Can you feel it when you walk outside?

There’s a certain crispness in the air. The wind is picking up. The leaves are starting to turn all shades of yellow, orange, and red. You no longer sweat the minute you step outside. Wearing your favorite pair of jeans isn’t as unbearable, because the scorching heat is gone…

Fellas, fall is here!

I live in NYC, and we New Yorkers generally have limited closet space. That means twice a year, we have to swap out our wardrobes. Warm-weather clothes are packed away in the fall and out comes the cold-weather wardrobe. And vice versa when springtime arrives.

(Ahh, the little suburban luxuries you miss when living in the city, but whatever, wouldn’t trade this life for some closet space, sheeeit)

So as I put off doing my twice-yearly swap, I wanted to help you dress sharp this fall and winter, so I put together this fall style guide.

This guide is packed with info! Here are links to the main sections if you want to jump around:

  1. Colors, Fabric, and Fit
  2. Outfit Specifics: What clothes should I add to my closet?
  3. Smart, Sharp Casual: How to dress sharp in cold weather
  4. Putting Together a Fall / Winter Outfit

Let’s get started, shall we?

Colors, Fabric, and Fit

The Best Colors for Fall and Winter Clothes

When you think of fall, winter, and cold weather, what images pop up in your head? For me, it’s stuff like this:

fall winter feelz

And when you think of spring, summer, and hot weather, what images do you think of?

spring summer feelz

When it comes to color, think of your wardrobe in this same way.

For colder weather and the fall and winter seasons, take advantage of darker, richer, and deeper colors: navy, charcoal, camel, eggplant purple, forest green, burgundy, these kinds of colors.

And for spring and summer, you’d obviously be going the opposite route, with lighter colors, pastels, bright and vibrant hues.

The Best Fabrics for Fall and Winter Clothes

In general, your fabrics will be heavier weight and thicker, plus warmer and more insular. This is, of course, to keep the body heat in as you’re braving the colder temperatures.

For suits and sport coats, we’re talking about winter-weight wools, flannels, and tweeds. And if you’re sporting an all-season wool suit, you’ll have to compensate for lack of warmth by layering up either with long johns and thermals, or adding midlayers such as a sweater or thin quilted vest underneath your suit jacket.

For casual clothing, you’ll probably be wearing denim and heavier-weight chinos, twill and flannel shirts, thicker wool, cotton, and cashmere, and heavier canvas and wool outerwear.

Fall, or as I like to call it, “Light Jacket Season” is my favorite time of year. You’re still dressing in a way that’s about style, not necessarily utility. You want to actually look good, not just feel warm. I like to play a game where I see how long I can wear my summer clothes, just by layering in cooler weather pieces. If the temperatures stay as warm as they’ve been, this year I’m shooting for November.

How Fall and Winter Clothes Should Fit

As I mentioned in my summer clothes article, I prefer my warm-weather outfits to be a bit looser and more breathable. I don’t like clothing that’s tight and restrictive especially when it’s hot and humid outside.

It’s the opposite during the fall and winter, especially as you layer. You want to make sure the layers closest to your skin are the most fitted. That way, you avoid any extra bulk or wrinkling as you put on more layers, which is SUPER ANNOYING and uncomfortable.

You may notice some parkas and wool overcoats are slightly oversized even when choosing your size. That’s most likely because they assume you’ll be layering underneath, and the coat is designed to accommodate those extra layers.

Outfit Specifics: “What clothes should I add to my closet?”

Formal and Business: How to wear a suit and tie in cold weather

A few years back, I attended a wedding in Mexico. I was one of the groomsmen, and we were all asked to wear mid-grey suits, white shirts, and a floral tie. Pretty simple.

I bought a Ludlow Traveler suit from J.Crew because I knew I had to:

  1. get that suit all the way to Mexico, and I didn’t want to worry about wrinkling, either while in my suitcase, or on my body… and
  2. The Ludlow Traveler is unlined and very lightweight, which was perfect for that hot Mexico sun.

