Trad Done Right

There is no better way for me learn to than by example. That is why I am going to take some to shine some light on my friend Chase H. Winfrey. This guy knocks consistently knocks trad looks out of the park and does it his own way.
ChaseI could spend this whole post waxing poetically about how Chase kills it on regular, but I won’t. I want to focus on one specific image. You know, the one above. In my humble opinion this is trad perfection. He holds it down on all three fronts. He has the right items in the right colors in the right fit.

First there are the trad aesthetics. It is clear that he knows what is what in the world of trad. He has the 3/2 sack blazer with patch pockets (the importance of patch pockets are underrated in my book), OCBD, flat front trousers with cuffs, and penny loafers.

Not only does he have all the right items, but he also has all the right colors. The blue blazer, blue OCBD, and blue emblematic tie all work really well together as there is enough contrast between the blues. Next up he incorporates olive trousers, off-white socks, and brown/burgundy penny loafers. From top to bottom none of these colors compete for attention, but instead they create a harmony.

I probably should have started with this, but the proportions are so on point here. Nothing looks too big and nothing looks too slim. To me this is the most impressive part of the whole rig. The fit and cut of those trousers are about as close to perfection that one can get. This is not easy to do!

If you, like me need the occasional style inspiration I encourage you to give Chase a follow on his Instagram (Chasehwinner). Not only will you find more great examples of trad done right, but also extremely cool menswear illustrations (Like the one below!) as well as some gorgeous items from Drake’s where he currently slangs clobber.
Chase H Winfrey Illustration

oxford cloth button down
Jerrod Swanton is a simple man interested in simple, classic, and traditional style.

23 Comments on "Trad Done Right"

  1. Randy Carson says:

    Great photos.

    I’ve added Chase to the short list of folks whose sites I check daily along with you and Tucker (


  2. LeeLo says:

    Another great post, Ox! Chase is a style inspiration for me too. It’s good to see him doing well and as you have pointed out, looking good doing it.

  3. Tim says:

    Got to disagree with you on the socks, they’re just plain wrong. Reminiscent of Micheal Jackson on the cover of “Bad” – match your sock to your trousers somehow- a pair of brown and green argyle would have just been the creme de la creme here but white/off-white is just naff and brings the whole aesthetic down. Save them for wearing with sneakers.

  4. Minimalist Trad says:

    Everything but the width of Chase’s trousers is just right.
    The trouser legs are far too skinny and out of proportion to the rest of his body.

  5. jon says:

    The look is great. But the overly tapered trousers with a lower vamp shoe (it appears to be an Alden penny loafer?) is distracting. When trousers are this tapered it works better with a more chocked up loafer, proper shoe or desert boot even.

  6. Dallas says:

    There’s a funny disconnect between online comments and actual heyday ivy style.

    White or off white socks were extremely common on college campuses in the early to mid 60s, worn with all colors of trousers, and this is what Chase is referencing with the sock choice shown in the photo above.

    Slimmer fitting, tapered, and no break trousers were what most students in the same era wore as well, and again this is what Ox is talking about with his commentary.

    As usual, Chase looks great.

    It’s like you guys haven’t even bothered to look at Take Ivy, or the thousands of photos available online from the heyday of the Ivy Look.

    • Tim says:

      Oh I’ve definitely looked, again I’m going to have to disagree. I happen to have my copy of “Take Ivy” to hand and whilst I’m not disputing the abundance of light coloured (impossible to tell the actual colour from black and white photos) socks – they are worn almost invariably with a lighter coloured trouser. Where dark trousers are worn, it’s a darker sock. The exception to the rule, at least within the confines of the pages of “Take Ivy” is when the ubiquitous jeans or sportswear (I.E. sweatpants) are worn. All due respect to Chase giving it the nod but the simple fact remains that light socks with dark trousers looks naff.

