roman Coin” brooge.
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.
Boots by Paul Smith. Overcoat by Rag&Bone (size 40). Grey hairline stripe shirt and grey flannel pants by Michael Andrews Bespoke (custom made, my own designs). Knit tie by Ralph Lauren Black Label. Leather gloves by Hugo Boss (size 9). Leather duffle by Kenneth Cole.
3. High Topsider
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.
Boots by Sperry. Moleskin peacoat by Fillipa K (size 50). Shirt by Steven Alan (size M). Cargo pants from Army/Navy Surplus store (size “38-40″).
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.
Suede chukka boots by Church’s. Corduroy blazer and grey flannel trousers byMichael Andrews Bespoke (custom made, my own design). White oxford shirt by Band of Outsiders (size 3). Cashmere cardigan by Brooks Brothers Black Fleece (size 2). Watch by Montblanc.
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 (custom made, my own design). Blue gradient trench by Burberry Prorsum (size 50). Grey oxford button-down by Onassis Clothing(size M). Corduroy vest by Michael Andrews Bespoke (custom made, my own design). Jeans by Polo Ralph Lauren (size 34).
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