Posted July 17, 2012 by YouPlusStyle in Fashion

The Guide to Summer Preppy


reppy has never gone out of style. Cardigan sweaters, pearls, madras shorts….all great wardrobe staples.  If going full-out prep isn’t for you, adopting one or two classic pieces to your eclectic wardrobe is always a good idea.  You never know when you might be invited to The Hamptons and suddenly have a J. Crew emergency. My advice?  Be prepared. Here are a few classic preppy looks to help you decide which key pieces need to make their way into your closet.

Monogrammed Tote

The monogrammed tote is a staple of prepsters everywhere.  If your initials aren’t embroidered on something….well, you are late to the picnic, my friend.  Pick a color you love and will carry all summer long. (Plus, you avoid mix-ups. No one is going to try and take home a tote with your initials on it. Hopefully.)




Tea-length dress


A tea-length dress is a must -have because:

A. It’s conservative enough for any and every event

B. It’s flattering to all body-types

To keep it from appearing too “Stepford Wives“, wear a modern heel and skip the pearls.

loafer or boat shoe



The loafer or boat shoe is another gotta-have item.  These are not only polished, but comfy!  Though I recommend buying a pair in the classic shades of brown, white, or navy, brands like Sperry-Topsider have colorful, metallic, and even patterned versions that are the perfect statement (comfort) shoe.

floppy hat and classic-cut swimsuit




Summer preppy means a classic-cut swimsuit and floppy hat to shield your delicate skin from the sun.  If wearing an all-black suit doesn’t suit your fancy, a gingham version like this one keeps it real and interesting.  (Or this bikini version by Rugby Ralph Lauren.)

Besides a simple floppy hat, bring that sunscreen in your monogrammed tote.  Sunburns are not chic.








Preppy means unashamedly pro-American, so don’t be afraid to sport at least one piece of red, white, and blue this summer.  From a silk scarf to a no-holds-barred shirt like this one, be proud to show you’re living the dream in the old U.S. of A.

(photos via)











-Hilary Kennedy is a contributing author for, focusing primarily on Style, Arts and Entertainment, and Dating and Relationships. Hilary also stars in many videos for YouPlusMedia and has her own show, The Hilary Kennedy Show.