2. ”Dressy” Casual

Combining dressy and casual elements, or dressing “down the middle” as we call it here at TSB, is a great way to create an interesting outfit that is appropriate for a variety of occasions.
Again sticking to lightweight fabrics here with a linen herringbone jacket, unlined chambray shorts, gingham poplin shirt and silk knit tie.

As always, fit is key. Make sure the shorts are slim through the leg so that they correspond with the silhouette of the jacket. Similar to trousers, inseam length is largely a personal preference. I prefer an 11″ inseam, which allows the shorts to hit a couple inches above my knee.
Featured Items:
- Brown linen jacket by JCrew
- Watch by Orvis
- Brown cap-toe shoes by Allen Edmonds
- Tie bar by TheTieBar.com
- Blue gingham shirt by JCrew
- Blue chambray shorts by JCrew
- Aviator shades by Randolph Engineering




53 Comments Add a comment
fugly
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.
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”.
Where can I buy the sunglasses of the first photos??
And to think my friends still talk trash when I break out the ice cream shorts. Thank you sir!
signature classics.. our main inspiration in producing these timeless slip-ons: http://chukutimes.tumblr.com/#!/post/24141046080/slipons
You are absolutely killing it in each of these shots – well done.
Townsend, please start your own blog. This post was absolutely awesome!
Best Post Ever
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.
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.
Best post on this blog ever!
Ester Pastel. definitely the best! Good Job!
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.
Nice! I’ve always had reservations about shorts with Blazers, but these are awesome!
Absolutely awesome! By far my favorite post!
BEST post yet. Really awesome looks and photos nice work styleblogger and Townsend!
Definitely I DO. I DO like short with blazer, cardigans & long-sleeve shirts.
Thx for the inspirational post!
:D
Cool man!
Greetings from
nomellameustedmoderno.wordpress.com
how do you like the color of your savile row co. double monk straps?
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.
http://urbanaesthetics.net/
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.
Best post yet.
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?
Nick Wooster does it quite often…
http://chinosandcheesecake.blogspot.com/
@justin k. yes and dan has done post wearing them. check the archives. cheers!
This is my favourite SB post so far. Excellent! Every outfit is a win in my opinion. Wanna see more posts from you, Townsend!
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…
Hahahaha. Yea my pasty ass could use a vacation.
It’s a good added tip though, a tan certainly helps.
Thanks for reading Michael
Dan, I must commend you on how gracefully you respond to posts. Best of luck with your collection!
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.
Look #1 is the perfect uniform to a spring polo match. Looking forward to seeing more posts from u.
Chinosandcheesecake.blogspot.com
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.
xoxo
http://www.thewrittenrunway.com
Hell..you’re a furry little man! Nice!
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.
Continuosly dropping jewels man. Another awesome post! Such inspiration.
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.
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!
Pants are unbearable in the summer. Nice to see a strong post highlighting shorts.
Personally I wouldn’t do the blazer/shorts thing, but I think the cardigan/shorts in look #3 is a winner..
What kind of shorts are you wearing in the last look?
Cut-off jcrew sweat pants. thanks for reading!
great post
The StyleBlogger is big on shorts… he just prefers them to hit a bit above the ankle.
nice one
A real winner of a post. A great subject/model and the look is right on! Thanks mucho!
shorts ain’t masculine and of course they ‘re not classy!
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!
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!
I’ve been strongly considering that J.Crew herringbone jacket for like 2 years now. Looks good here!
:) 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!
Best,
Adyna
Very Southern France. It still looks very smart. I wonder if us ladies can pull this off somehow.
I definitely think we can Gemma..just mix them and why not give it a try. It`s a confortable look.
http://pinterest.com/adynacbt/day-by-day/
Best,
Adyna