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 have limited closet space. 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)
As I put off doing my twice-yearly swap, I want to help you dress sharp for fall and winter. So I put together this men’s winter fashion style guide. Enjoy!
- Colors, Fabric, and Fit
- Fall/Winter Suits and Dress Clothes
- Smart Casual in Cold Weather
- How to Choose and Care for Fall/Winter Shoes
- EG’s Recommendations for Your Fall/Winter Wardrobe
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:
And when you think of spring, summer, and hot weather, what images do you think of?
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, go the opposite route – lighter colors, pastels, bright and vibrant hues.
The Best Fabrics for Fall and Winter Clothes
For men’s winter fashion, your fabrics will be heavier and thicker, warmer and more insular. This keeps the body heat in as you’re braving the colder temperatures.
For suits and sport coats, we’re talking winter-weight wools, flannels, and tweeds. Sporting an all-season wool suit? You’ll have to compensate for lack of warmth by layering up with long johns and thermals. Or by adding mid-layers such as a sweater or thin quilted vest underneath your suit jacket.
For casual clothing, you’ll probably be wearing:
- Heavier-weight chinos
- Twill and flannel shirts
- Thicker wool, cotton, and cashmere
- Heavier canvas and wool outerwear
Here are some ideas with for colors, fabrics, and patterns that don’t suffer from the sometimes dull palette of men’s winter fashion:
Windowpane Print Shirt – This subtle pattern isn’t as bold as gingham, but still adds a nice touch to your dress shirt style. The windowpane design feels like a bit of a throwback while still looking modern. Wear it under a sweater for a look that breaks away from the solid dress shirt most people expect.
Chinos in Fall/Winter Tones – If you love bright and colored chinos in the summer, keep that look for fall. Just switch to darker shades and earthier tones – like burgundy, slate grey, chocolate brown, muted blue, and hunter green.
Mid-Grey Flannel Trousers – This color and fabric are perfect for men’s winter fashion. It might not be the standout piece in your outfit. But the look and texture of these trousers go well with anything in your cold weather wardrobe. And they’re easy to dress both up and down – win-win.
Denim Jacket – On transitional days or when you need extra warmth over a lightweight sweater, a denim jacket is a classic look. You can keep it casual or even rock a tie with your denim – if you style it right, like in these five examples.
Grey Crewneck Sweatshirt – Athleisure is here to stay, but that’s no excuse to look schlubby just to stay warm. Expand your sportswear horizons with a grey crewneck sweatshirt that you can dress up or down with ease. Or rock a V-neck sweater for a similar layering effect but a different visual feel.
Shawl Collar Cardigan – V-neck and crewneck sweaters are great for layering. But if you want a piece with a more rugged edge, look no further than the shawl collar cardigan.
Leather Jacket – Outside of the suit, a leather jacket is one of the biggest investments in your wardrobe. Just like a suit, there’s something transformative about putting on a properly fitted leather jacket. There’s no other way to describe it: You feel like a badass. Check out our guide to choosing the right leather jacket.
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.
It’s the opposite for men’s winter fashion, especially as you layer. You want to make sure the layers closest to your skin are the most fitted. That avoids any extra bulk or wrinkling as you put on more layers – which is SUPER ANNOYING and uncomfortable.
Case in point: sweaters. Bulky sweaters with heavy fabrics and huge sleeves look bad and are no good for layering. To get the perfect fit, you want a slim profile with higher arm holes. It looks better and is much easier to layer over – maybe with a parka or coat.
Blazers give some guys trouble too. Summer-weight blazers are designed to stay close for a fitted look. But you need a bit more space in the winter so you can layer a sweater under it. Get the details in our guide to finding the perfect fit for your blazers – regardless of the season.
You may notice some parkas and topcoats are slightly oversized. You go with your normal size from a brand you know well, but it’s still too big. What gives?
Most likely because they assume you’ll be layering underneath, and the coat is designed to accommodate those extra layers. Choose your size accordingly.
Fall/Winter Suits and Dress Clothes
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:
- Get that suit all the way to Mexico, and I didn’t want to worry about wrinkling – either in my suitcase or on my body – and
- The Ludlow Traveler is unlined and lightweight, perfect for the hot Mexico sun.
One of the groomsmen had a mid-grey suit 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 so I didn’t sweat profusely. I felt so bad for this guy; I can’t imagine how hot he must’ve been.
If you don’t wear suits often, you don’t realize how many different types of fabric they can be made from. Something that’s appropriate for men’s winter fashion is definitely not one that can be worn to a summer wedding in Mexico.
Just like you have casual shirts that work better in winter than in 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.
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. That can work – but depending on how cold it gets where you live, you may need to layer up.
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 they’re 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.
