Fall will forever be my favorite season for style. All those clothing options – coats, boots, and my favorite, leather jackets, give you so much more opportunity to look amazing.

There is an unfortunate side to fall and winter style though. Men tend to gravitate towards black. I get it, it looks cool and is the easy choice. But you also run the high risk of looking like sad, dreary blobs in the gloomy winter weather.

This year I went back to the drawing board with my seasonal guide. It’s time to give you guys a kick in the ass and show you how to step up your fall/winter style game.

In this guide, you’ll learn:

  • Why the skinny look is dead (and what you should be wearing instead).
  • How to stop looking like sad grey blobs and wear more color this fall.
  • My favorite alternative to huge, awkward, rubber rainboots and a ton more recommendations to protect you from this seasons ugliest weather.
  • And much, much more!

Warning! This guide is huge. To make things easier navigate, I’ve put together a clickable table of contents. 

Part 1: How to Dress This Fall

This season we’re going to dip our toes into this Fall’s biggest trends to give your style a fresh upgrade.

The Skinny Look is Dead

Even as a guy that isn’t rocking 10% bodyfat, I can appreciate what the trend of skinnier cuts for clothes has done for men’s style. As I’ve said in the past, wearing clothes that fit properly is going to fix 90% of your style problems. Having clothes fit on the slimmer side helps.

But the trend toward slim clothes has been going on for nearly 17 years now. The guy that’s rocking head to toe fitted clothes has become almost a basic look.

So what’s the alternative?

The well dressed men of the world right now have been going oversized. But before you pull out your 90s era looks, there’s one key you have to keep in mind if you want to move away from skinny this fall.


In order to make oversized pieces, whether it’s your coat, sweater, or pants, you want a bit of contrast. Use these easy formulas to make sure your proportions are balanced:

Black is Boring: Wear More Color With These Fall Colors Mixing Recipes

I’m not going to sugarcoat it, this season I want you to wear more color.

Here are a few simple ways to add more color to your look without having to remember any complicated color theory concepts.

Easy Mode: Go For The Pop Color/Pattern

The most basic form of adding color to your wardrobe is putting together a mostly neutral outfit, then picking one (or a few) pieces in a high contrast color or pattern to “pop”.

The easy choices are your scarf, sock, or beanie. For something a bit more bold, you can opt for a high contrast sweater or even a jacket (like the gentleman in the suede leather jacket above.)

Screw The Color Wheel, Think Tried and True Combos

You probably know by now how much I hate the classic color wheel/theory advice on how to mix colors. (Spoiler alert: It’s bullshit).

I like to teach guys how to mix colors the same way chefs learn flavor combinations, something I call “Color Profiles”.

Essentially, they are tried to true combinations that have been passed on and stood the test of time. So instead of trying to learn about primary, tertiary, and all that color wheel b.s., let’s just follow great examples and call it a day.

Here are some of my favorites to get you started:


When In Doubt, Go Tone on Tone

Second to wearing a pop color/pattern, rocking tone on tone is another easy way to wear more color this fall.

The concept is simple: start with a color, like a brown coat, and pair it with pieces that are also brown but in different tones (or intensity). The trick to pulling this off is making sure there’s enough of a difference in a few pieces to give you some depth.

Part 2: Fall Essentials Your Wardrobe Needs

ACNE Studios Double-Faced Wool and Cashmere Coat, $1,150

The Oversized Topcoat

Traditionally topcoats (also called overcoats) are meant to be worn over your jacket (hence the name). Personally, I treat it like a long jacket, wearing it over sweaters or a button-up shirt to give my legs a bit more coverage from the winter chills.

This season I recommend going for an oversized topcoat for a more relaxed vibe. Remember to pair it with tailored pants to balance out the proportions.

One final important note – look for coats labeled “oversized” or described as having a “relaxed fit”. I don’t recommend buying a regular coat and sizing up, as the proportions will be off.

Budget: COS Raglan Sleeve Wool Coat, $275
Mid-range: Robert Geller Thomas Coat, $780 (Peter’s Pick)
Investment: ACNE Studios Double-Faced Wool and Cashmere Coat, $1,150

Engineered Garments Bedford Jacket, $477

The Patch Pocket Jacket

My usual go-to casual jacket has always been either a bomber or a denim jacket.

