The Fox Hole: Preppy News for the Week of February 23, 2020

Southern Tide Opens Store in Hilton Head
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Welcome to the Fox Hole! The Fox Hole is a weekly column loosely focused on events, news, and speculation surrounding preppy fashion, well-heeled lifestyle, and anything else that happens to strike our fancy. The subject matter and amount of content may vary from week to week, but our commitment to pseudo-journalism and irreverent commentary will never waver.

This Week's Theme: Prep is Dead. Long Live Prep!

Mood: Set to Vampire Weekend's Cape Cod Kwassa Kwassa

The last two years have seen much hand-wringing regarding the perceived decline of the preppy movement. Compared to the saturation of preppy styles (particularly the Southern variety) in the late aughts, the recent fashion shift to urban monochromes and basics have left many brands - ourselves included - concerned over the fate of pastels, bow ties, and boat shoes. Are we doomed to a palette of Brooklyn grays and blacks, beaten into submission by the $75 basic white v-neck tee? Has the Lululemon-led athleisure movement written the obit for the casual sundress? Do we really have to grow a beard?

Thankfully, recent news suggests that prep may have been down in some parts, but it was never truly out. Remember, preppy (or at least trad) style has been a staple of fashion for six decades. It's like Jason in khakis and a navy blazer - you just can't kill it! Much like the cargo shorts phase of the late 90s (that was JUST a phase, right? RIGHT?!), the monochramization of the the wardrobe appears to have been a cycle like everything else in the fashion world, and the world appears to be ready for bright colors and polo collars just in time for Spring.

Item #1: Rowing Blazers Gets It

Rowing Blazers pop up shop (Photo: Thomas Welch / Los Angeles Times)

One of the more interesting fashion developments in this space in the last two years is the growth of Rowing Blazers, an lifestyle brand focused on a "youthful, self-aware, and ironic take on 'preppy' style." We're not sure that "preppy" really needs the air quotes, but we couldn't agree more with the sentiment! Our motto of "Irreverently Preppy. Never Stuffy" matches well with the Rowing Blazers ethos, so we're excited to see the brand's success, as they recently opened a pop-up store in Santa Monica, CA of all places. Now if we could just convince founder Jack Carlson that preppy isn't a dirty word...

“I try to avoid the P word,” said the brand’s 32-year-old founder Jack Carlson. “But I guess Rowing Blazers is preppy because it’s rooted in classic East Coast American vernacular: seersucker, tweed, corduroy, rugby shirts. But I feel like what I’m trying to do with the brand is take all that good stuff and leave behind the stuffiness and sense of exclusivity that often goes with it.”

If blazers can make this kind of Mighty Ducks style comeback, the future looks bright for the next generation of don't-call-them-preppy-but-they're-actually-preppy brands. We look forward to watching Rowing Blazers grow, and we also look forward to an explanation of how this jacket isn't "preppy!"

Item #2: Of Ex-Presidents & Polo Shirts

Barack Obama Preppy Polo

(Photo: Getty Images via The South China Morning Post)

Quick disclaimer: this is a politics-free zone, and that also goes for the commentariat. Now onto the story!

Frequently criticized for his dad jeans and other less-than-stellar fashion choices, President Barack Obama might have turned over a new sartorial leaf during his retirement. In his own words to Vanity Fair in 2012:

“You’ll see I wear only grey or blue suits. I’m trying to pare down decisions. I don’t want to make decisions about what I’m eating or wearing. Because I have too many other decisions to make.”

Fair. Sometimes we feel the same when we're writing a blog post about critter pants in a local coffee shop. So many decisions.

But that Barack might be a man of the past! As an article in the South China Morning Post points out (that's right - we dig DEEP for your news), the former President has been making more of an effort of late, seen sporting cropped pants a la JFK (although without the yacht) and what may or may not be a classic Lacoste polo (we can't see a logo, and the collar might be a little too large, but we Barack would look good in the croc). Keep up the good work, sir. You're an unofficial prep ambassador, and we look forward to seeing your Nantucket Reds in the near future.

Item #3: Sperry Announces a New Global President

Joelle Grunberg Sperry President

(Photo: Sperry via Footwear News)

Coinciding with its 85th year in business, Sperry's parent company Worldwide Wolverine, Inc. recently tapped Joelle Grunberg to lead Sperry's global division. As reported in Footwear News, Grunberg is no stranger to the preppy space, having served as CEO of North and Central America for Lacoste after holding the same position in Lacoste's French division.

