Five years ago I wrote a series on my favorite pieces from each season. A lot of those items are still near and dear to me, but I thought it would be worth updating things to reflect my current lifestyle and wardrobe. My fall favorites have changed a bit, but many of the concepts are still the same – textured materials, earthy colors, and a bit of protection from inclement weather. Here are my go-to pieces for the cool weather ahead:
Waxed cotton jacket. Good outerwear is expensive, but it can really take a wardrobe up a notch. I love waxed cotton jackets for their mix of functionality and classic style – they’re a great way to stay dry in inclement weather without relying on tech fabrics. The jacket above is one of my favorite items, the Twin Track from the wonderful Private White VC (they currently are not offering it but you can sign up here for when they re-release next month). Barbour is another great alternative – the Ashby and Bedale are both classics, and the International gives a bit more of a moto vibe like the Twin Track above.
Washed jeans. I gave raw denim a good try, I really did. But after years of suffering through the break-in period and stressing over shrinkage (of the jeans, that is), I’ve moved on to washed denim. Washed denim doesn’t mean that the quality is any worse or that they won’t fade, it just means that the jeans spent some time in water before they got to you. I still like my jeans nice and dark to start with, but having them a bit softer helps a bunch. My Orslow 107s are breaking in nicely and are my current favorites.
Flannel shirts. While it’s true that a pair of gray flannel pants is a wonderfully versatile and comfortable piece of clothing, I just rarely have any need to wear them anymore. For me, flannel purchases have moved north into shirt territory. I have flannel shirts in a variety of patterns, colors and weights – I prefer the mid-weight ones to have a button-down collar and chest pocket like a classic oxford, while the super-heavy ones have two chest pockets and a point collar (like an overshirt). All of my flannels are made custom from Proper Cloth. Not only do I get to make everything exactly how I want it, but they also do a great job with pattern matching (which makes shirts with large patterns look much better).
Pebble grain boots. I like my boots to be tough enough to wear in wet weather, and pebble grain leather has always been a good candidate for that. Although it doesn’t really have any special resistance to moisture, the textured surface seems to hide it well. I like to pair them with a Dainite sole for added performance. This pair from Carlos Santos went all over Europe with me last year and still look great.
Denim shirts. Last year I discussed my rising interest in western shirts, and I’m happy to report that my first purchase has integrated seamlessly into my wardrobe. This one is from Proper Cloth, and is made up in a light blue slubby denim from Italy. It has broken in wonderfully and gets worn nearly every week, especially when the weather is cool. Of course, you don’t have to go full cowboy like me – if you tend to dress a bit more formal, try a dress shirt in denim. Or if even that seems like too much, opt for chambray (the only real difference between the two is the weave – twill vs. plain). I usually wear these with chinos as to not go full Canadian tux, but it’s up to you.
Suede shoes. It seems that there are still many differing opinions on suede – some feel that it is delicate and needs to be babied, others that it is tough as nails and can hold up to anything. I think the truth is somewhere in the middle (it can definitely take some abuse but will still need a lot of proper care), but hopefully we can all agree that it looks great. Colors like brown and snuff are a perfect pair for the textured clothing of fall. My favorite pair is my dear Alden unlined bluchers – about as comfortable as a welted shoe can get.
Shetland sweater. I’ve discussed my love of these delightfully scratchy sweaters many times, most recently here. Their rich, marled colors and hairy texture make them ideal fall knitwear, whether you’re wearing denim and boots or sportcoat and flannels. The one above is a personal favorite from O’Connell’s. If you haven’t tried one out yet, I highly recommend it.
Seasonal socks. I’m not yet a total convert to paying more than $3 for a pair of socks (shoutout to Uniqlo), but I was able to pick up a few fancier ones for this season and have been enjoying a break from solid colors. These are from Anonymous Ism (1, 2) and look great with the comfy seasonal clothing shown here.
Textured brown sportcoat. I don’t get as many opportunities to wear tailored clothing as I’d like, but I still find times to dress up a bit. A brown sportcoat with a bit of texture or pattern is great for this time of year – wear it above gray flannels, olive chinos, or jeans. Hard to go wrong as long as it fits well. This piece from Suitsupply is part of a suit, but it generally gets worn as a jacket. Another great source for high-quality sportcoats at a great price is Spier and Mackay, who has a great Fall lineup currently.
A tough watch. I love watches, but I don’t really have the funds to get too invested in the hobby. My watch collection is very small – only two at the moment – so I want each piece to be versatile. A Maratac mid-pilot is my choice for day-to-day activities – tough enough to take a hit, classic military-inspired design, and reasonably affordable. It also has a solid water resistance, so I don’t have to worry about it getting drenched in the rain.
Now, you may notice that plenty of things are missing here, especially classic cool-weather accessories like gloves, hats, and scarves. I love all these things too, but unfortunately the mild weather here doesn’t really require them. If your climate does, I envy you – until mid-winter, that is.
What are your essentials for shoulder season?
For more Seasonal Selections, click here.