I’ll be quite honest, I’m pretty bored of seeing guys in bomber jackets. That’s why this season my recommendation for your go-to casual jacket be something more tailored.

Some people call it at work jacket, others a chore jacket, or even a carpenter jacket.

Key Details of this style of jacket are the front patch pockets. You’ll often find this style of jacket in denim, but my favorite take on this jacket comes in more fall appropriate wool. Engineered Garments take on this style, their signature “Bedford Jacket”, features small peaked lapels and super functional patch pockets. They carry this jacket from season to season, offering it in all sorts of materials from unlined cotton to winter ready flannel wool.

What I love most about this piece is how versatile it is. Looks amazing with a pair of jeans and boots, yet if you wear this in place of a blazer you won’t look out of place at work.

Budget: COS Flannel Blazer with Patch Pockets, $225
Mid-range: Engineered Garments Bedford Jacket, $477 (Peter’s Pick)
Investment: N/A

J.Crew Twill Brushed Shirt, $79

The Brushed Twill Shirt

You can get away with using your cotton button-up shirts in the fall and winter if you add an extra undershirt layer underneath it. If you’re looking for a sleeker solution, it’s time to swap out that summer weight cotton (or linen) shirt for a brushed twill.

Brushed twill is a cotton fabric that’s passed through wire rollers to pull and fluff the fibers. What you end up with is an extremely soft and warm fabric, perfect for cold weather.

Budget: H&M, $24
Mid-range: J.Crew Twill Brushed Shirt, $79 (Peter’s Pick)
Investment: Bonobos, $98

Intermission: Why Cashmere is Still King

Despite all the advancements recently in fabric technology, there’s nothing quite like putting on a cashmere beanie when it’s cold out.

If you’ve already dreaded wearing anything wool because you always end up itchy with watery eyes, it’s time to become best friends with cashmere.

Before I give you some of my favorite cashmere essentials, let me show you why cashmere is still king of cold weather fibers.

Have you ever picked up a cheap synthetic beanie at Wal-Mart that barely kept your head warm and let tons of wind in?

The reason for this is because synthetic fibers like polyester are ultra smooth. Why does this matter?

Those little irregularities on the natural fibers like wool, alpaca, and cashmere create little microscopic air pockets that trap air molecules. These little molecules bounce around in these pockets, generating heat. Since synthetic fibers are smooth, they don’t create enough tiny air pockets, so they do a bad job as insulating.

Now compare the coarse and fine wool fiber with the cashmere, what do you notice? The cashmere fiber is made up of longer, smoother scales. This makes cashmere soft and less itchy. And a hell of a lot more desirable and expensive.

Luckily, you can find cashmere products from all types of brands. And while they might not all be equal, they’re still better than your run of the mill synthetic counterpart.

Uniqlo Cashmere Sweater, $99

Cashmere Sweater

The cashmere sweater is the perfect layering piece when you need extra warmth. It’s a lot more stylish and less bulky compared to a puffy vest and it’s a hell of a lot softer than a wool sweater.

Bonus: She’s going to want to keep touching you whenever you wear it.

Budget: Uniqlo Cashmere Sweater, $99
Mid-range: Hardy Aimes, $330 (Peter’s Pick) 
Investment: Massimo Alba, $640

COS Cashmere Beanie, $49

Cashmere Beanie

Fun fact: If you’ve ever felt itchy or uncomfortable wearing something like a wool beanie, don’t freak out, you’re not really allergic to wool. Your discomfort usually comes from the coarseness of the wool.

The solution is simple: Switch to a cashmere beanie this fall and your head (and eyes) will love you. Since finally investing in a beautiful cashmere beanie a few years ago, I’ve never gone back

Budget: COS Cashmere Beanie, $49 (Peter’s Pick) 
Mid-range: Margarette Howell, $115
Investment: The Elder Statesment, $280

Schott Sherling Trimmed Leather Jacket, $900

Sherling Lined Leather Bomber

In the past, my go to recommendation for a leather jacket has been a minimal café racer. If you don’t own a jacket and are looking for something extremely versatile, that’s the one I recommend you picking up.

