Have a Preppy Weekend…at the Cape!

From my own personal collection, a boy fishing on Earl Road Beach in Harwich, MA

There are many perks to living in the northeast, and specifically in New England. Besides having all four seasons, beautiful fall foliage, Plymouth Rock (it’s smaller than you think), some majorly awesome outlet shopping, and some really awesome cities, I also had the advantage of one other cool place: Cape Cod.

While the last few years I felt like I was “too old” to hang out at the Cape on vacation with my parents, on the bay side beaches of Dennis and Harwich (where we stay), alongside people just a few years older than me with their screaming toddlers, there is something so nostalgic and New England-y about the place I vacationed every summer growing up.

An idyllic pastel blue beach house on the Cape (from my personal collection)

Not only is it like a fairy-tale beachland, with pink and blue houses beach houses situated on top of hills on Harwich beaches, but there are mansions larger than any you’ve seen before in your life (also atop hills of the beaches), old-fashioned ice cream shops every fifteen yards, and of course: miniature golf. While the beaches are far from idyllic (believe me, you know you’re not in Tahiti) there is something so classic that screams “YOU’RE IN NEW ENGLAND!”

Something else you won’t see anywhere? The fashion on the Cape. While some tourists try to dress the part, most just rock the “straight from the beach” you-can-tell-I-didn’t-wear-makeup-or-brush-my-hair look, the folks that were born and bred Cape Cod, are a completely different story.

Cardigan, polo and a ribbon belt...on a guy? Totally acceptable for any guy on the Cape

Like straight out of an L.L. Bean catalog, there is preppy. There are polos, penny-loafers and madras-plaid, along with seersucker everything. You can spot Ralph Lauren, Lacoste, Lilly Pulizter, Kate Spade, Vera Bradley and Longchamp. It is perfectly normal to spot a person wearing a pair of shorts with  “insert sea-creature here” embroidered on them. Headbands and cardigans are staples of every Cape girl’s wardrobe.

While preppy=read “stuffy” the Cape prepsters are the furthest thing from it. There is a casual-cool, “I didn’t try that hard” look to the Cape’s preppy atmosphere.

Best Shopping on The Cape? While the #10 outlets in the country are located at the intersection of Rt 495 and Scenic Rt 1A in Wrentham, MA (a place you should stop on the way home), some of the best boutiques and stores are located in some of the fabulous small-towns, in beach-dreamy Cape Cod.

Decking in Lilly Pulizter... a common scene on the Cape

Visit Chatham’s Main St. on a week night for some fabulous boutique shopping; Chatham has a little bit of something for everyone. Another great shopping area is downtown Hyannis–while it’s geared more towards families, (there are several kid-friendly restaurants, a carousel and an arcade) there are also some fabulous boutiques. Additionally, Cape Cod’s well-known Provincetown also has some fantastic shopping.

My favorite’s?

Jackie’s a mid-priced fashion boutique at the top of Main St, with fabulous accessories and fashion finds you won’t find another girl at the bar wearing.

Puritan Cape Cod with five locations across the Cape (Chatham, Hyannis, Mashpee Commons, and Falmouth, plus “Vineyard Vines by Puritan” located in Mashpee (all mainland)) Puritan is a Cape Cod staple that has been around for more than 90 years! Puritan sells well-known, mid-high priced fashion brands like Burberry, AG Jeans, Vineyard Vines, Tory Burch, Velvet and many more. (I’m biased, but the Hyannis store is my favorite.)

The popular Vineyard Vines by Puritan in Mashpee

Indigo Lounge with two locations on the Cape (Chatham and Provincetown) Indigo Lounge is a fun boutique that I’ve shopped in for the last several years since it opened. With brands and styles that appeal to women from ages 15-50, Indigo Lounge is a great place to shop with teenagers and moms. They also usually carry funky jewelry that will be hard to find elsewhere!

Port Cargo a store mostly known by locals for its fabulous prom dresses, Port Cargo also carries fun tops, sundresses, and accessories (I have two uber-fabulous handbags from here!). Owned by a local Cape Cod family, you feel like you’ve known them forever when you walk in and begin to shop.

Main St in Chatham

Soft as a Grape the flagship store of this Cape Cod chain known for their ridiculously soft cotton t-shirts and sweats is located on Main St in Hyannis. While pricier than most other “sweats” you can buy on the Cape, Soft as a Grape sweats are high quality and will outlast the others (while still remaining ubersoft!) Best part: for Red Sox fans, Soft as a Grape carries one of a kind Red Sox apparel that no other Sox distributors make. Look for washed out Sox sweatpants and worn in hats.

