Winter Is Coming: Holiday Season Style Guide

Michael Satterfield The Gentleman Racer Winter Style Guide by Michael Satterfield

Winter is almost here, which means even if you are in warmer parts of the country, it is time to shift your wardrobe for the season packing. With the current pandemic, many holiday parties and events are still on hold, but that doesn't mean that you can't look you best for smaller gatherings, socially distant holiday shopping, or even those mandatory Zoom calls for work. 

While most guides want to share the season's latest trendy looks, my focus is more on timeless pieces that can be in your winter wardrobe for years to come. You can never go wrong with a classic Cable Knit Sweater, a vintage sweatshirt, or a nice pair of corduroys, they have been staples in menswear for decades and show no sign of going out of style any time soon. 

Button Up Shirts

Some of my favorite shirts are by Banana Republic, they are one of the better values with pricing ranging from $45-$90 and they have several fits you can choose from depending on your body type. I tend to choose color patterns that can be worn year-round. With or without a tie a nice patterned button-up looks great under a v-neck sweater or vest.


A classic shirt that never goes out of style this RRL plaid flannel workwear has become one of the dominant patterns of the holiday season. The pattern is actually a Scottish Tartan of the Clan McGregor and dates back to at least the 800s, so it has been in style for over 1200 years. While the RRL shirt is pricy, you will see the difference in the quality and be able to keep this shirt for many years. 


Every guy needs a few Mock-Turtleneck shirts in their closet, they give you that classic look without the weight or warmth of a knit Turtleneck sweater, making them perfect for parts of the world that get cool, but not cold. They also layer nicely under a leather jacket or blazer without looking as causal as a standard crewneck tee shirt. Be sure to get one in black so you can channel your inner James Bond or Frank Bullitt.



This classic Cable Knit Sweater by L.L. Bean has been a staple since the 1800s, the classic style, high-quality construction, and slim fit make it perfect for layering. Robert Redford, Steve McQueen, and Paul Newman were all fans of the classic Cable Knit, so you will be in good company.


It doesn't get much better than a classic french terry sweatshirt, and J. Crew has one of the best ones you can currently buy. This style of athleticwear with its fitted waistband and cuffs goes back to the 1930s and has a timeless look. I wear mine in Navy blue all the time and just ordered another in this Vintage Merlot, throw a vintage leather jacket over with a pair of dark jeans for your morning coffee run, or over a tee shirt with a pair of Chinos for a classic casual look.


Banana Republic is my go-to for Silk Cotton Cashmere and Cashmere V-Neck Sweaters, pick up a grey, navy blue, or dark red. Wear it with a crew neck tee, button-up, or dress it up with a tie. They work with dark denim or chinos and are great for layering. Here in Texas, they are light enough to wear late fall through early spring. 


Shawl Neck Cardigan's are a great way to give a more formal shirt and tie a causal look. Swapping your suit jacket out for a nice shawl neck cardigan gives you a professional look without the structure of a suite. This classic sweater by Charles Tyrwhitt is one of my favorites and come in wine or navy.


Winter Jackets

A quilted jacket like this Barbour Heritage Liddesdale is the perfect outwear for days when you need both weather protection and a sophisticated fitted look. I have a similar jacket from Charles Tyrwhitt's 2019 collection that looks great dressed up or down and is one of my favorite jackets for when the weather gets cool enough here in Texas or if I am traveling north.


RRL is the standard in classic American style and this classic fitted peacoat is an excellent winter coat, with a detachable down liner and unparalleled attention to detail. Anything with the RRL label is expensive, but it is such high quality you will keep it for a lifetime and pass it on to the next generation. 

A grey tweed patch pocket sport coat is one of my staples once the weather cools down. I have owned a jacket similar to this one by Studio Suits for years. Pair it with denim jeans, slacks, or chinos, elevate the look with a dress shirt and nice tie, or go more casual by pairing it with a denim shirt.


This a jacket that I will suggest you look for even though you will have to buy it used. The Mt. Washington Jacket by Ambercrombie & Fitch is an amazingly rugged and stylish parka if you need something for cold weather. Sold in 2006-2007 the Mt. Washington was offered in four colors, vintage blue, military green, vintage orange, and vintage red. I have had my Mt. Washington since 2007 and it has served me well on trips to Aspin, Whistler, and the Upper Peninsula. These parkas are so good they still sell for $75-$175 depending on size and condition. Look for them on Poshmark, eBay, and Mercari. 



Colorful Chinos are a great way to break up the grey/blue/beige tones that tend to take over most men's winter wardrobes. My favorites are by Charles Tyrwhitt, they are truly no iron and come in a great selection of colors like berry, teal, and stone. You can also get them in traditional tan, mocha, and dark blue. 


A classic Khaki is something every man needs in his wardrobe and Haggar offers one of the best iron-free Khaki when you want a more casual look. Another added bonus for the holidays these traditional looking pants feature a flexible waistband to make sure you get through those holiday meals in comfort.


Corduroy pants are a great way to add some style and texture to your winter wardrobe, sometimes you can't wear denim and you just don't feel like wearing a pair of traditional slacks, this is where cords come in. These super soft 12-wale cords from J. Crew are perfect for work or weekend. For a more formal look check out their collection of single pleat 10-whale corduroys.



The Chukka Boot had been around many years when soldiers during World War II discovered them, called Veldskoen, Dutch settlers had been wearing them since the 17th century to deal with the harsh climate of Africa. After the war, Clarks brought them to the masses and they have been a style icon ever since. While I have several pairs my favorite by far is made by a company that uses the original name, Veldskoen, and still makes the classic Chukka in South Africa.  


The Bryson Cap-Toe Boot by Ralph Lauren is another timeless piece of footwear that is versatile enough to be worn to the office and to the skeet range. Offered in dark brown or black, the brown is my personal favorite as it shows better and looks less like a police/military boot. If you really want to treat yourself, upgrade to the Purple Label Fidel Burnished Calfskin, which runs about $1,500 more than the standard boot.

New Balance has been my favorite sneaker brand for years, I wear my made in the USA 1540v3 when I workout and I am wearing my Pro Court 213 high tops as I write this. The All Coasts 574 is my by far one of the best looking casual low-tops on the market. In Cranberry suede they add a nice pop of color and you don't look like a Corvette Dad rocking the white sneakers. 



There is something to be said about buying nice accessories once and keeping them forever, this RRL Indigo-Dyed Cotton Watch Cap is the only "beanie" I own. I picked it up at an RRL store on a trip to New York in 2014 and the classic cap has done so well it has remained in collection for years and should be on your list too. 


My daily driver has a heated steering wheel, but a nice pair of driving gloves should be on your list as should some insulated winter gloves if you live somewhere it actually gets cold. Unless you are on a ski slope your gloves should be leather, nylon gloves are for kids. These two-tone leather driving gloves by Cafe Leather are incredibly well made and offered in a range of colors, they look great with anything, but the best accessory for them is a wooden steering wheel. For truly cold weather their Deerskin and Elkskin gloves are hard to beat and will last a lifetime. 


Another great way to add a pop of color and texture to your winter wardrobe is a classic wool scarf. I recommend getting a few colors and some timeless patterns so you have some choices. Buying high-quality scarves serve you well for years as, unlike ties, they never really change shape or width.