If you’re on your 2nd (or 10th like me) leather jacket, then I recommend a big bomber, preferably something with a sherling or fur trim.

This fall is all about more volume and pushing the envelope a bit more with your style.

Why did I recommend this over, say, a double rider jacket? Well, I just feel like a double rider is what everyone thinks when it comes to leather jackets. To be blunt, it’s a bit boring and expected, and this season I want us to stand out.

Budget: Schott Wool & Leather Sherling Trimmed Jacket, $585
Mid-range: Schott Sherling Trimmed Leather Jacket, $900
Investment: Loewe Sherling Trimmed Leather Jacket, $4,150

Need some guidance on buying leather jackets? Click here to check out my ultimate guide to buying a leather jacket. 

COS Pleated Chinos, $99

Pleated Pant

Earlier I called the end of the skinny look. This means it’s time to embrace the pleated, relaxed leg pant. But before you have horrible flashbacks of photos of your dad in the 80’s, you can rest easy knowing designers today aren’t putting out your dad’s pleated pants.

Today’s options are a lot more tailored and flattering. Pleated pants with a slight taper make it more stylish and modern.

This season we’re going to keep in mind balancing our proportions. Remember to wear these more relaxed pants with fitted shirts, sweaters, jackets and coats.

Budget: N/A
Mid-range: COS Pleated Chinos, $99 (Peter’s Pick)
Investment: Enlist Wool Pleated Pants, $275

Club Monaco, $100

Fall Colored Chino

I’ve mentioned before how if I had to choose only one pair of pant to own, it would be the chino. The most versatile pants you can own. If you’ve been smart enough to follow my advice on building a minimalist, versatile wardrobe, chances are you already have a few pairs in colors you can rock with anything.

Now it’s time to give your pants a bit of the fall treatment and pick up some cold weather colors. Brands like Bonobos put out amazing chinos in almost every shade.

A few color recommendations for your fall wardrobe? Olive, Maroon, and Brown.

Budget: Uniqlo, $49
Mid-range: Bonobos, $98 (Peter’s Pick)
Investment: Club Monaco, $100

Jean Shop Mick-Fit Selvedge Denim, $195

Washed Blue Denim

This is going to be a surprise to you, but I’m fully embracing the addition of some light washed denim into your Fall mix. Two reasons for this. First, you can totally rock these come springtime. Second, it gives your outfits a nice shot of brightness and color without going overboard.  You already have enough dark pants in your fall wardrobe.

Budget: Uniqlo, $49
Mid-range: Bonobos, $128
Investment: Jean Shop Mick-Fit Selvedge Denim, $195

Left to Right: J.Crew, $14 | Beams Plus, $20 | Uniqlo, $3/ea

Color and Patterned Socks

I believe your socks should be colorful and patterned no matter what the season. When it comes to your core socks, your black dress socks and the like, I actually recommending spending a bit more.

But when it comes to all the fun colors and patterns, I say go a bit budget, buy a lot more and mix things up. Uniqlo has always been my go-to for stocking up on colored socks, but I’ve been loving J.Crew’s offering lately.

Thursday Captain Boots, $199

The Perfect Boot

Fall without boots is like Summer without the sun. What makes a perfect boot? Versatility for one. It should look just as good with a suit as it does with a pair of jeans. Rugged. It should be able to take a beating, whether that’s deep in the woods or making your way through the city in a rain storm. Finally, it should be repairable. The best boots were made to be past down.

Thursday Boot Co’s have been the brand I’ve recommended to my clients for good reason: they’re extremely comfortable, look amazing, and such a deal. They’re really a great entry level boot for anyone interested in well crafted, goodyear Welt shoes. This season, they’re my only recommendation for boots. I’m confident you’re going to love them.

Intermission: Why I Don’t Shine My Own Shoes (And Why You Shouldn’t Either)

Check out any top 10 list of skills every man should know and without a doubt “a man should know how to shine his shoes” will be on there.

Look, I get the nostalgia tidbit, but it’s one of those things that I think sounds cool to recommend but people don’t actually do it. As a guy that does know how to shine his shoes, I recommend you don’t.

Why? Because it’s time consuming, messy, and you’re most likely not even doing it right.

