Win a FREE copy of The Effortless Guide to Graduating Your Style

April 22, 2012 · 269 comments

Hey gents,

So about a year ago, I had this idea.

It came about after receiving numerous emails with very similar questions revolving around these topics and thoughts:

I want to start dressing better, but I’m on a limited budget. How / where do I start?
What’s in my closet that’s worth keeping, and what should I get rid of?
I took your advice and started to buy classic pieces. Now I have a bunch of great stuff. How do I put it together?

It was amazing to see these same questions popping up, all worded a bit differently, but essentially having the same themes.

Then I realized, the answers to these very questions are the fundamental building blocks of creating one’s own personal style… Which happens to be part of the very mission that guides this site!

I had to wonder, why the heck hasn’t anyone written a guide on how to do this stuff?

Total lightbulb moment: If it can help the very readers (you) that ask the questions, why not spend a few days writing up something helpful?

Ha. I actually thought this would take a few days.

The Effortless Guide to Graduating Your Style was born

…but little did I know it would take MONTHS to finish.

Truthfully, I had the first draft of the manual written over the course of a few weekends, but what took the most time was perfecting it: finding links, illustrative examples, supporting photos, you get the idea… as well as formatting the book in a clean, presentable manner that was easy to read and follow. The more detail, the better and more helpful.

I didn’t want to just slap something together and release it into the world; it had to be of EG-level quality (and I’m a bit of a perfectionist).

There were periods of time where I had to put it away and not work on it for a few weeks. At one point, I had the thought of scrapping the whole thing.

Now that I’ve gotten great feedback by several readers who had early access, it’s crazy to me that I almost gave up on this… especially when I get these kinds of comments and emails:

It’s an excellent piece of work. Great information to begin a style overhaul. I highly recommend it.

–Christopher Dravus, the-approach.org

…if I had a copy of this guide two years ago, I would have saved a ton of money by avoiding stuff that caught my undeveloped eye. The guide has just the right level of detail and flair.

–David Li

The BEST Resource

I honestly believe GYS (as I’ve so affectionately dubbed it) is THE BEST resource out there that can kickstart your wardrobe and style overhaul. Once you finish this, you will have set up a solid style foundation for yourself that you can continually build on at your own pace.

Now that I’m older and wiser (and more handsome, ha!) than my 20-year-old self, this is the resource I wish I had back then. It would’ve saved me a bunch of money and time and stress, trying to figure out what I should be wearing and what’s not worth my time.

Not sure exactly where to get started? Covered that.
Short on time and just want an all-in-one, step-by-step solution? Done.
Want to know exactly what kinds of items you should be purchasing? Told ya, in the guide.
Need suggestions for putting items together into actual outfits? Totally covered that, too.

BOOM.

Your chance to win a free copy of your very own

I’m giving away three digital copies of GYS (retailing at $26, officially releasing on May 1). Here’s how you can win one:

Simply leave a comment below and let me know what your current style / wardrobe hang-ups are, and what you hope to achieve by reading and implementing the ideas in GYS.

What do you need help with most? What would you like to improve upon most? What kind of outcome would you like? No issues are too big or too small, so let it all out in the comments.

I’ll choose three winners this Monday, April 30, at 11:59 PM Pacific, so make sure to leave your comment in time.

That’s it!

I’ll announce the winners this Tuesday, May 1. Good luck! Can’t wait to read what you have to say in the comments.

Edit 4/23 10:52a Pacific: 103 comments already! Amazing. Keep them coming, guys. There are definitely some great ones in here already.

About Barron

Barron is the founder and editor of Effortless Gent, a site dedicated to helping dudes figure out what looks best on them. He also co-founded Fifth&Brannan, a menswear label based in San Francisco. Connect with him on Twitter and Facebook.

Joe Blute

I just graduated college and am working at a finance company. I am having trouble dressing professionally, yet not looking like I wear the same style as the 75-year-old CFO. What can I wear that is affordable, sharp, yet my age-appropriate?
Gabriel

What to fill this box with.
Well, I am in the Army and have a unique job where I have to go between an Embassy meeting with all the people you can imagine to being on a combat patrol and dealing with some unsavory characters. As such, my wardrobe needs to be ever changing and flow from tuxedo to suit to pant and shirt to a tshirt and jeans. I also work out and while I feel I have an athletic build, there is nothing I can get off the rack to fit well – even with tailoring. For example, my last suit purchased at Macys was a drop 11 and the pants were loose at the waist but I had to have them sized so my legs would fit. Rather than look disheveled or spend a fortune on clothing that has to be custom made, can you offer advise on what and how to wear clothing that will look good and function well. I want to buy what will work and what I need, not just something that fits.
Thanks
Gabe
Franklin629

The problem I’m having is I am not the 45 year old my father was. I was born in the era of hip hop and it is affecting the way I dress. I want to and need to dress my age without looking outdated. Look at Diddy. He can get away with almost anything because he always reinvest himself and he got $. I also would love to know what styles are still current and what is dead and never coming back. I think you are the new GQ and men will love your advice. Thanks George. Franklin620@clear.net
Adam

Thanks for creating this great resource. I’m a 36 year old soon to be dad. I’ve always liked the idea of have a classic, stands-the-test-of-time wardrobe, but too often I rush through a shopping trip and grab stuff that I later regret. GYS would help me identify items and looks that I want to create instead of just heading to the mall and figuring it out on the fly.
inspectorgadget12

