Bringing Class to School feat. Brady Pyfer

April 22nd, 2013

Brady Pyfer, long time Articles of Style reader and active commenter, is an elementary school teacher in Bloomington Indiana. Recently he cleared out his entire wardrobe and started from scratch by investing in affordable prep staples.

“I have always been into clothes, especially shoes, and from a young age I collected sneakers. But as I got older, my style needed to mature… I found Articles of Style when searching for men’s wardrobe essentials and I came across their “25 essential items post.” After looking through it I knew I hit the jackpot. I literally got rid of everything in my closet and started over again, taking Articles of Style’s advice. That was probably the best idea I’ve ever had.

Here’ s three examples of Brady’s new “dressed-up casual” look.

1. Sporty Layering


“I am an elementary school teacher and work in a very casually dressed environment. I gravitate towards the prep style because of the dressed-with-purpose yet still laid-back vibe.”


“The TAG heritage collection was my first real time piece. It was a gift from my father and one day I hope to pass it down to my son. Dan is always saying invest in quality items that will last a lifetime…it’s nice being on the receiving end of that investment.”


“Desert boots are so versatile and I love how the waxed leather sort of evolves with you. I have always tried to keep my shoes pristine [a carry-over from my Jordan collecting days], so it was tough to see every mark standing out, but it adds a personal touch. Now they have years of wear and are one of a kind.”


2. Grandpa Ivy


“I got this cardigan years ago from American Eagle, of all places. It was a bit too ballsy for me at the time and sat in my closet for years. Glad I didn’t part with it, now its one of my favorite items.”


The adventurous pattern-mixing brings this age-old look to life.


“Cant do prep without a pair of penny loafers. This is my first pair of Weejuns and I cant wait for the weather to warm up a bit so I can lose the socks. Talk about timeless, these are it.”


3. Professor Tweedy


“The prep look can be stiff or stuffy sometimes, but with the right fabrics it’s easy to give it a more casual feel, which is more work appropriate for me. Tweed, denim, oxford cloth, silk knit, sporty sweater…”


“I love the classic feel of the cricket sweater. Layering it under a jacket or with some worn-in denim tones it down a little. Definitely a prep staple.”


“This Swiss Army watch was also a gift from my father. He wore this for 15 years before he passed it down to me. I threw a new strap on it and now I wear it everyday.”



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


Yours in style,

Dan Trepanier


Photography by Katheryne Leslie. 

  • Mustafa

    Congrats on all 3 looks Brady. Your tie knots are on point in each look!

  • Parker

    Second look is my favorite for sure. Love the simplicity, love the sweater and tie, and I LOVE Weejuns. The shape is so perfect for penny loafers. I actually found an awesome shawl-collar sweater at American Eagle a few years ago, they can really surprise you sometimes!!

  • Gagan S.

    As a huge supporter of the prep style, I gotta say Brady nailed it. Especially love the third look!

  • KautiousNupe

    I REALLY like every look in this post. Those glasses are stupid fly. The fit in each look is seamless yet perfect. Nice color and shoe selections. Dope all the way around.

  • DP

    This looks like it was photographed at Princeton

  • http://undefined Mike D

    Great post (as usual)! Loved those wingtips in look #3.

  • Andrew

    I literally, (and I do mean literally) have never been able to say this before, but I own the cardigan from Look 2. And even though it is only from a well shopped nation-wide store such as American Eagle, getting it from Goodwill for $3.38 feels like such a steal. And it really is a great, versatile cardigan. One of my favorite cardigans I own.

  • Ricky Ricardo

    Brady- Well done! I am inspired by your looks. Thanks!

  • Collin E.

    Hey Brady,

    Great job putting the looks together. I’m from the notably unstylish state of Indiana myself, and it’s always nice to see guys taking the time and putting in the effort to unique looks. Bloomington is a lovely place, though. Do you stop into Andrew Davis at the center block of town often? It’s a highlight of my trips to B-Town. Cheers.

    • Brady P

      I always stop in there when I go to Briar and the Burley. It’s also the only place that sells menswear in town, def a nice little shop

  • Profound and Casual

    Nice outfits, especially love the tweed blazer!

  • Marcus Forlan

    Pretty gutsy move starting from scratch! Recall Brady P from the first giveaway. Classic prep is not quite my style, but it looks great and that is what I appreciate with all the different styles out there.

    Nice job.

  • FreshNeck

    Well done, sir. Way to represent the “dressy casual,” or as we call it as FreshNeck, #NewCasual. Time to step up your game fellas.

    2nd Look is my favorite. If I could make one (small) upgrade, I’d go with a non-silk tie, perhaps a wool or a knit.

  • Changingman

    I saw blazers at Target that look exactly like the Stafford one you have on. I’m probably gonna go back and grab a tan one.

  • Sergio

    Awesome to see another teacher being featured on the site! Brady your outfits are simply, great!

  • Justin

    Love the post at my alma mater, IU! Keep up the good work.

  • Garrett

    Cool stuff Brady! I actually go to school at IU and you dont see too many styling guys around campus. Maybe it’ll catch on eventually.

  • Joe

    Great post! It resonated with me because I have a similar story. I was searching the web for tips about buying a suit for an interview and found this site. I’ve also thrown everything out of my closet and started all over (over about a year) and this website was incredibly helpful in doing that. Though I have to admit I wasn’t as ballsy as you were in doing so, I had lost a lot of weight and nothing fit me anymore, so I didn’t have a choice in the matter. Hopefully I’ll be forced through another closet overhaul as I get to my ideal weight.

    Really nice choices for looking professional and mature in a casual environment. I work on the other end of academia and face a similar challenge in a very casual environment. Very well done – thanks for sharing your story.

    • Brady P

      Thanks for the kind words Joe. I have found that if you take yourself seriously and dress with purpose.. people around you will take notice and want to dress better as well, esp in very casual work environments.

      • FreshNeck

        Brady – I’m impressed. You are definitely FreshNeck material. Shoot us an email and we’ll hook you up with a free membership.

      • Joe

        That’s a good point. I’ve seen this trend in close family members as I began to dress with more purpose and attention (dressing with more purpose is much more accurate than saying dressing better isn’t it). I haven’t seen it so much at work because work tends to be more isolated (think mad scientist in a dungeon laboratory who occasionally rises from the deep to teach a course).

        The funny thing is that my grandfather has been preaching this for years (he didn’t mow the lawn in anything less than slacks, wingtips, dress shirt and stetson fedora). He always knew better.

  • LouCaves

    When I hear “prep” I think over-sized cricket sweaters from high school.

    This post and and others on TSB has changed that view.

    All great polished looks.

    Way to rep the Midwest, Brady!

  • Paul

    Love the looks – especially the windowpane cardigan and the cricket sweater.

  • Ian K

    Love the cricket sweater look. Can it be pulled off without a tie tho?

    • Brady P

      w/o a tie is my preference actually.. layered over a white OCBD and causal chinos. keeps it laid back and sporty, but still very put together. It’s a surprisingly versatile item imo

      • Ian K

        Thanks Brady. That’s the great thing about this site alot of what is shown is very versatile. Where did you pick up the sweater I’ve only seen them in white recently

        • Brady P

          Picked this one up online from Uniqlo. They have a red, white, and the navy blue. Im about 6′ and went w/ the medium since I like a slimmer fit

          • Ian K

            Thank you Brady!

  • http://undefined TimL

    Nice look in all.
    I especially like the lighter tone shoes with dark jeans in #3.