THE Fall Checklist

Fall – what a beautiful four letter f-word. I’ve never really done a “seasonal guide” before mainly because I think they’re pretty pointless (and annoying), but when I was up in NYC earlier this month Sloane (of Sailing The Sea in Style) gave me an idea. She said that she was a “closet overhaul” and instead of buying a bunch of seasonal items, she was going to stick to buying about a dozen pieces that she would wear on the regular throughout the fall, but styled in different ways. I thought it was a fantastic idea.  FINALLY – someone who actually gets the concept of building a wardrobe that doesn’t have to be replaced year after year.

And so I’m graciously “borrowing” her idea and putting my own spin on it. Below are thirteen core items for guys that are applicable not just for this fall, but next fall, and the dozen or so falls after that. Why? Because everything list below are core, timeless items that have high versatility and low maintenance for long-run. Below each pick is “the why” that includes two/three alternatives at different price points. Here we go:


1. The Topcoat: “Wool-Cashmere Topcoat” via J.Crew

Topcoats.  I love them.  And before you roll your eyes or scroll down because you think they’re for old men, hear me out.  While the purpose of a topcoat is to go over a suit/blazer/sportscoat, there’s no law in the books that says it can be worn with a great pair of denim and your favorite quarter-zip sweater. It’s a piece that not only elevates a guy’s wardrobe, but is far better than that North Face jacket you’ve been wearing since high school.  Guilty I have a handful of topcoats, but my favorite is definitely the one above.  I bought this same piece last year that I can’t wait to pull out once the temperatures drop.

Alternative 1  //  Alternative 2  //  Alternative 3


2. The Sportscoat: “Thompson Suit Jacket” via J.Crew

Heavy navy blazers are great, but sometimes – especially in the fall – you need something with a little extra protection.  As of recent, J.Crew Factory has really uped its offerings especially when it comes to suiting.  Now I admit that I haven’t seen this garment in person, but for a heavy, flannel suit the price-point is pretty great.  The best part is that you can make this jacket a full suit should you decide to invest in the respective pants.  In other words, you can nab a staple, fall/winter suit for around $400 if you buy during a promotion.

Alternative 1  //  Alternative 2  //  Alternative 3



3. The Vest: “Herringbone Puffer Vest” via Lands’ End

If you haven’t checked out Lands’ End most recent line you are absolutely and completely missing out.  This vest is one of the many fantastic pieces that they’re currently selling.  While the vest is a bit on the thicker side eliminating it from being used as a layer underneath a big topcoat, the price point is FANTASTIC – not to mention that it’s guaranteed to keep you warm at temperatures as low as 30 Farenheit.

Alternative 1  //  Alternative 2  //  Alternative 3


4. The Sweater: “Fisherman’s Sweater” via L.L. Bean

Fisherman’s sweaters are an absolute classic.  They’re fantastically textured and look great with just about anything in your closet.  What’s great about sweaters like these is that you can wear some of your lighter-weight shirts from the spring and summer without worrying about getting cold.  With L.L. Bean standing behind everything that they sell (they have a lifetime warranty FYI), there is zero reason not to buy this sweater.

Alternative 1  //  Alternative 2


5. The Jacket: “Quilted Coat” via Boden

I don’t know how many of you know about Boden, but I’ve mentioned the label here and there over the past year.  A great, quilted jacket is a fantastic fall (and winter) essential that goes well with any and all of your more casual pieces.  I think the red detailing, elbow patches, and stand-up collar are fantastic features that make this quilted jacket stand out in just the right amount.

Alternative 1  //  Alternative 2 (on sale)  //  Alternative 3


6. The Denim: “Resin Rinse Jeans” via Gap

Good jeans are hard to come by.  If there’s one thing I’ve learned about denim it’s that you should either buy the really cheap stuff or the really expensive stuff.  I admit that I favor denim by Burberry, but when you put your jeans through the ringer it just doesn’t make sense to pay $300+.  I’ve been wearing jeans by Gap for a couple of years after getting fed-up with J.Crew’s overpriced denim that fades after a couple of washes (just being honest, folks).  A pair of dark denim is necessary for the fall.  The pairings are endless especially if you’re going for a more comfortable/casual look.  Invest…and go dark – very dark.

