2025 Big & Tall Men’s Fall Fashion Guide

September 26, 2025

Football season approaches. School starts again for the youngins’. Temperatures are falling and pumpkin spice abounds…everything. Once again we approach a most versatile season in men’s fashion where we see a large shift in silhouettes, weight, fabric and color choices. Fall is arriving.

As always, somewhere deep inside is the feeling of impermanence and an urge to hold on to the last of summer while looking forward to something new. At Westport Big & Tall, we see a range of new (warmer) fall clothing options arrive on our doorstep, which primes us to think long and hard about what is heating up in fall fashion for the big & tall man. There’s no question that excitement comes with change.

When it comes to clothing choices, fall is a time to put away the linens and breezy tanks and shorts of midsummer and get ready to embrace the changes in the weather and your wardrobe. Warning - depending on your climate, and unless you go on a vacation, you may not see those swim trunks for a while. Let’s take a look at some of the basics of men’s big & tall styling for autumn before we check out some of 2025’s newest fall styles.

Autumn’s Evergreen Styles - the Basic tips

No matter the year, fall fashion is grounded in a few key concepts that keep men looking sharp and stylish, regardless of the outfit. In big and tall men’s fashion, fall’s new beginnings mean simple summer apparel gives way to more complex style opportunities: additional layers, texture experimentation, and longer shapes to match the lengthening evenings.

For most people, it’s best to look stylish rather than fashionable. Know the trends, but don’t chase them. It doesn’t pay to be trend averse, however - fully ignoring trends can lead to men dressing and seeming much older than their age or even looking like they’re in a sort of costume. A good technique is to borrow a bit from everything; each trend across the decades offers some universal stylistic truth, after all.

Fall Fashion & Color

Well-styled big & tall men will seek ways for their wardrobe to complement nature’s changing color palette, while strategically picking places to pop some unexpected hues. That means a cornucopia of golden browns and yellows with orange-tinted reds, darkening greens and mid-temperature blues, with blacks and grays tastefully peppered in. Accent colors can run the gamut, but be sure to keep strong contrasts as a small percentage of your outfit’s overall palette.

Fall Fabrics

When it comes to materials, your style needs to match the weather. It’s hard looking good if you’re too cold or too warm. Regardless of the season - but especially true in colder temperatures - dressing for style means dressing for comfort. Also remember that there’s a time and place to wear that sweatsuit that’s been sitting unneeded all summer.

For elevated style, fall lends itself well to experimenting with blending fabric choices. Flannels are an obvious choice, but mixing in touches of leather, textured wools and cotton blends can add a lot of flavor to your outfit. Corduroys start to come out of their summer hibernation as well, and can make for excellent contrast pieces.

Fit

Fit and style are synonymous. Unless you’re going runway avant garde, well-fitting clothes are the way. Big & tall men know this all too well: always opt for something that works with your body instead of fighting against it. A stout individual should not try to squeeze into skinny jeans, for example. Nor should a lean, tall man select baggy trousers or oversized sport jackets. Striking a good silhouette beats opting for the “perfect” shirt design or unique sweater texture if they don’t fit right.

Layering - a fall tradition

Layering articles is a hallmark of fall style, and only winter beats fall for layering opportunities. A simple shirt and overcoat pairing can go a long way in this manner. Adding a sweater or vest between adds warmth, of course, but also lends a chance to create some color, texture and fabric weight contrasts.

Layering Maxims

The general rule for layering is to go with thin fabrics nearest the skin to thick on the outermost layer. For instance:

Cotton Shirt, under a:

Cashmere Sweater, which layers beneath a:

Wool Blazer

Keeping a firm grasp on the basics of fall style ensures a well-considered appearance, even if you’re just throwing something together last minute. Since we’ve covered these basics, it’s time to look at what we’re seeing come down the fashion pipeline for fall this year:

What’s going on in Fall ‘25

Flannels

It wouldn’t be fall without flannel. With so many pattern options and colors available from a wide range of designers, the flannel shirt has become omnipresent in the colder seasons. If you’ve graduated stylistically beyond the thrift-store variety, a well-made well-fitting flannel from Westport Big & Tall can speak volumes. With a rainbow of colors and a range of thickness, the flannel shirt is always a great piece to have in your fall wardrobe. And when you’re kicking back, don’t forget the flannel pants!

