Fall Business Casual

We are coming dangerously close to the ‘glad I wore a sweater this morning, but regret wearing it this afternoon’ weather.  Crisp mornings call for a different kind of preparation than the warm afternoons.  It’s all about the layering game, which is a fun game to play.

Layers are great.  They are non-committal.  It’s two or three different looks in one outfit.  Most offices are moving to a business casual look where jeans are OK, so I put together an approved roundup.  Here’s the thing about business casual: stay away from the least common denominator.  Don’t be the guy that scrapes the bottom of the business casual spectrum by schlepping around in a pair of ill fitting jeans, busted up shoes, and an un-ironed shirt.  Instead, embrace it.  Take advantage of the breadth of choices.  Sport coat, vests, OCBDs, 5-pockets, and boots can all be interchanged and you’ll still screw up the bell curve.

Here’s how I like to do it this time of year:

From top left:

1. Tombolini Dream Sport Coat:  I’m telling all of you this little secret: Tombolini Dream sport coats are incredible.  When they are 70% off at YOOX, they are even more incredible.  Not too stiff, and not too soft…just right.
2. Brooks Brothers Original Polo Shirt Oxford:  I’m the most non-non-iron guy out there, and luckily Brooks Brothers completely compensates with these Original Polo Oxfords.  They fit GREAT, the fabric is just right, and the collar roll is just what the doctor ordered.  Wash, hang dry, and lightly iron for the soft, Fall look you want.
3. Levi’s Garment Dyed 501s:  Of course you have khaki, probably olive, and a light blue.  Add ‘pewter’ to your lineup.  It’s a great neutral this time of year, and goes with both black and brown shoes.  You’ll be surprised how often you sport these.
4. Barbour Lowerdale Gilet:  So far, the vest for 2017.  Orvis offers it in three colors (including orange), and it’s just what you need without all the bells and whistles.
5. Tudor Heritage Black Bay Blue Diver Watch:  Best diver watch value out there.  Why not go with the metal band….
6. Ball and Buck 6 Point Duck Cotton Pants:  I absolutely love a rougher canvas chino pant.  I think it has a rugged look that is really easy to dress up.  Ball and Buck do this effortlessly…and all the details (camo, rivets, shooter label) are just icing on the cake.
7. Holderness & Bourne Robbins Quarter Zip Sweater:  This time of year, I rarely leave the house without a quarter zip.  What sets the H&B Robbins apart?  It’s a little thicker than most on the market, which are basically a soft long sleeve t-shirt with a zipper.  This one does provide warmth, but not so much that you are sweating by the 14th hole 2:30 meeting.
8. Fifth & Fields Pelican Buckle Belt:  I’m a sucker for a cool belt, and the pelican buckle is as cool (and unique) as it gets.
9. Pantherella Socks:  If you have to wear socks, wear the best.  You absolutely can’t beat Pantherellas.
10. Loake 1880 Chatsworth Suede Chelsea Boots:  Chelsea boots help you look like you know what you are doing.  Suede chelsea boots are proof that you know exactly what you are doing.
11. Onward Reserve Jasper Flannel Blue Heaven Shirt:  A good flannel shirt can be worn on days when it’s cold, and on days when it’s warm.  They shouldn’t be so thick that sweating in 75 degree weather is an issue.  Onward’s Jasper flannels are just right: structured enough to look like a dress shirt, but brushed for that good flannel feel.
12. Filson 24-Hour Tin Cloth Briefcase:  The perfect size for that ‘Friday’ bag…laptop, notebook, and whatever else you need for the quick weekend trip.  Just leave straight from the office.
13. Oak Street Bootmakers Plain Toe Blucher:  I haven’t worn bluchers in some time, but I’m about *this* close to pulling the trigger on these.  The guys on Oak Street know what’s up, and these bluchers are great with jeans, khakis, with socks, #sanssocks, or whatever.  A very versatile shoe that cleans up with a little TLC.



  1. Nem
    10/06/2017 / 8:08 AM

    Look fella, I don’t know what you’re up to, but stay out of my closet.  Get your own ideas!!  I have 5 of these items in rotation already, including that Tudor and the pewter 501’s from Sid this summer.

    • JRS
      10/06/2017 / 10:09 AM

      Ha!  I know you have good style, but five items???  Those pewter Levi’s are killer…good call.

      • HLL
        10/06/2017 / 12:07 PM

        Blue or red on the Tudor? Need an addition to my rotation and I feel like blue is the safe option and red may be too much. I want the more timeless, yet dapper one.

        • Nem
          10/06/2017 / 1:55 PM

          Blue, no question.  With it you’ll get the white gold surrounds, and matte finish dial.  The blue bezel is subtle, appears black in some lighting, but never too blue. 

  2. CJW
    10/06/2017 / 9:33 AM

    Maybe it is just me but I think Chelsea boots are hideous. That being said, I just pulled the trigger on a pair of Alden 403. Hopefully they serve me well in the cold months as penny loafers aren’t suitable for the cooler months and bluchers are not my style.

    • JRS
      10/06/2017 / 10:10 AM

      403s are a great call.  

      • CJW
        10/06/2017 / 1:13 PM

        JRS, any thoughts on the Baracuta G9? Allen Edmonds has them on sale for $290, about $100 off reg. price. I love the iconic look but the cost still seems steep considering it is a fancy windbreaker.

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Close Me
Looking for Something?
Post Categories: