Maybe it’s because I was born in October, but fall has always been my favorite season. To me, it’s also the most exciting time of the year to get dressed — not too hot, not too cold. I like nothing better than banishing the shorts and short sleeves to the back of the closet and pulling out the flannel, corduroy, and dark denim. And even though I haven’t gone back to school in quite some time, every September, I still enjoy treating myself to some new pieces to fill any holes from the previous year. And you should, too. Here are a few tips for looking better this fall.

Embrace Color

Most guys seem to resist color for fear of being…colorful. But wearing color shows confidence, and if you like compliments, you will get them if you stray from your usual palette. Just ask a male cardinal or peacock. Add pieces to your fall closet that will turn heads when you’re out and about in October like Mr. Autumn Man with that pumpkin-spice coffee. Try a Levis red Trucker jacket, or an orange cardigan like this one from Thomas Pink. One of my favorite colors is teal, and while I might not have many opportunities to wear it, this backpack from Heritage gives me the chance to sling it over my shoulder. If you regularly wear khakis, lose the boring beige and go with some slim chinos from Original Penguin in bright blue or a pair of burgundy cords from J. Crew. You don’t really want to blend in, do you?

TIP: Don’t wear it all at once. Let one bold piece and an accessory like a tie or a pocket square do the heavy lifting.

Don A Henley

A Henley is often referred to as the most masculine shirt a man can wear. Perhaps that’s because they were first worn by the rowing team of the English town of Henley-on-Thames — you know, men being manly (nothing to do with singing drummers of 70's rock bands). They have a rugged, timeless appeal, like the type of garment the handsome, sweaty farm worker rips off as he seduces the wealthy land owner’s wife. Dressier than a T-shirt, and less prep-school than a polo, Henleys come in all colors, cuts, and weights. In short or long sleeves, you can wear one with just about anything — khakis, jeans, cords, or even trousers, like Ryan Gosling below. 

TIP: For fall, layer it with a printed flannel and a corduroy suit jacket, or even with a casual suit. Just unbutton a few buttons and the world is yours. 

Improve Your Sneaker Game

One of the best things about going back to school was getting new sneakers. There are endless choices of “fresh crepes” (sneaker slang) these days, but too many guys just go with what they know or think is comfortable (take a long hike away from the hiking shoes!). Having style is about looking for sharp alternatives and taking chances. So ditch safety this fall, and try a gum sole from Vans or Common Projects, or go for a high classic like Spring Court tennis sneakers in white (the “trainers” John Lennon wore with his white suit on the cover of Abbey Road — a truly iconic moment in men’s style). If you’re partial to more mainstream brands, Adidas Sambas in black look great with anything, or a pair of New Balance 410 Retros in blue and orange will tell the world that you’re a “cozy boy” (stylish yet comfortable – more sneaker slang).

TIP: Switch out the laces with different color laces after a few months. You’ll nearly trick yourself into thinking you got a new pair of kicks.

Go Wide

The Mad Men-style fedoras of the last several years were largely a welcome trend. It was refreshing to see something other than baseball caps on male heads. But now that every Tom, Dick and Broseph are sporting stingy brims (often in flip flops and shorts, no less!), you’ll want to up the ante. A wide-brim hat is less casual and takes a bit more daring, but who would you rather look like, Porky Pig going out for a Sunday drive, or David Bowie stalking Berlin in the late 70s? And the heavy felt of a wide-brim fedora is perfect for fall and winter. 

TIP: Eschew anything resembling Indiana Jones' or Garth Brooks' hat. Think rabbi or Al Capone. If you feel like the hat is wearing you, switch gears and try something a bit less conspicuous, like this driving cap on the head of Eddie Japan keyboardist Aaron Rosenthal. 

Beard Up

You’ve probably already seen the click pieces that say beards are over and that you should immediately shave. Perhaps that might be true of the ZZ Top meets Civil War general-style beards made popular by a certain demographic that I won't refer to as "hipsters," but a more modest beard never need go out of style. And there are lots of good reasons to wear a beard. For one, science says so. If you’d like to be seen as attractive to women, studies have shown that women prefer men with heavy stubble or a short beard. If you’re over 40, you’ve probably noticed that your face is starting to lose its youthful construction. A trimmed beard gives the face dimension and can sharpen a jaw that is starting to slip. It’s also a nice layer of protection from the oncoming cold and will mitigate your pale winter pallor. And you can shave it off in the spring for a new look. 

TIP: Don’t stop your beard at the bottom of your face unless you like the chinstrap look. Let it grow down your neck about a half inch or so above your Adam’s apple, and taper it up towards your earlobes. If you’ve got some gray, I say go with it!

Here we see George Clooney and Tom Ford getting it very right, as they usually do.

Drop 10

Most people wait until winter is over to lose weight, but why not get a head start as you go into the more sedentary, snack-filled months? Between the holidays, football parties, and the 12 feet of snow outside your door, it’s easy to put on the pounds between November and March. But if you knock off 5-10 pounds now, you might actually be inspired to keep them off. And you’ll look and feel better in all those new clothes you’re going to buy. 

TIP: Exercise is always important, but weight loss is mostly about diet. Make a few tweaks to what you usually eat (and drink!), and you should see 5-10 lbs pounds come off in a few weeks.

More About David Santos

David is a husband, father, real estate professional, and singer/songwriter with the Boston-based band Eddie Japan (2013 Winners of the prestigious Rock 'N' Roll Rumble). He also loves clothes. Be sure to click over to his new FB page - Dress Like A Man, where you'll find more grooming, health and lifestyle tips for the modern gentleman with an edge.

Photo Credits: All photos courtesy of David Santos