And They’re Off! TBB Day at the Races

the blogger boyfriend zara daniel wellington kyle hjelmeseth bow ties del mar

Thanks to my cousin in my 20s I started to develop this sickness that I couldn’t stop from spreading…The Prep Flu. I started desiring colored pants, polos and oxfords like I had never had an itch for before. I wanted to summer on the shore. I wanted to play preppy games. I wanted to dress in pastels and go to the horse races!!!

I’ve been slowly trying to make up for my lost childhood of not being a prep by hanging out on boats and buying more J.Crew. This year I turned another corner, put on my bowtie and grabbed my gorgeous girlfriend, and we went to play the ponies in our Sunday’s best… (more…)

Dear Cougar: Seersucker at an October Rehearsal Dinner…in Chicago?!

Please leave your questions for Dear Cougar in the comment section below, or feel free to email me at

DEAR COUGAR: I’m heading to a wedding in Chicago this October. Can I wear a seersucker suit to the rehearsal dinner? – SEER-SUCKER IN NORTH CAROLINA


Dear Seer-sucker,

Alas my friend I’m sorry, but no. I often joke that Chicago gets about 9 months of winter, which may not really be a joke at all. While us Californians can arguably stretch the usability of a summer seersucker suit (SSS) well into October with our lingering summer days, Chicago…not so much. The average temperature high in October for Windy City residents is, gasp, 60 degrees!

Now, the fact that you asked me if you could wear seersucker in the first place leads me to believe you want to make a statement. Two wintery wovens are perfect for making a statement and will keep you insulated as those temps drop to the 40s at night, Tweed and Houndstooth. eBay is the place to find jackets in either pattern that will be affordable, the rest of your ensemble might as well jump out of a J.Crew catalog.

This is how I would do it:

Paired to day with a great purple gingham J.Crew shirt, J.Crew slacks, a preppy as hell tie from Express and a purple paisley pocket square from around the LA Fashion District.

I hope that helps!

– Cougar

Perfectly Prep: The Kiel James Patrick Triton Bracelet

Going further down the rabbit hole of American prepdom I find myself in need of preppy accessories. Relatively new brand Kiel James Patrick caught my attention when a photo of this bracelet tumbl’d through my day:

Kiel James Patrick Triton Collection

The overall simplicity, and yet cool factor, instantly caught my attention and I had to have one. My mind wasn’t prepared for what I saw when I visited, which basically amounts to an explosion of preppy attitude and swag on a level I can’t come close to competing with.

So I ordered mine right away. I picked the ACK Latitude.

I think it took all of three days to get this little package in the mail from the time I order…all the way from Rhode Island.

That…is good shipping!

I was impressed by the little things, like taking the time to write thank you on the purchase order. You don’t see that kind of attention from brands any more and its the little things like this that build brand loyalty:

Service with a smile!

If you live the preppy life, or even want to just dip your toes in the waters of duck print wall paper I suggest starting here. At $38, this handcrafted little wonder is a steal, and you’ll find it in all of my style photos from now on.

For more excessive prep inspiration go:

Oh yeah, and here is a pic of it…had to go boating of course!

On the Duffy!

Today’s outfit inspiration is a little leftover from the Derby. What do you think? I love the alleyway behind my place. Plenty of great backgrounds for photoshoots in my neighborhood.

Where to get my prepster gear:

Dandiest at the Derby (please vote!)

Hey Tumblr/Internets Fam…

I’m in the Top 5 Finalists for Brooks Brothers Dandiest at the Derby! Please spread some love, click on this photo album link and LIKE my photo!

This was my submission. WINNING.

Garden Fashion. Today’s outfit was inspired by the plaid prepsters of the 80s.

I’m rocking a Tommy Hilfiger oxford shirt, a brown knit tie by…I have no idea cause I lost the tag, and plaid Express pants.

Of course, always shoed in Cole Haan.

Happy Friday everyone!

The Making of an American Prep: Part 3 – The Transformation

Read Part I | Part II

So there I was perched atop a mountain of clothes that I’d been collecting since I started in college. Work clothes…blah. My wardrobe is unevenly divided into “work” and “jeans/white tees.” No one except me thought my attire was boring. I get compliments on what I wear to work on a regular basis, but at this point I decided to change for me. To keep myself interested in myself.

So after being inspired to change it up, and doing my research like a good boy, finally the transformation was here…

In the top image I’m wearing a charcoal grey Kenneth Cole suit. I’ve got a good mix of patterns between the pink gingham shirt and blue polka dot pocket square, but this is essentially a typical European tailored suit and an average everyday office look.

Down bottom are the pieces of the Preppiest ensemble I could afford. Tweed two-button jacket, blue pin-striped shirt from J.Crew, Rooster red-and-blue bow-tie and my favorite blue polka dot pocket square. Prep perfection!

To illustrate the transformation I created this fancy grid:

Essentially I took my inspiration image and recreated almost to the T. Tweed jackets at retail can be ridiculously expensive, but I found the one pictured above for $40 on Ebay. Ebay has a HUGE selection of Tweed at reasonable prices. With minimal tailoring my perfectly fitted jacket cost a total of $90. A STEAL.

