Fashion Tips and Style Advice from America's "Best Dressed Real Man"
Thursday May 17th 2012

Keeping Cool: Tailored Shorts

I don’t wear shorts very often, but there are some days that are just too hot for anything else. When those days come around, you want to be prepared with the right shorts – ones that will allow you to expose some leg and still look mature and grown up.

Leave the basketball shorts for the gym, the cargo shorts for the high schoolers and the extra-short shorts for the beach. Find a pair of simple, not overly washed, cotton shorts that fit like a good slim chino – sit at the waist, slim through the leg and hit about 1-2 inches (2.5-5 cm)above the knee.

Shorts by Theory (size 34). Pinpoint oxford shirt by Band of Outsiders (size L). Sneakers by Converse Jack Purcell. Shades by Moscot vintage. Watch by Montblanc. Grosgrain ribbon watchbanc by Corvus. Bracelets from various street vendors.

It can take a while to find a tailored short that fits properly, but once you do, I suggest stocking up on the basic versatile colors, just like you would with chinos – khakhi, navy, grey, etc.

Pair them with a lightweight washed shirt (cut to a length that was meant to be worn untucked – see here), and a pair of classic sneakers for a simple, cool, summer-casual look.

Shorts by Theory (size 34). Blazer by H&M (size 40). T-shirt by Calvin Klein (size S). Belt by Ralph Lauren Purple Label (36). Tassel loafers by Johnston & Murphy. Linen pocket square by Paul Smith. Shades by Persol. Watch by Montblanc. Watchstrap from Thewatchprince.com

For a slightly moregrown-up-casual look, pair a tailored short with an unconstructed blazer, a basic t-shirt and a classic pair of loafers.

As I’ve mentioned several times before, mixing casual and formal elements like this is a great way to create an interesting look that is appropriate for a wide range of occasions.

Men don’t often pair  blazers with shorts, which makes it an interesting look – just make sure you choose theright blazer – fitted, slightly cropped, lightweight cotton, unconstructed and unlined.

And unless you work in a very laid-back, casual atmosphere (and you have legs that people wouldn’t mind seeing), I usually don’t recommend wearing shorts to the office – even if you’re pairing them with a blazer on top.

Thanks for reading – more on shorts and summer wear to come.

Also, my apologies for the delay in posts. I recently hired a new photographer, which should help with my posting consistency!

All the best. Yours in style,

SB

Leave a Comment

31 Comments

  • hisandherfashion says:

    Excellent article

  • Jonathan Charles says:

    This is really useful, as I’m going to London next weekend and the forecast has been very warm. Converse in this kind of outfit would be ideal – lightweight yet comfortable.

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  • Sabir P. says:

    Hey Dan,

    This is a well timed post, with the blazing temperatures that have been sweeping the east coast as of late. Like you I don’t wear shorts often but when I do i go for a more fitted and slightly above the knee look. The baggy cargo shorts look is made for kids and i think its funny it when I see grown men attempt to dress up a pair with a button up shirt. Good stuff Dan!
    http://www.thesocialcalendar.blogspot.com

    (Transfer comment from old site)
    Thursday, August 5, 2010 – 02:16 PM

  • ColorFool says:

    I am a big fan. Ths man has found a way to dress up a simple pair of short. I am amazed. Pefect combinations, awesome pictures, spot on blog, great suggestions and advice as usual.
    Keep up the good work Dan.
    I am humbled to be one of your fans and follower and been waiting for this blog. I never know how to wear shorts.

    In Dan We believe!!!

    (Transfer comment from old site)
    Thursday, August 5, 2010 – 03:07 PM

  • Fresh2death says:

    C’mon Dan, shorts? A valiant attempt, but you are too good for that! In the Sopranos, Carmine said it best, ” a don doesn’t wear shorts…” and Tony was a t a BAR-B-QUE, at HIS house!

    Here is your summertime wardrobe……

    Chinos
    T-shirts
    Golf shirts
    Linen shirts
    Linen pants
    Lightweight button-downs
    Loafers
    Boat shoes

    Be a man!

    (Transfer comment from old site)
    Thursday, August 5, 2010 – 03:17 PM

  • PawetZegarow says:

    Hi! Great trainers, i love it. Your outfit is very simple but style. This green shirt is realy, realy cool. I want this.
    http://www.pawelzegarow.blogspot.com

    (Transfer comment from old site)
    Thursday, August 5, 2010 – 03:31 PM

  • JMRouse says:

    F2D, I disagree. Shorts are a casual, summer staple for guys. You shouldn’t wear them all the time, but for walking around outside on a scorching HOT weekend afternoon they make sense.

