Upgrade Your Accessories: How To Survive Deep Winter And Still Look Good + 3 Looks to Pull It All Together

Upgrade Your Accessories: How To Survive Deep Winter And Still Look Good + 3 Looks to Pull It All Together
Tired of being cold and wet? These upgrades keep you dry, warm, and sharp as hell.

For many men who live in areas with true seasons, deep winter (December to February) can pose quite a style challenge. How do you look good while staying dry and warm? Sure, one could argue that it doesn’t matter, function should proceed fashion.

But then again, if you’re already going to buy gear to brace the rain and snow, why not buy something that looks good too?

Luckily for us, brands have been wising up and offering products that perfectly balance style and function. And while most people have the basics covered – from a proper down parka and plenty of sweaters, getting the last 10% right can mean the difference between getting cozy in the cold weather and literally freezing your ass off. Here’s how to upgrade your winter accessories without sacrificing function or style.


Sure, science has debunked the myth that most of your body heat escapes from your head, but proper headgear in deep winter is still vital.

I’ve whittled the choices down to two options – the beanie and the dress hat. Both are jack of all trades, pairing perfectly with casual or more formal business outfits.

The beanie has the added benefit of covering your ears, while you can add a pair of behind the head earmuffs to your hat ensemble. It might look a little silly, but assuming the rest of your outfit is sharp, the dressy nature of a fedora more than makes it forgivable. Plus it’s a much better option than the trapper hat, which I think most guys should leave behind in their college dorm rooms.

The Merino Wool Beanie

Men's winter accessories

Merino Wool Beanie: Norse Projects, $60

Take your beanie up a notch and opt for merino, the underrated rival to cashmere. Under the microscope, standard wools are thick and composed of large scales. These large scales are why standard wool sweaters, beanies and scarves are so damn itchy.

Fine merino wool is softer than your garden variety wools, as their fibers and scales are much smaller.

Natural fibers like wool have the added bonus of being naturally insulating. Wool fibers have small crimps in them, which create tiny air pockets that trap in heat. Once you invest in a proper merino wool beanie, it’s going to be hard going back to those $10 synthetics. Stay far away for acrylics, as their ultra smooth fibers don’t wick away moisture well and trap odors.

wool fibers under a microscope

The Cashmere Beanie

men's winter beanie

Cashmere Beanie: J.Crew, $68

While merino is soft, the title is still held by cashmere. Like other wool, cashmere has great heat retaining properties.

Under the microscope, cashmere fibers are made of even longer, smoother scales than merino, resulting in the soft plush feel they’re famous for. This also results in a much lighter knit cap without affecting the warmth.

The Water Repellent Fedora


“The Tino” Litefelt Fedora, Bailey Hats $77

Proper dress hats have made quite a comeback as more and more men explore classic menswear styles.

A proper fedora is made of tight fur felt, usually rabbit or beaver, both which have water repelling properties. The downside? These hats can get quite expensive. Litefelt is the next best thing. Wool felt is treated with a DuPont teflon coating. The coating repels water and helps the hat keep it’s shape. Not only is this a great introductory hat for men building their wardrobe, but also a great daily hat that can take a beating.

Scarves   Winter Accessories

Photo from Tommy Ton


Every winter, stores are flooded with cheap scarves made of synthetic or standard wools. Don’t fall into the trap.

If you want to stay warm without clawing at your itchy neck, this is where it helps to pay a bit more for nicer materials. Plus, scarves not only protect your neck from extreme windchills but also give you the chance to play with color and pattern. Your neck will thank you. Here are some of my favorites.

The Wool Knit Scarf

men's winter accessories

Wool Engineer Scarf: North Sea, $95

An extremely warm British wool, the birds eye pattern is a nod to the war-era sweaters it draws inspiration from. The subtle rib gives your look some much needed texture. Casually throw it around your neck and let both sides show through for some stylish depth.

The Double-Faced Cashmere Scarf

j.crew scarf

Double-Faced Cashmere Scarf: J.Crew, $118

Cashmere alone makes a great scarf – so how can you go wrong with twice as much? Doubling up cashmere serves a couple of functions. Not only does this add an extra layer of warmth to your neck, double-faced cashmere is also double the softness. It’s made from fusing two back sides of cashmere together (the less desireable coarser side). What you end up with is a scarf that is soft as it is warm no matter how you wear it.

