Big & Tall Men’s Winter Style Guide

December 09, 2025

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. Just like anyone else, big & tall men are looking for 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. With the proper style choices, your winter attire will be evergreen and in fashion.

Cotton

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

Wool is synonymous with winter warmth: ideal for socks, flannels, sweaters, vests, cardigans, lining, and outerwear. More than just a warm fiber, wool can look rugged or polished and can actually still insulate the body even if it’s wet. This makes it an effective winter material for many attire pieces. But at the very least, wool adds a bit of texture to your wardrobe. If you find wool itchy layering can minimize the itch by layering above other materials, or you can stick with cotton blends. Wool must always be dry cleaned.

Leather jacket

Leather

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 big and tall leather coat options, as you will be pleasantly pleased with the range of styles available. 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 flannel. You can even find insulated flannels designed as outerwear, made from a variety of fabrics.

Jacket

What’s going on in Winter ‘25

Styles of big & tall men’s clothes for this winter include smart layering and sleek silhouettes, while offering warmth and comfort to battle the weather. As always, key is to avoid bulky layers, and focus on long lines to match the long nights. Pants should fit well but not too tight, and making use of interesting textures to break up the feel of the outfit is always essential. Let’s take a look at some individual pieces:

Pants

Denim always works for winter, including the colored brown, grey and chocolate denims that have been popular the last few seasons. This season is one where non-denim 5 pocket pants are in the spotlight. The key to feeling polished and comfortable in these styles is to avoid oversized and baggy options. This season’s selections are often blended with a bit of stretch so that you can enjoy a classic 5-pocket trouser that is polished enough to wear to work and comfortable enough for casual days. If your climate is cold, layer thermal pants underneath or opt for a wool trouser instead of lighter cottons. Of course, comfy jogger-style sweat pants always work when it’s time to cozy up on the couch.

Some excellent winter picks for big & tall pants include:

Polo Ralph Lauren vest

Quilted Vests and Light 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.

Top picks from our curated collections are:

Sweaters

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. Crew or V-neck sweaters are a winter wardrobe staple but with each season the trends for texture, color, and finish vary. This year is a mix of small knits, solid colors or unique patterns and a fitted look, 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.

Great sweater options for this winter include:

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.

A quick look at our favorite picks for big & tall pullovers this winter:

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.

Here’s a selection of great suit and suit separate options for the big & tall this winter:

Peter Millar jacket

Outerwear

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 winter 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 a jacket with a rainproof shell 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 but casual enough to wear on a cold night out.

Great picks for winter coats and lighter jackets this season include:

Winter Outfit Inspiration from Westport Big & Tall

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.

Get in touch for a winter/holiday attire catalog from Westport Big & Tall.

Winter Style for Big & Tall Men

Winter Style for Big & Tall Men