Tag Archives: Preppy

Sailor Swing Dress by Pin Up Girl Clothing



Summer is just about here ladies, so that means it’s time for summer dresses! Today i’ll talk about an absolute favorite of mine, the Sailor Swing dress by PinUp Couture.

By now you may notice I am a fan of nautical pin up style, but I cant help if the dresses are so stinkin’ cute! Forunately this dress is a little less obvious as the Captain Dress, but still noticeabley vintage.

The dress comes in red and navy blue both with white trim on the top and down by the bottom of the skirt. There used to be a white one with blue trim but good luck finding it, its as rare as the white captain dress.

Another great feature is it comes with the white belt, an accessory that is a must for this dress just as much as the captain. It gives the dress shape with the simple yet effective contrasting white.

While this will primarilly be a summer/spring dress, in the sun it is as versatile as they come. Heels or flip flops are ideal to pair with and it looks great on any shape or size. You’ll be getting complimemts from other girls and heads turning from boys! (Myself included!)

Its only drawback is price as it sets you back $125 at full price. Fortunately vintage clothing sites like Mod Cloth and Pinup Girl Clothing have sales frequently especially right before the dresses prime season.

I recommend this dress to anyone looking for a fun dress to frolic in and enjoy the sunny weather! Enjoy ladies!


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!


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!