Dressing-Up Shorts feat. Townsend Smith

May 1st, 2012

Townsend here. Dan suggested I try organizing a post on my own, so here it goes…

Spring has arrived here in NYC and the weather has been heating up. It’s a great time to slowly unpack some pieces from the summer wardrobe and layer them up for a comfortable Spring look.

I hate to feel hot, so shorts are a mainstay in my warm weather wardrobe. I wear them almost every day, for all types of occasions, from roughly April to September.

Dan isn’t really much of a shorts guy (oddly enough, most of my friends aren’t either) so I figured I’d take the reigns on this one and showcase how a well-fitting pair of shorts can be appropriate for just about any occasion.

Hopefully you (and maybe even SB himself) will feel a little more inspired after reading this post.

1.  Bermuda Business

I wore this to a rooftop cocktail party last weekend.  It was the perfect way to dress up for a classy event while managing to stay cool in the daytime sun.

To make it comfortable and natural, it’s important to combine the shorts with other lightweight pieces. In this case the jacket is a fine wool with no lining, the shirt is a thin poplin and the tie is a cotton madras. Also remember to keep it simple. Wearing shorts with a jacket and tie is already a statement, so keep the color palette and accessories neutral and classic.

You don’t have to be in Bermuda (where this is considered a business appropriate look) to wear this for work. As Dan has written in the past, before deeming this proper “business casual” it’s important to understand the dress code and overall culture of your place of business, as well as your perceived role within it.

Keep in mind too, as it gets warmer dress codes typically loosen up.

As Community Manager for TheStyleBlogger one of my tasks is organizing reader correspondence – which is basically a full-time job on it’s own. A very popular topic this time of year is how to comfortably pull-off the popular “sockless” look. Dan and I put together some tips & tricks that can help fight odors, blisters and prolong the life of your shoes.

1. Make sure it’s temperature appropriate. If you’re baring your ankles it should be a comfortable weather to do so. It won’t look very natural in cold climates or with a heavily layered look.

2. WASH YOUR FEET!  The easiest way to avoid stinking up your shoes is also the most obvious. Bacteria feeds off the sweat and dead skin cells on the bottom of your feet creating that awful foot odor we all know too well.  Avoid this by thoroughly scrubbing your feet, preferably with a brush and good foot scrub, every time you take a shower. Make sure to get in between the toes too!

3. Let your shoes dry. Try not to wear any pair two days in a row. Give the lining a chance to breathe and properly dry-out by leaving them in an airy space with cedar shoe trees (which absorb moisture & odor while keeping them in proper shape). This will not only help with odors but also increase the life of your shoes dramatically.

4. Powders and Sprays.  There are plenty of powders (for your feet) and sprays (for your shoes) that absorb moisture and sweat which keep your shoes stank free and prolong their life. If sweating becomes a problem, try sprinkling a little Gold Bond powder on your feet to keep them dry and applying a little spray inside the shoes (I use Tineacide) once a week or so to kill the bacteria at the source of the stink.

5. Break ’em in first. If discomfort or blisters are an issue, wear your new shoes with socks until the interiors soften up and they mold to the shape of your foot.

6. If all these measures seam a little extreme, you can fake it by investing in some “no show” or “loafer liner” socks. Tommy Bahama makes a great liner sock with enough elastic support to keep them up on your feet (not scrunched down by the toes). Matching them to the color of your shoes will make them even more discreet.

7. Most importantly, be confident and embrace the look!  With the right attitude you can go sockless in any shoe in your closet. Loafers, desert boots, wingtips, monks, sneakers, etc. Give it a try!


  • Tortoise shell prescription glasses (w/ clip on shades) by Garrett Leight ·
  • Madras tie by Ralph Lauren ·
  • Navy wool blazer by Theory ·
  • Brown suede Ring belt by Brooks Brothers ·
  • Nantucket red shorts by J.Crew ·
  • White shirt by JCrew ·
  • No-show loafer socks by Tommy Bahama ·
  • Brown loafers by Johnston & Murphy

3.  Brunch Hour

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I wore this outfit to a casual Easter Sunday brunch among friends – probably the most appropriate occasion for pastel colors.

Although it’s nearly impossible to tell from these shots the shorts have little embroidered marlins on them, a cool little feature that gives them a little identity. With preppy embroidered shorts try to keep the rest of the outfit solid or very subtle in pattern or print.

Rather than a jacket, try a cozy cardigan sweater when the sun goes down on a cool summer evening.

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  • Faded pink oxford shirt by JCrew ·
  • Tortoise shell prescription glasses (w/ clip on shades) by Garrett Leight ·
  • Watch by Orvis ·
  • White boat shoes by Sperry ·
  • Light blue shorts by JCrew ·
  • Blue heavy knit cardigan by JCrew

2. On the Move 

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I wore this outfit for a late afternoon stroll with some buddies last weekend in the city.  It was starting to get a little chilly out so I threw on a jacket, which ended up giving the look a whole different feel.  Maybe it’s the sunglasses, or the combination of neat and beat-up, but something about this look just made me feel “cool” wearing it – you know the feeling. And, as Alex kindly and not-so-discreetly pointed out, I was “eyeballed” by several women AND men during our walk to the shoot location. Guess I was doing something right.

These are my favorite shorts. For years they have served as my trusty “beat-around” shorts. They bore the brunt of years of yard-work, painting, gardening, you name it. The blue and brown paint splashes are from helping Dan paint his apartment. The white paint is from my parents’ garage. The green is from the fence around my backyard. Each tear, fray, and stain represents a distinct memory from productive times with friends and family.

Fake distressing bothers me, as do articles on “how to give your clothing a used or worn-in look”. Just wear your clothes and don’t baby them, they will develop their own unique character with an authentic story that you can look forward to sharing

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This is actually not a legitimate pocket square, it’s a fabric swatch. With the proper fold you can use just about anything as a pocket square. I’ve seen Dan use a sock before. Sometimes when I forget one I’ll fold up a dinner napkin.

Fabric swatches are great because you can hand pick from endless colors and patterns and they are free from just about any fabric shop. The best part is, in a pinch you can actually put it to good use (wipe your hands, nose, clean off a utensil, etc.) without worrying about ruining a $65 piece of fabric.

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  • Grey flannel sportcoat by J. Crew ·
  • Green needlepoint belt by Smathers & Branson ·
  • Khaki shorts by Ralph Lauren Polo ·
  • Blue Chambray Shirt by JCrew ·
  • Tortoise Wayfarers by Ralph Lauren Polo ·
  • Tan leather double monkstrap shoes by Savile Row Co. ·
  • Striped pocket square made from scrap shirting fabric

As always, thanks for reading!

Yours in style,



Photography by Alex Crawford