Gents, it’s happening – Fall (not winter) is coming.
It’s time to put away the summer pastels and linen and pick fall dress shirts that fit the season – deeper colors, heavier fabrics, and patterns with some texture to them. That thin poplin shirt you wore all July looks flat and feels cold under a sweater in October.
Need help making the right choice? Have no fear – I’m here to help. We’re going through 5 men’s dress shirt styles you can rock this Fall.
1. Patterns: All About The Checks
Checks are a fantastic go-to pattern for men’s dress shirts. They’re incredibly versatile, yielding a plethora of variations.
There is a general rule of thumb to consider when shopping checks: the smaller, the more formal. 1/2″-2″ will tend to be more aggressive and thus suited for casual wear. If you find something under 1/2″ or even 1/4″, you’ve probably got something suited for the office (assuming the colors are subtle as well).
Gingham is probably the quintessential check pattern – used in shirts and ties alike. In some instances, you might even find subtle iterations on sport coats. They consist of tight overlapping lines in contrasting colors.
Windowpane patterning is common on casual suits, but it’s also acceptable on a dress shirt. My favorite, though, is Prince of Wales.
It started in Scotland as the Glen Urquhart check, a woolen estate check from the Highlands, and picked up its nickname from the British royals who wore it – most famously Edward VIII while he was Prince of Wales. On a shirt, look for a small, low-contrast version. It reads as texture from across the room and as pattern up close.
All-in-all, it’s all about the checks.
2. Colors: Go A Few Shades Deeper
Next, we have colors – yes, there IS a difference between hues and shades. A hue is the color itself – blue, green, orange. A shade is that hue darkened with black. Navy is a shade of blue. Forest green is a shade of green. Knowing this makes fall shopping simple: keep the hues you already like and go a few shades darker.
That being said, you want to look for deeper hues of blue, yellow, orange, and green.
Forest Green, Pumpkin, and Tomato Red are among several rich colors you can go for.
One warning. On a dress shirt, let those rich colors show up in the pattern, not the whole shirt. A navy-and-rust check, a burgundy stripe on a white ground, an olive oxford – that’s fall. A solid pumpkin dress shirt under a suit is a LOT of shirt. Let the tie, the sweater, or the jacket carry the loudest color.
Need more insight into color? I have plenty of info on how to choose a color based on your skin tone.
3. Cotton Flannel
The cool weather is setting in. Flannel’s going to be your friend if you’re going for a casual and more masculine look.
Flannel is traditionally made with either cotton or wool made into a thicker weave. It makes for a durable fabric that can be suitable for colder climates. During the manufacturing process, it can even be brushed for a more rugged look.
It’s great for a guy looking to be elegant with a dash of the outdoors in his look.
4. Twill
You need some texture in a men’s dress shirt for the fall, therefore, you’ll need twill.
Twill is a weave in which filling threads are passed over each other in such a way that resemble diagonal lines. The weft thread will go over, under, and over the warp in succession. It’s woven in a series of diagonal lines called ribs.
A few variations exist; Right Hand and Herringbone are a couple of examples. Regardless of your choices, you’ll nail the Fall look.
5. The Oxford Weave
Finally, we have Oxford. It’s akin to a basket weave. What makes it unique is the fact that the weft is dyed while the warp stays white. This makes for a lovely overtone of white in the texture.
Using this technique, for instance, makes for a much hardier shirt than most. It’s the perfect option for those men’s dress shirts you want as your workhorses. I kept it at number 5 because it’s tough, it gives a shirt personality, and you can find it in all colors.
Fabric Weight: Why Your Summer Shirts Feel Wrong In October
Most of the dress shirts in a man’s closet are poplin or broadcloth. Tight, flat, smooth weaves. They’re the right call under a suit all year and they breathe in July. But put one under a lambswool sweater in October and the collar goes limp and the wind cuts right through it.