The Extra Long Wool Scarf


Extra Long Windowpane Wool Scarf: Club Monaco $98

Clocking in at 80” long, a good 8” longer than your average scarf, the extra long scarf is one of my favorite accessories for winter. Why? The extra bit of length allows you to “stack” it higher, covering more of your face. As much as I love facemasks, it’s hard not to look like you just pulled off a heist. Combine the extra long scarf with a beanie to cover up your ears and you have the next best thing.


When it comes to protecting your hands from the chill, there really is no excuse to wear convertible-mittens or fingerless gloves anymore. Brands have adapted to the rise of touchscreens, incorporating metal fibers and special treatments on leathers that make them touchscreen compatible. Swipe away!

The Wool & Leather

Polo Ralph Lauren Gloves

Suede Grip Merino Wool Touch Screen Gloves: Polo Ralph Lauren, $30

There’s nothing worse than needing to take off your gloves to turn a freezing cold door handle. Leather grips on knit gloves solve this. Here, you get the best of both worlds: the flexibility and warmth of merino wool knit gloves with the grip of a beautiful suede leather palm.

The Leather And Cashmere

j.crew gloves

Cashmere-Lined Leather Touch Screen Gloves: J.Crew, $88

While leather gloves look infinitely cooler than knits, they’re just not as great as keeping your hands warm. This where you would traditionally go for a pair with fur lining. While luxurious, fur doesn’t sit so well with some people and can break your wallet. Luckily, brands are offering the next best thing: Cashmere lining. These gloves by J.Crew have U|R technology – a patented treatment throughout the leather which makes them fully usable with touch screen phones.

The Leather Grip Windstopper

winter gloves

Leather Grip Windstopper Gloves: Hestia, $90

For those days when pulling out your phone in the middle of a snow storm isn’t the smartest move, Hestra’s Windstopper are my glove of choice. These extreme condition gloves are made with Gore Windstopper Soft Shell – a breathable fabric that’s windproof and water repellent. It's also lined in a down-like material called Primaloft for added warmth. The leather grips ensure you’ll only need to take them off once you get inside, and the elasticized cuffs make sure no wind is sneaking in.

Base Layer

Uniqlo’s Updated Heattech Line: The Extra Warm

Uniqlo base layer

HeatTech Extra Warm Long Sleeve And Long Johns: Uniqlo, $9 Each

Boasting 1.5 times more warmth retention than standard HeatTech gear, Uniqlo’s Extra Warm line is a no brainer when it comes to updating your base layers.

There’s a reason why this is the only recommendation in this category. With its offering of long sleeved tees, sweatshirts and long johns, Uniqlo’s HeatTech Extra Warm line literally has you covered. With everything currently under $10, it doesn’t get better than this.


The HeatTech Sock

uniqlo socks

HeatTech Socks: UNIQLO $9.90 For 2 Pairs

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.

The extreme value of Uniqlo’s HeatTech line gives you plenty of opportunity to stockpile them for winter as well as experiment with colors and patterns.

The Really Darn Tough Merino Wool Sock

Darn Tough Sock

The Standard Issue Half Calf Sock: Darn Tough, $19

If you haven’t noticed by now, we’ve been recommending a lot of merino wool items. For good reason, they’re just the best value natural fiber material for the winter. Don’t make the mistake of trying to wear your cotton socks in the winter. Cotton fibers don’t stand up as well as wool fibers and lose “dead air space”, those magical air pockets that keep you warm.  Swap out your cottons for merino and your feet are going to be very happy.

The Boot Liner Sock

LLBean boot liner sock

Cresta Hiking Sock: L.L. Bean $32 For 2 Pairs

Boot liners serve a few purposes – first, they keep you warm like any other sock. Waterproof materials found in a lot of winter boots tend to be quite tough. Wearing the incorrect sock can make it not only tiring to tread through snow, but also increase your chance of blisters. Liner socks tend to be thicker, giving you some much needed cushion. Companies like L.L. Bean boots are often sized larger to accommodate for liner socks. Keep this in mind when you're shopping for either.


The Waterproof Boot

Timberland West Haven waterproof boots

West Haven Waterproof Boot: Timberland, $190

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.

The Waterproof Chelsea

cole haan chelsea boot

Warren Waterproof Chelsea Boot, Cole Haan, $248

I’ll be the first to admit that shoe choices in the winter are not the most exciting, especially if you want to dress it up a bit.