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 (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 either. Every element in your outfit needs to follow the theme of men’s winter fashion.
For shirts: Opt for a heavier dress shirt in pinpoint oxford, twill, or flannel. Curious about the characteristics of different cloths? Check out the reference guide from our friends at Proper Cloth. They’re 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.
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 Casual 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.
Compare that to my spring and summer clothing, which is mostly light colors – like white, light grey, light blue – plus a few pastels (lavender, light pink) and vibrant colors (orange, magenta).
Thickness: Men’s winter fashion has plenty of heavier cottons, wools, thicker knits, more substantial woven shirts, etc. All layers in general are thicker 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.
Smart Casual Accessories
You can elevate your smart casual look with a few carefully chosen accessories. Don’t go crazy here – but do make your outfit stand out with a few stylish touches.
Scarf – A wool or cashmere scarf is the perfect cold weather accessory. You can go with a fall/winter solid, neutral color – like grey – and your scarf will work with anything in your closet. Or choose a standout statement scarf in a colorful plaid. Our guide to scarves – with details on fabrics, knots, and more – can help.
Non-Boring Leather Gloves – Everyone has a pair of leather gloves with the three stitch design across the top. Upgrade to a pair that’s a little different. Think quilted cross stitching on the exterior, a racing inspired snap clasp at the wrist, or a combination leather and knit glove.
Weekender Watch – Even if you’re used to checking the time on your phone, your timepiece is a fun way to show off personal style. This unique strap goes well with the classic Timex watch and looks right at home as a fall staple. It may even become your new everyday statement piece.
Winter Beard – You don’t have to go full on lumberjack. But a bit of well groomed facial hair always fits in during the colder months. To stay professional and well trimmed, keep your neck shaved smooth and your beard lines well defined. The more stubble creep you allow, the less polished it looks.
Tired of the mess you see in and around the sink after trimming your beard? This beard and stubble trimmer from Philips Norelco comes equipped with a hair-capturing vacuum. At first it sounds like a gimmick, but after you use it a few times you’ll realize it cuts down on the mess by about 90%.
Flask – Taking pulls from a flask in the dead of summer means you might have a bit of a problem. But using a flask to carry and consume dark rum, whiskey, or bourbon after the leaves have started to fall is just too enjoyable to pass up. Use it to spike coffee or hot chocolate, or take it for a walk with you while you listen to a Saturday afternoon football game. Just be responsible, inconspicuous, and aware of your city’s public drinking laws.
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.
How to Choose and Care for Fall/Winter Shoes
The wet, slushy, snowy season requires some thoughtful footwear choices. I still see guys walking around in the rain with jeans, Vans, and a hoodie… which confuses me. Is your goal to absorb as much moisture as possible?
It comes down to dressing appropriately for every occasion, and canvas shoes don’t hold up well in a storm.
Start with Socks
Go with merino wool socks for a thick, warm feel without the massive bulk of most heavy winter socks. They can replace your typical summer cotton socks and will winterize even your lightweight sneakers and loafers. Just don’t wear them with a suit – that still calls for a dressier sock.
Winter-Ready Shoes and Boots
Timberland Earthkeepers – I still have my classic boot from the days when I used to wear baggier jeans. If I could remember to pull them out of the closet at my parents’ house, I’d wear them. If I had to start from scratch with Timberland, I’d pick up this pair.
UGG Hannen – These ain’t your usual sorority sister’s Uggs! Vibram soles, lined with sheepskin, and in a cordovan color (editor’s note: not necessarily made of cordovan leather, thanks to reader Andre), these boots look awesome and will keep you warm and dry. They’re in a different league than the ubiquitous slip-on model worn by sloppy American college students nationwide. Just sayin’.
Original Bean Boots from L.L. Bean – These are my rainy day go-tos. I slip them on and go jump in puddles. Sometimes I splash K accidentally, but I don’t always tell her because she’d probably get mad. So yeah, they’re EG tested and approved!
Hunter Original Short Boot – Caught in a downpour? Forced to wade in ankle-high water? Accidentally stepped in a deep puddle? No problem – as long as you have these on your feet.
Allen Edmonds Strand – Rock them with a suit to work or with a rolled pant on the weekend to show off the heft of the sole. Choose your socks with caution – a bold sock with a bold shoe is too much.
Personally, a chunky brogue is my go-to versatile statement piece for fall and winter. This brown color can easily pair with your suit – or be dressed down with jeans for a dapper happy hour look.
How to Wear Boots with Every Outfit
I once got an email asking: “What’s the best way to wear (these boots) with my pants?”
Sure, it may seem a little daunting. You’re accustomed to shoes ending at the ankle.
To be honest, the only right way is whatever keeps you most dry.
