If it seems like we’ve tried to cover a lot of ground in our #OOTD series this winter, well, that’s because … we have. From a guide on how to wear your new favorite sweater to today’s versatile-yet-rugged (and largely casual) set of winter style essentials, the stage is set for you to add another arrow to your quiver of menswear looks (yes, I went there). The best new men’s gear is here for you today, including an unexpected centerpiece: That of the surprisingly stylish hooded sweatshirt, and in fact … one of the best men’s hooded sweatshirts. No longer is the hooded sweatshirt to be relegated to wearing on those winter days when you can’t muster up the energy to leave the house — no sir, we’re wearing the perfectly rugged Flint and Tinder 10-Year Pullover just about anywhere you want. Heck, if you work in a casual, startup-type office environment, we’re wearing this look there, too (it looks a heck of a lot cooler than Zuckerberg’s hoodies, trust me). But mostly, we’re wearing the best hooded sweatshirt and other critical men’s gear picks anywhere you might wear a normal crewneck or V-neck sweatshirt — to brunch, to run errands, to grab coffee, to watch the ballgame … you name it, the Flint and Tinder 10-Year Pullover can probably take it on without missing a beat (aside from situations that definitely require a tie, that is). At any rate, your complete guide on wearing a hooded sweatshirt in style starts right here. Taking notes? Good, good.

The best way to wear a hooded sweatshirt comes down to the right essentials.

• The Stylish Hoodie: Flint and Tinder 10-Year Pullover, $98 — Is it worth it to drop nearly $100 on one of the best hooded sweatshirts around? Yes, of course — especially when it’s got a tailored fit and uses comfortable fabric that’s guaranteed to break in.
• The Jacket: Flint and Tinder Wool-Lined Waxed Trucker Jacket, $288 — The thing that’s really going to bring this rugged style ensemble together? Why, a classic trucker jacket, delivered in style from Flint and Tinder once more and lined in warm wool for your commute.
• The Base Layer: Faherty Brand Slub Cotton Henley, $98 — You’re investing once again here, but this time in one of the best men’s henleys on the market — one from Faherty Brand, no less. In the event you need to take off that hoodie, this is a perfectly stylish base layer.
• The Pants: Western Rise Alloy Chino Pants, $139 — The thing that takes this look from good to great? Some of the best men’s chinos from Western Rise — versatile enough to wear on a weekend hike, stylish enough to wear to drinks after (and yes, to the office, as well).
• The Stylish Boots: Astorflex Dukeflex Boots, $155 — If you read the blog, you know I’m all about adding a pair of the best men’s boots to any outfit — especially these rugged chukka boots that channel moc toe boots, all courtesy of Huckberry.
• The Rugged Watch: Luminox Modern Mariner Watch, $900 — For getting around in the snow, you need a tough casual watch — yet one that looks great, too. The Luminox Modern Mariner accomplishes that goal quite nicely, wouldn’t you say?
• The Grooming Essential: Duke Cannon Beer & Bourbon Box, $30 — The good folks at Duke Cannon know a thing or two about making the best men’s grooming essentials — this Beer & Bourbon Soap Kit delivers a trio of standout scents for every day this winter (and beyond).
• The Everyday Bag: Tanner Goods Simple Tote, $130 — No matter where you’re goiing, you need a tough everyday bag — and yes, the Tanner Goods Simple Tote is more than up to the challenge of hauling your EDC essentials.
  

No matter how casual this #OOTD might seem at first, it’s all about making the right choices in terms of your gear — hence, when it comes time to discuss how to wear a hooded sweatshirt, we’re starting with nothing but one of the best hooded sweatshirts around. Starting with a Flint and Tinder hoodie makes it all the easier to throw on the rest of your rugged gear picks, including (of course) a classic trucker jacket, also from Flint and Tinder. That one-two combo is accented quite nicely by both a pair of the best men’s chinos from Western Rise (for that casual office sort of versatility), plus one of the best men’s henleys (for when you need a stylish base layer). The overall effect is one that’s casual enough to hang with the guys, yet not sloppy enough that you’re confined to your couch — and only your couch. That’s where a pair of rugged chukka boots comes into play, helped along on the accessories front by a tough casual watch — the Luminox Modern Mariner, to be more specific. You’ve also got the right idea in mind in terms of hauling your EDC essentials with the Tanner Goods Simple Tote — it blends style and tough functionality with ease. To top it all off, the best men’s grooming essentials (by way of standout soap from Duke Cannon) are yet a final, fitting way to cap off this winter-ready ensemble. Where will it take you this season? Let me know on Twitter — until then, stay warm in style, and thanks for reading!