Two-Tone Riding Boots~ by Kipp

Flat boots make the most comfortable and warm footwear choice in the winter. My favorite pair are two-tone riding boots. Not only are they comfortable and practical, but they look stunning and can complete a plethora of outfit options. The brown and the black make them extremely versatile and even look great with a pair of tucked in skinny jeans. However, as always, keep your jeans dark, with no distress, and heaven forbid, holes!

Continuing my talks of proportions on the leg, the pair above, like my own, are cut at an angle. This lengthens the calf and does not cross the silhouette at the center. Boots that stop right under the knee sans this angle make your legs look wider and break up the fluidity of an ensemble.

The equestrian look is something that will never go out of style and will always look put together. Remember, always go for something classic over trendy.

Reader's Question ~ by Kipp

Since I always prefer a skirt or dress to pants, once the temperatures drop I live in black tights. I usually stick to solid black or herringbone tights in varying shades of brown. However, I have begun to contemplate more brightly colored hues of tights for this winter. What do you think?

Clearly An Oxymoron - by Richard

How can putting cheese on a triscuit be considered a cook book?

A Show That Needs Revising - by Richard

Five years ago, I was introduced to a show that had a lot of promise, Gossip Girl. Sure, the title seems feminine, but it only refers to a girl who runs a blog that tracks the elite private school and super preppy kids of the upper-eastside.

However, ever since the characters have graduated from high school, the show has dropped off my radar significantly. Sure, I still watch, but I haven't been interested in a while. Rather than taking the characters down their collegiate path, the show never focuses on their academic career. According to the show, they still attend but the story lines are never placed there. I mean come on, how many eighteen year olds run a billion dollar business (Chuck's story).

Finally, the clothes........Chuck Bass has lost his preppiness, and I have only seen one outfit worn by Blair this season that made me say, wow! So, Gossip Girl, if you need a writer or designer to give you a boost, give me a call. Otherwise, I think you may find yourself out of business really soon!

One of My Favorite Combinations - by Richard

A brown tweed herringbone jacket is a versatile piece, but I have always loved pairing it with a pink oxford cloth shirt (this one has a club collar) and a navy and yellow tie (bow pictured). Try it, you will love it!

Holiday Sweaters - by Richard

The Christmas Season is a wonderful time of year, and it is also the time to wear fun holiday sweaters. We here at WASP 101 encourage you to send us pictures of your favorite holiday sweaters, and they may be posted on our site. We will not reveal your name or identity, unless you ask us too! So send them in.....please :)

My New Favorite Skirt ~ by Kipp

Blackwatch always brings back memories of my old school uniform, but this skirt has a more grown up twist. I paired it simply for Thanksgiving dinner at my parent’s home and took advantage of taking a picture in their library. I was wearing a classic OCBD in pale yellow and pearls with simple grey suede flats.

I cannot get enough of the fact that this skirt has a bit of a ruffle on the hip. Since it is on the shorter side, it has to be worn with flats and not heels. Always keep the proportion on your leg in mind. If I were to wear heels with this it would look vulgar. If the skirt were knee length then it would require heels in order to elongate my leg and for me not to look too matronly.

The blackwatch can be easily paired with almost any color. I feel I may even wear a pink OCBD next time I wear the skirt out. However, if you want to tone down the schoolgirl look I have also worn it with a pussybow blouse for a more put together and older look.

Remember, plaid can be done with out looking like a school girl. Do not be afraid to borrow the tartan from your youth and wear it today!

Happy Thanksgiving - from Richard, Kipp, and Crawford

I hope all the readers of WASP 101 have a blessed Thanksgiving with all your family and friends! We will see you back tomorrow on Black Friday, and don't eat too much turkey.

Bringing Color to Winter ~ by Kipp

Even though it is getting to be winter it does not mean you have to stick to blacks and grey. In fact, I whole- heartedly encourage you not to be bland and dreary. Just because it is not spring it does not mean that these types of colors are out of bounds. The traditional winter and spring color palette are good guidelines but not rules. My favorite way to incorporate color in the winter is a bright and bold wool peacoat. A red such as the one shown above and a mustard yellow are my two favorite hues for winter coats. They also go perfectly with your favorite OCBD and tartan plaid skirt!

Your winter coats are the most visible and vital part of your ensembles during the winter months. Why would you ever want to wear something as boring as black?

Plaid Shirts Under Tweed - by Richard

If you are looking to change it up a bit, and you find your blue OCBDs a little boring, then try a plaid shirt under your tweed jacket. Personally, I find it to be a nice look, but picking the proper tie can be tricky. I find that one has three choices:

1)Solid Color Tie
2)Solid Color Club Tie
3)Yellow Foulard Bow Tie

So, the next time you feel like adding some excitement to your day, try a plaid shirt under your tweed jacket.

There Is Just Something About Women In Plaid - by Richard

There is just something about women in plaid skirts, or plaid anything that I love. However, I have always found it interesting that men can dress in the same preppy clothes from birth to death, but women on the other hand throw in some tweaks. We never abandon our blazers/uniforms, but women seem to grow away from theirs. Personally, I wish it wasn't the case.

The Christmas Party Season Is About To Begin - by Richard

As Thanksgiving (the forgotten holiday) approaches, we are quickly entering the Christmas Holiday Party Season. Of course the season is a wonderful time to sport tartan, drink egg nog, and kiss under the mistletoe!

However, some may not feel comfortable wearing heavy tartan, and for those people, I suggest a subtle houndstooth tweed or a double breasted blazer (cashmere DB in photo). Either choice will look appropriate for the season, but neither will scream look at me.

