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It is arguably the best style season of the year. Fall. Cool enough to wear layers and perhaps mix in some patterns, but not so bitter that the goal is to ward off hypothermia instead of looking your best. And this year, we’re going to divide this pile of autumnal temptation into three different posts:

  • The Clothes
  • The Shoes/Boots/Accessories
  • The Outerwear (coming soon)

Even if the climate in your neck of the woods hasn’t even begun to approach autumn yet, that doesn’t mean you can’t look forward to it doing so. So get ready, get excited, and here come the new arrivals. As always, brand new stuff can usually take a little while to drop in price or go up for codes, so keep that in mind when the sticker shock hits you.


J. Crew Goodyear Welted Kenton Horween CXL #8 Chelseas – $298

J. Crew Goodyear Welted Kenton Horween CXL #8 Chelseas

Boot of the season contender. Very, very high hopes here. Goodyear welted, made out of Horween’s famous burgundy #8 shade, and a subtle lug sole to keep you upright on all the slickery-ness that is fall (and winter) weather. Drops to $200ish during sales.

BIG IMPORTANT NOTE: Our man Brandon D. purchased these during the big 40% off Labor Day sale, and he’s reporting that J. Crew emailed him to extend the backorder date. They were originally supposed to ship over the weekend, but they send him an emails saying they’ve been delayed again. They also said if they don’t ship them by early October, they’ll cancel his order. So the supply chain madness of 2020 seems to continue, at least for J. Crew, and these could be a sticky proposition. Big thanks to Brandon for that heads up.


Dan Henry 1963 Pilot Chronograph – $280

Dan Henry 1963 Pilot Chronograph

Seiko Mecha-Quartz movement. Sapphire Crystal. 12-hour rotating GMT bezel. 40mm options, but also updated in a blue color scheme that comes in a 42.5mm diameter for those that like the larger pilot-style thing. Lots of fun, or a reasonable cost. But if this is a little too big, bold, and casual for you, can’t go wrong with their 1937 Dress Chrono. It was a sleeper hit from our annual Dads and Grads watches post.


Nike Air Max Pre-Day LX – $140

Nike Air Max Pre-Day LX

For your athleisure days. These are George Castanza kicks if Seinfeld had been set in the year 2150.


Taylor Stitch Goodyear Welted Chukkas in Weatherproof Loden Suede – $298

Taylor Stitch Goodyear Welted Chukkas in Weatherproof Loden Suede

Weatherproof suede uppers. Goodyear welted. Vibram mini lug sole. Sheepskin lined. Hand made in the famous shoe and boot hub of Leon Mexico. Can go on sale for around 20% off from time to time, or, 20% off if you’re a new customer and sign up for their email list.


Flint and Tinder Made in Japan Camp Socks – $18 FINAL

Flint and Tinder Made in Japan Camp Socks

If a pair of socks could represent fall and winter, then these would be them. 78% acrylic/14% wool/7% polyester/1% spandex. Final sale, since they don’t want people sticking their feet in them and then sending them back.


Merrell Moab Speed Mid GTX – $160

Merrell Moab Speed Mid GTX

Lighter weight hikers from a legit outdoor shoe/boot company. Love that black/gray scheme with the white sole. “But the sole will get dirty.” That’s the point! And you should get them dirty. They look pretty capable from here. Gore-tex lining makes them breathable and waterproof. Padded collar and toe cap for comfort. Hit those trails before they turn to impassable muck.


Hook & Albert Black Leather Briefcase – $299

Hook & Albert Black Leather Briefcase

There’s just not a ton of good looking, classy briefcases out on the market right now. They’re all either backpacks, super casual, or on some weird luxury high end where the price is laugh out loud stupid. Three hundred bucks isn’t cheap, but if you sign up for their emails you’ll save 20% off. Plus, Hook & Albert are the originators (I think?) of those garment duffel hybrid bags, which have taken off in popularity. So while this is a simple briefcase, H&A know a thing about bag design.


