There was a time when I believed that if I had a wardrobe that had enough blazers, trousers, shirts and shoes to wear a different combination every day, I’d be content forever. I’d look at guys online who wore tailored clothing so elegantly every day and yearned to do the same without having to wear any one jacket twice in a week.
I achieved that years ago … and of course my desire for more never ceased. As with all pursuits, life gets dull without some form of growth, and our appetites grow—for more, for better, for different.
And looking back these last few years, my style has evolved to incorporate more modes of dressing beyond tailoring. Mastering a tailored look feels daunting at the beginning, then after a time, feels rather simple in hindsight and doesn’t provide the same rush. In my case I’ve gotten really into sweet knitwear, casual forms of outerwear, etc.
But heading into fall this season there have been a handful of classics I’m really appreciating all over again. Here are those icons I’m getting excited for all over again this season.
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Mid-gray flannel suit
Seeing the suit above on a form at Anglo-Italian earlier this month felt like a revelation. Theirs was actually taupe according to the tag. And when I looked for a similar cloth, Dugdale has an extremely similar one that’s made from un-dyed wool. In fact I have a length being sent to Besnard, who will be making a suit for me, as I type this. Besnard has a great house cut that I reviewed 4 years ago, and which I’m excited to add to my closet.
I’ve never owned a mid-gray flannel suit. I do own a light gray POW flannel suit. But the plain pattern of nailhead makes it more sober, and should wear a little more easily with different patterns of shirt and tie if I’m so inclined. That said, the way Anglo styled it is exactly how I’m excited to wear it—sky blue end-on-end shirt and navy tie, or possibly a navy ancient madder. I even look forward to wearing it with black balmorals—shoes I pull out approximately once per year for things like funerals.
Here are gray flannel suits of this season from the makers I recommend the most (Anglo’s was sadly just an MTM/MTO, not off the rack):
Cavour (a little darker)
Spier & Mackay (in double breasted)
Anglo-Italian (also in double breasted)
Berg & Berg in taupe or in mid gray
Proper Cloth (their tailored jackets can look great on some, though I haven’t yet dialed in mine to be satisfactory) with code MUSINGS10 for the discount
Brogue boots
Roughly halfway between Edinburgh and Inverness is a mecca of Scottish retail called The House of Bruar. I stopped there on that drive, getting some spiced pumpkin soup (highly recommended—and they even host their recipe online), and perusing their vast collections from mens and womenswear to art to potted plants and tourist tchotchkes. I bought an inexpensive lambswool sweater and a wool throw for friends back home in their namesake tartan, but dreamed of buying the Crockett & Jones Islay Scotch grain brogue boot.
I’ve long favored suede shoes, for being the most versatile dressed up with tailored trousers or down with denim. But pebble grain calf leather comes after that in versatility. Brogued wingtips are a classic part of British tailored history (the holes originally were there to let water drain out), and in boot form they deliver a chunky, masculine feel that grounds selvedge denim as well as flannel suits. I once owned a pair from a different maker in a lighter tan color, but the fit just wasn’t great so I sold them. I still think on them fondly however, and so perhaps this season is the one I finally get the ultimate.
Crockett & Jones’ Islay [linked at their own website] is the platonic ideal of the category, and worth the price. But if that’s too steep here are some alternatives:
Velasca (smooth, not grain, sadly)
TLB Mallorca will make you a custom pair for $575
Cobbler Union (smooth, not grain, sadly)
Ancient madder neckties
For the decade plus of dressing up in menswear, I’ve long favored sportcoats worn somewhat casually with denim, chinos or the like. I’m now filling my closet with more suits (see note above), though ironically I used to wear ties far more regularly. Here’s a pic of me in an ancient madder tie I was excited to have gotten from Brooks Brothers 12 years ago. So when I do wear neckties these days, it’s the more formal occasions we all think of: worship services, funerals, weddings. Given that relative infrequency, the last few years has seen me heavily favoring much more plain ties—solid navy twill, or grenadine in navy, brown or green, or maybe a solid navy knit.
The appeal of ancient madder, however, is evergreen, and once again I’m being drawn to its matte, chalky pleasures. I have a handful of ancient madder ties already (that one linked from 12 years ago I have in two other color ways). But here are some of the best makers for ancient madder you should shop:
Spier & Mackay (surprising but they sourced high quality silk in Italy and made beautiful ties. They’re not marked as madder, but the matte finish gives it away)
Tweed everything but jackets in particular
Summer 2026 was the summer of linen for me. I leaned hard into linen for suits, jackets, and shirts (while in years past I’ve often worn garments made in blends of linen with other material—cotton/linen for shirts and chinos and wool/silk/linen for tailoring). As I’m heading into fall and winter, I’m finding the default fabric I’m yearning for is tweed. Its characteristic scratchy hand has a warmth and charm to it that can’t be compared to anything else. Harris Tweed’s cottage industry is a wonderful example of traditional craft maintaining a foothold in the era of industrial production—literally, as all the weavers must weave the tweed by foot, in their own homes. Besides Harris tweed are other wonderful traditions: Donegal tweed from Ireland, Lovat tweed, Abraham Moon tweed from England, and more. Here are some tweed (or tweed-adjacent—some Italian mills create tweedlike cloths that are great, too).
