Your Guide to Fall Wedding Style

Getting dressed between late August and, say, mid-October is the best time of the year for having fun with your clothes, where the weather doesn’t really hold you back in terms of what you can wear. Similarly, weddings offer an opportunity to flex one’s sartorial muscles — are you dressing up an elegant cashmere polo for a more casual affair or have you opted for an immaculate silk tie for something more formal?

In the Venn diagram of getting dressed, then, a late summer to mid-fall wedding is nestled right in the centre. It’s an elite time of year to pull on your best wares. With the weather and the occasion affording so many possibilities, there are countless ways to put your best foot forward.

For starters, it’s important to consider which pieces to turn to, depending on what the appropriate level of formality might be: is the reception at an exclusive, wood-panelled members-only golf club or at a smaller, more intimate setting like one of the happy couple’s favourite restaurants in the city? For weddings whose setting hews closer to the former, there’s really no beating a pair of hard-bottomed leather shoes, a sharply-cut suit, pressed shirt and a tie. As the setting becomes less formal, you can eschew the tie, while the variable weather opens the door to pairing a suit with a sweater or polo and even a more laid-back pair of shoes. Should you wish to trade the suit for a sport coat or blazer with a pair of trousers, you can consider a shirt without a tie a safe and stylish bet.

Next, it’s time to think about the fabrics that you’ll want to wear — both in terms of weight and texture. Midweight pieces are your safest bet, offering breathability during the day, without leaving you underdressed when the sun goes down. In an ideal world, your suit will be cut from a wool blend fabric. If the weather is going to be warmer, a linen shirt offers a great solution, with superior breathability and luxurious texture. But, if you want to wear a tropical wool suit you can pair it with something heavier, like an Oxford cloth shirt or a cashmere sweater. The key to — or, rather, the fun part about — fall style is the freedom to mix and match textures and that extends to footwear, where a pair of pebbled leather derbies, suede chukkas or nubuck dress sneakers can go a long way to levelling up your look.

Last, but certainly not least, comes the consideration for the colour palette. If spring and summer are the seasons to inject pops of colour into your looks — hues that call to mind colourful ice cream or a seaside resort town — then late summer giving way to fall ought to be a call to opt for something richer, rooted in neutral and earthy tones but elevated with deep blues, hearty reds, deep greens and sumptuous browns. Even if it’s no longer the season to pull out your electric blue knit tie or a cream-coloured linen suit, you can still have fun! With that in mind, these are our favourite pieces to build the best late summer and autumn wedding looks.

Brunello Cucinelli Cashmere Turtleneck Sweater

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Embracing a new, more modern wedding dress code, consider swapping out your collared shirt for a turtleneck sweater as we move deeper into fall and the temperature drops — especially if you’re only attending an evening dinner and reception or if a portion of the festivities are outdoors. Brunello Cucinelli is renowned unflinching commitment to luxury and for its mastery of cashmere: there’s a reason that Mr. Cucinelli is colloquially known as the King of Cashmere. All of that comes together to make this chic cashmere turtleneck an ideal choice for fall weddings, offering sumptuous comfort and refined elegance in equal measure that can be worn casually or paired with even the most formal of smoking jackets. ($2,500)

Gucci Men’s Loafer with Horsebit

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If there’s a time to wear rich burgundy red shoes it’s a fall wedding. Here, Gucci’s iconic Horsebit motif is applied to a sleek loafer made from premium leather and done up in Rosso Ancora, the standout colour of Sabato De Sarno’s inaugural menswear collection. Owing to their superior materials and meticulous craftsmanship, these loafers will get better with time, meaning they can be your go-to shoes for fall weddings for years to come. These can be worn more casually, with a slightly shorter trouser in a lighter colour and white dress socks, or more traditionally, with a darker wool suit and trousers that have a slight break. ($1,425)

BOSS Cotton-Cashmere Corduroy Jacket

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Corduroy is a regal fabric, drawing its name from the French word for king: roi. Often thought of in retro terms, sometimes seen as being a bit kitsch, it’s an underrated fabric that always surprises people (in a good way) when used to create modern tailoring. It’s also perfect for fall, owing to its texture and warmth. Case in point: this smart slim-fit BOSS double-breasted jacket, crafted from a cotton-cashmere corduroy in a dusty shade. While the jacket can be paired with matching trousers to create a suit, consider pairing it with a darker pair of trousers and brown suede shoes with a shirt and tie for a look that can play in formal and casual spaces alike. ($1,795)

Bontoni Suede Leather Brogue Oxfords

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A perfect pair of autumn dress shoes, made in Italy with Goodyear construction and Vibram sole. The brown suede and rugged Vibram sole give these elegant wingtip brogues a slight casual touch that means you’ll be able to wear them with jeans after the wedding’s over — particularly convenient for that destination wedding you’re trying to only pack a carry-on or weekender for. Lighter contrast stitching where the midsole meets the upper facilitates wearing these with light grey trousers, but they can easily be paired with a navy suit to great effect. ($1,875)

Atelier Munro Pine Green Polka Dot Silk Grenadine Tie

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The texture of this grenadine tie gives it an elevated air that’s perfect for fall, while the darker shade of pine green pairs well with a range of suit colours, from dark navy to earthy browns. With the subtle polka dot pattern, this tie can be worn with shirts both solid and striped, but ought to be paired with white or blue for the most stylish look. ($169)

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