Photos:

Tweed Houndstooth Sport Coat - Brooks Brothers
Navy Chino Trousers - Polo
Extra Slim Fit OCBD - Brooks Brothers

Tweed Herringbone Trousers - Polo
DB Crested Blazer - Polo
Suede Penny Loafers - Lands End

We Will Be Back In Full Swing In The Next Couple Days - by Richard

I have had to do some serious reflecting the past few days, and I decided to bring WASP 101 back with a new fresh look. We will be up and running full throttle in the next couple days. Thanks for being a loyal reader.

Reader's Question ~ by Kipp

Hello Kipp,

Would love to get your take on the WASP POV on thigh high stockings.

Given the conservative reputation of a WASP, thigh highs could provide that secret naughtiness.

Would love to see your thoughts shared on the blog.

Cheers.

This is a fun question if I do say so myself. Yes, WASP style is always conservative and proper. However, there is an element of secret sexuality that can, and should be explored. Personally, I quite enjoy wearing thigh highs such as the Wolford ones above. The lace is an essential choice since it gives more of a romantic and sexy touch.

The crucial element lies in how you wear them. They should NEVER be exposed. To the normal passerby it should appear that you are wearing full tights. They are to be enjoyed only by you and the lucky gentleman in your life. Therein lies the key to properly combining conservative elements with a little rebellion!

Plaid Seating To Die For - by Richard

These lovely furniture items are available at One Kings Lane. The furniture is designed by K. Cooper Ray, founder of Social Primer.

If I were feeling a little less frugal this weekend, the plaid seated gray flannel chesterfield would be mine. However, if you choose to be froggy, jump quickly, the items go off sale November 14th.

The Holidays Are Coming - by Richard

With Thanksgiving and Christmas around the corner, it is time to start thinking about Holiday attire. One of my favorite holiday items is tartan, and in this photo, I am sporting my tartan wool bow tie. My advice is to only sport one tartan item at a time (sport coat, trousers, tie, etc.) Unless, you are brave enough to go for a full tartan suit, which I have often contemplated. If you choose this route, my advice is to stick with a dark tartan like Blackwatch.

Shorts for Fall ~ by Kipp

We have been experiencing some unseasonably warm weather, which to me, is highly disappointing. However, it did allow me to wear my new Brooks Brothers lambswool shorts. I will continue to wear them in colder weather, but tights will be necessary!

At this time of the year there is always some fluctuation in weather. Even if it is the 65 degrees we endured today one has to be season appropriate. These shorts are the perfect way to incorporate fall fabrics and colors with a traditionally warm weather classic. They are a luscious green broken bone herringbone, as you can see below.

I normally do not like to wear shorts at all, I much prefer skirts. It is truly the cuff that make these shorts perfect. The cut is very well fitting and I love that they are high-waisted. The shorts are a tad bit on the short side as well, but they are just long enough to be conservative and flirty. They are quickly becoming one of my new favorite items!

The Signature Piece ~ by Kipp

Jewelry is one of my favorite reasons for being a woman. Gentlemen, yes, you have the signet ring but we have so much more. Jewelry can be the most complete expression of who you are conveyed through a material possession. It is of even greater value when passed down through generations and is a statement of your familial ties.

However, with jewelry, I honestly believe that there should be a piece that you always wear. May it be your favorite diamond or pearl studs, or a necklace, this item will become your signature. A token that shows your loyalty, who you are, a sense of meaning, and tradition. It should not be your engagement/wedding ring.

Personally, I have three stacked rings (above) that I hold dear and that create my perfect signature item. I have always been partial to rings. When I was finally given this set after my grandmother’s passing I have yet to let a day go by that I do not wear them.

Your signature item must be something that is simple yet elegant. Something that is appropriate for everyday use without ever looking vulgar.

Taking The Day Off

Shoes I Desire - by Richard

In my opinion, Ralph Lauren makes high quality shoes, or to be more accurate, he signs contracts with high quality shoe makers and then applies his name. However, I have always desired the Ralph Lauren Butler Shoes with the yellow, blue, and red grosgrain ribbon displayed above. I do own a pair of Butler Loafers, but mine have the green and red ribbon.

If anyone out there knows where or how I can acquire a pair, please let me know.

Reader's Question - by Richard

Richard, what was your first preppy outfit you can remember?

The first outfit I can remember is a navy blazer with brass buttons, a navy and red regimental bow tie, khakis, and wee little penny loafers. If I recall correctly, I was about four years old. In addition, my mother was a Beatles fan, and I had the hairdo to match.

Topic of Debate #16 - Will The Ascot Ever Fully Recover - by Richard

Will the current preppy movement restore the ascot to the prominence it has restored the bow tie? Personally, I will wear the traditional clothing I have always worn with no consideration toward popular culture. So, in conclusion of a few days of Topic of Debate, what are your conclusions in regards to the ascot?

Topic of Debate #15 - Ralph Lauren Rugby Patchwork Tweed Tie - by Richard

Recently, I went on a quest to acquire the patchwork tweed necktie I saw on the Rugby website. However, the tie was only displayed and not offered for Internet sale. In part, that is why I accepted my friends invitation to visit the Rugby Cafe, but to no avail, I didn't find the tie in the D.C. store.

With determination in mind, I called all Rugby stores until I finally located the tie at the San Francisco store. It arrived yesterday.......thoughts?

Topic of Debate #14 - Outfit by Tailor Caid Days- by Richard

Thoughts?

Time to pull out your old college scarf - by Crawford

I must confess to enjoying wearing my old college scarf -- it is not only a way to subtly show your support for alma mater, it is also a way to stay warm!! I particularly like that my college scarf is longer than my other scarves -- which makes it easier to wrap around my neck once (or twice on windy mornings) and still tuck it into my top coat. J. Press is the traditional American maker of the college scarf, and Luke Eyres is one of the oldest makers in England. The above photo from the Yale Alumni Magazine shows 15 of the scarves by J. Press.