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

    18 copy

    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.

    19 copy

    • 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 

    07 copy

    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

    08 copy

    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.

    09 copy

    • 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

    • Bo

      I appreciate the looks here for sure (particularly the cardigan combo) but does it not look to anyone else like the fit of the jacket in the last set of photos is too big? Too wide in the shoulders? Sleeves are too wide? Maybe that’s just because it’s unbuttoned, but thought it was worth pointing out! Solid combos otherwise, though.

    • AFJ


    • James

      Loved the post, especially the Easter Pastel look.

      I was having problems with my uncomfortable new boat shoes while going sockless, then one day I put them on straight after coming off the beach and the sand turned them into some of the most comfortable shoes I own. Not a technique that is accessible to everyone but it wore them in like nothing else I’ve ever tried.

    • AMProf

      No, just no, to the blazer and shorts thing (the cardigan and other sweater is fine). Its a really immature look– think high school seniors being “zany”.

    • jack

      Where can I buy the sunglasses of the first photos??

    • Dan

      And to think my friends still talk trash when I break out the ice cream shorts. Thank you sir!

    • Ema

      signature classics.. our main inspiration in producing these timeless slip-ons: http://chukutimes.tumblr.com/#!/post/24141046080/slipons

    • H

      You are absolutely killing it in each of these shots – well done.

    • Sidd

      Townsend, please start your own blog. This post was absolutely awesome!

    • Anonymous

      Best Post Ever

    • Alex

      Dig the Allen Edmonds. Are they the strands? walnut? Was thinking of buying a pair to suit up with. Also, how do they hold up sockless? I can imagine the sweat could do some damage to a decent pair of leather shoes.

      Great post though! SB should utilize the rest of his team more often.

    • Dennis

      Best post ever!

      Though this is not really something you guys blog about, I would love if you could give some tips about you hair. I really dig it but can’t seem to make it hapen by myself.

      Keep up the good work all of you.

    • Andreas

      Best post on this blog ever!

    • Anonymous

      Ester Pastel. definitely the best! Good Job!

    • ANH Style

      Mr. Smith- you would definitely catch my my eye if we passed on the street! I really like the Bermuda Prep and Easter Pastel looks. Well done.

    • Carlo-Antonio

      Nice! I’ve always had reservations about shorts with Blazers, but these are awesome!

    • Booth

      Absolutely awesome! By far my favorite post!

    • Reader

      BEST post yet. Really awesome looks and photos nice work styleblogger and Townsend!

    • Emanuel Iuhas

      Definitely I DO. I DO like short with blazer, cardigans & long-sleeve shirts.
      Thx for the inspirational post!

    • Iván

      Cool man!

      Greetings from


    • tee

      how do you like the color of your savile row co. double monk straps?

    • Ariel.

      After now seeing two posts up on dressing shorts from more “dressy” approach/paired with blazers and full on prep inspirations to styling them so casually, I just have to give it a shot now! I honestly think this is such a daring look not fit for every man, but is absolutely nailed here and is definitely worth a try soon. Bravo Townsend.


    • Atticus

      Hey Townsend I’m reading this as follower of SB from Bermuda! I had to smile when I saw the “Bermuda Prep” because it looks like you just walked out of the Royal Bermuda Yacht Club. Excellent representation.

    • Anthony

      Best post yet.

    • Justin K

      Is it ever appropriate to wear short-sleeved button-up collared shirts? With shorts or pants? How about ties or jackets? I know it can look terribly immature and car-salesman like, but can it ever work?

    • Kris

      This is my favourite SB post so far. Excellent! Every outfit is a win in my opinion. Wanna see more posts from you, Townsend!

    • Michael

      Good post. These shots illustrate the importance of having somewhat human-colored ankles if you’re going to rock the sockless look. Whenever I see Dan’s whiter-than-white ankles (as in the last post) it kind of freaks me out a little…

      • http://www.thestyleblogger.com SB

        Hahahaha. Yea my pasty ass could use a vacation.

        It’s a good added tip though, a tan certainly helps.

        Thanks for reading Michael

        • Daniel

          Dan, I must commend you on how gracefully you respond to posts. Best of luck with your collection!

    • Kevin

      Love the Tommy Bahama loafer socks. I enjoy the sockless look, but think it’s bad for the shoes especially since my feet sweat. Unlike other loafer socks, these have a deep toebox and actually stay in place.

      Good investment to save your shoes.

    • Desmond

      Look #1 is the perfect uniform to a spring polo match. Looking forward to seeing more posts from u.


    • Ambyr

      My favorites are Bermuda Prep and Rooftop Relaxing. This Bermuda Prep look is so chic with the colorful tie and shorts. And of course the Rooftop Relaxing is so easy but still well styled. There’s nothing like a man who can dress up nicely to go out and find a casual way to still have sex appeal, like he’d want from a woman.


    • Billy

      Hell..you’re a furry little man! Nice!

    • Reader

      Good post. But you should add more brand diversity to your wardrobe. You look like a J. Crew model basically. Appears as if that’s all that’s in your closet.

    • Mrjbeee

      Continuosly dropping jewels man. Another awesome post! Such inspiration.

    • Alan

      Awesome post. Good looks. You pull off all the looks but some guys just can’t pull off these looks. I’m one of those guys. Keep up the good work.

    • Kyle

      Really diggin’ the third look. The rest, though, are just not for me. In my eyes, “dressing up” a pair of shorts never really works. I prefer a more casual approach, like outfit three or Wes’ look @ http://www.thestyleblogger.com/wp-content/uploads/2011/08/08-11-11014.jpg.

      Townsend, even though the looks aren’t something I would personally sport, I really dig the post! I hope to see more from you in the future!

    • Jack

      Pants are unbearable in the summer. Nice to see a strong post highlighting shorts.

    • Miguel

      Personally I wouldn’t do the blazer/shorts thing, but I think the cardigan/shorts in look #3 is a winner..

    • Arron

      What kind of shorts are you wearing in the last look?

      • http://www.thestyleblogger.com Townsend

        Cut-off jcrew sweat pants. thanks for reading!

    • Scott

      great post

    • Khalid

      The StyleBlogger is big on shorts… he just prefers them to hit a bit above the ankle.

      • Drew

        nice one

    • Paul

      A real winner of a post. A great subject/model and the look is right on! Thanks mucho!

    • Evangelos

      shorts ain’t masculine and of course they ‘re not classy!

    • joey dee

      all solid looks, can’t wait to put it all together. target has some great colored ‘cut off’ shorts available now in a bunch of colors, going out to stock up now!

    • Dave

      the casual looks are great! still not sure how the shorts look goes down in the city though, wish i had the weather to try it at least!

    • Sam

      I’ve been strongly considering that J.Crew herringbone jacket for like 2 years now. Looks good here!

    • Adyna

      :) Congrats Towni! Luv the post, informative and so well organized. I personally like when men are wearing shorts, it looks good and you showed it here too well!


      • Gemma

        Very Southern France. It still looks very smart. I wonder if us ladies can pull this off somehow.