A blog by "America’s Best Dressed Real Man". Fashion tips, answers to your questions, and all things men’s style
Sunday January 22nd 2012



Recent SB Tweets

Follow SB on Twitter

Fall/Winter Headwear, Part II


The weather in NYC has been a little bipolar lately – it’s that time of year – but as today reminds us, it’s still February.

Therefore, as discussed in “F/W Headwear Part 1″, I’m still wearing alot of hats.

Part 2.

1. Worsted Cadet Cap

Cool, similarly-shaped but slightly more unique, warm and “style-forward” than your typical every-guy baseball cap.

This olive cadet cap is cut from a traditional menswear blazer fabric (olive worsted wool with subtle yellow windowpane pattern) which looks great with a casual, laid-back look.

I slip this thing one whenever I’m rushing out the door without time, or will, to style my hair (at times I miss having a short buzz-cut…considering bringing it back for summer 2011).

*New Feature: Where I Wore This: Menswear illustration class at FIT.

Olive wool cadet cap by Hats in the Belfry. Wool herringbone down vest by Penfield (size S). Chambray shirt by Rag&Bone (size M). Henley by Polo Ralph Lauren (size M). Brown corduroys by H&M (34). Belt by Banana Republic. Shoes by LL Bean. Leather wrap bracelet from NYC street vendor. Watch by Montblanc.

2. Cashmere Ivy/Driving Cap

Black cashmere ivy cap by Hats in the Belfry. Grey suit, white shirt and herringbone tie all by Michael Andrews Bespoke (custom made, my own designs). Loafers by Bally. Leather gloves by Saks Fifth Avenue. Cashmere scarf by Johnston’s of Scotland. 2″ silver tie bar by Tiffany & Co.

The “Ivy” or “Driver” is a traditional cap that can be worn for a number of occasions, depending on the color and fabric. A black 100% cashmere, for example, works well dressed-up. A herringbone Harris Tweed, on the other hand, works better casually (see look 4 below).

Bonus tip: this is not a “newsboy” cap. The ivy cap has a one-piece top making it slightly more sleek and streamlined than the traditional newsboy (also called a “cabbie” or “Gatsby” after the Great Gatsby) which has a rounder, fuller, paneled top with a button.

Where I Wore This: corporate event where I gave a presentation about building and accessorizing the “perfect” business wardrobe.

3. Corduroy Trapper

On those “freeze your #$% off” kind of cold days, you need all the help you can get. It doesn’t get much warmer than a fur trapper hat, especially one rendered in a winter-weight fabric like wool flannel, knit cashmere or this brown corduroy.

Bonus Tip: I picked up this vintage military parka for $40. It was bulky and oversized. I had both the body and the sleeves tapered and now it’s one of my favorite outerwear pieces for blizzard-like conditions. This is the warmest coat I’ve ever owned, and I’ve worn it with just about everything this winter, from a sharp business suit to a chunky knit cardigan.

Where I Wore This: running errands/grocery shopping (on a cold winter afternoon).

Corduroy/fur trapper hat from NYC Street Vendor. Vintage olive parka. Cardigan by Caufield Prepatory (size 3). Jeans by APC (“new standard” 32). Boots by Kenneth Cole. Gloves by Hilts & Willard.

4. Tweed Ivy Cap

As mentioned above in look 2, a tweed Ivy cap is a traditional rugged cap that works best with a casual look.

Bonus Tip: wearing an ascot (especially a silk one) with a casual look can be fairly tricky as it inherently implies formality. A “neckercheif” (cotton bandana or small square scarf) loosely rolled and tied around the neck is a more casual, rugged, and surprisingly “manly” alternative. If you’re going to try it: just like with an ascot, unbutton only the top shirt button and make sure to push the wrap as low as possible on your neck, so that it just “peeks” out subtly. On top of being an unusual accessory, I like the neckerchief because it keeps the neck warm without the hassle of taking it off and storing it indoors (as with a traditional scarf). More on neckwear coming soon.

Bonus Tip II: it’s always nice to implement something with a little sentimental value, or a piece that has a bit of a story into your look. This “neckerchief”, for example, is an old bandana that my oldest brother Leo used to wear on his head during his days as a local soccer star.

Where I Wore This: casual meeting with workshop pattern-maker to finalize production details.

Tweed ivy cap by JCrew. Oxford shirt by Thom Browne (size 2). Tweed vest by Michael Andrews Bespoke (my own design, part of THIS three-piece suit). Chunky sweater by Polo Ralph Lauren (size M). Neckerchief vintage bandana. Belt by Banana Republic. Brown cords by H&M (34). Boots by Kenneth Cole. Wooden bead bracelets from NYC Street Vendor.

Thanks, as always, for reading.

Yours in style,


Photography by Alex Crawford.

Leave a Comment