    • Tim says:

      P.S. I agree with you on the trousers however, the silhouette looks spot on to me, although maybe (and it’s a pretty small maybe) they could be 1/2 an inch longer to just give a wee bit more coverage to the back of the shoe.

  7. Dutch Uncle says:

    Since many of us Ivy/Trad aficionados don’t want to look like we’re going to costume party or acting in a period drama, we don’t feel obliged to dress like carbon copies of 1960s college students. Chase would definitely look better if his trousers were cut in proportion to his shoulders and his entire torso.

  8. GTwig 63 says:

    Agree that the trousers look too “pegged,” but also agree that in the Ivy heyday (I know I lived through it) trouser legs were slim and tapered as his are. But we probably did not wear white or off white socks when wearing a tie though. But the great thing about his outfit is that his jacket is long enough to cover his rear and does not pull at the middle button!

  9. oxford cloth button down says:

    I think that we all learned a valuable lesson here in that we all have different ideas about what silhouette’s look good. There is no perfect for everyone just perfect for you.

    I like Chase’s look because it is not a carbon copy of 1960s college students or Ivy Style reenactor, but a modern trad look.
    In my opinion Chase’s pants don’t look too pegged or short. I think he looks cool. I rarely if ever see someone so well put together in our style on the internet or in real life which is why I featured him in this post.

  10. Len Longville says:

    Chase is so well-dressed that we owe it to him to make a few suggestions as to how he could look even better: the more I look at that second photo, the more unbalanced (top-heavy) it looks.

  11. Richard aka Tweeds says:

    Jerrod I prefer your trad style much better. Your color preference is always spot on, keep it real. Dont change.

  12. Lennart says:

    From the other side of the Atlantic I’d say, our fit in general is slimmer and more tapered. From my point of view the pants are great looking. Today I have a pair of khakis with more or less the same fit on paired with brown weejuns and orange socks. Also, the blazer is a bit to bulky for my taste but I realize most of you guys would disagree. At the end of the day we can all agree that we disagree even if we all like the same…

  13. Philly Trad says:

    Allow me to agree with “Richard aka Tweeds.
    Jerrod, your look is far preferable.

  14. Woofboxer says:

    Maybe the angle of that photograph isn’t doing him any favours, but it is clear that Chase is a short, stocky guy, this is confirmed by looking at his other pictures on Instagram. Unless you are fortunate enough to be of proportionate build, average height and weight, then you have to pay attention to the way clothing can emphasise aspects of your figure. There is one shot of him on Instagram where he is in khakis and a plaid shirt, he looks a whole lot better in this picture because he is wearing high waist trousers ( make your legs look longer) and because they are not so tight fitting and sharped tapered they even out the disparity between his upper body and legs.
    There are very few pictures of well dressed people in Take Ivy, mainly students wearing whatever they grabbed from the closet that morning. Some of them manage to look cool, but a lot of them look awful.

  15. Boston Bean says:

    Might I suggest that Chase pay a visit to Charlie Davidson of the Andover Shop in Harvard Square. Charlie could help Chase find trousers that would complement his look rather than detract from it. He has done so for many men for many years.

  16. Don says:

    OK, so I’m old.
    What does “slangs clobber” mean?

  17. Old Trad says:

    Some of us survived the heyday and know better than to take Take Ivy as a bible.

  18. Franz Faber says:

    Are we obliged to share your admiration of Chase’s style even when the cut of his pants is so unbecoming?

  19. Steve L. says:

    At the risk of seeming to pile on the fellow who was unwittingly made the subject of this post I’d have to agree that, while peg-legged pants such as those shown above may hold some appeal in the abstract, they simply do not match all of the bulk that’s above them. If he likes the look that is of course 100% his prerogative and he isn’t harming anyone. But he’d look so much nicer in cuffs that were a still-trim 8″ or so in width.

  20. Greg Summers says:

    Steve L.:

    Chase’s top-half is so well-dressed that we owe it to him to make a suggestions as to how his bottom half could look better:

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