While you can buy rubber slip on covers for your dress shoes, let’s be honest, that's not the best look. They're essentially condoms for your shoes. Leave it to Cole Haan to innovate with their Waterproof Chelsea Boot. Not only are these perfect for trekking to the office on a rainy day, they’re also part of Cole Haan’s Grand.OS line. The Grand.OS line offers lighter, more flexible shoes, hidden inside classic silhouettes. They might make you panic and feel like you showed up to work wearing sneakers.

The Updated Duck Boot

Sorel Duck Boot

Caribou Wool Boot: Sorel, $170

How do you improve the classic Duck Boot design? By adding a removable wool InnerBoot and an ice gripping proprietary AeroTrac sole. Sorel offers the Wool Caribou in two fantastic, timeless colors: a deep chestnut brown and my personal favorite, the army green. At 10” high, it’ll keep your pants dry, and with the ability to withstand temps as low as -40, there’s no chance of your feet getting chilly.

Putting It All Together:

3 Looks To Get Inspired As You Get Deeper Into Winter

The Daily Go-To

Men's Winter Style Look

Cashmere Beanie, J.Crew $68 | Hooded Wool Jacket, J.Crew $298 | Heattech V-Neck T-Shirt, Uniqlo $12 | Cashmere-Lined Leather Gloves, J.Crew $88 | Engineer Wool Scarf, North Sea $95 | Heattech Socks, Uniqlo $12 For 2 Pairs | Slim Fit Jeans, Levis $50 | Lambswool Sweater, J.Crew Factory $32 | Waterproof Boot, Timberland $198

Casual workplace? No problem. HeatTech t-shirt and lambswool sweater covers your base. Timberland’s waterproof boot has you covered for those pesky black puddles. Nothing looks better with a brown leather boot than dark blue jeans, and a pair from Levi’s is as classic as it gets. Luxe it up a bit with the cashmere beanie and cashmere lined leather gloves. Throw over an easy wool coat and you’re good to go.

The Rainy Day Office Meeting

Rainy Day Men's outfit

Thinsulate Herringbone Topcoat, J.Crew $149 | Wool Check Suit, Suit Supply $499 | Spread Collar Shirt, J.Crew $88 | Fedora, Baily Hats $77 | Suede Grip Merino Wool Touch Screen Gloves, Polo Ralph Lauren $50 | Tie, Suit Supply $69 | Double-Faced Cashmere Scarf, J.CRew $118 | Merino Wool Socks, Darn Tough $19 | Waterproof Chelsea Boots, Cole Haan $248 | Traditional Auto Open Umbrella, Shedrain $26

For those that wear a suit daily, staying dry and warm while keeping it sharp can pose a challenge. A Topcoat, like the J.Crew Herringbone, is a formal option to the winter parka standby. The Thinsulate lining adds extra warmth without increasing the bulk. Wrapping a double-faced cashmere scarf around your neck keeps the standards of this look high. And while most men are dealing with the weather wearing knee high rubber boots, you got a secret weapon: Waterproof chelsea boots.

Bar Blizzard Trek

Men's winter style outfit ideas

Merino Wool Beanie, Norse Projects $60 | Waterproof Faux Fur Trim Down Parka, Timberland $348 | Heattech Extra Warm Long Sleeve And Long Johns, Uniqlo $9 EACH | Corduroy Work Shirt, J.Crew $88 | Windproof Chinos, Uniqlo $29 | Extra Long Wool Scarf, Club Monaco $98 | Windstopper Gloves, Hestia $90 | Cresta Boot Socks, L.L. Bean $32 FOR 2 Pairs | Caribou Wool Boots, Sorel $170

Your friend’s decided to gather at a bar for his birthday, and mother nature decided it was time to dump a few more inches of snow. Don’t be the guy that just doesn’t show up. Instead, bundle up. A proper base layer is the key: Long sleeve HeatTech Extra Warm shirt and long johns and merino wool socks. There’s no way the wind is getting through Uniqlo’s triple layered chinos or your Windstopper gloves. Ankle deep snow is no match for the Caribous boots, so stack your extra long scarf high and pop your hood on, go out and celebrate.

BONUS: Enjoyed the post?

I put together a special page for Primer Magazine readers, where you can get a FREE 10 PAGE BONUS GUIDE with even more recommendations on upgrading your winter gear beyond accessories – from outerwear, to dress pants, to essential gym gear. These are “The Essentials” I’m packing to help me get through the next few months in style.


Peter Nguyen

Peter Nguyen is a Personal Stylist for successful entrepreneurs, and founder of The Essential Man. He lives and works in New York City.