Alternative 1  //  Alternative 2  //  Alternative 3


7. The Gloves: “Deerskin Driving Gloves” via Ralph Lauren

Ever. Guy. Needs. A. Pair. Of. Gloves.  Key word here is “a”…single…one…not twelve.  I’ve been wearing the same gloves for the past 3+ years sourced via Ralph Lauren.  Unfortunately, those gloves were lost in the backseat of an Uber that were never found…and so I must buy a new pair.  The reason why I chose the pair above is because of the details – they’re great. Sure they’re a smidge on the pricey side, but Ralph Lauren is offering 25% off your order that puts them a little over $100.  My point?  You won’t need to buy a new pair of gloves for awhile – unless of course you lose them in the backseat of an Uber.

Alternative 1 (on sale)  //  Alternative 2  //  Alternative 3


8. Pants: “Garment Dye Chinos” via Brooks Brothers

You don’t need half a dozen pair of navy chinos…you need one (preferably these).  These Darment Dye Chinos via Brooks Brothers come in a number of different colors so if you’re already set in the navy department, go with another practical color like olive, khaki, or burgundy if you’re feeling on the bolder side.  A staple pair of chinos goes great with anything, so make sure you have a couple of pairs in your closet.

Alternative 1  //  Alternative 2  //  Alternative 3 (on sale)


9. The Crewneck: “Merino Wool Sweater” via J.Crew

Merino wool is fantastic.  It’s as soft as silk, but the price is comparable to that of a common, cotton sweater.  I’ll be honest in that I have at least six versions of this sweater, but merino wool is what I live in during the fall (and even winter).  These crewnecks will probably go on sale at some point over the next couple of weeks so keep an eye out.  I’ve scored several for under $45 since J.Crew usually has 6+ promotions going on at the same time.

Alternative 1  //  Alternative 2  // Alternative 3


10. The Boot: “Desert Boot” via Clarks

Do these even need a comment?  If you’ve followed me for awhile, you’ll know that I swear by these shoes.  I have two pairs – one in beeswax and another in suede – that I wear at least once or twice a week.  They’re fantastic shoes that are not only warm, but don’t break down after a couple of seasons.  Mine are going on year four (or maybe it’s year five) without any sign of letting up.  Buy them if they’re not in your possession already…

Alternative 1  //  Alternative 2 (on sale)  //  Alternative 3 (on sale)


11. The Scarf: “Check Blanket Scarf” via ASOS

Here’s the thing about scarves for men…they’re too short.  You wrap them around you neck once or twice and the ends stick out to the right and left mirroring some horribly tied bow on a present.  My advice is go with the longer option – like this one via ASOS.  The plaid pattern is appropriate for the fall that adds a nice texture to whatever you’re wearing.  If plaid isn’t for you, go with something like like a tan or navy.

Alternative 1  //  Alternative 2


12. The Shades: “Bates” via Warby Parker

Just because you’re not at the beach doesn’t mean you shouldn’t have a great pair of shades resting on the inside of your coat pocket.  Club masters are alright, but Warby Parker came out with an awesome line of sunwear for the fall.  All sunglasses aren’t for everyone, so know what compliments your facial features and go with something that you’re going to love instead of just like.

Alternative 1  //  Alternative 2

Dress Shoe

13. The Dress Shoe: “Britton Bit Loafer” via Cole Haan

I don’t know about you, but living in DC without a car means I do a fair share of walking.  With that being said, a comfortable (and durable) pair of dress shoes is a requirement.  A few weeks ago, I came across this Britton Bit Loafer at Nordstrom and picked them for a little under $100 (sorry…not on sale anymore).  After breaking them in (it wasn’t as painful as slippers) they’ve become a great, go-to shoe.  While the bottoms aren’t made of leather, the rubber soles will give good traction when the weather turns from nice to not-so-nice.

Alternative 1 (on sale)  //  Alternative 2 (on sale)


  1. Kyle

    Any recommendations for a rain jacket? I thought of Barbour but I’ve received mixed reviews on their waxed jackets.

    • Dean

      Hey Kyle,

      I have a couple of suggestions:
      1. “Heritage Park” by Lands’ End – Great jacket that’s affordable, well built, and in a pretty simplest design that will easily pair with the basics in your closet.
      2. “Stockholm Bla Raincoat” by Stutterheim – This is suppose to be a FANTASTIC brand. If I didn’t already have a great raincoat from Brooks, I would totally have bought this one. Price is a little steep, but it’s worth it (at least in my opinion).
      3. “Long Waterproof Jacket” by Rains – Basically the same design as the Stutterheim, but at a fraction of the cost. Simple design and decent for the fall when it’s not yet cold.

      Let me know if you need some more recs, Kyle.


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