One of the groomsmen had a mid-grey suit, but it was made from a winter-weight wool (poor guy). This was, legit, something you’d wear to work in the wintertime.

I was DYING in my (lightweight, unlined, unstructured, breathable) suit and had to stand still as much as possible when in direct sunlight so I didn’t sweat profusely. I felt so bad for this guy; I can’t imagine how hot he must’ve been.

winter vs summer suiting

One suit is wool flannel, the other is a lightweight wool… can you tell the difference between the two, just by looking at them? (left, right, both via Brooks Brothers)

If you don’t wear suits often, you don’t realize how many different types of fabric they can be made from, and something that’s appropriate for winter is definitely not one that can be worn to a summer wedding taking place in Mexico.

Just like you have casual shirts that work better in winter than summer (and vice versa), you will have suits that are better for colder weather.

“What kind of fabric should my fall / winter suits be made from?”

Wool flannel is among the comfiest and warmest suiting fabrics.

Also, remember that 100% wool cloth comes in different weights, with 12 oz being the minimum you want for a winter suit. Any lighter, and you’re in “all-season” weight, which also works, but depending on how cold it gets where you live, you will need to layer up.

mtm winter suits

a nice selection of fall and winter fabrics for MTM suits, via Black Lapel (top) and Oliver Wicks (bottom)

If you’re buying suits off the rack (or even MTM), you most likely won’t have to worry about picking a specific weight, as suits will be categorized by season. So you simply shop for fall / winter suiting, or spring / summer suiting, and you’re good.

Once you start going custom, that’s when you can select the specific cloth and weight.


MTM Showdown: See our reviews and first impressions of Black Lapel and Oliver Wicks

“Are some colors better than others for fall and winter suits?”

For a Lean Wardrobe, regardless of season, you’ll want a standard navy and / or mid-grey suit. Other colors that work for fall and winter weather specifically? Brown, rust, forest green, even an ash (light) grey.

If you wear suits every day, you have more options as far as color and pattern (stripes, checks, herringbone, houndstooth… the list goes on), since you have the opportunity to wear them all. But if you don’t wear suits often and you’re concerned about versatility and not looking like you own only one suit, stick to a simple navy and / or mid-grey color with no obvious pattern. A bit of texture, on the other hand, can’t hurt.

“What about shirts, ties, and shoes?”

Everything in your outfit should match the common theme… in this case, weather.

Not only should your suit be cold-weather appropriate, so should your shirt, tie, coat, and all your accessories. Meaning, you’re not going to wear a thin linen shirt with your wool flannel suit. You won’t be rocking unlined suede loafers in the snow with your heavy wool coat. Every element in your outfit needs to follow the theme.

For shirts: Opt for a heavier dress shirt in pinpoint oxford, twill, or flannel. While I won’t go into the details, if you’re curious about the characteristics of different cloths, I suggest checking out the reference guide from our friends at Proper Cloth. Proper Cloth is a great option for MTM shirts. For a nice selection of OTR shirts, check out The Tie Bar.

For ties: I looove wool ties. They produce a substantial knot and look great with heavier-weight suit jackets and sport coats. Grenadine knits (navy and burgundy are perfect Lean Wardrobe staples) also work well in the winter… actually, year-round. And you can’t go wrong with a standard silk tie; just make sure the color palette makes sense with the rest of your outfit.

For shoes: Leather oxfords in brown or black. Make sure to wear overshoes to protect them from water and salt.

A super simple secret to creating a sharp, layered outfit for fall is choosing pieces with different textures. Tweeds, chunky knit sweaters, flannels, wool overcoats, denim and chambray shirts all stack to build an intentional look.

Smart, Sharp Casual: How to dress sharp in cold weather

First, let’s cover a few basics about your casual clothing: Colors, fabric thickness, and amount of clothing.