The shirt and pants again came from J.Crew. Thanks to working in education I get a 15% discount on all purchases, and lucky for me there is a J.Crew premium outlet not too far from where I live.

The shoes again are from Cole Haan. I also found these at a premium outlet that was having a store-wide 50% off sale, so they were about $98.

So total to “go Prep” I spent a little less than $300. That is a cheap as hell when you really think about what it would cost to revamp your whole look. Using my research and deal finding skills I picked pieces that are versatile, stylish and classic. I can pair them in different ways creating many new looks and they’re all pieces I can keep in my closet for a lifetime.

If you have any questions about how to change your style, where to look, etc. please don’t hesitate to ask!


The Making of an American Prep: Part 2 – Research

Read Part I | Part III

The Cougar 4-Point Style Research Plan:

  1. Investigate the components of your intended style switch. For instance if its Preppy, sign up for the newsletters of some of the preppiest brands you know, and read them!
  2. Compare trends across different brands. Look for similarities. Preps tend to like common trendy items like “Tweed” and “Boat Shoes” and “Chinos.”
  3. Know the terminology of your new style so that you’re looking and asking for the right things. For aspiring preps Brooks Brothers has a great glossary on their blog that with a little study will have you talking of gingham and madras with confidence and ease.
  4. Establish what your likes and dislikes about the new style you’re attempting to adopt. Don’t adopt aspects of the style you don’t care for because you won’t wear those items with confidence. The man makes the clothes.
  5. Shop! Visit the stores (on-and-offline) of your target brands. Look at the sales associates and what they’re sporting, look at the catalogs, even the decor. You don’t have to purchase anything yet. But shopping is the main tenant of style research.

When changing one’s life, in any way, research is necessary so that mistakes aren’t made. In this case I was decidedly changing my closet from Euro to American Prep. I had to be sure that this was the right move, especially socially.

Growing up I had very few fashion influences. I lived a humble rural life with my parents in Washington State, which is largely void of fashion sense. My older cousin took me under his wing and introduced me to suits and finer things when I was around 15, and that I think spurred my interest in overall “looking good” and “dressing well.” But I shunned his preppy oxford shirts and loafers as old man style and not for me.

Prep is so much more than that. As I started to get bored with my every day suits I realized that it is because they’re so plain jane. There is no flair, there is no punch. I would add things to make my outfits more stylish such as an occasional bow-tie or pair of brightly colored socks, but that’s about as good as it gets. I needed more.

Although some might find pretentious, in American Preppy closets you’ll see styles that “normal” folk just won’t wear. The chartreuse and dusty berry colored pants, top-siders, lobster or spouting whales over everything is just not normal. But I was seriously tired of blending into the crowd.

So, how to go Prep. The first move is research. I started with what I call the HOLY QUAD OF PREPPY FASHION: Tommy Hilfiger, Ralph Lauren, Brooks Brothers and J.Crew. We already know I’m in bed with Cole Haan when it comes to shoes. There are plenty of other Preppy labels out there, but for research sake I decided to focus on those four key brands.

I signed up for each brands e-newsletter and watched the sales and styles that came through each week. I was able to compare and contrast trends across brands, and honestly that helped me establish what I wanted my look to be. Plus you can’t beat weekly deals.

Through researching this Prep thing I wanted to get into, once I started collecting pieces of a new wardrobe, I did so with confidence and I’ve found a style that I can now call my own.

Next week: The Transformation

Stay tuned.

– Cougar

A Making of an American Prep: Part 1

To read Part II | Part III

Last year I started getting a bit restless.

Guys, for the most part, aren’t as gung-ho about shopping excursions as our better halves are, especially in the clothing department. Surprisingly, I’m no different. Those who know me well know that my style hasn’t changed too much over the last few years.

My sense of fashion had plateaued.

As an office dweller I’ve been used to European-cut suits since the day I graduated from college. For the last seven years I’ve been wearing two-button two-and-three piece suits. And they’ve been awesome. Simple and classic. Those to adjectives have been my mantra.

Last year though…I started to get an itch. I was bored. Bored with a lot of things, but especially my wardrobe. Then someone introduced me to The Preppy Handbook.


That book, coupled with an uber-prep outfit I saw in a GQ magazine seriously changed my life. Mind you, this was on my trip over to the Middle East for two weeks, so I had plenty of time to ponder the next stage of my style evolution.

Red pants. GTFO. What a-holes wear red pants? Well, preps wear red chinos. And green chinos. And assorted other things with anchors and lobsters and whales on them.

Top-siders, bloodies, friends named Chip & Muffy, Squash, Flotillas and duck print motifs. I have a lot to learn.

Well, maybe I’ve got the bloodies down.

The transformation to American Prep is going to be a rough one, but I’m determined.

Stay tuned. 

*the first being, I Hope They Serve Beer in Hell.

When you are branding and building a brand, remember that fashion is very much a part of it, but fashion is fleeting and style is forever.

Tommy Hilfiger