Fall/Holiday Men's Fashion Guide

The Fall Holiday Men's Fashion Guide

The Westport Big & Tall Fall and Holiday Fashion Guide

By Stephan Belov


Welcome to fall, gentlemen. It’s time to start transitioning out of the bright colors, shorts, and summer linens towards something that’ll keep you warm and comfortable in the cooler months to come. Fall and winter are really great seasons for menswear. There are a lot more options when it comes to what you can wear, and how to put all of the layers together into a cohesive look. You can put some individuality into your outfits and experiment with different sweaters, vests, jackets, and coats to create a look that will not only suit your style, but also maximize your comfort against the unpredictable elements. We've put together a collection full of the best men's fall attire to start your search.

Nowadays, with the exception of law offices, investment firms, banking and financial institutions, as well as some senior level management positions - suits are no longer the standard attire of the modern workplace. In the last few decades, most of corporate America has instead adopted “business casual” as the dress code of choice.

All of these choices can be a bit overwhelming – but that’s why we’re here to help. This article will break down a few trends that we’re seeing in menswear today that we think our customers will appreciate. We don’t believe that every trend out there in the marketplace is worth chasing, but we do encourage every guy to learn a few and see what works for them. Even if your taste is more conservative and traditional, you might find a great new way of doing something different.

In general, fall and winter are a time for thicker fabrics and darker, richer colors. Leather, shearling, luxurious wool or cashmere yarns, flannels, and corduroy fabrics will keep you warmer when the temperature drops. These materials are also very plush and comfortable, and can look quite elegant and put-together. Our collection of fall jackets and coats will keep you warm. Spring and summer are great for pastels and bright, almost neon-like colors. However, the fall and winter lend themselves more to saturated hues like dark green, deep red, burgundy, purple, indigo, brown, or camel. Neutral colors like black, navy, charcoal, light grey, or white are great as well; they can serve as a good foundation for mixing other colors into your outfit. 

Without further ado, here are five interesting trends that we’ve seen and found relevant enough to add to our collection.

Tech Fabrics

Tech Fabrics and Athletic Performance Garments

"Athleisure" is a buzzword we’re hearing quite often in the men’s clothing industry lately. Basically it’s all about using traditionally athletic-inspired apparel to create a clean, put-together casual look that serves as an alternative to the standard uniform of jeans and a t-shirt that most guys go to.

The key here is to pay attention to the fit. Yes, you can wear sweatpants and a track jacket when you’re out watching the game at the bar or running errands on a Sunday – as long as your clothes aren’t too baggy and unkempt-looking. You don’t need to go for a slim-fit, but a pair of sweatpants with a slightly trimmer leg silhouette, or even a banded ankle cuff, will work great. The accompanying tops should also fit well and have a clean-cut appearance. Comfortable athletic sneakers naturally fit right into this look. Overall, the athleisure look is cool, casual, and comfortable - with plenty of youthful and modern appeal.

Similarly, many gentlemen are incorporating technical golf apparel into their casual wardrobes. Many polo shirts, sweatshirts, shorts, pants, sport shirts, and even underwear is now being made with a variety of technical stretch fabrics. Although these designs were originally conceived for use out on the golf course, many gentlemen find that they are elegant and dressy enough to wear to the office or around town.

Many forward-thinking brands are now promoting clothes with this kind of versatility. You can throw on a dressier stretch sport shirt and some performance pants in the morning, and look absolutely appropriate for the office. When you need to take a client out on the golf course or go to the driving range with your boss at lunchtime, you can just play in your work clothes without worrying about sweating a bit, or having your clothes constrict your movements. In other words, this apparel can pull double or triple duty: it works just as well out on the course as it does at the office or at happy hour. This can be considered a more mature, professional alternative to the “athleisure” look, which similarly emphasizes comfort and practicality while looking sharp.


Investment-Worthy Outerwear

Coats and jackets are staples in pretty much every gentleman’s fall and winter wardrobe. And if properly cared for, a quality piece of outerwear can take care of you for many seasons – perhaps even a lifetime. It’s great when you can find a garment like this that you truly love and can come to rely on when the weather gets rough – whether it’s a shearling-lined leather topcoat or a sueded leather jacket.

When you find a great-looking piece of outerwear that’s made with the best materials, with excellent craftsmanship, and that fits you like a glove - the only downside is that it’s usually quite expensive. However, we consider this to be a great investment that can actually pay off in the long run. Something like a genuine shearling-trimmed leather coat is not only rich and luxurious, it can stand up to repeated wear in adverse conditions - and will gain character and look even better with age. And as I mentioned before - if you take care of it, it’ll take care of you for decades.

This is why we love giving our customers plenty of choices in investment-worthy outerwear: leather, suede, or cashmere-blend jackets, topcoats, vests, and more. “Taking the plunge,” so to speak, and putting the initial investment into these pieces can be daunting at first. However, we know from first-hand experience that if properly selected and sized, these pieces become true favorites in men’s closets.

The key to properly selecting a piece of outerwear is to first find something that resonates with your tastes and style. Consider how it will work with what you like to wear and what’s currently in your closet. For example, if you go casual quite frequently - a leather or suede jacket can be a perfect complement to your look. Similarly, if you work in a dressed-up office environment, and are looking for something elegant for the colder months of the year – a cashmere topcoat can be a worthy accompaniment to a suit, a blazer, or a sportcoat. 

