Tag Archives: Shorts

The Boss’ Back to School Style Guide via Vineyard Vines

As prep school orientations are wrapping up and classes are just around the corner, many preps are finding their summer outfits of choice (button downs and bathing suits) don’t quite meet dress code. So, here are a few back to prep school wardrobe ideas for all of our readers and fans.

For the nautical boarding schoolers. St. George’s. Tabor. You know who you are. You spend your summer days sailing off the shores of Newport, and by night you charter helicopters to local parties. For the fall, trade in your Rainbow flip flops for boat shoes and button up your button down.

This look is strictly for the adrenaline-junkie prep schoolers. I see you on the ISL ski teams. I see you VT, NH, and ME boarding schools, where 1 out of 10 alums become ski bums living off trust funds. You spend your summers on a lake up north, or chilling by the ocean with George Bush Sr. Your school has a somewhat casual dress code and this outfit gives you a rebellious, earthy crunchy look.

What’s up Mid-Atlantic preps? New England preps reign supreme, but I know you’re down there trying hard. Dad works in D.C. so you can enjoy crab cakes on the Potomac at the family estate. You a little geo-curious–much like your forefathers. You can’t decide if your Northern prep, or Southern. So, you bring the two styles together.

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Filed under Prep School Life, Swag for the gents, Swag for the ladies

The Confessions of trueprep

Dear Readers,

I have a confession. I was trifling through my things getting ready to leave my house for a day trip and came to the realization that I have a serious problem. It’s called monogramitis. This terrible disease is basically the need to monogram everything one owns. From pillow cases to gym shorts to my backpack, I have my initials on practically everything. Not only is monogramitis a personal issue, but it is infectious and has caused many of my friends to start down its dangerous path. It has proven quite difficult for me not to adore things that are specifically mine and cannot be mistaken for anyone else’s so I have decided that, despite how risky this is, I need to share my love of monogrammed items with all of you. I have found Converse shoes, iPhone cases, virtually indestructible “Roadie” cups, and rain boots that can be monogrammed to your liking. (By the way, Vineyard Vines also has phone cases that make me happier than a five-year-old in Disney World.) If monogrammed things aren’t for you, that’s fine too. I discovered some classy knit bow ties to keep you/your guy’s preppy neck warm for the fall and winter and some tacky shorts to watch the London Olympics in. Enjoy!

Send in pictures of your favorite monogrammed item to the Twines & Vines Twitter page and you may be featured on our Instagram!

<3 Stay Preppy


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Filed under College, Fashion, Girls, Guys, Prep School Life, Random, Relationships, Swag for the gents, Swag for the ladies, Technology, Travel, Uncategorized

1984 City of Angels Olympics Shorts

The Story: Awarded the games by default after the withdrawal of Tehran, the Games of the XXIII Olympiad also saw a boycott by 16 countries (mainly those of the Eastern Bloc) and truly represent a historic moment in Olympic history.  Since the United States’ withdrawal from the 1980 Olympics in Moscow, 1984 would be the first time since Montreal in ’76 that American athletes would have an opportunity to represent their nation in sports competition.  On a shoe string budget, Los Angeles hosted one of the most successful Olympics for the United States to date, winning a total of 174 medals, a staggering 115 medals more than West Germany’s second most of 59.


Streaker Sports, one of The Boss’ favorite athletic apparel companies is owned by former prep schooler Grant Hewit. Grant attended the Delbarton School in NJ before playing lacrosse at Princeton. Oh, and his bro (same schooling) starts in cage for the LXM Pro Tour. If you aren’t wearing these shorts cheering on USA in London, you should just quit.

Get yours here!

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Filed under Sports, Swag for the gents, Travel

Pick up the Lighthouse Linen Shorts by Castaway Clothing

Featherweight and cool, you’ll be relaxing next to the water this season in these linen shorts. Featuring a classic flat front, fully alterable waist and seat, and slash pockets. Machine wash. Inseam 9”. Available in five colors.