Mass Bay Company also located on Main St in Hyannis, this half-boutique, half-thrift shop, Mass Bay Company is a pretty unique store. Half of the store has resold army uniforms, new sports apparel and accessories, baseball cards, and a million other things you can think of, while the other half of the store is a fashion boutique carrying popular mid-priced brands like Free People, Juicy Couture, Joe’s Jeans and Reef flip-flops.

Many of the shops in Provincetown are dynamic and constantly changing, but are definitely still worth checking out. Provincetown is a fun and unique town, located on the tip of the Cape. Be sure to check out the Dunes in Truro on the ride there!

Possibly my two favorite things to do on the Cape: Eat ice cream and play mini-golf (in my madras plaid shorts, cardigan and headband, of course)

For some reason, the ice cream on the Cape doesn’t seem to have calories in it, and you never feel too old to play a round of miniature golf.

Places to visit:

Sundae School in Dennisport, MA, Cape Cod

#1 Sundae School with three locations, Dennisport, Yarmouth and Dennis Village/Harwich, the sundaes and homemade ice cream at this place are TDF. (To die for) I highly suggest a coffee Oreo frozen yogurt sundae, with hot fudge, whipped cream and a cherry. I promise, you have never had hot fudge or whipped cream like you’ll have there. (In addition to the ice cream being homemade, the whipped cream and all toppings are homemade too, and the cherry? A real cherry, with a pit)

#2 Blondie’s located in Harwich, Blondie’s has about a gazillion flavors that are all delicious and fairly inexpensive if you just want a few scoops!

I only have one favorite mini-golf place on the Cape, and I think most people who’ve been will agree:

Pirate’s Cove takes the cake. With two courses in South Yarmouth, this somehow always somewhat challenging mini-golf course never gets too old for me. Not only will you see families with their young kids here golfing, you’ll see teenagers with their friends, college students with their friends, married couples, and older couples and families all mini-golfing here.

Apparently, I’m not the only one that it never gets too old for! (Pirate’s Cove also has locations in Arkansas, Florida, Georgia, Iowa, Maine, Michigan, Minnesota, Missouri, New Hampshire, New York, South Dakota, Virginia and Wisconsin, so if you don’t live in the Northeast, check their website for a location near you!)

So, put on your madras plaid skirt, a cardigan and a well-matched headband with penny loafers and hit the town!

I’m off to the Cape….

xo xo,  E

More scenes of the Cape from my personal photo collection (click to view larger):

This entry was posted in Fashion/Style, New England, Summer, Travel, Uncategorized and tagged , , , , , , , , , , , . Bookmark the permalink.

2 Responses to Have a Preppy Weekend…at the Cape!

  1. Hey E,

    Great write up! You’ve helped me decide on a short weekend getaway!!!

    Love your stuff.


  2. Ella Mode says:

    I miss home (Massacuhsetts).

    I lived on the cape from babyhood to kindergarten and summered there until 15, after my grandfather died. We actually lived in Harwich!

    I never noticed the fashion there, as it was always outside of the chic world for me. I’m often about designers, and the only COACH is in department stores. But I love places like in Chatham.

    Also, as a teenager with the Harwich Jr. Theatre, fashions were different for theatre kids.

    Additionally, the cape broke the tip off of a kitten heel of mine, so it has mostly been seen by myself as an escape from fashion (which I don’t need but I love it anyway). Some cobble stone or sand areas just don’t work with heels or even kitten flats, as I call them. But I love it anyway. It’s not like I hate preppy by any means (I just love heels?), but I normally don’t treat any event as a sort of costume opportunity. Usually I stay in my style, although my style is fairly compatible.

    I just see it as a place where I’m allowed to look as I please, at least due to no judgement. (How I used to see NYC before fearing it for all the Yankees.) It’s always been that kind of haven. Although one adult Summer I was obsessed with getting the perfect summer tote, perhaps that old pink/straw one from Coach. Hah. I also liked this certain pink/straw one in a Brighton boutique in Hingham’s Derby Street Shoppes.

    I want to remind readers that the Wrentham Outlets are well outside of Cape Cod, but awesome of course. Where I live now, we at least have the biggest, no exaggeration, outlet mall. Also has outside shops, but just partly.

    Oh and btw, Sundae School takes the cake! #1 all the way.

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