Hamilton Khaki Field Mechanical Bronze – $825

Hamilton Khaki Field Mechanical Bronze

They took their classic Hamilton mechanical hand-wind field watch, and bronzified it. 38mm case. Leather NATO strap. H-50 hand-wind movement has an 80(!) hour power reserve. Will develop an individual patina over time. That… is something.


Banana Republic 100% Cashmere Fisherman’s Beanie – $98.50

Banana Republic 100% Cashmere Fisherman's Beanie

BR’s cashmere usually doesn’t disappoint. And if you’re gonna splurge on cashmere, it might as well be on a hat that’s touching the skin on your forehead. Fingers crossed these come up for some sort of code, and aren’t excluded between now and the end of time.


Allen Edmonds Higgins Mill Weatherproof Boot with Chromexcel Leather – $370 w/ FALL75 ($445)

Allen Edmonds Higgins Mill Weatherproof Boot with Chromexcel Leather

The Higgins Mill is a classic, and they’ve equipped it this year once again with weatherproof leather. Chromexcel this time around, and that super-dark brown option is beeeeeautiful. Subtle studded Dainite rubber sole for traction and durability in fall and winter weather. Not quiiiite sure what’s going on with the rest of AE’s new arrivals so far, but, maybe it’s early and there’s more to come.


Timex Waterbury Traditional Automatic 39mm – $259

Timex Waterbury Traditional Automatic 39mm

A nice, classy classic (is that redundant?) smart casual to slightly dressy watch from Timex. 39mm diameter leans more towards the classic (there’s that word again) size. Miyota automatic movement. And that “W” counterbalance on the seconds hand is pretty cool.


Orvis Battenkill Cashmere-Lined Gloves – $98

Orvis Battenkill Cashmere-Lined Gloves

Strolled over to Orvis to see if they by chance had brought back their old driving gloves. They have not. But they do have these two toned, full grain, cashmere lined gloves. Just different enough.


Red Wing Classic 6-inch Moc Boots – $279.99

Red Wing Classic 6-inch Moc Boots

Having a bunch of boots in a fall round up WITHOUT mentioning Red Wing seems like blasphemy. So here we are, before we get too carried away with more (and more) boots. Classic American made beauties here. Six colors to pick from including the modern navy shade shown above. But if you want browns, they got browns.


Spier & Mackay Pocket Squares – $28

pier & Mackay Pocket Squares

One of the secrets to standing out quietly is to wear mostly solid, classic stuff. Navy or gray suits (or sportcoats). White and blue shirts. Nothing crazy. But then put a pocket square with some color in your breast pocket, show just a bit, and you’re golden. Spier’s pocket squares are terrific for this sort of strategy. Made in Silk or wool, with patterns that look like they came out of some high end haberdashery, and NOT the clearance table at your local department store.


Greys Outdoor Slipper Boots – $108

Greys Outdoor Slipper Boots

2020 was an absolutely good for nothing year. But at least these felted wool blend indoor/outdoor capable slipper boots came along. A small consolation considering the emblazoned crap-pail of a year, but they really are an incredible at home slipper/shoe/hybrid-thingy. Full review coming from Adam tomorrow. He was super impressed.


L.L. Bean Waxed Canvas Duffle Bag – $159

L.L. Bean Waxed Canvas Duffle Bag

Looks like it should cost more. Super glad it doesn’t! Good for those autumn weekend adventures. Not some massive thing. 10.5″H x 22.5″W x 10.5″D = Just over 2000 cubic inches. So don’t expect a battleship of a bag. Ships and returns for free via Nordstrom.


Danner x Huckberry – Vertigo 917 ‘Gold Rush’ – $245

Danner x Huckberry - Vertigo 917 'Gold Rush'

The Danner Vertigo 917 is a perfect blend of sneaker comfort and waterproof boot performance. They’re not super heavyweight, clunky mountaineering boots. But they’re more capable than “outdoorsy” attempts made by the big sneaker companies. And the Huckberry gold rush color sure does leap off the monitor.