Fall fabrics are different in two ways. First, the weave has visible texture – twill, oxford, herringbone – which gives the shirt depth next to wool and tweed. Second, many are made from heavier yarn or brushed on the surface. That brushed nap is why flannel feels soft and why it holds heat.
Here’s the rule I use: the more texture you can see from three feet away, the warmer and more casual the shirt. Poplin sits at one end, flannel at the other, and everything else falls in between.
One option most guys never think about is a cotton-wool blend shirt. A little wool in the mix gives you real warmth without the bulk of a thick flannel, and it’s still sharp enough to wear under a sport coat.
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| Fabric | Warmth | Formality | Wear It With |
|---|---|---|---|
| Poplin / Broadcloth | Low | Most formal | Suits and ties. Your year-round office shirt, not a fall statement. |
| Oxford | Medium | Business casual | Chinos, a crew neck sweater, a navy blazer. The workhorse. |
| Twill | Medium | Office to weekend | Sport coats and knit ties. Holds a collar well under layers. |
| Herringbone Twill | Medium | Office to weekend | Tweed or flannel jackets. Texture that matches the season. |
| Cotton Flannel | High | Casual | Jeans, boots, a field jacket. Lightweight versions under a sport coat. |
| Cotton-Wool Blend | Highest | Smart casual | Cold days under a sport coat when you want warmth without bulk. |
| Bottom line | The more texture you can see from three feet away, the warmer and more casual the shirt. | ||
Warmth depends on fabric weight too – a heavy oxford can be warmer than a thin flannel.
How To Layer A Fall Dress Shirt
Fall is layering season, and the shirt is the foundation. Get it wrong and the sweater or jacket on top can’t save you. Here’s what I look for.
Under A Sweater: Go Button-Down
A button-down collar is your best friend under a sweater. The buttons hold the collar points in place so they don’t wander out of the neckline or flip up by lunch. With a crew neck, only the collar should show. With a V-neck, either wear a tie or leave the top button open – buttoned to the top with no tie looks like you forgot something.
Skip the wide spread collar under a sweater unless you’re wearing a tie. Without one, the points have nothing to hold them and they collapse. Need a refresher? Here’s my guide to dress shirt collar types.
Under A Sport Coat: Match Texture With Texture
A tweed or flannel jacket has a lot of texture. Put a shiny poplin shirt under it and the shirt looks flat and out of place. A twill, an oxford, or a small check holds its own. Keep the shirt’s pattern smaller than the jacket’s pattern, and you won’t have the two fighting each other. If you’re not sure what your jacket is made of, read up on sport jacket fabrics.
Fit: The Rule That Doesn’t Change With The Seasons
Heavier fabric means more bulk. Every extra inch of shirt around your waist bunches up under a sweater and makes you look heavier than you are. So fall shirts need to fit closer through the body than you think.
If a shirt billows at the waist, take it to your tailor and have him take in the sides. It’s one of the cheapest alterations there is, and it changes the whole look. And with flannel, expect some shrinkage – wash it cold and hang it to dry.
Fall Dress Shirts FAQ
What color dress shirt is best for fall?
Go for deeper versions of the colors you already wear – navy, forest green, burgundy, olive, and rust. White and light blue still work, as long as the fabric has some texture. A check that mixes a light ground with a darker fall color gives you the best of both.
Can you wear a flannel shirt as a dress shirt?
A fine, lightweight flannel in a solid or small check can go under a sport coat, and with a knit tie it looks great. A heavy plaid work flannel can’t. If it’s thick enough to wear as a jacket, it’s not a dress shirt.
What is the warmest dress shirt fabric?
Flannel, especially a cotton-wool blend. The brushed surface traps heat. After that, heavy twills and oxford cloth are your next warmest options.
Summary – Men’s Dress Shirts For Fall
Gentlemen, when it comes to looking great this Autumn, it comes down to deep colors, hardy fabrics, and lots of checks. Need to turn some heads come October? This’ll get you there.
What to read next?
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