I have a confession to make...

I still have some of the same shirts I’ve owned since high school.

If you’re an average guy, you can probably relate.

On one hand, this seems charming. I’d like to think that some of these items have a sort of timeless appeal – the soft black t-shirt that, when you put it on, reminds you of late night teenage summer drives and kissing your high school girlfriend; a well-worn flannel that feels like what you would imagine it’s like to wear a cloud from Oregon.

Then there are those other pieces that, knowing your luck, you would probably be wearing when you got into a car accident on laundry day.

A sport coat with the fit of a cardboard box or a shirt that you might as well have borrowed from Tim Duncan.

I would never call myself an optimist, but I am a prisoner of hope. And, I believe that this upcoming season offers some hope for men who can find themselves in a bit of a style quandary that might induce a panic-fueled reintroduction of these into your wardrobe (just kidding, I hope it’s not that bad).

Anyway, here is a list of what will take your style game to the next level this winter:

A Proper Hat

If you’re worried that you might end up looking like Dick Tracy or a retiree on his favorite golf course, let me take a moment to calm your fears.

Sometimes the finest style improvements are all about subtle, time-tested classics paired with a modern aesthetic. A fresh hat is a great way to enhance any outfit and put extra swagger in your step.

Whether you are pairing a fedora or other wide-brimmed variation with some black jeans and a patterned button-down or sporting a fitted knit with some fresh white Jack Purcell’s and a solid gray tee, all I am asking is that you give it a shot.

But please, promise me you won’t check it in every mirror or window you walk past. That, I can assure you, is not a good look.

Style in Action

The Oversized Crewneck

Menswear has gravitated toward slim, tailored lines for some time now. And it isn’t a bad call (remember,Tim Duncan). I rue the day I will be on here writing about how every one of us needs to wise up and spring for the perfect Zoot Suit.

But, I think fashion has always had something to say about being inventive, and I’m hear to make your life a little easier when you decide it is time to spring for some new clothes. Besides, the fact that you are already Google-ing what to wear this winter tells me that you don’t want to walk outside every day in sweatpants and a Trogdor t-shirt, so let’s keep giving this a go.

Winter Saturdays in 2014 = oversized crewneck sweatshirts.

This might be the most versatile item in your closet this season. It can be paired with jeans, chinos, worn over shirts with collars, layered with jackets, coupled with boots or sneakers. It’s ingenious and simple. Buy one. Now.

Style in Action

Gym Bag

The phrase “gym bag” probably has you thinking of a dingy Adidas duffel, or maybe it is code language for “that thing in the back of my closet that’s full of old socks and a smelly shirt from the 5k I did in 2001.” But the gym bag is a classy and legitimate option for carrying all your essentials like an iPad, laptop, notebook, folders, and Cormac McCarthy’s All The Pretty Horses.

In keeping with these style options, these bags go with just about anything – from a suit to a bomber jacket to your trusty sweater. I recommend grabbing one in leather if you tend to live on the “dressy” side, and waxed canvas is a perfect option for someone who spends more time looking casual.

Style in Action

The Right Coat

This is a broad category, which is actually a good thing. I’m going to throw out a few ideas, and you can either snag one or all of them, based on what you want and need.

We’ve been hearing that quilted jackets are feeling strong this season, and it is no surprise. Their blend of rugged and polished personality makes them a strong frontrunner. Also, bomber jackets certainly deserve mentioning. If you’ve never put on a leather jacket, I recommend you to do so sooner rather than later. It’s the style version of eating a red mushroom in Mario Bros.

For the more gainfully employed among us, why not try a double-breasted overcoat or a duffle coat?

Style in Action

Bonus Points for Reading this Far

Just so you all know, greens, oranges, and florals are going to be big this season.

If you’re looking for a way to spice things up and feel confident doing it, grab a few items in these colors/patterns, and you’ll be on the right track.

A Solid Pair of Boots

In case you haven’t noticed, 2014 is a great year for menswear, and this is true all the way down to your feet.

In the winter, boots make for great fodder to show off your seasonal know-how and are great conversation starters. Like a clean pair of Jordans, boots are practically eyeball magnets for passersby. Go chukka or duck boots when you’re hanging out, Chelsea boots when you feel like you want to ditch the laces, and a tan/brown brogue boot when you are in the office or dressing up.

Style in Action

At the end of the day, if you are wearing your clothes with confidence and pride, you’re going to make the clothes you wear look good.

So, above all else, love your clothes and love yourself. Happy outfit hunting!

And always remember...

Lauren Hutton Model / Actress

Fashion is what you’re offered four times a year by designers. And style is what you choose.

About the author

Brandon Brown

Brandon Jordan Brown was born in Birmingham, Alabama, and raised in the South. He moved to California to pursue his MA in theology and currently lives in Los Angeles. Brandon is a 2014 PEN Center USA Emerging Voices Fellow, and his work has been published or is forthcoming in The Bakery, Day One, decomP , The Rufous City Review, Winter Tangerine and Cultural Weekly. He also curates a book review series for Fox Hunting, the corresponding blog to Foxing Quarterly, a print literary journal based in Austin, Texas. Currently, Brandon is writing his first full-length book of poetry.

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