Since C.C.Prep's inception in 2012, we've witnessed several changes in Sperry's leadership team. Previous regime changes have manifested themselves in interesting ways, from Sperry's re-branding to Sperry Topsider (and then back to Sperry) to a shift away from its boat shoe roots to a more sporty and urban aesthetic (and then back to boat shoes). Given Lacoste's long history and dedication to its enduring style, we suspect that Grunberg will place a renewed emphasis on Sperry's preppy inclinations, and we look forward to one of our favorite brand's next steps. Incidentally, if you're curious about Sperry's founding and the creation of the boat shoe, we've got you covered!

Item #4: Move Over, High Heels. Bean Boots Own the Runway.

Bean Boots on the Runway

(Photo: Victor Virgile/Getty Images via Town & Country Magazine)

A vignette:

JUDGEY GIRL AT COFFEE SHOP: "Ewwww. What are thoooose?? Did you kill a lumberjack and steal his boots?"

ME, A PARAGON OF STYLE: "Bean Boots. It's called fashion, sweetie. Look it up."


If you've ever personally been victimized for wearing your duck boots (or for any reason by Regina George), your long national nightmare has come to an end. DUCK BOOTS OWN THE RUNWAY. As reported by Town & Country Magazine, fashion designer Todd Snyder recently collaborated with LL Bean for his 2020 Fall Collection, finally pulling Bean boots out of the puddles and ... splashing ... them on fashion's center stage (had to do it. not sorry). And Todd didn't stop there! Surely galling the Miranda Priestlys of the world, Todd added Bean's signature red flannel and trapper hats to his display.

This is it people. This is your sign. If you've been sitting on an idea for years, waiting for the perfect time to unleash your genius upon the world, delay no more! Bean boots on the runway prove that the masses are ready for anything. And if you need an expert guide to duck boots, we're you're Huckleberry.

Item #5: Southern Tide Follows its Destiny, Opens Store in Hilton Head

Southern Tide Hilton Heads Store

(Photo: Lisa Wilson via The Island Packet)

Rowing Blazers opening a store in Santa Monica? A bit of an odd couple. But Southern Tide opening a store in Hilton Head? Where the brand also sponsors the RBC Heritage golf tournament at Harbour Town (where we have been their grateful guests)? Just a few hours from its South Carolina HQ? Where you can't swing a golf club without hitting a magnolia tree? If it were a jeopardy category, it would be "Obvious and Amazing Ideas for $100."

Southern Tide has expanded its retail storefront aggressively over the last two years, following in the footsteps of fellow Oxford Industries stalwart, Tommy Bahama. Tide now boasts at least 15 Signature Stores and a single corporate store. The Hilton Head location appears to be a Signature Store, which will be operated by Palmetto Dunes and located in Shelter Cove Harbour and Marina. More specifically, as The Island Packet reports, the store will be located "adjacent to the Neptune statue," which is one of my favorite sentences in this article.

 Item #6: According to GQ, Preppy is BACK.

Eddie Redmayne

(Photo: Getty Images via E! Online)

Well, duh. That's the entire theme of this article. But don't just take it from us. Let's hear what our sartorially inclined friends at GQ have to say on the subject:

It’s not only on the runways that the preppy vibe is making a comeback, either: “The look seems to be picking up momentum as people move away from streetwear and are looking for something smarter but not formal,” says Daniel Kearns, the creative director of Kent & Curwen. “Like Tyler, The Creator wearing a cricket sweater with a tweed suit and sneakers or Eddie Redmayne in his off-duty looks.”

The way to wear the Ivy League look in its current iteration is with a hefty dose of irony – in the mode of the aforementioned Creator – and with a dash of high-fashion nous, in the mode of Redmayne. Your fits should be close, but not too close, hues should be pastel and your attitude should be anything but WASP-ish.

Hey! That's what we said! Preppy should be fun. And it has been fun for years. Go bright or go home. If you're curious about the looks that GQ selected as emblematic of the preppy renaissance, you can check those out here. While we're at it, you could also check out Glamour's take on the preppy situation, as the magazine offers nine ways to work preppy style into your wardrobe (with celebrity examples to reinforce the point). We feel like adding plaid and pastels to your closet might be low-hanging fruit to our readers, but to each his or her own!

Final Thoughts

So there you have it! Not a bad week for preppy news, all in all. The trend line for preppy style appears to be pointing up and to the right, so we expect to see a ton of color and Navajo Sandals this Spring. Who knows - maybe it's time to break out the bow ties for those Summer weddings? The only thing we know for certain is that, thanks to readers like you, prep most certainly is not dead.


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1 comment

  • Author image
    john carlos: February 26, 2020

    Matt, I enjoy your clever writing style and it has to do with one of my favorite subjects: trad/preppy clothing. I just turned 70 years young so I may be a little long in the tooth to be a prep. Plus I live in Texas. Go figure. But my closets are full of khakis, OCBD’s, madras, tartans, and Reds. I’m a big fan of all things madras. Keep up the good work, you young pup!

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