Men's Winter Wardrobe Essentials

Men's Winter Wardrobe Essentials

"Winter is Coming..."

Ah, wintertime. From the warm fireplaces to the holiday (disclaimer: is a non-denominational men's fashion resource) lights glistening on the fresh, powdery snow to the general retirement of pumpkin spice (thank god), winter is a season everyone can enjoy. Subdued colors, more pronounced textures, and an emphasis on not freezing to death are accentuated as we make the shift to a colder weather wardrobe. As always, this men's winter wardrobe essentials post is by no means an authoritative guide on what you must wear to be stylish; treat it only as a reference. Let's begin.

Table of Contents


Before I even jump into apparel categories, I'd like to go into the actual composition of our clothing. The chillier winter weather allows one to layer considerably more than summer or spring. What's the difference between an undershirt made of polyester as opposed to cotton? A leather jacket to a nylon one? A wool sweater, or one made of tears? To put it simply: plenty. Different textiles have different inherent properties, which means they'll all perform distinctly in varying conditions. A fundamental grasp of materials and their applications can save you from sweating right through a shirt or losing the rest of your toes to frostbite. 

Cotton: The backbone of the clothing industry, cotton makes up the vast majority of all apparel, and for good reason. It's inexpensive, relatively soft, retains color well (depending on dye), durable, and generally easy to clean. The downside to this material is that it wrinkles easily, shrinks/stretches, and is very absorbent, which results in body odor retention and lengthy drying. Do note that not all cotton is created equal, and many factors determine the material's softness, color retention, and durability. Pima, for example, is long-staple cotton that's very soft to the touch, and more expensive than traditional cotton. Kirkland makes a solid pima T-shirt for under $10 if you're looking to try the material.  All in all, cotton's a time-tested, versatile fabric with plenty of uses. 

Flannel: Contrary to popular belief, flannel is actually a type of fabric and not a pattern (e.g plaid). It was originally made of woven wool, but more modern compositions consolidate different fibers like cotton, nylon, and polyester. Flannel is finished with a process called napping, which gives it its iconic "fuzzy" appearance. This process allows flannel to be very warm and soft without being too heavy. A downside to flannel is that it can pill easily. Flannel is a staple fabric for colder weather and looks great without sacrificing utility. I'm a fan of Woolrich flannels as they're available in a ton of designs, though they're 100% cotton and fit a bit boxy. 

Wool: Chances are, you own an article of clothing made of wool, but there's quite a bit more than meets the eye with this peculiar fiber. Wool comes from sheep, goats, alpacas, and rabbits, though wool from sheep is by far the most common. The type of wool (graphic) varies from the type of sheep it comes from, and the properties of each vary too. Wool is animal friendly (the sheep is unharmed if properly sheared) and environmentally sustainable. It's very warm, hypoallergenic, odor/stain resistant, and insulates when wet. In fact, wool doesn't feel wet to the touch until it absorbs 60% of its own weight in water. The material's high water and nitrogen content even allow to be fire-resistant, which is great if you're someone who catches fire frequently! I can go on and on about why wool is a seriously cool fabric, but just know that it's a great material for sweaters, shirts, and especially socks. If you're prone to sweaty (therefore smelly) feet, wool socks might change your life. 

Polyester/Nylon: I'm choosing to include these fabrics together because they share multiple characteristics and are similar enough. Both polyester and nylon are synthetic fabrics spun from chemical solutions. Advantages of these fabrics include: inexpensive production, moisture-wicking, strong shrink resistance, and stretch. Synthetic fabrics are often shiny or reflective in appearance, which may deter some. Polyester is often used due to its remarkable moisture-wicking properties. A good example is in Uniqlo's Airism boxers, which are great and very comfortable. Nylon, on the other hand, is more often used with outerwear and "shells" of clothing. For instance, this Alpha Industries bomber has a nylon outer shell, but polyester lining because the nylon is more durable. Something to note is that these materials, nylon especially, tends to make that swooshy swoosh noise when rubbed against itself (and yes, that's definitely the technical term). 

Leather: To clarify, I'm referring solely of animal leather here, and not the artificial/faux/"vegan" substitute, which has different characteristics altogether. There are tons of different kinds of leathers, each with differing heat insulation, durability, softness, color, etc. Generally speaking, however, leather is strong and has great heat insulation. Leather fibers hold large amounts of water, which allows them to absorb perspiration and later dissipate it. Something I strongly urge is to not buy cheap leather. Not only will it likely be of inferior quality, but cheaper leather often comes from places where ethical standards for animals are non existent. 


