High Risk/High Reward: Jackets & Shorts

August 24th, 2011

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Menswear (or fashion in general, rather) is very much a game of high risk/high reward.

Take a jacket + shorts look, for example. Although it is much easier to get the look “wrong”, if performed correctly it can be very chic and set you apart without looking out of place.

As the age old saying goes, “you have to know the rules, before you can break them.” That is to say, if you understand the basic elements of mens dress (fit, fabrics, pattern mixing, color coordination, accessorizing, seasonality, etc) there is a much better chance that you will be able to bend the rules to achieve a desired outcome. (Rules is italicized because there are no actual “rules”, only a heavy dose traditional conformity).

Here, some looks and tips to help you pull-off a jacket with shorts.


1. Heat Wave Business 

The trick is to have the proportions right. The jacket is an “modern” length (but not trendy short or “cropped”) so the shorts should have the same look and feel; about 1-2 inches above the knee.

The slimness of the shorts should also be cohesive with the jacket. They should be cut as if they are the matching pants of the suit, just chopped around the knee.

Bonus Tip: It’s already a look that can very easily look “affected”, so keep it simple with classic pieces, neutral colors and toned-done accessories.

Bonus Tip II: If the pieces aren’t tailored well it can look very amateur.

Bonus Tip III: Loafers are a lot easier than lace-ups. Think of shoes that look natural without socks.

Bonus Tip IV: Make sure the jacketing fabrics are summer appropriate. Think cottons, linens, tropical wools, etc.

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  • James

    Hey, I really like your blog. It’s very helpful.

    One question though: Could someone please point out the brand/store where I could get the shirt and shorts combo in look 2?

    The only thing I have to say about the article (and keep in mind that I don’t know shit about fashion) is that in my opinion, many of these looks would look better and more natural without the jacket. To me the jacket comes off as very odd in almost all of these pictures.

    Still a great article though.

  • Adnan Hassonjee

    Great combination! I generally get such different and stylish combinations at http://www.iknowboutique.com.and I feel they will have something similar to offer.

  • Sandeep Jain

    what a concept and what a style i am impressed.I just bought some very nice shots by monteil brand. I will definitely try this my self with those monteil shots.

  • austin edward

    I have more shorts with different color and i have good match with this khaki shorts, the most valuable advantages in this brand, there giving at a very reasonable cost.

  • raj

    Hi SB,

    im teaming up a pair of white shorts with a grey v neck tee and a blue denim jacket. do u think thats a good match. im going for a cafe opening party and i dont feel like wearing trousers or jeans. i was hoping to do something un conventional. need your inputs asap. the party starts in 7 hours from now

  • Jim

    Wish I could pull this off!

  • ark

    Way too adventurous for me!

  • Windsor

    These looks would be better if you guys shaved your legs.

  • michael

    your business casual outfit, is damn HOT. LOVE IT, till hurt.

  • FrankB

    I totally disagree with the idea that this look is difficult to pull off. I think it is impossible to pull off. Unless you are Angus Young, shorts and a jacket never look good.

    Of course, I still think that men should not being wearing shorts when not involved in an athletic pursuit.

    I do love the jacket in the second look, but you are an adult male. Get some pants.

  • Fred Krugger

    Its kind of cool but I agree the sandals dont work for me.

  • Joey Dee

    Numbers 1, 3 are the best. The plaid jacket on 3 is so Sinatra, couldn’t stop looking at it. Sunday brunch is killer, don’t know if i can pull off the sandals, though.

    I have always wondered how to pull this look off; this gives some ideas.

  • Zach Raymond Boroff

    Something doesn’t add up, party down below, business on top….a little effected, or is it affected, who no’s.

  • pickle cracker

    style blogger, nooooooooooooooooooo!!!!!

  • Emanuel Iuhas

    I love the first outfit Dan!
    That jacket with the tie and the loafers with the shorts…Awesome!!!

  • Mr. Andy

    Forgot to add the importance of wearing minimal sock with the airy trouser. Bare ankles exposed while sitting (or walking) can signal confidence, among other things. Sartorial success to all.

    • Briar

      believe this is 1 of by far the most vital information for me. And i’m glad redaing your post. But must remark on some general factors, The site style is perfect, the articles is definitely terrific : D. Good job, cheers

  • Mr. Andy

    Another option for battling summer heat would be trousers with a gracious leg width (baggy). Think airy, vice tight and restricting.

  • oliver

    Loving the look in #2. Just plain classic.

    You guys…nice accessories here http://www.artofgear.com/

  • Darius

    Not really feeling shorts + jacket.

    It’s going to be affected no matter what you do because if it’s hot enough to have to wear shorts it’s going to be too hot for a jacket.

    • http://www.thestyleblogger.com SB

      I disagree. There are jackets made for all types of weather.

      I also enjoy wearing shorts when its a little cooler out.

      Thanks for reading.


  • Jason

    Mr.Nick Wooster would be proud of you in these photos!

  • EmoGuy

    Yo Dan, you need a tan. I know this white man can jump, but can he tan?

  • jim

    What would you say is the appropriate (modern as you put it) jacket length (in inches) for a guy around 6′?

    • http://www.thestyleblogger.com SB

      Depends on your proportions. The jacket should just cover your seat (ass).

      All the best,

  • TO

    Loved all these looks, especially the first and LAST (damn! Sunday brunch is the perfect way to describe it)
    Advice is very on point!

  • Leroy

    Great post Dan, the first look is killer. By the way what style name are those Fabulous Fanny frames?

  • Mori

    I like the final look the best. You are already going out on a limb with this look and Esquire is telling us not to do it. The matching looks makes it appear like it was meant to be.

    I also like the second look – casual sort of thrown together for a warm day.

    I’ve heard that in Melbourne, the shorts/jacket look is perfectly acceptable in business. It’s time that we adopt this look in the U.S. as the planet continues to heat up.

    Great work Dan!

  • Pat

    so much awesome in this post its not even funny. great work.

  • sincere

    No, you did not!!!

  • jesuisunprince

    I have also tried it out, here is the result :-)



    • TO

      Looks Great man!

      • jesuisunprince

        Thank you so much!
        It’s so rare that people are kind to me on the internet, so really thank you!

  • Mike

    The sport coat/ blazer look is just something I can’t get behind, but I have no problem with the first and third looks (or even the fourth if not for the footwear). They actually don’t look too affected, but once you add the henley, espadrilles, and SANDAlS, it just skews things a bit too far for my taste.

  • cam


    thanks for the post and i look forward to my new purchase. some of these looks work great. i’m thinking unlined/unconstructed blazer though. no?

  • Vidal

    I remember years ago trying the shorts with a long sleeve shirt look and couldn’t sell it. Of course I didn’t really ‘know’ the rules yet then, and thus, had no business ‘breaking’ them.
    As for the looks presented here, I dig it, but still have reservations about trying it myself. I think it may work for a guy who is short to average height, but at 6’8″, I’d be baring a lot of leg, while rocking a lot of sleeve! I think I’ll leave this one to the ‘less vertical’ fellows.
    I certainly agree with the brown shirt tips though! (I’m rolling in a deep caramel one as I type this.)
    Thanks Always!

  • khordkutta

    Look #2…KILLER

  • Cory

    I’ve never liked the jacket and shorts combo. For me, warm enough for shorts = too hot for a jacket. Anyway, you seem to make it work here, especially the seersucker “suit” in the last photo. Bonobos should sell that as a three-piece (jacket, shorts, and pants). :-)