Shorts: Dressed Up & Down featuring Townsend Smith

May 1st, 2012

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5. Rooftop Relaxing

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This is what I wear when I’m just hanging around my apartment/roofdeck with no need to dress up or be in public.

Espadrilles, cut-off sweats, a tank and a breezy linen shirt are perfect for a lazy Sunday in style.

These used to be my sweatpants for jogging/working out. After a while they were stained and ripped but rather than throwing them away I decided to repurpose them. Now they are my go-to shorts for lounging around the apartment.

Before throwing away or donating old pants (whether they are khakis, sweats, or even suit trousers) consider having them altered to fit differently, or cutting them into shorts. If you don’t like the frayed bottom, your tailor can always help you finish them properly with a plain hem or cuff.

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  • Red espadrilles by Stubbs & Wootton
  • Grey heather tank top by American Apparel
  • Navy linen shirt by Uniqlo
  • Watch by Orvis
  • Aviator shades by Randolph Engineering

As always, thanks for reading!

Yours in style,

Townsend, Dan and the SB Team


Photography by Alex Crawford

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  • 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:!/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…

    • 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’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 @

    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?

    • 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.