One of my favorite aspects of cold weather fashion is the reintroduction of coats. Not only are they functionally great for breaking wind and storing leftover Halloween candy, but they're excellent statement pieces that can really make your look stand out from the crowd. Not to mention, the sheer variety (infographic) of different outerwear available is impressive, so you're able to experiment and figure out what compliments your personal style best. Aside from design, color, and fit of your outerwear, textures play a much bigger role in your look as opposed to the warmer seasons. I'll be highlighting a few different types of jackets that can diversify your winter wardrobe. 

Technical Jacket: We all need a reliable jacket to combat wind and rain. I've been enjoying the look of technical jackets a lot more recently, and they're top notch when it comes to functionality. This category of outerwear is probably the most technologically-advanced, usually boasting Durable Water Repellant (DWR) coating and wind resistant outer shell. The Patagonia Torrentshell takes at least 30 minutes of consistent rainfall to saturate its fabric. These are great jackets to save for a rainy day (literally), but you may not want to!

Bombers: These have come a long way since their introduction. They were first manufactured 100 years ago for pilots in World War I. Planes had open cockpits back then, so flyboys had to endure the elements all while dodging enemy planes and flak alike. Flight jackets combated this problem with thick, sturdy leather and fur lining to keep pilots warm in the skies of no man's land (you can totally tell these sick facts to the hordes of ladies lining up to ask about your jacket).

War - war never changes, but fortunately bomber jackets did. Though traditional leather models are available, modern bomber/flight jackets are typically composed of nylon or polyester. My recommendation for a solid bomber has to go to the Alpha Industries model. It's available in both regular and slim fits, and comes in six colors. A more budget-friendly alternative would definitely be the HM version, retailing for about $50. If you're geared more towards the more traditional look, this nylon/cotton bomber from J Crew could interest you. I love these jackets because they're so easy to pull off. Whether you choose to layer it over a simple T-shirt or hoodie, the bomber is always a stylish look. 

Field/Military: These military-inspired jackets have a lot of different names, and even more kinds of styles and variations. Specifically, the M-65 (stands for M-1965, the year it was first introduced to US troops) is likely the predecessor of most army-type outerwear seen today. They're not typically very warm, so it's definitely a jacket to layer over a sweater or flannel shirt. Essentially every large brand has their own variation of the M-65. J Crew, Urban Outfitters, Rothco, and Levi's offer modified versions of the classic jacket. Aside from fashion retailers, it's also possible to obtain a military surplus jacket for a fraction of the price of competitors (and they're often brand new). 

Peacoat: If I had to pick a single coat to wear for all of winter, it would definitely be the peacoat. Originally worn by European and later American sailors, the peacoat can be traced as far back as the 1700s. Like the M-65, this jacket has its roots tracing back to military use, and has also been transformed into a modern fashion staple. Pea jackets are made from wool (at least they goddamn better be). The ideal composition of a peacoat is 70-80% wool to ensure warmth without sacrificing the durability that some 100% wool coats do. Peacoats usually have two outer pockets (either slant or horizontal) as well as inner pockets for storing things like wallets, keys, or flasks of liquor - 'cause sometimes you need that extra warmth. Typically, these coats are worn with the collar down, but some wear it up when the weather gets tough. Those looking to try out a peacoat without investing too much could opt for an Old Navy model, which retails for $80, but can be had for much less on sale. Personally, I'm a fan of Seibertron and Schott peacoats, though they're considerably more expensive. Like the M-65, it's also possible to get military surplus peacoats for relatively cheap. Check if you have a local Army/Navy store; they can be a great place to stock up on men;s winter wardrobe essentials.

Photo credit /u/thecynicroute on Reddit

Parka/anorak: These are hooded coats adapted from traditional Inuit tribe outerwear, and can range from light fishtail parkas (pictured) to heavier fur-lined ones. Parkas are found in nearly all branches of men's fashion, and are often a staple in winter streetwear. A heavier, puffier model like this N-3B is a great bang for the buck for staying warm in the winter months, though they typically run large so be sure to size up. There's a considerable range of prices, features, cuts, and materials when it comes to parkas and anoraks. HM, Zara, and other fast fashion retailers introduce new parkas every season. For beginners, I'd recommend the Alpha Industries N-3B linked above (be sure to size down), an HM parka, or this Penfield Fishtail


