Hunter Original Tall Rain Boots




orig_white_largeIf you were to ask me right now my favorite clothing piece in my closet, it is without hesitation my Hunter Rain Boots. These stylish boots are now a near daily staple of mine and a top recommendation for any and all people, they are that amazing. This post will cover the original tall line of boots.

Before i get into them, a little back story on the famous wellies. Hunter is based in the UK where welly boots are common as a pair of tennis shoes. They are hand crafted and meant to last generations. Some testimonials from people have claimed to owning pairs for 30+ years! The brand is recognized world wide as top notch and has kept the reputation for decades.

In the last few years they have boomed in America, particularly to younger women looking for both cute and practical boots with color pallets not offered anywhere else. You cannot go far in a mall or city without seeing multiple people sporting them. And while the trend is primarilly popular amongst women, they are designed and acceptable for men too (my pink pair would like to concur as well!).

So when is the most appropriate time to wear Hunters? Its simple: any time! Aside from formal attire, you can find hunter boots for any situation or season.

For fall, dark colors like black, maroon, and navy will help compliment the usual jeans, khakis and jackets worn in the cool air. In winter pairing your favorite colors with one of the many styles of welly socks will help keep you both warm without sacrificing fashionable appeal. In spring and summer a bright pair, such as white, yellow, pink, or turquoise with a matching print sun dress can add some brightness to the sunshiney days and keep you equipped for the rare rainy occasions.

A favorite outfit choice of mine is wearing a navy blue blazer with dark jeans and a polo that matches the color of the boots i’m wearing to give it a great two tone color scheme while maintaining the preppy flare i enjoy expressing.

Please share your hunter boots purchases and favorite outfits! I would love to hear everyones take on these phenomenal boots!



Tatyan Boutique’s Captain Dresses


Ahoy there ladies! If you plan on sailing the high seas or enjoy a little nautical/pin up flare in a dress then you will love the Captain Dress by Tatyana Boutique!

The dress is styled like a sailor with its collar and buttons adorning the top with white piping along the collar. The dress transitions to its skirt with the white belt that accompanies every copy and the skirt comes in a pencil style or a circle flare skirt for adding a crenoline to make it a full vintage style skirt. The dress comes in either bright red or navy blue and is made from a stretchy bengoline material.

Celebrities alike from Leighton Meester to Holly Madison to Chaka Khan have been seen donning this beauty and it looks incredible on every woman brave enough to give it a shot. Do not be intimidated by its costumey appearance, this dress is more than just a classy sailor costume.

Pairing the navy blue dress with red heels, white gloves or a red ascot gives it a pop of color commonly found on most pin up style dresses. Leaving the flare skirt open makes it a great dress to move around and swing dance in. And yes, it makes for a drop dead gorgeous halloween costume too.

The dress comes in sizes XS-4X so it will fit nearly every size of woman. I emplore any girl out there looking for a way to spice up their wardrobe to give this dress a try. It can be a bit expensive at full price, but it is often on sale for under $100 at the right times. I will gladly salute any lady with the guts to try this beautiful dress!

Preppy Essential: Barbarian Rugby Shirts



Autumn: Too warm to wear a heavy jacket and too cold for a basic polo shirt. What is an aspiring prepster to turn to to accomodate for weather and still look fashionable while the leaves fall? Ladies, gentlemen and everyone in between, look no further than Barbarian Rugby Shirts.

Rugby Shirts were primarially worn by rugby players alike back in the day but are now relegated to a fashion piece worn by college band members and prepsters like myself. The simple yet noticeable style of them are what have kept them a staple in a prepsters closet for decades.

Often just confused as long sleeve polo shirts, the relationship ends at the fact they both have collars. Rugbys sport a heavier cotton material for cooler weather but breath like a polo shirt. As with nearly every rugby shirt, there are 4″ stripes, elastic cuffs and a white tweed collar.

A few things to note about rugby shirts:

– Some rugbys come with options for solid colors. Avoid that. Keep solid colors to polos and stripes to your rugbys. It allows them to be distinctful.

– All rugbys MUST have a white collar only. Its what the name indicates.

– Stick to bold stripes around 3-4″ if wearing a different brand other than Barbarian.

The long sleeve striped shirts with white collars have been a preppy staple since about the 80’s. The often bright colors fit the preppy style with the white tweed collars providing great popped collars that require much less maintinence than polos to stay neat and straight.

Other brands such as Ralph Lauren and Tommy Hilfiger have offered their own takes on rugby shirts, but after my first purchase through Barbarian it was clear their quality met no match. Every shirt is hand sewn and will last you years longer at a much lower price of ~$50.

Just a few color combos to consider for the stripes are gold/navy, red/navy, navy/grey and my personal favorite, pink/green. They should primarly be worn with khakis and jeans to keep te autumn feel consistent. Another way to add some color is is to wear a polo that matches one of the stripe colors and pop the collar with your rugby collar for an uber preppy appeal.

Thank you for reading, comments are always welcome!

Preppy Essentials: Ralph Lauren Big Pony Polo Shirts

Ralph Lauren is quite possibly the ultimate staple for any preppy wardrobe, the brand has created some amazing quality and fashionable clothes with its iconic polo player logo donning every piece. It’s most common staple is obviously their polo shirts, of which there are practically thousands of options. This post i will be discussing my favorite style of polo shirt, the Big Pony Shirt.


Big Pony is an obvious variation of the standard polo, where it separates is in its ballooned size logo. The enlarged polo player covers the right breast with contrasting color to make it stand out on the shirt. Often the big logo comes with various other embroideries such as the common number 3 on the left sleeve, country flags on the right breast or back, or even custom names and crests. These really add a uniqueness to each shirt and creates hundreds of color options.


ou can style the shirt down with a common pair of jeans and tennis shoes or style it up with a blazer, khakis and riding boots. Ladies can pair a pleated skirt and heels for a casual look or color match it with jeans and a pair of Hunter Boots. Also popping the collar adds a bit of flare to it as these shirts arent generally worn to casual events. Save your more subtle polos for that.

Most Big Pony polo shirts run at about $98-120 but cheaper options are available during clearances and on ebay. Macys carry them most often as well as occasionally Nordstrom as well as the Ralph Lauren Factory outlet.

Any opinions or ideas are welcome in the comments! Thank you for reading!


Hello folks and welcome to my new fashion blog, Rainy Day Prepster! I am new to this so bear with me as i develop my penchant for typing blogs.


First a little about me, I am a guy from Seattle (choosing to keep my personal info private) that is in love with fashion. A friend recently inspired me to start this blog as a way to help put ideas out there for men/women that may have overlooked a style that they would like. I particularly will be centered around preppy/country club attire as well as vintage/pin-up styles so if thats your cup of tea please stick around, if not I hope you’ll find something you never thought you’d like!


I will slowly be trickling out posts as I have time but please remain patient, I will also try to respond to every comment as possible. Thank you for taking the time, and enjoy!