Summer Staples feat. Alex Maier

September 2nd, 2013

Chicago native Alex Maier grew up studying music and art in the windy city. Like a lot of creative guys in the business, he fell into the menswear industry and is trying to make a name for himself. He’s off to a great start, in my opinion, by organizing community-building events like THIS.

“My interest in menswear and fashion didn’t materialize until I moved to NYC and couldn’t find a job… I was blogging at and by a stroke of luck, tumblr invited me to cover NYFW for them. After moving back to Chicago I was offered the chance to be Creative Director at Haberdash. It was an amazing experience, however, I recently left to pursue more freelance opportunities, the most current project being this week’s Fall Classic; a streetball game between #menswear’s biggest tastemakers and influencers.”

We got together a few weeks back to discuss the bball game, the menswear industry, and life as a free agent. He was only in town for the weekend – one of the hottest of the summer. These are the three simple & smart looks he packed in his carry-on.

    1. Meetings with Sponsors


    Hard to go wrong packing a solid navy suit for a business trip.

    This tropical wool 2-piece by L.B.M 1911 is great for traveling because the high-twist fabric is naturally wrinkle resistant and the soft construction of the jacket makes it a great blazer as well (with the jeans from look 2, or khakis from look 3, for example).


    Alex’s style is simple and effective, he sticks to well-tailored basics.

    Check out the midsection suppression on this jacket – that’s a serious drop.


    Tassel loafers, especially in this beautiful shade of light brown, are a great choice for traveling because of their versatility.

    He could easily wear these with any of the three looks in this post, or with any other combination of the pieces he packed.


    2. ‘Dad’ Jeans Done Right


    The light wash, or “dad”, jean is back!

    Alex sharpens his up with a classic horsebit loafer and an awesome silk/linen soft blazer.



    There is said cary-on; a medium-sized waxed canvas duffle by Ernest Alexander.


    The belt selection here is genius: just enough energy to bring some life to a simple outfit, while hinting at the jeans’ “hippie” vibe.

    And contrast all that with a steady business loafer… Well played.


    3. Back to Basics


    It doesn’t get much simpler than a navy polo, khaki chinos and white sneakers.

    The trick is getting the fit right: find a brand that works for your body type and don’t skimp on the alterations if necessary.



    I think we’ve said more than enough about white low-cut canvas sneakers…


    Thanks, as always, for reading and special thanks to Alex for participating.

    Hope to see you all this Thursday 5pm at Tompkins Park – I’ll be the one getting BUCKETS.

    Yours in style,

    Dan Trepanier


    Photography by Alex Crawford

    • David

      Great looks! I have that same LEC belt from look #2. :)

    • Dit

      Superdanger, great to see you in your daily outfits again! Man, I seriously miss your wiwt posts. Such great inspirations.

      Anyway, good luck with your future endeavours!

    • http://undefined Big Jon

      I’ve been following Alex’s tumblr for some time. He always brings his A game and this was no different. The first look was the best.

    • Kyle Leon Norville

      Amazing post! Especially with the summer still in full swing for a couple more days.


      Look 2:

      “There is said cary-on; a medium-sized waxed canvas duffle by Ernest Alexander.”

      Cary-on… or carry-on?

    • Christian Davis

      One of the people I idolize most! I’ve spoken with him on Tumblr a few times and has always had great and extremely nice things to say from tips, advice, and some small talk.

      Keep it up Alex.

    • Theguybehindthelens

      The second look is killer. I am in love with that mid brown and blue houndstooth blazer. It is a perfect casual piece. The washed jeans, pocket square, and o ring belt are killer. They all play so well together in terms of context. The whole look strikes a perfect balance between relaxed and put together.

    • SidP

      Great effortless style Alex…keep rockin’

      Look #2 is solid…well done


    • Justin T

      Don’t you just hate it when you forget to pack your socks.

      • Alex

        not when its 100+ degrees out.


    • BF

      No DB jacket and shorts?????? WTF…

      As a streeterville resident, I’m proud to say this how we bring it in the Windy City.


      • Alex


        chicago represent.


    • James

      Great to see Alex on here, found him through his brother Marcus on tumblr actually when I was going through the “thrift” tag, great instagram as well. Good job Dan & TSB, as always.

    • Brady P

      Really like the light wash jeans and look 2 in general

    • TO

      Love this guy’s style- truly understated with a great fit. Can’t go wrong.

      • Alex

        thank you for the kind words.


    • cam

      checked out his blog…nice classic style he has going

      • Alex

        thanks cam!


    • Alex

      To get the fit of jeans like this do you just go to a tailor and ask for a taper?

      • Alex

        these jeans are old levis 511s.

        but if you have a great pair that you are willing to tailor, you can ask to get them tapered from the knee down.

        not all tailors are familiar with denim though so make sure you go to the right guys.


        • Adam

          Who do you recommend in Chicago (for denim, but also for general work)? I have yet to settle on a go-to guy, still shopping around. Would love your suggestions!

    • BougieHippie

      Look 2 is the coolest. relax, modern and wearable.

    • John B

      Great looks! Packing clothes that can be mixed and matched is essential for (short) trips! I’d probably pack one (maybe two) pair of shoes though!

    • Tom

      Whatever happened to the monthly competition…or are people too scared when I bring the heat

      • Robert

        Hey Dan, where did the monthly competition go?

        • Dan Trepanier

          I’ve been a little consumed with our relocation to Los Angeles and the re-vamping of the website…

          It will be back soon!

    • Gary

      Great looks, but the half-tucked tee/polo is contrived.

      • Alex

        contrived is my specialty.

        • Gary

          Why is it that whenever I offer an opinion about something I don’t like, I get a snarky reply?

          • http://undefined TimL

            snarky is MY specialty….. lighten up :)

          • Michael

            Your opinion is a criticism…what else would you expect but a snarky remark? ;-)

          • http://undefined TimL

            Hey Alex…. quit being so snarky! ;)

            • Not Gary

              Like a Boss. Well played Alex.

          • Ethan

            That response is embarrassingly insecure, Alex. Criticism is a great agent for positive change. The correct response to that criticism is: Thanks for checking out the post. Agree to disagree though on polo.

            Not an emotional tangent, literally laughable.

            This comment will likely not be posted.

            • Tribeca, NYC

              It seems to me that Gary was indeed adding to the discussion. The fact that one person considers it a “selfish act” does not mean another person won’t find the comment to be a valuable opinion. It was no more unnecessary than Alex’s response.

    • Tom

      Any idea where you can get the navy polo or is it vintage?

      • The Other TO

        JCrew sale racks.

        • TO

          Good look

      • Alex

        the other TO is right, got it at

        • Tom

          Could you post a link at if you could. I couldn’t find it.

          • Alex

            they must be sold out.

            sorry man.

            better luck next time.


    • Ken

      Is the slideshow sequence off on this post? Not seeing first 2 looks. either way, good luck balling. Is there a track Team Indigo is thinking to come out to?

    • Shaboo

      Boo, can’t go into 2nd and 1st :( something’s broken

    • Sal

      I don’t know about everyone else, but I can only see one look here. Website glitch?

      • Dan Trepanier

        Apologies, should be fixed now!

    • BG

      Can’t wait for the game!

    • Brent Kuz

      This is only showing look 3?