The High/Low: Tailored Jackets & Hoodies

February 5th, 2012

As I’ve written many times (since 2009), my favorite way to dress is what I sometimes call High/Low. A classic silhouette with a combination of dressy/casual and luxury/affordable. It’s an easy formula for an outfit that is stylish but not “too much” in any direction.

An example of High/Low is a simple hoody (preferably neutral and solid) combined with a tailored jacket (suit or blazer).

I am partial to this particular combination because it is very me and represents my style influences – mixing athletic elements as a former basketball player and tailored elements as a current menswear designer/ “tailor’s apprentice”.

Here’s a couple examples I wore last week.

    1. Grey on Grey

    I hear it from guys all the time: “I want to wear suits and tailored pieces more often, but I never have occasions to wear them.” Here’s an easy solution: you don’t need an “occasion”,  just wear your suit. Men look good in suits. Girls like it. Your parents like it. And most importantly, YOU like it.

    The best part is, it’s easy. The jacket matches the pants…75% of your outfit is already put together.

    There are plenty of “laidback” suits on the market now – from Uniqlo to Michael Bastian. Soft shoulders, partial lining, textured fabric, slim leg, etc. These are the easiest to wear casually – with sneakers, for example.

    However, that doesn’t mean you can’t dress-down a sharp suit. This charcoal grey peak lapel number sometimes serves as my “semi formal” suit.

    As always, fit is critical.

    • Grey hoody by Theory
    • Tortoise shell prescription glasses (w/ clip on shades) by Garrett Leight
    • Grey wool suit
    • Oxblood loafers by Scarpe di Bianco
    • White sneakers by Nike
    • White t-shirt by Alexander Wang

    2. Navy on Navy

    The right blazer can sharpen a very casual look and take it up a level. This is just a simple casual look – hoody, jeans, boots – with the “perfect blue blazer” from my collection over it.

    Sometimes going without a pocket square is more natural. When it’s a really laid back look, you don’t need to add a fussy accessory like a pocket square.

    • Navy pullover hoody by Club Monaco
    • Light grey wash jeans by Ralph Lauren Polo
    • Black leather wingtip boots by Paul Smith
    • Black aviator shades by Persol

    3. Suit & Sneakers


    Like I said, easiest done with a more casual suit, like an olive green cotton.


      Thanks for reading.

      Yours in style,

      Dan Trepanier


      Photography by Alex Crawford.

      • cutting men’s

        Something that I never ever really understand is why some discussions are
        incredibly lousy – and yours is definitely not! Appreciate your sharing a superb article with us all!

      • sleeveless hoodie

        Nice hoodie – looks really good, not to mention comfortable. The double zip really does add to the outfit, I have not come across many hoodies that are even remotely as wearable as this one.

      • Trustivia

        That looks fucken fresh! I love it.

      • Rusty

        Zip hoodies look lazy, the shawl collared photo was by far the best. I’d just invest in waistcoats.

      • Arshat

        Wow! Awesome experiments! Too bad I couldn’t find any half-linen jackets here in Bangalore. Do you know any place online when I could get them?

      • ark

        Looks sharp but i dont think i have enough swagger to pull this off without looking conflicted.

      • Cooper Smith

        Love the looks and reading the blog. Didn’t realize there were so many ways to wear a hoodie. I recently bought a hoodie from Alex Maine. It has buttons down the front and is great to dress up or down. Definitely would look great with these looks because it isn’t bulky. Great work. Their website is if you want to check them out.

      • Zac J

        wow, great looks! i love every styles in this posts. its just perfect. i so love the tailored hoodie 2.

      • Anonymous

        Amazing looks. Also I just wanted to know what brand was the sweater in the first look. It does look quite amazing with the suit because of it’s thinness and the ability to not add any bulk along with it.

        • SB

          Sorry, hoody in look 1 (and 2) is by Theory.

          Thx for reading,

      • Anonymous

        nailed it on the 3rd look

      • Jose F

        I like (LOVE) all these looks…. side note, are you going to be doing any appearances/events during NYFW?

      • Blake

        The purple hoodie with complimenting pocket square and khaki suit is simply exceptional! Never would have thought to do that. Excellent post.

      • Justin K

        The hoodie/jacket combo is something I noticed in large Eastern cities back in 2005 when I studied abroad in China. The Koreans I knew in China LOVED this look, baseball caps and all. I traveled to Hong Kong, and guys were rocking it there, too. Very cool post. Love the looks, especially 1 and 3.

      • D6bells

        If all the jackets are really awesome, I think that the combination is not that good… Nevertheless, I like the combination between a hoodie and a shirt…

      • Mrjbeee

        Love your updates. Kep up the awesome and inspirational work,

      • Dani

        I know quite a few men that will be upset with you for even considering that combination but I beg to disagree. I think for life in the city, a high and low combination is mandatory…

        My personal favorite is look #2, grey layers always capture my eye…

      • J. Prep

        Rocking “J’s” I salute you. Gotta get a pair of 7’s up here soon.

        J.P. Lee

      • Anonymous

        Your eye for styling is NEXT LEVEL

      • Every Man’s Closet

        Great fresh idea for layering. And I’m having heart palpitations over the grey shoes! Nicely done.

      • Ambyr

        Loving the brisk corporate morning look. The colors and fit of the hoodie under your blazer looks great.


      • Anonymous

        About a year ago i decided to stop wearing hoodies, didn’t realise i could rock them like this!

      • DP

        love the blog and this was a solid post, but what kinda throws me off is the structured-ness of the shoulders of the suits jackets. How do you, SB, feel about the relatively newer Italian deconstructed/unstructured suits and blazers… Like of the L.B.M 1911 or Boglioli variety… (p.s. I know you have your own suit collection and all)

      • Anonymous

        Your blog is nicely written!

      • TO

        Funny timing, I just decided today to cut the sleeves off a hoody I have for which the arms had become a bit too small, and also saw the advantage of layering…and wore it on a last-minute date with shirt and tie under a jean jacket that would have been to “full” otherwise.

      • Sean

        I thought the lapels looked a little meagre on #1, then I noticed it was your first custom suit. Very cool to see the evolution of your style.

      • Felix

        Cardigans yes, hoodies, hell no.

      • cam

        hey dan, as usual thanks for the post. i think this looks best with a blazer or sport jacket and jeans. the full suit and hoody just doesn’t seem to look right. the inspiration however is greatly appreciated.

      • parker

        What brand are the wingtip boots? By the way – greatoutfits and suggestions in here.

      • bbqsanchez

        great post as always. looking forward to a new episode its being almost two months man!. definitively will take a lot of points from this post. i really would like to see a post on more laid back clothes. maybe jordan’s jeans and sweater etc. nonetheless you and your team are top shelve. keep it up Dan.