Fall Essentials from a Menswear Stylist


A change of season is once again upon us. Here in New England, my backyard is slowly turning orange and yellow from fallen leaves and I am (thankfully) grabbing a sweater more and more before I leave the house. As a menswear stylist, transitional dressing is one of the most common concerns clients come to me with, especially this time of year when summer weather hasn’t fully released its grip on the five-day forecast. The same holds true for later in the year when we slide from comfortable fall temperatures to slushy winter weather. And it’s understandable: when the weather demands something different from us day to day, sometimes hour to hour, it’s tricky.  

Because you can’t outsmart the elements and you can’t outdress mother nature. That doesn’t mean taste has to suffer. By contrast, dropping temperatures mean more options; fall is, in my professional opinion, the most stylish season. It’s all about cozy layers and rustic textures. Aesthetically, few things are as pleasing to my eye than tweeds layered with wool layered with subtle but rich flannel. But vanity aside, the art of layering and investing in good layering pieces is also a matter of strict practicality: the walk from the car to the restaurant might be cold but at the table you might find yourself overheating and needing to shed a layer, ditto the office where the heat is certain to kick on (prematurely) any day now. The secret is not just that you need to layer, but how to layer: how to pick the right fabrics, textures, colors, and pieces so that you can move seamlessly through your day – and through different temperatures – without ever looking out of place.

I get that these calculations are perhaps not as second nature to someone who didn’t grow up being forced into L.L. Bean Boots (before they were influencer favorites) so I love applying the savvy I’ve learned in my thirty two years in a climate that is as demanding as it is dynamic to ensure my clients look as good as they feel in what they’re wearing. Here are ten essentials that look effortlessly stylish and that can sustain some wear and tear from the elements. 

The Shaggy Dog Sweater

Shaggy Dog Sweater

J Press

The perfect sweater is a non-negotiable for fall and I adore the iconic Shetland-made Shaggy Dog sweaters which have been a J.Press staple for over 80 years. It comes in every color imaginable and I’d recommend starting with a few basics like the navy or tan. The rustic texture makes these sweaters ideal as a standalone or as a layering piece; one of my favorite ways to add interest to a fall outfit is to layer neutral pieces in varying textures so I’d recommend pairing a neutral Shaggy Dog with a wool blazer in herringbone or harris tweed. 

Ralph Lauren Corduroy Pants

Ralph Lauren corduroy trousers

Ralph Lauren

Speaking of texture, I have always had a pair of corduroy pants in my closet for fall; in high school I lived in a pair of corduroy five pocket pants from Ralph Lauren’s Rugby (RIP) because they were warmer than chinos or jeans, and they still looked polished – allowing me to adhere to my prep school’s dress code without sacrificing on practicality. Thankfully, in Rugby’s absence Ralph Lauren continues to carry a great selection of cords, my favorite being this relaxed fit, pleated pair that comes in a great selection of colors. 

Barbour Waxed Jacket

Barbour Bedale

Barbour

As soon as the temperature drops below sixty, I always throw a jacket in the car and the one I reach for most and the one I recommend most often to clients is the same: the classic Barbour Bedale Barn Jacket. It’s virtually impossible to kill this jacket and the removable insert means that, depending on how cold weather hearty you are, it can carry you from early fall all the way into snowier days. 

Woolrich Flannel Shirt

Woolrich flannel shirt

Woolrich

For chillier days, swap out your poplin button downs for a high quality flannel. I find Woolrich’s wares outside of their winter coats to be criminally underrated and the flannels they offer are no exception. My very particular New Englander father stocks up on them every year despite the fact that ones from the year before still look and wear like new. They’re great both layered over tees or lightweight crewneck knits or on their own.

Anderson & Sheppard Merino Polo

Anderson and Sheppard

Anderson and Sheppard

One of my absolute favorite cool weather wardrobe staples is a knit, long sleeve polo. Another piece that’s great as a standalone or under a blazer, these are easy to pair, and look more refined than a simple crewneck. I recommend most of my clients have one at least in navy, but they pair well with everything from jeans to trousers so I’d never discourage picking them up in a few colors. 

Fortela Houndstooth Jacket

Fortela Houndstooth tweed jacket

Fortela

A plaid or tweed blazer is a nonnegotiable as far as I’m concerned. There is something so timelessly collegiate about this piece; it can be dressed up with trousers and a formal shirt, or styled with a more relaxed vibe a la Robert Redford in Three Days of the Condor with jeans and a sweater. This brown, green, and subtle purple in this double breasted option from Fortela make it a unique but incredibly wearable option. 

The Andover Shop Windowpane Wool Trouser

Andover Shop tweed trouser

The Andover Shop

Practically every Harvard professor is on the client roster at the Andover Shop and with good reason – among their countless collegiate essentials are these windowpane wool trousers which are one hundred percent lambswool so perfect for the cooler months. 

Caroline Andrew Field Jacket

Caroline Andrew field jacket

Caroline Andrew

A field jacket is one of the most essential pieces in any man’s wardrobe as far as I’m concerned and my absolute favorite on the market is this beauty from one of London’s best bespoke tailors, Caroline Andrew. Available in a variety of materials, I’d recommend a lightweight wool or wool blend for chilly fall days. 

Alden Rubber Sole Boot

Alden Rubber Sole Boot

Alden

To my mind, few things look sillier in fall and winter than a fussy leather soled shoe. Whether it’s to accommodate thick socks or brave a slick sidewalk, a rubber sole boot is something you simply cannot go without in fall. And while I will always and forever be a ride or die for the classic Bean Boot, it doesn’t hurt to have a boot for slightly less inclement weather that blends a little more seamlessly with your wardrobe and looks less utilitarian.





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