Some great big & tall flannel options at Westport include:

Cardigans & Pullovers

The classic cardigan has seen a resurgence in popularity and offers a great layering opportunity for big & tall men. Its versatility lends to its stylishness, so feel free to pair it with jeans, chinos or slacks. The pullover is a more modern take and finds itself equally at home on the golf links as at a fancy dinner. For either, a solid colored t-shirt works well underneath for a casual weekend look, while a collared button-down layered beneath a pullover or cardigan can achieve a more elevated style.

Select cardigan & pullover options at Westport Big & Tall:

Sweaters

When the wind whips up, there are few things that fit the fashion mold like a quality sweater. With a sport shirt tucked under, a big and tall man can use this adaptable fall staple to look studious and slightly dressed up. Layer it with a blazer or a sport coat and a man can look downright professorial. From cable-knits to turtlenecks and quarter-zips, the sweater is always a useful piece of fall apparel.

A selection of great fall sweaters this year includes:

Pants: Chinos & Five Pocket Styles

Since we’ve largely put away our shorts for the summer, each fall offers plenty of opportunities to try different styles and color pairings of big & tall chinos. The five-pocket pants design has moved from being the providence of denim, so we’re seeing these styles in all sorts of fabrics and colors. Paired with a t-shirt, polo or button down and some casual shoes, these chinos are a simple option that can get thrown together while still looking intentional.

Get the look at Westport Big & Tall:

Jeans: What Fit & Wash is Right for Fall?

In terms of style and versatility, few items have stayed at the top of the fashion list as long as jeans. With a few exceptions, we feel that a jean’s cut is a matter of personal preference and comfort, so whether you opt for an athletic fit or a simple tapered silhouette, going with what you’re most comfortable in is often the best route.

Lately there’s been a resurgence in experimenting with different colors and wash styles, which is an exciting opportunity. In fall, try a middle ground between light washes of summer and the dark washes that take over in winter.

These jeans options will fit the bill for fall:

Big & Tall Fall Outerwear Style

Leather and Shirt Jackets

Owing to a resurgence in 90’s styling, we’re seeing the elevation of cord, denim & leather jacket options this year. What’s different from the Clinton-era is the reduction in bulk for these throwback styles. Leather is king in the fall, but denim or corduroy sport jackets work great for both casual and semi-casual settings. Having a great variety of fall jacket options is key.

Here are a few selected options:

Fall Blazers & Sportcoats

Before the weather gets too cold, a smartly-matched blazer and sweater or shirt combo can offer endless possibilities for the well-outfitted big & tall man. A cotton polo works or plain button-down always pairs nicely with a light sport-coat, or you can go with a colorfully printed sport-shirt beneath a blazer in muted tones.

Sportcoats and blazers we like for fall:

Bomber Jackets

Once again, classic bomber returns for another run this fall! The latest take on this iconic piece tends to offer slimmer silhouettes, but is (as always) highly complementary to everything casual, from a t-shirt or henley and jeans to a sport shirt with a pair of well-fitting chinos. Look for interesting modern interpretations of this utilitarian, stylish garment.

Great bomber jacket options for this fall:

Long Overcoats

A car coat, trench or shearling never seems to go out of style, and we’re seeing a heavy lean on these types of outerwear as a good alternative to the shorter bomber or trucker jacket. For the big & tall man wearing a suit, a long topcoat or trench is an essential pairing. But he can also mix it up and pair a leather shearling coat with a fall-hued cardigan and a pair of dark jeans for a more rugged, casual feel.

A variety of long overcoats to keep you warm this season:

Footwear for Fall

Fallen leaves crunching under your steps is a hallmark of autumn. So is splashing through mud and puddles. Naturally, autumn brings a change of footwear: sandy toes in flipflops are quickly replaced with more substantial footwear to handle the changing weather. Slippers also come into vogue at home as you relax and watch the big game.

Stylish footwear options for autumn include:

Big & Tall Fall Fashion: 2025

Big & Tall Fall Fashion: 2025