Colors: My winter wardrobe consists of much darker colors. Lots of navy, black, brown, forest green, burgundy, etc. My staples (like chambray shirts, OCBDs, and grey T-shirts) are the lightest colors that stay in the closet.

spring vs autumn colors

Great example of a spring / summer palette (left) vs. a fall / winter palette (right) (via The Sartorialist). Want to learn how to match clothes like a pro? Check out our eGuide

Compare that to my spring and summer clothing, which is mostly light colors like white, light gray, light blue… plus a few pastels (lavender, light pink) and vibrant colors (orange, magenta). I even put away my dark denim and swap them with my lightweight, stretch, light-wash denim. The only dark colors I have during the spring and summer are my olive and navy linen shirts.

Thickness: The fall and winter wardrobe has plenty of heavier cottons, wools, thicker knits, more substantial woven shirts, etc. All layers in general are thicker, obviously, to keep in warmth.

Contrast that with my spring and summer clothing, which is all lightweight EVERYTHING, from my denim and chinos, to the linen shirts I wear. And forget about layering; I avoid more than one layer unless I absolutely have to (like if I’m going to a nice dinner or getting drinks, I’ll throw on a linen or lightweight, unlined wool sport coat).

Amount: I generally just have more fall- and winter-appropriate clothing. Maybe that’s because there’s more layering involved (although you’d think I would have more spring / summer clothing, since I’m not layering as much…) Anyway, might be a different case for you. Let me know in the comments.

The ideal number of clothes in your lean, minimalist fall / winter wardrobe will depend on your situation, lifestyle, and surroundings. If you’re still in the process of building your minimalist wardrobe, read through all the articles here.

I think a natural tendency for a lot of guys is to grab their puffy coat when it’s cold outside and call it a day. They’re missing out on an opportunity to create a more interesting look with layers, especially when you contrast things like casual and formal pieces.

A great example recently when it was cold: I threw a double breasted blazer over my denim jacket and got a ton of compliments. You can do something similar – wearing a leather jacket under a topcoat, or swapping in a flannel henley in place of a plain undershirt, unbuttoning your dress shirt a bit and letting the henley peak out. What’s great about adding more layering to your fall style is that it lets you wear some of your spring/summer clothes that would normally be too thin when it gets cold out.

Putting Together a Fall / Winter Outfit

As I always say, if you have a lean wardrobe, putting together outfits is simple. And transitioning them from spring / summer to fall / winter? Just as easy!

In general, for colder weather, you’re going to be working with thicker and heavier fabrics, as well as doing a bit more layering.

Y’know, to stay warm.

But the additional benefit to layering is that your outfits look waaaay more interesting than, say, whatever you’d wear during the summer (typically one top and bottom layer BORRRING)

So for this example, I’ll use my lean wardrobe outfit as an example. I’d consider this my base uniform, as I wear some variation of this most days.

default fall winter outfit

Buy Levi’s Denim (similar)
Buy Uniqlo OCBD
Buy SuitSupply sport coat (similar)
Buy Allen Edmonds Loafers

If you look at each piece of the outfit separately, you’ll see that each one can be swapped out with items that are similar, but more appropriate for the season or the venue.

So with every suggestion below, imagine swapping it out with the default option above. And for items that don’t exist in the default option (midlayers), you’d simply add it in (i.e. shirt, VEST, sport coat)

So let’s fall/winter this bitch up! In terms of weather-appropriateness (thicker, warmer layers), here’s what I would do:

Fall / Winter Shirts

fall winter shirt options

Buy Bonobos Chambray Shirt
Buy Bonobos Twill Shirt
Buy Todd Snyder plaid flannel shirt

Ok, so chambray isn’t exactly a fall- and winter-specific shirt. But! I think of them like jeans: easily worn year-round. So if you already have a favorite chambray, keep on wearing it through the winter months, if you please (I know I do).

As far as OCBDs, brands do make lighter-weight versions for spring and summer, but your standard Oxford cloth is pretty substantial and a great option for fall and winter.

I’d also consider flannel and twill shirting; both will keep you warmer during the winter months. Both casual and more formal options exist in both fabrics.