Do what I do, find yourself a local cobbler who has a huge stockpile of polish in all shades/brands and drop off your shoes every few weeks. My cobbler are magicians and can condition, buff, and polish the driest of leather shoes I have in the time it takes for me to scroll through my instagram feed.


Nike Internationalist iD (Custom Suede Colorway), $125

Suede Sneakers

I’ll admit that I’m a sneaker guy. You’ll probably find me in sneakers 90% of the time (the rest in a military boot).

How do we make sneakers interesting for fall? Add a bit of texture by going with a suede sneaker. Grey or Cream are both  great versatile color choices as they show off the texture of the suede better than white, but don’t be afraid of something like a maroon which can add a bit of pop color to your look.

Budget: Converse Suede One Star, $90
Mid-range: Nike Internationalist iD (Custom Suede Colorway), $125 (Peter’s Pick)  
Investment: Common Projects Achilles Suede Sneakers, $425

How to take care of your suede shoes: Suede shoes are a reminder that there’s no such thing as a free lunch. Suede, while beautiful, has one enemy: water.

Get water on these things and what you’ll end up with is a crusty shoe reminiscent of a scab. That’s why I recommend picking up a suede waterproofing spray and treating your suede sneakers (and anything else suede you might have) immediately. Do them in a few coats. And if you do get water on them, it’s not the end of the world. A suede eraser can buff and revive suede nape to almost new.

The Art of Layering

Great fall style is all about the layering.

One key to layering that most guys often overlook: layering is not just about a jacket over a button up. You can add some super interesting depth and style to your looks layering different jackets and coats, formal with casual, on top of each other.


More Tips on Layering From Barron Cuadro of Effortless Gent


I reached out to my fellow men’s fashion expert Barron over at Effortless Gent to swap some advice on layering. You can read what I wrote for him on his site here. Here’s what he had to share for Essential Man Readers:

“Fall and winter are obviously great for layering… not only for warmth, but for the opportunity to put together outfits that are more visually interesting. There’s a subtle art to layering, but beyond pairing up great combos of color, pattern, and texture, considering each garment’s fit and thickness is equally important.

For max comfort, make sure the layers closest to your skin (whether they’re long johns or a T-shirt) are the thinnest and most form-fitting. From there, everything else you put on should be a bit thicker and looser-fitting. Thicker for warmth, and looser to accommodate the layers underneath and minimize the potential bunching and wrinkling.

That way, when you put on your button-up shirt, sweater, vest, coat, and scarf, everything will fit comfortably and you’ll be nice and warm.”

3 Situations, 3 Looks

Jacket: Engineered Garments Bedford Jacket $477 | Shirt: J.Crew Brushed Twill Shirt, $79 | Pants: Club Monaco Chinos, $100 | Socks: J.Crew, $14 | Belt: J.Crew, $45 | Boots: Thursday Boot Co., $199 | Cologne: Commes Des Garcon Kyoto, $95 | Pocket Square: Paul Smith, $60 | Bag: Want Les Essentials, $250


Coat: ACNE, $1,150 | Shirt: J.Crew Brushed Twill Shirt, $79 | Jeans: Jean Shop Mick-Fit Selvedge Denim, $195 | Scarf: J.Crew Wool/Silk Scarf, $80 | Belt: J.Crew, $45 | Socks: Mr. Gray, $25 | Shoe: Converse Suede One Star, $90
Jacket: Schott Sherling Trimmed Leather Jacket, $900 | Sweater: COS Cotton and Yak Sweater, $89 | Shirt: COS Granddad collar shirt, $89 | Pants: Enlist Wool Pleated Pants, $275 | Socks: Uniqlo, $3 | Sneakers: Nike Internationalist, $125 | Cologne: Frederic Malle Vetiver Extraordinaire, $215

Part 3: Fall/Winter Reader Questions, Answered

How to Pick The Perfect Fall Scent

Question: “Hey Peter, I’d love some advice for getting some fall colognes. Thanks!” – Craig

Men, it’s time to put away your shower fresh citrus heavy scents. I reached out to my go to scent expert, Rachel Beider, a certified aromatherapist and owner of Massage Williamsburg and Massage Greenpoint.