Black and white glen check sportcoat at Spier & Mackay
Antiqued gray herringbone sportcoat at Spier & Mackay [this has been a favorite of mine]
Gun club jacket at Spier & Mackay
Brown donegal-style tweed suit separates in DB at Spier & Mackay
Russell check jacket at Anglo-Italian
Glen plaid tweed jacket at Sid Mashburn
Green windowpane Lovat tweed jacket at Sid Mashburn
Green windowpane jacket at Spier & Mackay [similar to the tweed at Sid just above but not actually tweed methinks]
Brown houndstooth tweed jacket at Cavour
Herringbone tweed jacket at Cavour
Gray glen check sportcoat at Buck Mason
Tweed herringbone raglan coat at Cavour
Tweed flask with four mini cups (I bought this at a tourist shop—best flask ever)
Raw selvedge straight-fit denim
Comfy, broken-in and faded denim has been the name of the game for myself and many others these past several years—and I even gave in about 3 years ago and accepted stretch into the denim I’ve been wearing. And while selvedge denim hasn’t gone away, the appeal of a stiff pair of jeans you treat as a project has ebbed a bit, admittedly. Maybe my shifting perspective on what I consider an appealing fit—a little less slim, a little higher rise—has brought them back into my graces. Who knows. But thankfully the selvedge denim makers are still out there doing their thing, and there are more of them now than ever. Here are the ones I would steer you towards:
3-Sixteen – any of their SL (Straight-Leg) fits
Imogene + Willie – I have a tapered leg jean of theirs, and wish now I’d done their straight leg
Buck Mason – their full saddle jean is a great fit in my limited experience
Gustin – their American One Five stocked denim is on sale for $99 and their Okayama Standard is maybe my favorite color of selvedge denim for me no matter what maker
Cordovan full strap loafers
Perhaps these aren’t “classic” in the same way that a gray flannel suit is, but of course penny loafers are among the most iconic of shoes, and shell cordovan leather in color #8 is too. While suede is still king to me in its ability to dress up with tailoring and down with denim, something about cordovan makes it look amazing with denim (and still be dressy with tailoring too). Especially dark, selvedge denim. For about a decade my brother has owned a pair of Alden-made cordovan #8 tassel loafers (made under Brooks Brothers’ now-defunct Peal & Co. brand), and they look fantastic with jeans.
Lately I’ve had a hankering for the full-strap penny from Alden in shell #8. The curve of the extra-long penny strap gives it a little extra sauce.
Alden is the icon—buy them at The Shoe Mart or Sherman Brothers
Crockett & Jones makes one for Anglo Italian called Bradbourne
Crockett & Jones also has one in their catalogue called Yale
Allen Edmonds their “Randolph” loafer in cordovan if its less refined stitching is your thing
Carmina Shoemaker makes a sumptuous one
The other miscellaneous “basics” I’m excited to wear this fall
Besides these newly rediscovered classics above, there are the ones I’ve never un-discovered in the first place:
Blue Oxford shirts (the royal blue color Oxford at Proper Cloth has been my favorite of late)
Favorite OCBDs are from: Proper Cloth (dressy or casual depending on fabric) | Wythe (casual and soft) | Spier & Mackay (affordable and either casual or dressy) | J.Press (original and iconic) | Kamakura Ametora (vintage inspired)
Shawl collar cardigans (ideal for a cozy morning by the fireplace)
The shawl collar cardigans to buy: Buck Mason | Kent Wang | The Armoury (in cashmere!) or in Lambswool | Permanent Style (somehow $700 more than The Armoury’s cashmere | eHaberdasher
Suede chukka boots (with the gray flannel suit is gonna be so sick)
The suede chukka boots to buy: TLB Mallorca | Myrqvist (my personal faves) | Sid Mashburn | Morjas | Crockett & Jones Chiltern
Crewneck cashmere sweaters (navy is my go-to but beige/tan/taupe is on my list for this season)
Crewneck cashmere sweaters to buy: Todd Snyder | William Lockie | Le Connaisseur (this is a brand of a guy I met at Pitti who was all about getting the best, most excellent so I am recommending them based on that!) | Brooks Brothers
The gray herringbone raglan coat
Where to buy one all listed here.. As usual Wythe’s looks amazing. Cavour’s looks awesome this season too.
