The High/Low: Tailored Jackets & Hoodies

February 5th, 2012

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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.

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

Here, Alex and I got together to shoot a few examples.


1. Brisk Corporate Morning

This has been one of the mildest winters I can remember. When heading to a business meeting, in February, I can use a hoody under my suit jacket rather than a bulky overcoat.

The hoody has to be slim through the body and sleeves, you might want to consider sizing down.

A full-zip hoody is ideal because you can zip it down to create a v-neck shape similar to that of a cardigan.

A double zip is even better since you can open the bottom as well – creating a silhouette even more like a cardigan (on which you shouldn’t be fastening the bottom button – the same rule that applies to a tailored jacket).


This is a new feature we might start including once in a while in posts.

You’ve heard it a million times. “The shoes make the man”. “A women notices a mans shoes first”. Etc.

All cliches aside, your selection of footwear really can make or break (or complete change the feel of) an outfit.

For the three outfits in this post, I styled them with two different shoes, giving two quick variations on the same look.

The first look above – with the wingtips – is something I would wear to the office (you can always take the hoody off when you get there).

The second look – with the sneakers – is something I would wear to an event, or a show, or a nice restaurant. Or, on my commute to work since I always leave a pair of dress shoes at the office/studio.

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  • cutting men’s

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    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.