Men's Winter Style Guide

Winter Style for Men

As the weather cools down it’s time to rethink your wardrobe. Winter is all about layering in a way that is warm, comfortable and reflective of your personal style. Just how cold it gets in your region will play a vital role in what new pieces you select for your wardrobe. Not to worry as our winter clothing collection has plenty of options to ensure you look your best at work, play, and for special occasions.

Leather jacket

Winter Fabric Choices

Let’s first begin with fabric choices. What you are looking for are options that are warm and comfortable. Even if you aren’t someone who is typically suited-up for work, expect to send more to the dry cleaners during the winter months as many of your winter items require professional cleaning. With proper care the items you add to your winter wardrobe will last many years.

Cotton is king all year round as it is breathable and comfortable, found in your wardrobe for every layer, underwear, undershirts, socks, button downs, sweaters, and even your outerwear. This includes cotton blended with polyester, nylon, and anything with a bit of stretch. These blended fabric choices enhance fit, minimize wrinkles, and create structure where needed.

Wool is synonymous with winter warmth ideal for socks, flannels, sweaters, vests, cardigans, lining, and outerwear. More than just a warm fiber but one that can be rugged or polished. At the very least wool adds a bit of texture to your wardrobe. If you find wool itchy layering can minimize the itch, or you can stick with cotton blends. Wool must always be dry cleaned.

Leather is essential for your winter boots, dress shoes, and casual sneakers. While not suitable for getting wet, a fleece, fur, or wool-lined leather glove is ideal for formal occasions. Regardless of your fashion sense every gentleman should consider adding at least one leather jacket to their wardrobe. If you’ve never considered a leather jacket explore designer options as you will be pleasantly pleased with the range of options. For year-round use, leather is a must for your belts, briefcase, and weekender bags.

The Non-Flannel Flannel Button Down

Winter fashion is all about layering. The goal is to create warmth, but you don’t want to overheat—which is why we suggest investing in a few button down shirts that are patterned like a traditional flannel but made from cotton. Traditional flannel can of course be layered but is designed to be warm enough that you only need an undershirt. Layer your non-flannel flannel button downs under everything from sweaters to vests, cardigans, leather jackets, and athleisure wear. For a bit of texture, choose a soft brushed cotton or cotton and polyester flannel opposed to a traditional wool flannel. You can even find insulated flannels designed as outerwear, made from a variety of fabrics.

Corduroy Pants

Corduroy Pants

Denim always works for winter, including the colored brown, grey and chocolate denims that have been popular the last few seasons—but this winter is all about corduroy. The key to feeling polished and comfortable in corduroy is to avoid oversized and baggy options. This season’s corduroy is blended with a bit of stretch so that you can enjoy a classic 5-pocked trouser that is polished enough to wear to work and comfortable enough for casual days. If your climate is cold layer thermal pants on underneath or opt for a wool trouser instead of corduroy.

Quilted Vests and Outerwear

This year’s quilted options provide the warmth of quilting without the bulk. They are sleek enough to wear in the city but still functional enough for the outdoors. Consider a quilted jacket, either cropped or hip length—and add at least one quilted vest to your wardrobe. Vests can be worn both open or zipped depending on the look you want to achieve. You can even find hoodies with soft cotton arms and hood, and a quilted chest and back. At first glance quilted hoodies look like a vest, but they have the added warmth of sleeves and a hood.

Sweaters and Plaid shirts

Sweaters In A Variety Of Styles

Sweaters are a must for winter, and you have plenty of stylish options to choose from. Chunky knit cardigans are a sweater option that never goes out of style. The key is in selecting a color that looks good with your skin tone—with navy, grey and black being top picks. Round or V-neck sweaters are a winter wardrobe staple but with each season the trends for texture, color, and finish vary. This year is all about small knits, solid colors, and a fitted not baggy. You still want to layer a button-down underneath, but you don’t want to look bulky. If you opt for a cable knit opt for skinny texture. If you select a pattern, make sure the design lines are thin. Pullovers, like a sweater hoodie, are also popular this season, which we detail a bit more below.

The Pullover

There are a variety of pullover options this winter, with either a half or quarter zipper. Zipper pullovers aren’t just comfortable but easier to put on, without worry of messing up your hair or stretching out the neckline. We like the polished look of a small knit sweater but be sure to explore your options in athleisure wear pullovers in a variety of materials. Always be sure to layer a button down underneath for both warmth and style.

Your second pullover option is a thin hoodie in cotton or a knitted sweater. Think beyond the standard casual hoodie, which has its time and place, to creating a layered look. Start with an untucked flannel button down, then add a thin layered hoodie, and finish your look off with a leather jacket.

Suited Up For Winter

If your job requires you to suit up daily the options above may only work for the weekends and after-hours, but layering sweaters and vests are still part of the mix. Instead of a flannel-inspired button down stick with classic solids, patterns, and prints. We like a checked button down layered under a V-neck cashmere sweater — with or without a tie. When suiting up for winter, wool is your top choice. However, a pair of thin thermal pants can make many of your lightweight slacks a year-round option.

Don’t feel confined only to darker colors as winter is the perfect time to mix and match your suit separates. A dark grey slack with a navy sweater, neutral button down, and a medium brown blazer look good on every gentleman. Now is the time to pull out your plaid suits, but not to wear together, to mix and match with solids. Like a solid grey slack with a solid maroon sweater, neutral button down, and a plaid grey sportscoat.

Outerwear and boots


With a minimum of three layers per look, your top layer may be a casual leather or athleisure jacket designed to wear all day, or to keep you warm when walking the short distance from your car to the indoor location you are heading too. While layers alone may work in some climates it certainly won’t work everywhere, so consider your need for a heavier jacket.

When selecting your outerwear focus first on function. Wool is great for cold climates but if you live somewhere cold and damp you may require rainproofing too. When wet, don’t just pop your coat in the coat closet as it needs airflow to properly dry—you also don’t want to get your other jackets wet. If you live in extreme cold you may want a high neckline or hood built-in to minimize your need for accessories. If you live in a city where you commute via public transportation, consider where you will stash your phone and headphones.

Once function is determined explore this year’s options in outerwear. You can always stick with a classic long trench or peacoat, but this year has countless options in cropped and hip-length jackets that make your outerwear a part of your complete look. For maximum versatility select a jacket that is refined enough to wear to the office. As we mentioned earlier, this year’s quilted options are both functional and polished.


This season’s boots are rugged and sleek. Made from smooth leathers and soles with traction built-in. Dark and medium brown are the most versatile, but you can never go wrong with a classic black. Be sure to spray your boots with a sealant so that puddles and rain don’t ruin the leather. You don’t have to do this yourself as a local cobbler can do it for you. While sealing your boots will protect them from the elements, on days that it’s snowing, wet, or icy leave the leather at home—and choose a waterproof option instead. Waterproof options aren’t as stylish so feel free to slip your leather boots or dress shoes on when you get to work.

For outfit inspiration, we invite you to browse this season's new arrivals we have put together from Westport Big and Tall’s top designer brands. Not only is this the perfect place to shop for complete looks but every item we select is one that can be mixed and matched in your wardrobe in a variety of ways.