For fall Rachel recommends going for scents with notes of leather, dirt, earth, wood or incense. She’s broken down a few of her favorites below.

Warm Woods:
Tom Ford Oud Wood, $230: Smells like powdery, warm, wood.
Commes Des Garcon Hinoki, $120Smells like walking through a fresh, soft cedar forest.

Commes Des Garcon: Kyoto, $95:
Smells like you’re burning incense in a Japanese temple in the winter. It’s warm and spicy. One of my favorites.
Ds & Durga: Mississippi Medicine, $260Smells like camping in the woods with an old book; cedar, tar, incense.

Warmth, Musk:
Sophia Matthias: 1509 with Sage, $90
Smells like warm amber with a touch of sage, dark.
Histoires De Parfums: Ambre 114, $35Smells like powdery, warm amber, with a bit of citrus.

Frederic Malle Vetiver Extraordinaire, $60 (.3oz):
Smells like citrusy, freshly cut grass with some warm wood.
Terre d’Hermes, $58: Smells like dried orange peels, fresh bright scent with a touch of warmth. A lighter

How to Properly Apply Cologne:

Again, over to Rachel!

“The over application of scent is my biggest no no. Scent should draw you in, not repel you. It should have a very nuzzling and embracing quality.

Some do’s and don’ts:

  • Don’t use too much! Your neighbors shouldn’t be able to smell you.
  • Don’t spray it on your wrists. The idea about spraying fragrance on your wrists was started by department stores. Every time you grab a new item of clothing and check it out, the motion wafts the wrist scent toward your direction. They want you to keep smelling it as you shopped and entice you into buying.
  • Spraying in the air and walking through is a bit of a waste.

To start, I’d suggest ONE spray onto your shirtless chest, or ONE spray between the shoulder blades. (Just reach over your head and spray towards your shoulder blades.)

I like scents on the back for a man, because when I go to give them a hug, I get a whiff of their scent from over their shoulder. It’s not too overwhelming.

Be cautious about the neck (especially if you’re on a potentially amorous date – no one wants a mouthful of scent).”


How to Avoid Looking Like an Old Man This Fall

Question: “How do I rock chunky sweaters and cardigans without looking like Mr. Rogers?” – Andrew

First, how dare you. Mr. Rogers is a national treasure and a style icon.

My advice if you don’t want to look like an old man is to make sure the rest of your outfit is a bit modern. If you’re rocking a knit cardigan with ill fitting flannel pants, loafers, and New Balance sneakers, it’s hard to avoid looking like you smell like Ben Gay.

Keep in mind balancing proportions this fall. If your knit is chunky and big, make sure your pants are tailored and fitted. If your rocking a slim/tight sweater, you can go with pants with a bit more volume.

On Staying Dry and Stylish

Question: “Hi Peter, on the subject of fall clothes: what about raincoats? Or do we just take umbrellas?” – Martin B.

The first recommendation I have is to upgrade your umbrella.

Repel Teflon Umbrella, $21

The Repel umbrella is one of the highest rated umbrellas in recent times, why? This Teflon coated compact beast of an umbrella has been dominating top 10 lists for good reason. It’s teflon coated, so it beads off rain better than anything else in the market. 9 reinforced ribs prevent it from turning inside out. Most importantly it open and closes at the touch of a button, a godsend if you ride the subway.

Second, I agree about traditional and trendy raincoats like the Sutterheim. It can sometimes feel like you’re wearing a body condom. Luckily, you have a few awesome traditional, like the Mackintosh coat, as well as modern techy options from brands like Arc’Teryx Veilance.


Timberland Waterproof West Haven Boot, $109

If you’re like me and hate rainboots, companies like Timberland have been releasing some awesome rainboots in disguise, like The West Haven ($109)

There are some days where wearing snow boots is overkill. While wearing sneakers makes you look like a tourist who’s never seen snow in his life. Timberlands waterproof boot is a rainboot masquerading as a rugged, everyday casual boot. Waterproofing is done during the tanning process of the leather, going beyond the topical coat that over-the-counter sprays offer.

The West Haven’s have sealed seams throughout to keep your feet completely dry. Timberland’s trademark Gripstick sole spreads water away, giving your foot more surface contact with the ground preventing slips.