I am a big fan of Castaway Clothing (as you can tell from the Castaway sticker on the Swag Surfer), but I am an even bigger fan of linen. Yes, linen wrinkles like it’s its job, but nothing is cooler when things heat up. Mother Nature teased us a few weeks ago, but warm weather is coming soon. So visit Castaway Clothing today and pick up some of their linen shorts before they’re gone.


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Filed under Fashion, Prep School Life, Swag for the gents

Fresh Off The Boat

Vineyard Vines put out some prep new releases this spring! They combine island style with prep style and tie it all together with a classic feel.

I was just in the VV store at the Prudential Center in Boston yesterday and picked up a Mariner 1/4 Zip for the spring. Check out the above styles and get yourself some ASAP! 

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Filed under Fashion, Swag for the gents

Krass & Funnell Releases New Site!

Today, Krass & Funnell, a small preppy sports label, relaunched their website and released their new line of shorts for the Spring and Summer! Krass & Funnell have a very interesting background and are both graduates of prep schools.


The concept for Krass & Funnell originated in 2009 by two high school friends and teammates, Pierson Krass and Sam Funnell. They felt that athletic shorts currently on the market lacked a certain style and flair they were looking for. This inspired them to create the first pair of Classic Embroidered Lobster Shorts, which laid the foundation for what was to come; a brand focused on blending high quality products with a flashy style.

Pierson is now a Junior at Lehigh University where he has joined a fraternity and relishes in the full college experience. His design ideas tend to err more on the wild side and are influenced by his passion for extreme sports. This is balanced out by Sam, an avid lacrosse player , and freshman at Trinity. Having grown up on the Cape and attended prep-school, Sam brings a more refined and traditional style to the mix. Combined, they are able to strike a perfect balance, that is Krass & Funnell. With a work hard, play hard mantra, their goal is to continue to try and design original products for their peers.

Feel free to reach out about anything to Pierson and Sam at their personal emails: pierson@krassandfunnell.com and sam@krassandfunnell.com. If you are interested in learning more about them or Krass & Funnell in general, definitely check out the K&F blog for frequent updates.


Krass & Funnell shorts are not the typical athletic shorts you find at a sporting goods store. They provide an element that stretches beyond high quality and high performance. Whether you are going to school, heading to the beach, playing a sport, or just lounging around, our shorts keep you looking good and feeling comfortable wherever you go. They combine timeless, beach influenced, preppy style with an unquestionable flash that is suitable for any adventure.

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Filed under College, Fashion, Sports, Swag for the gents

Get up for Gingham

Like it or not, Gingham is the next big hit in the prep style world. Gingham is a plaid-woven medium-weight cotton fabric. Perfect for warm spring afternoons and walking from class to class, you can’t go wrong  rocking a Gingham shirt with linen khakis, jeans, or  pleated shorts.

Check out Southern Tide’s take on the Gingham trend with their sport shirts and seersucker shorts.

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Filed under Fashion, Swag for the gents

Get what you really wanted

Aunt Edna didn’t come through on with the shorts on your list for the Holidays?  Never fear, from now until January 6th, grab the gear you really wanted at never before sale prices.
No discount codes, no limit on which items, just a good old fashioned end of the year sale to brighten up your post holiday slump!
Only at Streaker Sports

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Xmas Flow

Check out LFC’s new styles including the Les Marc shorts and Liquid Flow Cap

LFC is offering a few Xmas Specials, so be sure to check the site everyday. Offers include free thsirt with purchase, rush shipping, as well as discounts. There is a limited supply so order now!

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Liquid Flow – Sanabel Navy

Yes LFC spells their shorts ‘Sanabel,’ but I believe these shorts are based off of Sanibel Island located off  of the west coast of FL. Sanibel is well known for having extremely shelly beaches, hence my spelling assumption. LFC makes the most versatile, comfortable, and functional shorts you can find. They can be rocked on land, in water, outer space, or just about anywhere else you can wear clothes. Like all LFC shorts they are fast drying and have a waterproof pocket for your phone, wallet, etc. I know it is winter, but has anyone noticed the weather? It was 65 degrees in MA today and I wore shorts twice this week. Make sure to grab a pair of the Sanabel Navys before winter really comes.

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