Shirt (n.): a garment for the upper body made of cotton or a similar fabric, with a collar, sleeves, or buttons down the front. Now that we have that out of the way, let's get into it:

Button-down: This is a pretty large category of shirts, so I won't be going too in depth on them. Whether you have a job/internship or you simply have a need for dressing up every once in a while, a button front shirt is a necessity for every season. The biggest difference in how you wear this type of shirt during the winter is the material it's made of. Hang up your linens and chambrays and replace them with heavier fabrics like oxford or broadcloth. A popular style is to layer a sweater over your OCBD, which can create some interesting color and pattern combinations. Light blue and white are definitely the most adaptable.

dexter with henley

Henley: Not everyone's a huge fan of this type of shirt, but I happen to love 'em. They're incredibly versatile and make a great layering undershirt. Typically, henleys are made of cotton, wool, or a mixture of the two. You can also totally pull off the Dexter aesthetic (vigilante homicide optional though encouraged). American Apparel makes some great henleys, and I believe it's the one Dexter wore in the shore if that matters. 

Flannel: Flannel shirts are, in my opinion, an essential in a winter wardrobe. They're easy to pair with pretty much anything, come in a wide assortment of colors and patterns, and the ladies love 'em (subjective to wearer's attractiveness, wealth, muscularity, facial hair, car, and Battlefield 1 kill-death ratio). Uniqlo makes some great flannels, and they're often on sale for less than $20, which is an incredible value for the quality of the shirt. 

Photo from

Sweaters: Chances are, sweaters will be a large contributor to your winter looks and there's really nothing wrong with that. They're clean, effortless garments that are warm and cozy - what's not to love? Cotton, wool (merino or shetland), or cashmere are common sweater materials. Patterns aren't uncommon for sweaters, and fairisle is quite popular during the colder months. Sweaters typically come with either a crewneck, V-neck, or shawl collar. The knit type (infographic) of a sweater also serves to differentiate it from the pack. I'm a big fan of cableknit sweaters as they can add some awesome textures to your fit. This No Nationality sweater features a pretty sick structured pattern. I'd recommend having at least 2 or 3 sweaters in varying colors and knits to maximize versatility in your winter wardrobe. 

Hoodies: 'Cause let's be honest: you're not gonna dress up every day. Normally, I'd factor in hoodies into the outerwear category, but the winter season inhibits wearing just a sweatshirt at least where I'm from. Hooded sweatshirts are great for days when you just blatantly give up (we all have those days), though they can certainly be fashionable with the proper execution. My personal favorite sweatshirt, especially for the price, is the American Apparel California Pullover. It's medium weight and has a well-balanced slim fit, which makes it a great piece to layer underneath a bomber or M-65 and it's around $25. Those seeking a more premium sweatshirt can check out Reigning Champ


Left to right: Levi's 511, Nudie Steady Eddie, Woolrich Wool Pants, Assorted chinos

Left to right: Levi's 511, Nudie Steady Eddie, Woolrich Wool Pants, Assorted chinos

Unfortunately, societal standards require us to wear pants (total bullshit, I know), but that doesn't mean we should be stuck with sweatpants and bootcut jeans all winter. In fact, the cold season permits the most experimentation with different pant styles and fabrics. 

Jeans: Likely the cornerstone of every man's trouser ensemble, denim hasn't changed much since its inception more than a century ago. Nowadays, jeans have evolved into a myriad of cuts, materials, colors, and scratch-and-sniff scents (Naked & Famous, y'all wild). For winter, darker washes are definitely the fashionable choice. Lighter washes in winter aren't unheard of, but it's definitely easier to pair darker denim with other, more neutral winter colors. My go-to for denim (and always will be for many reasons) is Levi's 511 in Rigid Dragon. They're an awesome cut, fade well, and are unbeatable for the price. Check out my mini guide to Levi's jeans for more information on the different cuts and styles of the brand. A step up to Levi's would definitely be Unbranded denim, which also offers an gateway to affordable selvedge jeans (read my introduction to selvedge denim here). You definitely don't need to go overboard with jeans in your wardrobe. I'd aim for solid pairs in dark indigo and black.

Wool Pants: Depending on your climate, investing in a dependable pair of wool pants can be a power move. They're incredibly warm, and provide some awesome texture to your outfits. Wool pants pair perfectly with your favorite boots, chukkas, dress shoes, or even some sneakers. When a regular pair of chinos simply isn't warm enough, I find myself opting for wool pants quite often. I'm a fan of both Uniqlo and Woolrich's pant offerings, but it's best to try on a pair in store. 

