Tuesday, January 17, 2012

Preppy Style 101

In the past couple of weeks, I have gotten a lot of messages on Tumblr about the fundamentals of preppy style for women. So, here is my master post of everything I can possibly think of that relates to dressing the part of a preppy woman!!

I think of preppy as being split into 2 major seasons: fall/winter preppy and spring/summer preppy. Fall/winter is the more traditional "northern" stereotype, full of androgynous and classic pieces rather than the "southern" spring/summer preppy where Lilly shift dresses and Jack Rogers are in abundance. 


In the fall, I find myself to be in a constant blur of navy. Everything is navy, or close to it. It is the ideal "prep" color in the colder months. As well as navy, hunter green, camel, burnt orange, and slightly off-white are heavily emphasized through the abundance of thick, cable-knit sweaters from Ralph Lauren or Rugby. My favorite items are: my Rugby dark green cable-knit crewneck sweater, my Ralph Lauren orange cable-knit crewneck sweater with the suede gun-patch, and my classic navy Ralph Lauren cable-knit crewneck sweater. As y'all can tell, the classic preppy sweater is the cable-knit crewneck, whether it be wool, cashmere, or cotton. Otherwise, I am a huge fan of the L.L. Bean Norweigan sweater as well as the L.L. Bean Fisherman sweater. I usually just go straight to the mens section on the L.L. Bean website since their sweaters are the best (and reallyy classic prep).

Tartan is the essence of fall preppy. I have my favorites, as everyone does, but I'm going to list the most popular/well-known tartans in case y'all don't know them.

1. Black Watch

2. Campbell

3. Gordon Dress

4. Macdonald

5. MacLachlan

6. Royal Stewart

7. Mackenzie

8. Gordon

9. MacFarlane

10. Morrison

11. Stewart Black

12. Stewart Dress

13. Stewart Green

These tartans can be found in blouses, some dresses, scarves, coats, and skirts. I love, love, love tartan and there honestly can never be enough in the preppy fall wardrobe (as well as interior decorating)!

For the bottom half, corduroy pants are usually the way to go in terms of pants. Leggings aren't preppy (even though I find myself constantly wearing them due to how comfortable/easy they are), and jeans aren't either...but let's be real, it's impossible to not wear jeans. When wearing them, make sure they are in a dark rinse and that they aren't distressed, ripped, or bedazzled (haha). The simpler the better!! Also, you can wear traditional skirts such as the J. Crew wool miniskirt and corduroy skirts (in grey, black, and navy).

via Matchbook Mag
L.L. Bean Boots and equestrian inspired boots are the typical classic footwear. It's pretty hard to get Bean Boots this time of year, though, because they're usually on back-order due to their popularity, but Sperry also makes a suitable alternative. The perfect riding boots are hard to find (trust me....it's taken me 4 years to find my ideal boots), but they are so, SO worth it. You can always go the authentic riding boot route, but be warned: they are very expensive. So, in order to save your wallet and your sanity, check out places like J. Crew, Madewell, and Frye. My favorite pair are from Madewell. 

via Unabashedly Prep
As much as I like fall/winter clothes, I find spring/summer clothes to be much easier and much more fun. Pink and green! Finally! Obviously I love pink and green (hence, the Pink and Green Prep)...but there are other colors that can be worn besides this dynamic duo. Springtime is the time to bring out the pastels (light pink, yellow, light blue, pale green) and after memorial day, white!! 

via Tumblr
The Lilly Pulitzer shift dress. Possibly my favorite article of clothing. EVER. I love it so so so so much. Darling Lilly has made the preppy world a brighter place through this dress. Vintage is always better, and I find past seasons of Lilly much more classic in terms of the shift dress. Head on over to Re-Lilly on Facebook as well as eBay to find marked down, older Lilly dresses to make your closet happy. The Lilly shift dress is ideal for the preppy woman's wardrobe. 

via Vineyard Vines
On top, depending on the weather, you can wear polos (from Ralph Lauren, Lilly Pulitzer, or Vineyard Vines), oxford button downs (from Ralph Lauren or Rugby), cardigans (from Lilly Pulitzer), or cotton cable-knit crewnecks/v-necks (from Ralph Lauren or Vineyard Vines). The combinations are endless!!