Clarks Desert 2 Chukka Boot – $150

larks Desert 2 Chukka Boot

Love the look of the oft-mentioned Sanders Chukka but you’re like “Joe you absolute dillweed I’m not paying $250 for suede chukkas shipped in from England“… then here’s your alternative. Ships and returns free from Nordstrom, and they were a big winner in Adam’s round up of all the Clarks chukkas and desert boots. This new Desert 2 is a real winner, and the switch from a light crepe to a darker less textured sole means you can dress them up a little bit.


Christopher Ward C63 Sealander GMT – $950

Christopher Ward C63 Sealander GMT

Hey look it’s a Rol… no it’s not. Swiss made, GMT function, 39mm case diameter leans into the “less is more” thing, and it’s under a grand. Not bad for a high end watch that steers clear of the price points big luxury brands charge. Plenty of strap options under a thousand, with those on a stainless steel bracelet running $1070.


Cobbler Union Made in Spain Benjamin Chelsea Boots – $199 ($425)

Cobbler Union Made in Spain Benjamin Chelsea Boots

New to the sale section I believe. Free shipping and Free returns. Cobbler Union shoes have really impressed. And these, on such a mega discount, might look mighty fine against dark wash denim or flannel trousers. They do recommend suede protector though. These need a little help when it comes to fighting the fall weather elements. Fit recommendation from them is to take a half size smaller than your normal US size.


Target Goodfellow Faux Sherpa Gloves – $23

Target Goodfellow Faux Sherpa Gloves

These are either gonna be a great, cheap way to insert a little mountain/rugged style into a fall/winter look… or they’re gonna be a hot disaster. All poly! “Pull on style.” As opposed to gloves that teleport onto your hands?


Grant Stone Diesel Boot Storm Suede – $285

Grant Stone Diesel Boot Storm Suede

Super capable boots in an unexpected shade of suede. Suede can do just fine in the elements. All you have to do is protect it. Should look terrific with olive chinos, dark wash jeans, etc. Full review here, albeit in the sand suede option from the summer.


Huckberry Made in Japan Acrylic, Wool, Nylon, Spandex Beanie – $28

Huckberry Made in Japan Acrylic, Wool, Nylon, Spandex Beanie

They’re back. And in new colors! Flat out terrific. Picked up one of these on a whim and it’s seriously impressive. Japanese fabric is just the right weight, and feels good and strong. Sometimes beanies can look good but then slouch and/or shrink. Not these things. Perfect fall/winter hats here, and the price is nice and affordable too.


Nordstrom Dane Cap Toe Oxford – $99.95

Nordstrom Dane Cap Toe Oxford

Dress shoes might not scream fall like a pair of boots do, but these are still an important decision. Because sometimes you have to dress up and look your best. And not everyone has $200 – $400 for a pair of Allen Edmonds. Perfect toe shape. No chisel nonsense. True oxford lacing. They’re dress shoes. And they’re under a hundred bucks. Ships and returns for free like everything else from Nordstrom.


Timex Expedition Sierra 40mm – $79

Timex Expedition Sierra 40mm

Pretty sure this Expedition Model or some highly similar incarnation of such has been around for years. But they sure nailed the colors this time. Orange seconds hand, EXPEDITION at six o’clock, and 12 o’clock indice. Brass case. Equipped with Indiglo. The matte (is it sorta kinda sandblasted looking?) case and hardware on the strap is pretty darn perfect too. An educated guess says that this is one of the cheaper movements, so… expect the loud-ish Timex “TICK” when all else is quiet.


Good Man Brand Legend Z Low Top Modern Core Sneaker – $198

Good Man Brand Legend Z Low Top Modern Core Sneaker

Good Man Brand makes some really nice luxury sneakers for under two hundred bucks. Made in Italy. Nice leather. Classic styling. Extra padding on the tongue. And for about as half as much as that other brand that stamps weird gold numbers on the outside of their rear quarter panels.