Chinos/khakis: The sheer versatility of chinos is unparalleled; whether it's business casual with a pair of oxfords or paired with boots or sneakers, chinos have you covered. Similarly to jeans, khakis come in varying cuts and styles, so choosing the right pair for you may be a trial-and-error predicament. Personally, I'm partial to J Crew's 484 cut chinos and Banana Republic's Alden cut. They're definitely a bit higher on the price spectrum, however. Cheaper alternatives include Levi's, Uniqlo, HM, and Zara. 


White sneakers: There are some who believe white shoes should be constrained to the warmer months. I am not one of those heathens. White, minimalist sneakers absolutely have a place in winter fashion. They're clean, simple and can really help balance out an otherwise overly-dark outfit. The cheapest, reliable pair of white sneakers would have to be Vans Authentics followed by the super popular Adidas Stan Smith (I'd go for the all white, blue or green accent colorways). More upscale models include the Buttero Tanino and Common Projects AKA "Dev's favorite sneakies". 

Nike Flyknit Racer "Oreo"- Photo credit:

Casual Sneaker: It's always wise to diversify your wardrobe, especially when it comes to your shoes. Having a comfortable sneaker for long days full of walking can be a lifesaver, so opt for a shoe with a comfortable, supportive sole. Adidas' Boost cushioning is great for casual use and is very comfortable. Ultraboosts and NMDs are the brand's flagship models utilizing the boost technology, and are very popular but may be difficult to obtain. Nike's Flyknit material is meant to fit snug on your foot and is used in some great shoes like the Flyknit Racer and Lunar.

Dress shoe: Even if you don't need to dress up often, it's essential to at least have the means of doing so. It isn't totally necessary to drop a ton of cash on a really nice dress shoe, either. A simple Bass oxford or JCP Stafford wingtip will do the job just fine if you only dress up occasionally. However, if you're in the market for a nicer dress shoe, check out the Johnston & Murphy Conard oxford or even the Allen Edmonds Strand. Do your research before committing to a nice dress shoe; a quality pair can last you well over a decade with proper care. 

Boots: Hands down my favorite part of fall and winter fashion, boots are the MVP of my footwear lineup. They're comfortable (at least they should be), warm, and build character with each wear. For an introductory pair of boots, I'd personally shoot for a pair of the ever-so-popular Clarks Desert boots in Beeswax or some Chippewa Apaches. There's a lot to say about boots and all the different types, so check out my fundamental guide to boots if you're looking to learn more!


Watch: Well, a watch isn't totally an essential, but it can really add a noticeable aspect to your look, even if it's a cheap Timex. I'd recommend a modest, white-dialed watch with a brown leather strap. I absolutely recommend picking up a few NATO straps. They're inexpensive and easily alter the appearance of your watch with minimal effort. In my opinion, the best entry-level watch would be the Timex Weekender, though the ticking is very loud (especially in a quiet room laying in bed waiting for Stacy from calculus class to Snapchat back....sigh). Anyway, watches are a whole different discussion altogether, but the fellas over at have a ton of great watch resources and reviews. 

Mink Oil: This is an oil derived of mink fat removed from fur pelts. Besides being a great dip, it's also very good at conditioning and waterproofing leather. I recommend picking up a small tin to prepare your boots for the snow, or just to condition them a bit. Be careful, however, as mink oil is known to darken leather slightly. 

Warm socks: A lot of guys wear whatever socks are cheapest and come in the largest quantity, and while I can understand this because I used to do the exact same thing, I've since been indoctrinated to the ideology of wool socks. Seriously though, these are a total game changer, especially when cold weather. If you're prone to smelly, sweaty socks and feet, you may want to give the natural odor and moisture-repelling properties of wool socks a try. I'm a big fan of Smartwool's MiUSA socks, but have heard great things about Costco's house brand, Kirkland. 

Backpack: Alright, most people already have one of these and it isn't necessary to go out and purchase something 'cause some dude on the internet told you too. That being said, if you are in the market for a new bag, Everlane's Snap is a clean, stylish alternative to that old Jansport you've lugging around.

Sunglasses: Contrary to popular belief and the fact that it depressingly sets at 5PM every day, the sun does in fact exist throughout winter. I'm a firm believer in eye protection, so I'd consider a polarized pair of sunglasses a wardrobe essential. More info on sunglasses, facial shape, and the sun's effects on your eyes here.

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