Dappered Classics: The Dress Shirt Top 10 Hierarchy

What you should have on hand first, plus affordable examples for each.

Originally Published 3/28/12

#1.  White, semi-spread, light to mid-weight Poplin/Pinpoint/Twill

Nord. Trim Fit – $65. Pricey, but worth it.

Quick, think of a white dress shirt.  Yahtzee.  There’s the #1 shirt we should all have in our closet.  The collar does not button down on these, and the fabric is a mid to lightweight (we’ll get to the thicker “oxford cloth” soon).  Some call these “oxfords” even though that’s not quite right.  It’s a shirt that’ll look equally as good with a suit as under a v-neck with jeans.  It’s crisp, it’s clean, and you want a collar with enough beef  to look substantial.  Use some wurkin’ stiffs to keep it framing your face when tieless.  Melt your brain with the differences between poplin, pinpoint, & twill here, here, and here (scroll down a bit on that last one).

 

#2. Light Blue, semi-spread, light to mid-weight Poplin/Pinpoint/Twill

BR Stretch $47.60 w/ BREXPLORE (exp. 4/1)

Pretty much the same thing as the white dress shirt at #1, only in a real light blue color.  Not royal blue, not kinda light blue with grey buttons, light blue with standard off-white/bone colored buttons.  Slightly less formal than white, but still able to be dressed way up.  The BR shirt above doesn’t come in neck-and-sleeve measurements, but it can get cheap when on sale.  It’s also been quite durable on this end, after a ton of beatings in the washer & dryer.

 

#3. White, mid-weight to heavy-weight Oxford Cloth Button Down

J. Crew Factory – $26.50.  Slightly fitted.  Keep that logo hidden.

The OCBD.  Which surprisingly, wasn’t a member of the WuTang clan.  OCBD = Oxford Cloth Button Down.  And the “button down” part refers to the collar, not the fact that you button the shirt in front.  The term for that would be “button up” (even, if like me, you start at the top and button down.  Let’s move on.)  Is it a “dress” shirt?  That can really depend on how thick the fabric is.  If it’s like the J. Crew Factory above, or maybe the options from Old Navy, Bonobos or LEC, the thickness and rumpled-ness (not a word) of the cloth will make it hard to dress up.  But lighter, pressed OCBDs can pull some duty at the office.  A workhorse for layering.  Think grey jeans with a blue cotton blazer.

 

#4. White base, blue windowpane / tattersall, non-button-down

Boden French Cuff – $47.60 ($68)

Lots of white and blue right?  Well, yes.  An orange and green check just won’t go with as much stuff in your closet.  Meanwhile, a windowpane or tattersall is just different enough from the usual striped shirts most guys default to.  When under a jacket of some kind, they’ll give your look a bit of depth.  And unlike gingham (we’re getting there) they’ve got plenty of white which is more business ready.  When it comes to the office, for paterns, Tic-Tac-Toe > Checkers.  And for the size of the squares, the ideal size is between a pencil eraser and a quarter.  The perfect example:  Ratio’s.

 

#5. The Bold Gingham non-button-down

Color is up to you.  Black and white obviously offers the most contrast, but deep blue, red, even purple can deliver.  It’s a dressed up version of a dressed down pattern.

 

#6. White base, thin stripe non-button-down

Alfani Fitted French Cuff – $24.75

The stripes on these are thin enough that white base is dominant, but the stripes add a bit of depth and maybe some more color.  Thicker striped ties look just fine on top.  Just keep the thickness of the patterns far enough apart.  Keep your stripes slim and you can even take some color risks, like the tan stripe on the pictured cotton-blend, cheap Alfani Red.

 

#7. Thick/bengal stripe non-button down

Target Merona – $19.94. Try in-store.

The stripes on these are much thicker than the pin-stripe at #6.  Thick enough that from a distance, the shirt looks to lean more towards the color of the stripe, than the white base.  There are button down versions as well, but with a good pair of collar stays (or wurkin’ stiffs) those buttons will be unnecessary, and could limit it’s use.  If you’re always in a tie, and want some European flair, opt for a full spread for the collar.

 

#8. The Grey

Target Merona – $22.99

No, not the Liam Neeson punches wolves flick (which on a sidenote, got surprisingly good reviews).  A grey or even grey chambray that still has a sharp collar with collar stay slots is a good shirt to have on hand for under black sweaters or black sportcoats/blazers.  Not a bad getup to wear when grabbing a cocktail post sunset.  It’s still put together, has an evening out feel to it, but it’s thankfully still very far from clubby when tucked in and layered over.

 

#9. The cleaned up, light to midweight, non-button-down plaid

1901 Trim Fit – $49.50

This is a collision of workwear and business-wear.  The shape, collar, fabric, and details of the shirt are similar to the #1 shirt on this list.  But the pattern is straight out of a workshop.  Steer clear of oxford cloth, button down collars, or God-Love-It flannel/brushed cotton shirts.  Those’ll spill you into the Al Boreland category.

 

#10. The Pink or Red Subtle Patterned Shirt

J. Crew – $59.50 ($41.65 during the next extra 30% off sale)

Because no matter what your sexual orientation is, wearing pink doesn’t make you effeminate.  And wearing pink every now and then is a good way to flush out the knuckle draggers.  Anyone that says something to the effect of, “Dude, you’re wearing PINK!  BRO!”  might be worth, y’know, not spending a ton of time on.  At least for now.  Some of us whiter dudes (y’know, us crackers) might not look so great with a solid pink.  Lil’ too close to the skin tone.  So a red micro pattern on white, like this, helps make the pink look less like flushed flesh.
UPDATE:  This one is back to full price.  They moved some shirts out of their sale section for a 2/$120 promotion.
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Final Notes
  • 2 is the magic number:  Less is more.  Two is sort of the speed limit when it comes to dress shirts.  Meaning:  Anything more than two colors or two different thicknesses of lines in a pattern on a shirt and things can get weird.  There are exceptions, but solids, and pattern shirts with just one color on a base are safest.
  • Try and stick with all cotton:  Prices are rising (evidence is up above…) but limiting the level of poly used in your dress shirts will keep you cooler.  Sometimes synthetic just can’t be avoided, like in the shirts from Target.
  • Neck and Sleeve = More dressed up:  Sometimes a S/M/L/ neck will fit.  Sometimes it won’t.  Try it on.
  • No-Iron is up to you:  Some people love wrinkle free.  Some hate it.  Up to you.
  • Collar Stays:  Always.  Unless it’s a button down collar.  Wurkin Stiffs are even better.

Anything missed?  What should have made the top 10 that wasn’t?  Leave it all in the comments…