Huckberry All-Weather Duckboot II – $188

Huckberry All-Weather Duckboot II

Incredible comfort. Classic but still modern looks. (How the heck did they do that?) Waterproof. The next generation of Huckberry’s super popular duckboots have arrived, and they’re ready for all that fall and winter weather can throw at them. Full review here.


Allen Edmonds Park Ave. or Strand in Mahogany – $395

Allen Edmonds shoes

They’re not weatherproof, but they are spectacular. And a deep brownish red shade sure feels like fall. Do note that they do make weatherproof Park Avenues, if you’re in need for some.


J. Crew Waxed-canvas duffel bag – $198

J. Crew Waxed-canvas duffel bag

For those crisp fall weekend away adventures. Go somewhere and put your feet up and just enjoy the air.


Banana Republic Realy Leather Chukka Boot – $178

Banana Republic Realy Leather Chukka Boot

Don’t sleep on these. If you can get them on a sizeable discount, then they could be a very nice surprise. BR shoes have impressed in the past. Are they gonna carry with them the hallmarks of higher priced footwear like really nice leather and substantial welts? Nah. But they don’t cost nearly as much either… assuming big sales/codes/promos.


Seiko Presage “Style 60’s” SRPG line – $525

Seiko Presage "Style 60's" SRPG

Brand new from Seiko, and an affordable alternative to the new Heritage (can new + heritage be a thing?) Omega Seamaster 300 line. Plenty of 60s dive-style. 50m water resistance. Seiko 4R35 automatic movement. Rotating bezel with an aluminum insert. Box-shaped Hardlex crystal. 40.8mm diameter hits that sweet spot for many. And holy smokes look at it. But where’s the black one which is shown above? At post time, white, blue, and green options are available. But no black with the simple dial and NATO strap. Hmmm.


Banana Republic Winstan Leather Sneaker – $148

Banana Republic Winstan Leather Sneaker

If Air Force 1s and the Nike Killshot had a baby. A baby sold by Banana Republic. Which of course, again means, we’re crossing fingers for a sale or promo code or something.


Alden Indy Boots in Brown – $521.10 w/ TODD10 ($579)

Alden Indy Boots in Brown

It’s been a hell of a year(s). If you hit some goals, didn’t give up, and instead chose to use this period of history as “active” time, then maybe a reward is in order. Or maybe that’s enormously unhealthy rationalization. Full review of the Alden Indy can be found here. Tough to find on sale, but the 10% off code at Mr. Snyder’s shop seems to be applying at checkout.


The Tie Bar Vitale Barberis Wool Ties – $24.50 ($35)

The Tie Bar Vitale Barberis Wool Ties

A seasonal favorite that appears to be on the way out, and thus, on sale. Seems to have been made in only skinny widths, so, best under a sweater or worn more casually than dressed up. Terrific for the smart casual workplace.


Nike Waffle Trainer 2 SP – $100

Nike Waffle Trainer 2 SP

Classic Nike Sneakers, waffle sole and all, in fall appropriate “velvet brown” and “dark sulfur”? Dang right.


Lorier Hyperion GMT Watch – $799 (restock = Sept. 2021)

Lorier Hyperion GMT Watch

A huge hit when it was released in late 2020. And for good reason. Swiss Soprod C125 movement. 24 hour red and blue 48-click bi-directional bezel. 39mm case diameter. Has that vintage thing going for it. Full review here.


Suitsupply Dark Brown Double Monk Strap – $249

Suitsupply Dark Brown Double Monk Strap

Suitsupply shoes have been a bit wonky in the past, so here’s to hoping they corrected those problems. Ships and returns for free, so in case they show up and they’re a weird fit, you can send them rocketing right back. Simple cap toe here, and unlike a lot of monks, these actually come with a rubber sole. Which is much needed once the leaves start to turn and thereafter.


Taylor Stitch Minimalist Wallet in Navy – $58

Taylor Stitch Minimalist Wallet in Navy

Usually Spring is when we all do a bit of cleaning. No time like the present though if you’ve got a wallet overflowing with old business cards, receipts, etc. Made in Spain.