It’s the perfect rainboot if you hate rainboots.

Part 4: Winter is Here

For those who don’t have four true seasons, the fall wardrobe essentials will get you through winter no problem. But if you’re like me who live in places like New York where we can wake up to knee deep snow, you might need to stock your closet with some winter essentials.

Winter Essentials

The Fur Trimmed Parka

There’s just no way around it, the parka is a necessity if you live in a place where the temperatures dip below 30.

Thanks to advances in technology, you no longer have to deal with big puffy parkas. Wind and water repellent materials, along with warmer fillings, have made these guys sleeker than they’ve ever been.
The parka has been a men’s winter staple for the past 65 years, and is a more than acceptable replacement for a tailored top coat, even when you’re donning a suit.

Biggest Tip: Break the monotony of winter blacks and stick to the traditional army green. It’ll give your look much needed color and contrast.

Woolrich’s iconic version of the parka is made from a breathable cotton/nylon, and finished with Teflon to protect you from snow, rain and wind. Duck down and feather filling keeps you extra warm on the inside, while the coyote fur trim will keep any droplets of rain or snow from your face. Pick up this classic and you’ll never have to buy another winter coat for the rest of your life.

Budget: Vince, $499
Mid-range: Woolrich John Rich & Bros, $765 (Peter’s Pick)
Investment: Yves Solomon Fur Lined Parka, $3,050

Uniqlo, $59

The Packable Puffer

There are times where your parka can be a bit overkill. In this case, an ultra light down jacket will turn any piece of outerwear in your closet into a proper winter jacket.

Uniqlo’s ultra light down is sleeker than traditional counterparts, making it the perfect layering piece for your wardrobe. The nylon shell is water-repellant and packs into a small portable pouch.

(Bonus: Makes a totally useable pillow on flights in a pinch.)


Sorel, $170

The Serious Snow Boot

While L.L.Bean is most people’s go-to when it comes to wet weather boots, I’ve never got over how mediocre their signature chain sole was.

Sorel’s AeroTracs, however, give me a lot more grip confidence on the black ice of New York streets. The removable liner (felt in the original, wool in this model that I own) provides a much needed, cushy barrier between you and the rubber lower shell.

And while Sorel doesn’t have the lifetime repair/replace warranty that L.L.Bean has, Sorel owners have shared stories of owning the same pair for over 20 years. It was the snow boot I recommended last year, and it’s the one I’m recommending again this year. It can’t be beat.


Uniqlo Heattech, Price Varies

Heat Tech Everything

Uniqlo HeatTech clothes have become a winter staple for me here in New York since they launched in 2010.

Developed in conjunction with textile manufacturer Toray, Uniqlo’s proprietary blend of acrylic, cupro, nylon, polyester and spandex traps heat through their air pockets. It’s essentially a blended, synthetic alternative to wool that feels more like a cotton.

Heattech are the perfect solution to staying warm without adding bulk, or needing to buy new winter specific clothes. Throw a pair of Heattech tights under your jeans or chinos and you’re good to go.


Your Short Guide to Better Winter Gloves


Uniqlo’s Heattech gloves got a bit of an upgrade this season. Conductive fibers woven into the gloves allow you to use your touchscreen without needing to take off your gloves. Perfect for Instagramming that snowstorm. Uniqlo


If you need something a little bit more grown up, these knit wool lined leather gloves from Dent are perfect.


Designed for people who like to climb snowy, freezing mountains for fun. Nuff said. (And yes, they are also touchscreen compatible!)

What Are Some of Your Favorite Fall/Winter Gear?

This essential guide will cover most of your bases when it comes to kicking up your fall/winter style. But I’m not done yet. Over the next few weeks I’ll be sharing more fall/winter style tips and recommendations.

In the meantime, I’d love to hear from you. What’s some of your fall/winter style favorites or recommendations?

Was there anything I missed?

Leave a comment below, I’d love to hear!



Hi, I'm Peter. I spent 11 years as a menswear designer here in NYC. Now, I help some of the most successful men look really good as a Private Personal Stylist and writer of The Essential Man. You can learn more about what I do by clicking here