I recently received this question from a reader named Alexa…
I have been looking around the web about preppy fashion and most sites mentioned that the door to preppy style is to have polo tee, and probably not just one but many! However, I have seen many people wearing polo tee, and I don’t think they have attained the preppy look; rather, I think they look rather casual. Do you have any suggestion to spice up a simple look into something preppy? How can one look preppy in polo tee?
To me, dressing preppy is all about wearing traditional items of clothing in a new and exuberant way. We’re talking bright colors, bold patterns, bows, ruffles, cable knits - you have it. I recently came up with a huge wish list of preppy items for spring, which will be a good start.

L to R: Another Day to Dress Up, The Owls Are Not What They Seem, The Glamourai, Coco Canal
I personally don’t like wearing polos too much - I prefer a button up or soft and snuggly tee. But for some direction on incorporating polos into your wardrobe, let’s look back to Ralph Lauren’s Pink Pony campaign from last September. 100 bloggers were asked to style the Pink Pony polo to raise awareness for breast cancer (and a portion of proceeds from sales of the line is donated to cancer care and prevention.) While most of these bloggers probably wouldn’t identify as “preppy,” they all took the preppy spirit to heart when styling their plain black polo with wild patterns, playful skirts, and reinvented classic items, like a scarf worn as a belt. Here’s a whole file of inspiration for you!
If you have a fashion dilemma or just want to say hi, shoot me an email or use the ask box!
I recently received this question from a reader named Paola…
I’m a sophomore in high school and I am going to attend a new school next year which is a lot bigger than my school now. I wanted to change up my style a little bit and go for the preppy look. Right now my style is somewhere between prep and hipster, mostly I just shop at places like Forever 21 and the Gap. But lately I’ve fallen in LOVE with the preppy look. I’ve been looking online a lot and J Crew, LL Bean and Anthropologie are my favorites so far, but I don’t know where to start!? So what do you think are the main essentials that I should have?
Thanks, Paola, for writing! I answered a similar question regarding preppy staples for the fall season, but I thought I’d give you some more ideas for the warm weather months. Even though you’re on a student’s budget, keep in mind here is that preppy style is classic - you’re investing in some items you’ll use for years and will never go out of style. I included practical purchases as well as a couple of lustworthy inspiration pieces.
1. Seersucker and Madras

clockwise from left: lands’ end canvas mini, juicy couture blazer, j crew top, tahari shirtdress, ae sandals, kjp headband, anthropologie sandals, old navy shorts, j crew shorts
These classic fabrics are the most cheerful way to dress for sunshine. Plus, patchwork madras and naturally wrinkled seersucker will travel well on weekend getaways —no need to iron to look polished.
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