Huckberry Rhodes Tyler Chukka – $175 | Blake Chelsea – $198

Rhodes Boots

Huckberry’s Rhodes brand of boots keep cranking out hits, and these “Caliber” collection boots keep that trend rolling. Head here for Adam’s review of the chukkas. Meanwhile, I bought the chelseas for myself during Huckberry’s summer sale a couple months back, and they quickly replaced a pair of old Red Wing Weekender chukkas that had seen better days. Super comfortable. Substantial without being gunboats. Soles are inspired by workwear boots that cushion, and look pretty darn good.


Allen Edmonds Hamilton Weatherproof Oxford Dress Boot – $370 w/ FALL75 ($445)

Allen Edmonds Hamilton Weatherproof Oxford Dress Boot

More weatherproof leather from Allen Edmonds, this time in a true-oxford boot. Chili, Brown, or Walnut available. Think of these as your crap weather strands, only with more ankle protection, a waterproof membrane lining, and a Dainite rubber sole.


Hamilton Khaki Field King Automatic 40mm – $545

Hamilton Khaki Field King Automatic 40mm

Hamilton’s Field automatics are getting harder and harder to find via gray market dealers, so going full price here via Nordstrom. Free shipping, free returns, AND it comes with the factory warranty (can’t say that about gray market shops). Rugged good looks, day and date cutout at 12 o’clock, and a vintage-y but not faux vintage beige dial.


J. Crew Goodyear Welted Kenton pacer boots in Horween Chromexcel leather – $298

J. Crew Goodyear Welted Kenton pacer boots

Indy boots for the still quite fortunate, but not quite as fortunate as $500 Aldens requires. Will drop under $200 with codes on occasion. Note that the estimated ship date isn’t until October 12th, and J. Crew has been emailing buyers on other boots bumping back ship dates. Could be a long wait on these.


Target Goodfellow Textured Knit Scarf – $20

Target Goodfellow Textured Knit Scarf

That’s a lot of texture. Cable knit, waffle knit, ribbed… this thing has it all. And it’s cheap. 100% acrylic, which is no surprise here thanks to the cost.


Grant Stone Diesel Boot in Crimson Chromexcel – $340

Grant Stone Diesel Boot in Crimson Chromexcel

Goodyear welted, chromexcel leather, and a construction and attention to detail rarely seen at this price point (which, admittedly, is an investment). Full review from our shoe expert can be found here.


Made in Japan Hario V60 “Buono” Drip Kettle – $50

Made in Japan Hario V60 "Buono" Drip Kettle

Try one of these and you’ll never head back to a screeching/whistling kettle ever again. Slim spout makes for perfect pours. Ergonomic handle won’t heat up. Yes, you sort of have to keep your eye on it, but the steam will let you know when it’s ready to go. That, and maybe slowing down and intentionally waiting for water to boil (it will eventually) is one way to being a bit more in the moment. Great for pour-overs, tea, toddys, etc.


Made in Italy J. Crew MacAlister Boots – $158

Made in Italy J. Crew MacAlister Boots

J. Crew’s flagship desert boot. Italian suede uppers, stitched out welt construction, three fall-ready shades, and made in Italy. Just be warned that crepe soles don’t do so well on wet surfaces. So once that fall drizzle starts to spit, keep these on the shelf.


Khaki Aviation Converter GMT Automatic Leather Strap Watch – $1445

Khaki Aviation Converter GMT Automatic Leather Strap Watch

For those that like their wristwatches blue and busy. Shades of a Breitling Navitimer. 44mm diameter plays into the “big” pilot style. Swiss automatic GMT movement. Rotating bezel is actually a slide rule. For, y’know, in case you’re flying a plane somewhere and all the instrumentation goes out and… oh hell I dunno, but it looks cool.


