Shoes?  Check!  Pants?  Check!  Shirts?  Hmm…  Compared to picking out shirts, pants and shoes are easy.  Shirts are a lot more personal, and from what Dan has shown us, he seems to be ok in this department.  Sure, there is room for improvement when it comes to fit and construction, and that is why we’re here, right?

Now that Dan has proper fitting pants, he needs a few (note – just a few) new shirts to round out the look.  And while we’re at it, perhaps we can help him pick out a sweater that shows off a bit more of that shirt.  And for those days when there’s a nip in the air, or some rain, but too warm for a sweater…well, Dan could probably use a new jacket. 

But first things first.  There’s no need here to go crazy over shirts.  A few basic styles and colors should be able to get Dan through the work-week and into the weekend with ease. 

The Solid Shirt

As I mentioned previously, shirts should be simple.  It’s hard to go wrong with a few clean-cut, nicely fitted solids like the ones shown above.  For work, Dan should work with a mix of solid and pattered shirts.  The Tailored Fit Solid Original Oxford from Lands’ End is a great starter for most days.  It comes in white, light blue, and dark blue, and costs less than $30.  This is the most versatile shirt of the lot, and can be worn with any of the pant options I gave Dan yesterday.

For dressier occasions, J.Crew now makes their dress shirts in numbered sizes; so rather than S, M, L, you can get a closer fit combining neck (16, 17, etc) and sleeve (34, 35, etc) sizes in the same great fabric they’ve been offering for a few years now.  The white spread collar shown above would go well with the dressier options I gave Dan yesterday – the Bowery twills or wools, and perhaps even the rinsed 501’s when worn with a blazer.  This will also be the perfect option when we cover getting Dan into a suit (Thursday).  These shirts are also available in a variety of colors and patterns, and are discounted when you order more than one.

On the more casual days, I go back to the oxford, but this time from Lands’ End Canvas.  Again, this shirt comes in a variety of colors and patterns, but is more relaxed than the version from its’ parent company making it a prime candidate to be worn tucked or untucked, with the casual chinos or jeans, on a casual work day, or into the weekend.

Lands’ End Tailored Fit Solid Original Oxford | $29.50,

J.Crew Spread-Collar Regular Fit Dress Shirt | $75.00,

Lands’ End Canvas Heritage Oxford Shirt | $39.50,

The Patterned Shirt

Introducing patterns into one’s shirt collection should be done with some caution, but should still infuse a little fun into an outfit.  Dan should avoid stripes that are too thick, bold, or colorful, and instead concentrate on a finer stripe shirt like the one shown above from L.L.Bean Signature.  It’s billed as a pinpoint oxford dress shirt, but can be worn with dress pants, under a suit, or tucked into chinos or jeans.  Because of the fabric and styling, I would avoid wearing it untucked.

For that, I have included a plaid shirt, and a mini gingham shirt, each from Lands’ End Canvas.  I know it seems like I’m favoring LEC quite a bit, but for the price it’s hard to go wrong.  Should Dan wish to branch out or avoid LEC completely, everyone else makes shirts that look like these from Old Navy  to J.Crew to Steven Alan.  Mixing plaids and ginghams into dress vs. casual wear should be done carefully.  Make sure the style of the shirt is crisp enough to wear with dress pants (or a suit), and either pattern will look great!  J.Crew, Brooks Brothers, and many other shops offer gingham and plaid dress shirts.

L.L.Bean Signature Pinpoint Oxford | $59.00,

Lands’ End Canvas Patterned Heritage Poplin | $12.99 – $39.50,

Lands’ End Canvas Poplin Button-down Gingham | $39.50,


With Spring in full force, the last thing most of us wants to think about is throwing on a sweater.  But we all know that sometimes there’s a cool nighttime breeze when we’re out for dinner, or you’re running out first thing to get bagels, or it just brings the outfit together.  Luckily everyone makes a cotton sweater, or a light cashmere that is perfect for such things.

Dan seems to favor the classic v-neck.  While there is nothing wrong with this look, the one in his photo seems a bit big, and doesn’t show enough of his shirt.  One surefire option is to try a cardigan.  I know, these tend to look old manish, but the new slimmer versions like the one shown above from Lands’ End Canvas (yes, again!) is slim, and lightweight.  The deep V up top helps draw attention away from the gut, and directs it towards the chest & shoulders – something Dan (and I) would surely prefer.  Dan could throw this on over any of the shirts shown above, and any of the pants shown in yesterday’s, Big Dan Pt 2.

Should Dan choose to stay with the v-neck look, GAP has a nice, lightweight cotton version that has a deeper v, but is still fairly conservative.  This would also work with any combination of shirt and pants.

I also recommend the stand-up collar half-zip like the one shown above from J.Crew.  This is a staple piece for them, and comes in a cotton-cashmere combination (shown above in lambswool.)  The cotton makes it nice and light, while the cashmere adds softness.  They tend to stretch because of this, so I also recommend sizing down.  Again, this sweater would work with any combination – dressed up or down.

Lands’ End Canvas Cotton Heritage Cardigan | $59.50,

GAP Cotton V-Neck | $39.50,

J.Crew Cotton-Cashmere Half-Zip | $85.00,


For the same reasons Dan needs spring sweaters, he needs spring jackets; and then some.  Sweaters will keep out the cold, but not the elements.  For rain (and sleet, like were supposed to have tomorrow) Dan needs a solid raincoat.  This one from Lands’ End is made of polyester twill – so it looks great, has a removable lining – so it can be worn nearly year-round, and it’s waterproof – so, it does its job.  This should not be limited to being worn only on work days – a fine-looking coat like this can be worn with any combination from wool pants to jeans.

The Harrington jacket – made popular in the mid 20th century by Baracuta, and worn by the likes of Steve McQueen, James Dean, and Paul Newman is popular again today.  Dan could drop over $300 on one by Baracuta and others, or he could go back to the good old standby, Lands’ End Canvas to pick one up for $69.50.  In beige or navy, this jacket is extremely versatile, and could be worn with any of the mid-dressy to casual looks.

Valet Magazine recently endorsed the classic Military M-65 Field Jacket introduced during the Vietnam War, made popular by Robert DeNiro in Taxi Driver, and again over the last few years with the sudden craze for all things military.  At the end of the day, it’s a comfortable and practical lightweight weekend jacket that works perfectly for running errands, doing outdoor house work, or just taking a walk with the wife and kids.

Lands’ End Stormer Raincoat | $99.50,

Lands’ End Canvas Heritage Harrington Jacket | $69.50,

Vintage Light M-65 Field Jacket | $44.95,

Check out Big Dan’s Ramblings later today for Dan’s response, and back here again tomorrow for a few suiting options.