A year in review: my favourite outfits of 2021

Despite the year being a dumpster fire in many ways, 2021 was a good year for my style.

It felt like the year where I really felt that my tastes had developed and consolidated into a cohesive point of view. Having spent the past couple of years soaking up knowledge every way I could manage, this year I I experimented with a wide range of influences and styles. It was a year where I was able to round out my wardrobe much better than before, and was able to acquire a number of garments that better fit my own approach to silhouette, proportion and overall style.

In previous years, I made do with too many items that weren’t an ideal fit, didn’t have the ideal proportions or design considerations. I spent much of this year culling the pieces that didn’t suit me or my tastes, and did what I could to create a better rounded wardrobe without buying too much. 2021 was the year where I really nailed down my preferences on fundamental details like shirt collar proportions, jacket feature placement, favourite shoe styles and makers, my preferences for ties and favourite types of fabrics for each season.

I realised that pant style and silhouette isn’t a one size fits all deal for me. What I found is that I like a variety of shapes, depending on the outfit I’m creating. I found some chinos that I like, for the first time, and I’ve become quite the chino wearer in the summer. I realised that I don’t like big wide jeans, and prefer a normal straight leg like can easily be found with vintage Levi’s 505s, jeans which I developed a penchant for wearing with tailored jackets. I also tried flared pants, expecting that they’d never work on my frame, but in the end I loved them.

I did a number of design exercises working in the made to measure tailoring industry. I learned much from each item that came to fruition; the summer suits (one brown, one tan check) became instant favourites and have stayed that way, while two that I did in the winter and loved at the time – a corduroy western style suit and a grey flannel with bellows pockets – have become expensive tales of loves lost, as I stopped consuming dairy late in the year and the jackets from both suits are now unalterably big for me*.

The following ten outfits are some favourites of mine from throughout 2021. I believe they make a good showcase of how my style evolves through the cool and warm seasons.

Made to measure suit style with vintage details and vintage coat
The grey flannel suit I did during winter, paired with a NOS German cavalry twill coat, suede derbies and conservative Armani tie. The oversized collar is somewhat noticeable since the lapels aren’t sitting flush with the generous shirt collar.
Navy blazer and jeans - double denim Ralph Lauren style
I developed a preference for camelhair over cashmere when it comes to winter warmers. Seen here is a vintage Polo camelhair blazer, over double denim and black cowboy boots. The denim shirt was bought by my dad sometime in the early 1990s, and handed down to me last year.
1940s buffalo plaid lumber jacket style Polo Ralph Lauren tweed pants and cowboy boots
I got this beautiful 1940s buffalo plaid jacket from Midwest Trader late in the winter. Here it’s paired with a western shirt I designed, an old Hanes tee, Polo tweed pants and western belt/boots.
Flared jeans and cowboy boots style l'etiquette Belvest jacket and black turtleneck
I never expected flared pants to work on me, but I really wanted to try them anyway, since I could see that they were having a big moment. I was pleasantly surprised with this pair of late 1960s Levi’s Sta-Prest pants and how good they looked, especially paired with heeled boots. I got the inspiration from this outfit from the French magazine L’Etiquette.
Big vintage shearling coat style 1970s 1980s western shirt cowboy Americana
On one of the year’s coldest days, only the warmest clothes would do. This vintage shearling coat was a welcome companion on many occasions, paired with that favourite heirloom western shirt of mine and the increasingly present black cowboy boots.
Tuxedo dinner jacket and jeans style black watch tartan
I picked up my first dinner jacket last year; this vintage Brooks Brothers blackwatch tartan sack jacket. I enjoyed wearing it with an open collared white shirt and a variety of denim. The shoes are embroidered velvet slippers with proper soles, from Stubbs & Wootton.
vintage McGregor wool robe English aristocrat style
I’m not usually an outfit repeater, but I wore this for at least a small part of every day during the winter. We all had to be stuck at home for some period of time during the year – some more than others – so I wanted to do it in maximum comfort. The robe is a vintage McGregor heavy wool which I found in a thrift store for something like $8.
1980s 1990s movie detective style power shoulder tweed jacket
I’d been on a spree of watching 1980s and 1990s cop movies, many at the time featuring Michael Douglas, and the style of the hard-boiled lead characters often involved an outfit like this. Strong shouldered tweed jacket, western shirt, knitted tie, jeans and boots. This particular jacket is a vintage Polo Shetland, and the boots are Thomas George Collection.
check suit with check shirt and check tie style, pattern matching with checks
Most of the year’s favourites were cold weather outfits, because we didn’t really see the start of summer until it was almost Christmas here in Australia. What I did feel a little pride at was this all-check affair. I don’t usually get complimented on outfits when I’m out or at work, but this one garnered a couple; it was a calculated risk to leave the house with more checks than an old-time bank.

*If you’re wondering how jackets could become so oversized as to be lost causes, it’s because I lost a good two inches from my waistline after halting dairy consumption. This dropped my neck size by around one and a half centimetres; the two suit jackets were already a little large in the collar, and the loss of neck size means both wear with too much collar gap now. If I’m lucky enough to a) find more of the cloths and b) have the ability to finance it, I’ll hopefully remake the jackets.

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With content features ranging from appearances on popular menswear hubs (The Rake, StyleForum, Put This On) to French perfume newsletters and university course readings, Sam is a writer, designer and enthusiast in the fields of menswear and fragrance.

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