via Just Madras
In summer, we switch tartan for madras, yet we still wear it in abundance. I love Just Madras for their skirts and dresses. The nice thing about having a madras skirt is that there is an abundance of outfit options in terms of sweaters, polos, and oxford shirts. I have a madras skirt from Just Madras that is navy, pink, green, yellow, and white. I can wear a trillion different things with this skirt and never get bored!! Also, madras Bermuda shorts are very cute!!

via J. Crew
If you're not up to the ultra-girlishness of the Lilly dress, you can always switch the shift for the chino shorts!! J. Crew has made fantastic chino shorts (in 3 different lengths) for years, and they are honestly the best. The must-have colors are navy, khaki, white, and pink...bonus points if you have the old J. Crew critter chino shorts!! Besides J. Crew, Lilly Pulitzer and Vineyard Vines have great shorts. 

via We Heart It
Footwear in the spring and summer is typically the Jack Rogers Navajo sandal or the Sperry Topsider. I've also heard that there are monogrammed Jack Rogers....YES. This is also the perfect segway to the importance of the monogram: if there is any possibility that a sweater/bag/polo/button down/headband/ANYTHING can be monogrammed, have it done. Just do it. 


Pearls are the essential piece of jewelry for the preppy woman. Pearl earrings, pearl necklace, pearl bracelet. All day, every day. Besides pearl earrings, though, diamond studs are a great alternative. Kiel James Patrick sailor bracelets are good, as well as Tiffany charm bracelets. The main thing is to keep it simple. Necklaces should be pearls or a monogrammed chain necklace. Other jewelry/accessories include signet rings, A. Tierney ribbon watches, leather watches, ribbon belts, and needlepoint belts.

via Tumblr
Tote bags (especially from Lilly Pulitzer, L.L. Bean, Vineyard Vines, and Vera Bradley) are great. Bermuda bags are perfect purses for spring/summer, too.

Via Tumblr
HEADBANDS. Love them to death. They are very classic and lovely and are definitely a staple in the preppy girl's wardrobe. My favorite brands are: Kiel James Patrick, J. Crew, High Cotton Ties, Southern Proper, and Lotus and Lilly.

Beauty (Hair/Makeup)

Hair and makeup is low maintenance and very clean looking. Makeup should be minimal (or minimal looking) for every day use. Nothing fake looking...nothing cakey or too heavy. Hair should look natural...now, that doesn't mean that you shouldn't fix it if you don't have naturally perfect hair. But, over-curled and over-straightened hair isn't really ideal. Hair color shouldn't look fake either. If you color your hair, natural is better!!

I hope I haven't forgotten anything!!

Have a great day!!

xoxo, Hannah


  1. Thank you for writing this very informative blog! I enjoyed reading it!

  2. great post! easily my favorite post of yours ever! :]

  3. I too adore Spring/Summer preppy items more!

    Love and Hugs,
    Mrs. Kindergarten...aka...Madam Spoiled

  4. LOVE! I am longing for the days of Lilly shifts!!

  5. Super post! I really enjoyed reading it - because as a Brit it was reassuring - I own tons of navy (RO cable V and round neck, navy RL cable dress etc etc), my house is full of blackwatch tartan, etc etc. The RL pic you used at the start of the post os iconic - and as for Princess Grace - well, the icon of icons for me. Lovely post - looking forward to reading mroe as a new 'follower' !

  6. Great list--reading this post brought a huge smile to my face! The Lilly shift is one of my personal faves as well!

  7. love this post! so so so accurate and describes my year long style perfectly! LOVE IT!!!

  8. Great post! Haha, I pretty much own all of this. Cannot wait for Lilly season. :)

  9. Thank you for the mention of Re-Lilly! I just found your blog and adore it already. I look forward to following. xx Sue

  10. ahh, I adore your blog! and this post is amazing. I love the fall/winter season portion of this post. Keep up the good work! xxx

  11. Love your blog! I have been trying to figure out where to get those flip flops for years! Thanks Hannah!

  12. This is a fantastic 101 post! I've been researching preppy styles all day long and this is EXACTLY what I was looking for. Great for the basics.