Once you find a piece that suits you, it’s just a matter of trying it on and finding the right fit. You can reference my previous article, The 5 Steps to A Great Fit, for some specifics on what to look for.

The final step is to make sure that you take good care of whatever you purchase. This can mean finding a dedicated specialist to clean and condition your leathers, or going over cashmere fabrics with a gentle brush once or twice a season. Then, you’ll have a piece of outerwear that’ll eventually pay for itself and keep you looking sharp for years to come.



We’ve seen a surge in popularity of sleeveless sweaters and outerwear for a couple of seasons now, and it doesn’t seem to just be a passing trend. It’s hard to deny the practicality of a vest. If you’re a guy that overheats easily when bundled under a ton of layers, it’s pretty much a dream come true. The vest will keep your body’s core warm, but its lack of insulation around the arms and underarms allows you to vent away excess body heat quite easily. Not only that, but it’ll allow you to show more of the shirt or sweater you have on underneath, making for some interesting options for matching pattern and color.

Sleeveless sweater vests come in a variety of different styles. A v-neck sweater vest is a traditional choice, and always looks great layered over a sportshirt or a dress shirt. It’s a mature and conservative choice to wear to the office, around town, or any other occasion that requires a dressier, more sophisticated touch. Merino wool and cotton fabrications are the most common here.

Similarly, sweater vests with a quarter or full-zip trim will still give you the dressy look of a traditional v-neck vest, but with a modern touch. This is another great option for the business casual office, and it has a slightly younger, more contemporary appeal.

There are many casual vest options to choose from as well. You should be able to tell these apart from the thinner, dressier sweater vests mentioned above. They may appear more rugged and outdoors-inspired, and can be slightly thicker. These pieces are a great complement to a casual pair of jeans and a sportshirt, or even a polo.

There are also plenty of vests that are actually outerwear pieces. Puffer vests stuffed with packable down, waxed cotton, or even leather vests all make for great-looking top layers. They work well during the milder fall weather, or in climates where it doesn’t get too cold during the winter.

Quilted Fabrics

Quilted Fabrics

Another trend that we’ve been seeing a lot of recently is the use of quilted fabrics on sweaters, or more commonly on outerwear pieces like jackets and vests. The fabric is usually done in a diamond-stitch pattern along the entire body of the garment, binding two layers of cloth over a layer of padding. The padding gives the quilted fabric extra insulation, but the stitching keeps the overall bulkiness of the garment to a minimum.

This takes a lot of the hassle out of layering up for the cold weather. The compact, low-profile thickness of a quilted garment makes it easy to throw on over a sportshirt and a sweater without making you feel like you’re constricted or over-layered. This also makes quilting well-suited for the transitional fall weather, where it can be windy, chilly, and rainy one moment and sunny and balmy the next.

Not only are these garments functional, they can aesthetically complement many different styles of dress. Most quilted jackets and vests trace their origins to outdoor sporting activities like hunting or shooting, and have a certain charming, rugged appeal to them. As such, they look great layered over a flannel shirt and some worn-in denim. You can add a pair of leather boots to get a look that’s comfortable, functional, and unarguably masculine.

Some quilted pieces take a more elegant approach. These garments look more like something that you’d wear to work or around town, rather than on the hiking trail. Many times, they come with special trim like corduroy or suede, and they’ll pair well with a merino wool sweater, a sportshirt, or a dress shirt. However you choose to wear them, quilted fabrics will always be a great choice if you’re looking for a comfortable, functional garment with a unique look.

Outdoors-Inspired Apparel

Outdoors-Inspired Apparel

Clothing inspired by being in the great outdoors always works well for the fall and winter. The same clothes that you might take with you on a mountainside cabin trip or out hiking also work well for casual occasions around the city. Cotton canvas or twill khakis, rugged denim, thick woolen sweaters, and sportshirts made from denim, corduroy, or flannel can be combined with leather boots and belts to create a great casual outfit. Outerwear is a big category here as well. Waxed cotton, canvas, or leather jackets and vests are all great options to complement this look. The pattern and color styling here is usually a bit more restrained, which is great if you’re a guy that isn’t drawn to overly bright and flashy patterns.

You don’t need to be an active outdoorsman to appreciate the rugged durability and comfort of outdoors-inspired apparel. However, its biggest appeal is its practicality. These clothes are designed to keep you protected from the elements and stand up to the pressure of repeated use, and are made with great attention to detail and workmanship. You can buy a great flannel shirt or a pair of canvas chinos, and they’ll keep you warm and comfortable for years. The garment will even break in and get better with age - becoming a truly distinct, vintage piece that you’ll love wearing as much as you can.

Final Notes

Our philosophy at Westport is to keep up with the trends in the marketplace, but always stay true to what our customers love. If we bring a trend or a new style into our merchandising mix, you can be sure that we did so because we find it relevant to our customers’ tastes, as well as what we stand for as a brand.

Individual style is personal, and can evolve over time for many gentlemen. Sometimes a new trend is a truly innovative way to do something new and different. However, not every gentlemen needs to adopt every trend out there. Again, that’s why we encourage everyone to try something new every once in a while and find out what works for them – what they’re the happiest and most comfortable wearing. Fall and winter always offer a large variety of options in menswear - and we’re genuinely excited to see which styles endure year after year, and discover the ones that come out of the woodwork to become new favorites.