    Dan, any recommendations, besides H&M, where to get good fitting unconstructed & unlined blazers? H&M’s sizing typically does not agree my long arms.

    Keep up the good work Dan. Hope the unusually hot NYC summer is not killing you yet.

    (Transfer comment from old site)
    Thursday, August 5, 2010 – 04:38 PM

  • ColorFool says:

    Watch it Fresh2Death…Just watch it!!!!! Grrrrrrrr
    I hope your comment was not to criticize Dan. You are talking to a messiah of fashion, style and etiquette.
    Watch it there buddy.
    Dan is the Man and we are his followers and fans for ever and ever ever!!!!

    (Transfer comment from old site)
    Thursday, August 5, 2010 – 04:45 PM

  • TO says:

    Hey Dan,

    Great post as usual! However, I’m not sure if I understand the use of the term “washed” that gets thrown around when referring to oxford shirts, chinos, etc. and as you use in this post. Also, this reminds me of an old post of yours (http://mensstyleblog.blogspot.com/2009/05/stand-out.html to be exact) that I loved which points out the ballsy formal version of the second look, which you may want to revisit for us!

    (Transfer comment from old site)
    Thursday, August 5, 2010 – 07:18 PM

  • Victor says:

    fine post, I would neatly cuff my shirt though, to sort of match the cuffed shorts. You can still look rugged and casual because your shirt is not ironed well, and I would took in the shirt aswell.

    (Transfer comment from old site)
    Thursday, August 5, 2010 – 07:53 PM

  • Fresh2death says:

    COLORFOOL: I’m a fan, not a blind-follower….If you were a true fan, you would realize that Dan encourages his readers to foster their own sense of style through their sartorial choices…I bet you are the guy I will see this weekend, at the bar, trying to mimick this look…

    Also..although I am a relatively recent reader, I have gone to Dan’s old website and read ALL of his posts….

    AND..

    I check the site daily (sometimes multiple times a day) for updates…. : )

    (Transfer comment from old site)
    Friday, August 6, 2010 – 09:26 AM

  • RobfromDC says:

    COLORFOOL– You are a tad on the stalkerish/creepy side, in regards to your comments??????

    I must say Dan, I am a little surprised you did not go with a more bold choice of color.

    Anyways, great post as always, Cheers!

    (Transfer comment from old site)
    Friday, August 6, 2010 – 01:37 PM

  • ColorFool says:

    Hey Fresh2Death,

    You are my buddy now too.
    We are all fans and followers of Dan Trespain for ever and ever ever again.

    (Transfer comment from old site)
    Friday, August 6, 2010 – 08:10 PM

  • Thatguy says:

    wow SB, you shave your legs?

    you should start making video episodes or something

    btw… I know someone else mentioned this as welll.. could you do a segment on sandals… how do you rock them? thats one thing I hate about summer and addiing them into my shoe rotation without messing with my style

    (Transfer comment from old site)
    Saturday, August 7, 2010 – 02:53 AM

  • JMRouse says:

    ColorFool, laying the compliments on a little thick, don’t you think? lol

    (Transfer comment from old site)
    Sunday, August 8, 2010 – 04:13 PM

  • Anonymous says:

    Save Khaki, best shorts hands down, great slim fit, more tailored then your Theory’s…

    (Transfer comment from old site)
    Monday, August 9, 2010 – 10:33 AM

  • A. Sahan says:

    Easy on that ledge Dan, we don’t want to lose you!

    p.s. all those suit have you pasty, hit the beach!

    (Transfer comment from old site)
    Monday, August 9, 2010 – 12:52 PM

  • ColorFool says:

    JRMouse,
    I think the compliments are well deserved.

    You guys may not know this, but I consider myself…a bit of a loner. I tend to think of myself as a one man wolf pack. But when I first started reading Dan’s blog, I knew he was one of my own. And my wolf pack, it grew by one. As I read more of the blog, I was not alone in the pack, more wolves were in the pack. Now were a pack of wolves for ever and ever ever best friends.

    (Transfer comment from old site)
    Tuesday, August 10, 2010 – 09:59 AM

  • FRESH2DEATH says:

    @COLORFOOL: Wow brother…I don’t even know where to begin with you. The Hangover reference was well-delivered, but take it easy tico-broham

    (Transfer comment from old site)
    Tuesday, August 10, 2010 – 10:42 AM