Fall / Winter Midlayers

fall winter midlayer options

Buy J.Crew Factory Walker Vest   Buy SuitSupply Padded Vest
Buy J.Crew Merino V-Neck

Midlayers are the secret sauce of perfectly-layered wardrobes. Instead of wearing one thick, heavy coat, wear a midlayer and a jacket (or a coat that isn’t so thick and heavy).

Having two warm layers makes it easier to regulate body temperature, vs. just a shirt and a thick, heavy coat.

If it gets too warm and you only have a coat on, you’re out of luck. You basically have to take off the coat, and… that’s it. That’s all you have. With no midlayer, you’ll get cold 4 minutes later and have to put the coat back on, and then take it off when you get warm again… it’s a vicious cycle.

From an aesthetic perspective, you can put together a more interesting look with multiple layers.

So really, sweaters and vests not only regulate body temps better, they also add extra oomph to your outfit.

It’s important to make sure you have 2-3 versatile middle layers, such as vests and quarter zip sweaters (which are pretty much interchangeable). To maximize versatility, stick with neutral colors like grey, navy, black, tan or brown.

Most guys have a plenty of inner layers (like button up shirts) and outer layers (lightweight jackets), but the crucial middle layer is sometimes overlooked. My current favorite affordable middle layer is the J. Crew Factory Walker Vest.

Fall / Winter Pants

fall winter pants options

Buy Franklin Tailored Flannel Trousers
Buy Bonobos Bedford Cords

Denim is obviously a great option for fall and winter. If you get the right pair of denim, you’ll be able to wear it casually (T-shirt and sneakers) and more formally (dress shirt, sport coat, and loafers, just like my default Lean Wardrobe outfit at the beginning of this section).

You can also find heavier-weight chinos, and for a dressier option, you can’t go wrong with flannel trousers like the pair from Franklin Tailored, above.

Fall / Winter Shoes

fall winter shoe options

Buy Chippewa Work Boots
Buy Allen Edmonds Strand Brogues

I typically wear brogues during the colder months, as I prefer a lighter-weight unlined leather or suede loafer when it’s hot out.

For a dressed-down shoe that you can wear with all the pant options above (yep, even those tailored trousers! High / Low FTW), you can go with a work boot or a Chelsea boot.

And for a smart, sharp option, go with the Allen Edmonds Strand, an awesome cap toe with beautiful brogue detailing. You’ll see the dark brown model above, but my favorite is the Strand in Walnut.

Fall / Winter Outerwear

fall winter outerwear options

Buy Barbour Quilted Jacket
Buy Todd Snyder + Private White Wool Pea Coat
Buy Polo Ralph Lauren Wool Flannel Down Jacket

By the way, here’s a little tip when it comes to sport coats: Look at them as jackets, instead of “half a suit”. This will help you to not be so intimidated by them. Treating them as jackets makes it easier to incorporate them into more outfits, thus making you look sharper even if the outfit has plenty of casual elements (like denim or white leather sneakers).

For extra warmth, opt for sport coats in a winter-weight wool or tweed. And for a smart, sharp, casual look, you can layer up with a V-neck sweater and a quilted jacket (like the one above), or Ultra-light down vest and a field jacket.

Depending on where you live, during the winter, you may need to go a bit heavier with a top coat, pea coat, parka, or down jacket. The pea coat and down jacket you see above are two of my current favorites.

How do you dress for fall and winter?

What it really boils down to is this: The perfect outfits for you will depend on 1.) weather and 2.) formality.


  1. Weather: If you’re in Minnesota, your fall and winter wardrobe will look a bit different than someone from Miami, or even Manhattan, for that matter.
  2. Formality: And if you’re usually in business formal environments, your everyday outfits will look different compared to, say, a freelance web designer who works out of coffee shops.

Start with a base outfit from your Lean Wardrobe (your uniform, what you typically wear most days) and Autumnize it (I just made up that word) by adding warmer, thicker, softer fabrics.

Where do YOU live? And what’s typical winter wear for you? Tell me below in the comments.

If you found this article useful, make sure to check out our Lean Wardrobe resources page.