It’s funny how men’s style, and largely ALL style, is cyclical. We all tend to gravitate to a core set of pieces that we like (good jeans, blue OCBD, loafers, blue sport coat…), but the edges become susceptible to influence. I remember back in ’10-’12 when Prep was all the rage. The Preppy Handbook, KJP, argyle, and Shaggy Dogs were all the rage. It’s fun, but it seemed to putter out in favor of more Italian/European influences from the major brands.
Whatever.
I still like a preppy look. There are quite a few pieces that I’ll NEVER put in the back of my closet, and I’ll proudly keep in the rotation. Here are a few of those elements that stand the test of time (and influence):
From top left:
1. J. Press Shaggy Dog Sweater: The brighter the color, the better. Purple (seen here), emerald green, royal blue…bring it on.
2. Ray Ban Wayfarer Sunglasses: Classics. Since that picture of JFK these have become a staple.
3. Vintage Corduroy Hat: I love these. They remind me of the old mountain climbing culture that took over in the 90s. These hats only get better with age. Extra credit if you sport one of these at the beach.
4. Repp Tie: As if I have to justify a repp tie.
5. Brass Plaque Buckle + Strap: Don’t sleep on brass. It has a life of its own… You can let it patina and dull out, or you can shine it for a more dressy look. Either way is A-OK.
6. Withernot Rugby Shirt: It’s nice to see rugby shirts as a mainstay. I’ll categorize them as more ‘preppy’ than anything else, but these bad boys are tough as nails, and look great as a sweatshirt/Q-zip replacement.
7. Pennbilt (Cuffed) Chinos: Good chinos. Not slim. Not tech. Cotton chinos. Cuff ’em.
8. Yellow OCBD: I love a yellow OCBD. It adds just the right amount of punch without being obnoxious.
9. LL Bean Boot Mocs: Eh hem. The best slip ons ever.
What did I miss?
New Balance 990s. Imo these are synonymous to the odd blend of prep and fraternity culture that exists in SEC country. .
I’d add a navy blazer to this and its perfect.
OCBD, chinos, and camp mocs have been my non-work “uniform” since high school, and I’m 41. If it ain’t broke, don’t fix it. I went to school in Virginia, so I’ve always skewed more eastern preppy than Southern frat. Would certainly add an all-cotton polo and wallabees.
6 out of 9 I would send to goodwill-
JFK wore American Optical Saratogas, not Ray Ban Wayfarers.
https://aoeyewear.com/product/saratoga/
This may be your best clothing post. Love everything here and glad to see J. Press getting some love. Hoping they stay true to their roots with their new boss. Regarding KJP, any experience with them? I had one flannel shirt from a while ago that was very nice quality but haven’t tried anything else. Not a fan of the logos they seem to put on their stuff now.
The KJP quarter zips are great, and have a normal fit. My limited experience with KJP is that it runs very slim. The hats are also really great- all cotton that break-in nicely.
The KJP quarter zips are great, and have a normal fit. My limited experience with KJP is that it runs very slim. The hats are also really great- all cotton that break-in nicely.
Love this. Classic is timeless for a reason. Although you’re pretty bold to go with the cuffs these days! 😉