Cuff up your denim, let them sit in between the boot’s tongue and back tab, or tuck them in if you have to. What matters most is not arriving dry.
If your cuff naturally drapes over the boot, that’s fine. But if your pants get wet, start rolling them up! Don’t stress about the rules of men’s winter fashion. Adapt, my friends. Adapt.
Protect Your Leather Shoes from Wet Weather
Shoe trees. Rest for a day.
Dealing with Salt
Peeps in snowy areas, watch out for salt on your leather shoes. Salt + leather shoes = sad face, big time. This is all the more reason to NOT wear your nice leather shoes when you’re commuting by foot.
If you absolutely must wear your leather shoes when braving the elements, treat them with care as soon as you reach your destination. A simple wipe-off should suffice.
Be thorough – any stray slush or salt water will stain your shoes. And getting that stain removed is a pain in the butt.
Conditioning and polishing the leather will help keep your shoes in tip-top shape and ready for whatever you throw at it. This is another reason (if you haven’t yet been motivated) to polish your shoes regularly.
Think of it like moisturizing your skin after showering. If you don’t moisturize, you dry out, your skin gets rough and cracked, etc. Your leather shoes work the same way.
Want a step-by-step solution for de-salting (that’s not a word) your shoes? Check out this concise guide from Valet Magazine.
How to Avoid Slipping on the Ice
If you’re more concerned about your own safety (walking around on wet, icy, or snowy ground with leather soles is not very fun or sexy), then you have some alternatives.
- Take your leather-soled shoes to a cobbler and have a thin rubber layer added. Many places do this and it shouldn’t be tough to find a cobbler who knows what you’re asking for.
I’ve heard arguments for and against this method. Some say it’s perfectly fine and they haven’t experienced any problems. Others have said adding a rubber layer decreases the breathability of the leather and can trap in moisture which leads to rotting, curling of the rubber, and in general, ruins your shoes long term.
I’ll leave it up to you to do the research and decide whether or not this is a good solution for you.
- Another option is to use Swims, which are overshoes (aka galoshes) that protect your shoes from the elements. They also increase your sole’s grip so you don’t slip and slide.
Some people think this is super nerdy. Others (like myself) think they look kinda cool. I don’t yet own a pair, but I’m inclined to pick some up and try them out. I encourage you to do the same; feel free to report back to me for extra bonus points.
For me, the best solution is a pair of dress shoes with a rubber or combination rubber/leather sole that you use on rainy and wet days. (More on that in our complete guide to brown leather shoes.)
The grippy rubber keeps you safe, minimizing slippage as you walk around. Aesthetically, you get the same look as your other dress shoes. The only difference is the less formal – but grippier – rubber sole.
EG’s Recommendations for Your Fall/Winter Wardrobe
If you have a lean wardrobe, putting together outfits is simple. And transitioning them from spring/summer to fall/winter is just as easy.
For men’s winter fashion, you’re going to be working with thicker and heavier fabrics. And doing a bit more layering.
Y’know, to stay warm.
YOU’LL LOVE THIS ONE, TOO
The additional benefit to layering is that your outfits look waaaay more interesting than whatever you’d wear during the summer (typically one top and bottom layer. BORRRING).
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.
Each piece of the outfit separately can be swapped out with similar items that are more appropriate for the season or the venue.
With each suggestion below, imagine swapping it out with the default option above. And for items that don’t exist in the default option (midlayers), 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
Chambray isn’t exactly a fall- and winter-specific shirt. But… I think of it like denim: easily worn year-round. So if you already have a favorite chambray, keep on wearing it through the winter months.
As far as OCBDs, brands 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 shirts as men’s winter fashion appropriate; they keep you warmer during the winter months. Both casual and more formal options exist in both fabrics.
Fall / Winter Midlayers
Midlayers are the secret sauce of perfectly-layered wardrobes. Instead of wearing one heavy coat, wear a midlayer and a jacket or light coat.
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. Your only option is to take off the coat. 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.
Aesthetically, 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
Denim is 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 choose heavier-weight chinos. For a dressier option, you can’t go wrong with flannel trousers like this pair from Franklin Tailored.
Fall / Winter Shoes
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 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
Here’s a little tip when it comes to sport coats: Look at them as jackets, instead of “half a suit”. That helps make them less intimidating and easier to incorporate into more outfits. They’ll make 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, 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 men’s winter fashion for you will depend on 1.) weather and 2.) formality.
- Weather: If you’re in Minnesota, your fall and winter wardrobe will look a bit different than someone’s in Miami or Manhattan.
- Formality: If you’re usually in business/formal environments, your everyday outfits will look different compared with that of a freelance web designer who works out of coffee shops.
Regardless, this is how it works: 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.