Today, my friends, we’re doing something that might seem a bit out of left field in these increasingly casual days. We’re going to tell you all about how to wear a blazer, and not just any blazer — a slightly bold, very sharp Todd Snyder Madison Suit Jacket that injects your next fall #OOTD with some serious style and a bit of flair. It’s one of the best men’s blazers for a reason, and you’ll see why below. To keep it casual — perhaps, as you head back into the office or head out of town for a socially distanced wedding or road trip (those are still happening, right??) — we’ll team it up with your favorite blue jeans and a pair of the best chukka boots for men for the ultimate in rugged, versatile fall style. After all, you’re going to have really get dressed again eventually, and if that timing has caught you off guard, you might as well go with tried-and-true classics to help get the job done.

Elsewhere, we’re talking all about one of the best weekender bags for fall trips, available at a discount from Boarding Pass NYC when you use the code BEAUKNOWS. How cool is that?? Naturally, classic picks like one of the best Oxford shirts help to ground this outfit even further, and in a way that’s cool and fall-friendly. When it comes time to look sharp and to look put-together, you really can’t go wrong with one of the best blazers for men, so let’s get you geared up for the occasion. How about it? And hey, here’s a reminder to follow me on Twitter if you like the look of this ensemble below.

The perfect way to wear a blazer this fall? You be the judge.

• The Blazer: Todd Snyder Madison Suit Jacket in Brown Houndstooth, $398 — So, is this stylish blazer a bit of a bold leap? It sure is, but when it’s made by Todd Snyder, the quality is as good as it gets. And when you style one of the best men’s blazers with classic men’s style pieces, it’s a recipe for success.
• The Shirt: Flint and Tinder Garment-Dyed Oxford Shirt, $98 — To team with that Todd Snyder suit jacket, get a certified menswear classic, one of the best Oxford shirts. The folks at Flint and Tinder know how it’s done.
• The Classic Denim: Mott and Bow Slim Crosby Denim, $108 — Yes indeed, some of the best blue jeans for men, especially a pair of Mott and Bow jeans, are going to help ground this outfit in perfectly classic fashion.
• The Boots: FRYE Bowery Chukka Boots, $328 — What you need to really keep this #OOTD rolling is a pair of the best chukka boots for men, and my friends, that’s exactly what you get with the FRYE Bowery Chukka Boots.
• The Belt: Billykirk No. 117 Mechanic’s Belt, $99 — One of the best leather belts for men is an oft-overlooked accessory that can make a big difference in tying an ensemble together, so make sure you’ve got this Billykirk leather belt.
• The Watch: Timex Navi XL Red Bezel Watch, $259 via UNCRATE — That’s right, folks — we’re going with a classic brown leather watch from Timex, as sold by UNCRATE. This is one of the most rugged men’s watches out there, yet it’s also nice and versatile for a fall business casual look.
• The Socks: American Trench Merino Activity Socks with Silver, $19.50 — You should never overlook the details, and these days, if you want the best men’s socks to wear with boots, well, you want American Trench. In fact, the American Trench Merino Activity Socks are easily some of my favorite socks out there, seriously.
• The Getaway Bag: Boarding Pass NYC “Work Hard, Play Hard” Duffel Bag, $79 — My friends, here’s the thing with Boarding Pass NYC. They’ve long been a favorite brand of mine, and seeing as this #OOTD is well-suited for a fall getaway, you need the “Work Hard, Play Hard” Duffel Bag in your life. In fact, you can use the code BEAUKNOWS to get $10 off any purchase over $70 … so, this stylish duffel bag works out mighty well. One of the best weekender bags for fall trips? Easily.

My friends, how are we doing out there? Are we ready, slowly but surely, to dress again in style for fall with one of the best men’s blazers, teamed up with perfectly casual and classic menswear picks? I know I sure am, and I couldn’t be more excited for you (any one of you!?) to try out, say, the Todd Snyder Madison Suit Jacket for a bit of bold fall style. Of course, it’s all grounded the right way with one of the best Oxford shirts, not to mention the best blue jeans for men and a fitting pair of the best chukka boots for men. Each of those pieces are so classic and so well-made, you can wear this look just about anywhere (but especially to the office or to a casual country wedding this fall). It all gets even better with one of the best leather belts for men, a critical pairing alongside a classic brown leather watch from Timex. And it really wouldn’t be a fall outfit without the best men’s socks to wear with boots, courtesy of my friends at American Trench. If you can believe it, it’s all tied together by the “Work Hard, Play Hard” Duffel Bag from Boarding Pass NYC, one of the best weekender bags for a trip out of town or a day on the road (don’t forget the discount code BEAUKNOWS for $20 off!). So, folks … what do ya say? Who’s ready for fall dressing in earnest? I know I am. As always, thanks for reading!