I Love Fall Style.

As a man, dressing for Fall is one of my favorite things.

This is literally what I wore on Tuesday.

I love Fall (or Autumn, as it’s known where I grew up.) I love the crisp, cool weather as a change from the heat and humidity of Summer. I love the afternoon light from the sun low in the sky, washing over the golden and browning leaves of the trees under the clear, startling sapphire blue which deepens into the cold cobalt of evening. I love the darkening skies and sudden rain showers and the occasional thunderstorm.

And I love that after long months of stifling heat I can finally start layering up what I wear, mixing patterns, colors, textures, and accessories into outfits which are both practical and (to me) fun.

There’s something about Fall which makes it the best time of year for male style. In summer, it’s about keeping things light and minimalist, staying fresh and not looking like you’re trying too hard — cottons and linens in plain colors, with the occasional bold print thrown in for effect, maybe a raw silk shirt with a couple of bracelets you bought in St Lucia or Sao Paulo. In Winter, all anyone can see is your outerwear, and who cares about the stitching of your boots when you’re ankle-deep in icy slush (not to mention the time spent scrubbing said boots with saddle soap and boot wax to prevent the salt from destroying them). And Spring … well, thank god Winter is over, but with more cold showers than a group of priests at a porn convention and the trees looking about as interesting as the Dalai Lama’s sex life*, it’s just not that fun.

Fall is like the morning after the awesome party of Summer, where you’re still rolling with the energy of drinking pisco sours while salsaing by the pool, sleeping in a hammock, and then toasting the sunrise with Champagne. It’s a t-shirt which reads “Smokin’ Hot Yesterday, Still Cool Today” worn under a tuxedo jacket. It’s the breakfast after the party-after-the-after-party, so it’s worth dressing well for.

Fall style is fun because it also needs to be practical. It’s cooler, but the weather tends to swing from warm to chilly so layers are a good option. Coats tend to be worn open, allowing the rest of your clothing to be seen. Particularly later in the season, scarves, gloves, hats and umbrellas are pragmatic additions. It’s a time for dusting off the heavier fabrics, opening up the opportunity for denim, corduroy, velvet, leather, and of course wool in all its variations: tweed, twill, herringbone, checks, pinstripes, tartans, plaids and the whole variety of knits to name a few.

My style used to be fairly bland. I’d choose good clothing which fit properly, generally in nice fabrics and solid colors which would look good for more than one season. Clothing in Winter was dark; in summer it was light. I can’t remember exactly when I began to embrace patterns, but if I have to put a pin on it I’d say it was 1996, when I bought a silk tie from Liberty in London which was completely outside my comfort zone and utterly beautiful. It’s electric blue, finely embroidered with climbing roses of gold with red buds, and I still have it. Somehow, nothing patterned was quite as unapproachable thereafter (although sometimes I made some pretty horrible choices).

Enough about me! On with some of the things I’ve learned about styling for Fall. I mention a number of traditional style “rules” below — just think of those like The Matrix, where some can be bent and some can be broken … if you’re the Morpheus or Neo of men’s fashion.

Fit is the Foundation. No matter what you pick, your clothing needs to fit both your body and the occasion. If you’ve tended to pick your clothes to fit you, it’s much easier to combine them in different ways. You’ll likely also select different clothes if you’re meeting friends for a walk in the park than a night at the opera or a business lunch. There are some basic rules, such as don’t wear a baggy sweater under a fitted jacket, and make sure that the lengths of various items work together. If you look in the mirror and things don’t seem to mesh, it’s likely going to look more dorky than trendy.

Layers. The trick I’ve learned with layers is to recognize what people will see most of, and which parts of your outfit will really be highlights. For example, light sweaters and vests will have a more dominant effect with the shirt only showing collar and cuffs, so there’s no point picking a shirt with lots of detail on the body. There are many shirts which do have interesting cuffs and collars, such as Stone Rose and Robert Graham, and it’s worth looking at some of the excellent range of fabrics from Charles Tyrwhitt. A good tip is to lay things out before you put them on to see if it goes together the way you expect — a valet stand is a good investment — and always check yourself out in the mirror.

Patterns. The traditional rules are to only have two patterns and have the rest of your outfit be solids. That’s good advice and certainly if you’re just starting to explore patterns it’s worth following while you explore what works for you. As you get more confident, these rules can be bent and ignored by adding in the elements of color and texture, which can be used to both soften and visually blend different patterns into a more coherent combination.

Colors, Tones, and Hues. It’s useful to understand the color wheel and complementary and contrasting colors. The general rule is to have most of your items complement each other, with a single item or color for contrast. Within colors, the tone (the level of paleness or grayness) and hue (tinting of a different color) can be used to ensure that the items in your outfit fit within a common range — a selected spread of colors, for example blues, tans, and greens, with highlights of red. Choosing a range helps the patterns work together: for example, a navy blue paisley pocket square will work with a mid-blue herringbone jacket over a blue and burgundy check shirt.

Fabrics and Textures. Most fabrics have a combination of color, hue, and pattern. For example, wool fabrics ranges from plainer varieties like twill and flannel to tweed and herringbone. Other fabrics including treated leather, suede, buckskin, cashmere, corduroy, cotton, denim, silk, and velvet, each of which have a distinct texture ranging from smooth to rough, shiny to matte, soft to hard. A sheer shirt can complement a matte pincord jacket; suede can pair well with silk and knits; velvet adds a visually intriguing shine without becoming a human disco-ball.

If there is a downside to having a well-developed and playful Fall style, it’s that people will want to talk to you and possibly even fondle your fabrics (especially if soft knits and velvet are involved … some people just can’t seem to resist). Any negative comments or snide remarks you receive will most likely be sourced from some variation of envy at your taste and confidence, so are an opportunity to ignore or deflect with charm and humor — you won’t want to detract from the image you’re projecting by resorting to defensiveness or nastiness. The chillier the weather, the more your warmth will be appreciated.

* This is a little unfair, as the Dalai Lama seems to be an amazing person and pretty much has sex with the universe, which must be awesome judging by how relaxed and smiling he is.

Liam is an avid traveler, thinker, and regular contributor to The Modern Dandy’s Guide to Manliness podcast, which explores the challenges, choices, and commitments of being a man in the modern era.

Thinker. Technologist. Tasmanian.