Allen Edmonds Weatherproof Daltons in Brown or Chili – $349.97 ($495)

Allen Edmonds Weatherproof Daltons in Brown or Chili

The AE German sourced Weatherproof leather is a revelation. Super soft. Super supple. And ready to handle the elements along with the interior membrane sandwiched between the leather lining and exterior. Incredibly comfortable. Available in brown or the reddish brown “chili” option. Also happens to be shown (as a worn pair from last year’s debut season) at the very top of the post.


Huckberry Polarized Weekender Sunglasses – $35 (or two pairs for $60)

Huckberry Polarized Weekender Sunglasses

Huckberry’s weekender shades have been around for a while now, but the more recently released “Matte Cola” frames will give someone who wants to buy into the browns + earth tones trend that’s happening this fall the ability to do so, at a low price. Polarized, which is a nice plus.


Charles Tyrwhitt Goodyear Welted Chukkas – $249

Charles Tyrwhitt Goodyear Welted Chukkas

In case you don’t want to go digging around for Loakes. I don’t think these are made by Loake. Pretty sure they’re not, in fact. But, knowing CT they might go on sale at some point? Maybe? They’ll run a sitewide code from time to time. Cork lining between the insole and sole which will mold to your foot overtime. Subtle studded rubber outsole.


J. Crew Braided Italian Suede Belt – $49.50

Braided Italian suede belt

A little intention, but still laid back. Italian suede with a warm gold-tone buckle. J. Crew is leaning HARD on these three colors this season. But they do look great.


Allen Edmonds Weatherproof Park Avenue – $299.97 ($445)

Allen Edmonds Weatherproof Park Avenue

Gets mentioned plenty, but worth a reminder since the cold and wet weather is coming up quick.  These things are legitimately the most comfortable pair of dress shoes I’ve ever worn. The German leather they’re using here is extraordinarily soft, while also being weatherproof. Subtle Dainite sole gives you good grip too. These went on mega sale not that long ago, and thus, got bought up pretty quick, but there’s still some common sizes available at post time.


Shinola Canfield Traveler Briefcase – $1,395

Shinola Canfield Traveler Briefcase

FOURTEEN HUNDRED DOLLARS?!? The only way this dips into the “affordable” realm is if no one buys it (possible), it heads to Nordstrom Rack on a significant discount (could happen), still no one buys it (now we’re getting somewhere), it goes on clearance (not looking likely) AND it’s part of a “clear the racks extra 25% off” event. So yeah. Maybe it’ll happen in… April?


J. Crew Wallace & Barnes camp moccasins in suede or leather – $198

Wallace & Barnes camp moccasins

Camp mocs that are more rugged for that late summer –> fall period. Can’t speak for them in terms of quality, but usually J. Crew’s Wallace & Barnes line feels, wears, and looks a bit more rugged/upgraded than the rest. And those suedes look terrific.


Crown & Buckle’s Supreme NATO Straps – $34

Crown & Buckle Supreme NATO Straps

They just got restocked, and they look just as good on a Casio as they do on a Rolex. Switching out the strap is one of the easiest and relatively cheapest ways to refresh the look of a favorite wristwatch. And NATO straps make doing so even easier, thanks to not having to remove any spring-bars in the process. Crown & Buckle’s supreme NATO straps are a noticeable, big step above the competition. They’re soft but still substantial. The hardware is nothing short of excellent. And the edges don’t cut into your skin or feel rough/unfinished. Multiple widths. New options shown above, but yes they have the classics too like gray and black stripesolive/red/black, etc.


Spier & Macaky Jumper Boot in Mocca Suede – $278

Spier & Macaky Jumper Boot in Mocca Suede

Not sure if these are brand new or “new-ish”… but suedeifying (not a word) their jumper boots was a heck of a move. Water resistant suede from Germany. Studded rubber outsole. Goodyear welted. Made in Portugal.

And that’s just the first wave. We miss something? Something just come out that should have been mentioned? Send any and all of those tips into joe@dappered.com … apologies if we did miss something obvious. New Fall arrivals have been pretty late this year, industry wide. Stay tuned for outerwear up next. 


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