Just found this site and looking forward to it helping me reinventing my style as I transition from post graduate student to professional having to switch from wearing casual to dressy clothing. I hope to find recommendations and also am eager to see if you have tips on helping me perhaps bring out my old dress shirts and other clothing to make them work for today’s outfits since I don’t have too much extra cash to buy new stuff yet. I look forward to reading your site everyday!
http://www.adapterdesign.com/ AdapterDesign

I’m still having troubles with patterned shirts. I can pull off a windowpane or pinstripe, but any more than that and I just feel like it’s too much.I’m hoping that the ideas in GYS help me get away from blindly following advice I see online and help me stand on my own with the knowledge of some fundamentals.
http://www.facebook.com/profile.php?id=608483082 Shane Bennett

I’m struggling with how to maintain style with a good budget in mind. In addition to that I would like to learn how to maximize the life of my wardrobe
wardrobeman

I’m about to graduate college and start a job that requires a wardrobe that I currently don’t own, or completely understand. I’ve perused the pages of this website and dappered.com in an effort to try and improve, but not having a book readily available makes it hard to get things to stick. I would love to have a copy so that I can start all over from the ground up, and make my wardrobe efforts truly “effortless” with your help.
http://www.facebook.com/profile.php?id=1150763853 Rafael Antonio Castillo

I have a ton of resources I can wade through, websites, blogs, mags, books, but I can use one quick access guide that can cover my basic questions and that I can recommend to all the young guys I know who may need help growing up their wardrobe. Also I can use more help figuring what tie to wear with what shirt and suit or sport coat. Also, I need to improve my wardrobe on a very tight budget keeping in mind that I cannot sacrifice too much quality for low price. And I need to keep my outfits minimal.
JTUSAF

My wardrobe consist of Chive T’s, Express button ups, Express slacks, one pair of dress shoes(which I hear do not work for me), American eagle jeans and I can never find a pair of shoes that fit my wide foot. I’m not into that skater look, but the only thing I wear are the Nike 6.0 which are getting worn. I’m constantly trying to update my clothing so I can be present myself more as an adult/impressive. The problem is the wardrobe that I’ve built is from listening to blink 182/Football teams. So pretty much I need help w/ the right fit of jeans for the style that i’m looking for which is the buttoned down look. I wear a size 12.5 and I said I can never find a pair of great casual/dress shoes that work for me. I just would like to have a great sense of style where I get I’m getting that second look. To finish up, my day to day mainly consist of me wearing my ABU’s (Air Force Uniform) so I never really know what works for me. Help Please!
crockeronline

I’ve been reading Effortless Gent, as well as other menswear blogs, for the last year now and they have been essential to making me feel better, dress better, and enter a room with more confidence. Girls compliment me on the changes and guys, while it’s not always vocal, have started to feel like they’ve got to pick up the slack.

My current quandary is that now I have a good idea what I’m doing and what NOT to buy, but I’ve gotten stalled in the purchasing department. I want everything I get to be as versatile as possible. I’m happy to pay for the good leather shoes, the well-made shirts, and the excellent denim, but I get overwhelmed by the options (mostly that I see and hear about online) and don’t end up buying anything.

When I was just starting out building a wardrobe, I was happy to get cheaper experimental pieces. But now that I feel confident in my personal style, I want to take the next step, and I keep hesitating.

Thanks for all the great work, Barron! Congrats on GYS.
Paul

Love the content!

For me, the hardest balance comes from an ethical desire to mostly purchase used clothing, express a handsome playfulness, and still dress like an adult. I’m not sure if this guide will give me all of that, but I can certainly tell you how I incorporate your ideas into my style.

Thanks for all the great work!
http://twitter.com/BroSnake Bro Snake

My job is a Sales Engineer and I am constantly visiting difference types of customers. This may range from CEO/Presidents down to the maintenance technician. I greatly struggle with how to dress better, but not look too schnazzy to scare off the lower level technicians.
Thanks, can’t wait for 5/1!
Dom H

My problem’s with appropriateness. I’m in college, being pulled in quite a few directions at once. It’s like, what can I wear that will be acceptable everywhere? In a day I might meet with department heads and with truckers, with amateur filmmakers and my D&D group, I might interview for internships or attend a house party or just lounge on someone’s couch playing N64 all day. So my problem is, I guess, that I can’t dress for everything, so I usually end up over- or under-dressed for a given occasion.

I want to know how I can… I don’t know, find a happy medium? If ‘medium’ is even what I should be shooting for? And how to dress so I don’t look like a goof?
Remu

I haven’t updated my wardrobe in the last 5 years (except
for the odd socks and gym shorts), and considering I’m now a college graduate
with a job I really need to get my act together. Cargo shorts and graphic tees
just aren’t cutting it anymore!
Unfortunately starting off from scratch is a daunting task,
and I really need something/someone (GYM maybe?) to give me that push towards dressing
like a (classy) grownup. Hell, I’ll even throw in a before-after picture if it
helps!

Thanks, and keep up the good work.
http://www.facebook.com/people/Jon-Helmkamp/617257122 Jon Helmkamp

Hey Barron,

As you know, I found this site a few ago, and I absolutely love it. Your insight on things makes it really easy to follow concrete information, yet encourages me to keep exploring with style in order to develop my own personal style.

As of right now, I have more questions than answers! What color shoe do I wear with what shirt? What type of shirt? How do I mix colors and textures in general, especially with shirts and ties? How do I look presentable but still casual (when appropriate)? And more specifically, what type of of collar do I wear? What size tie? What type of knot? How do I piece everything together, head to toe, to make sure all my colors jive with each other? There’s a lot of questions, and it will take a lot of time in order to acquire a good wardrobe, but I want to start now. I’m at a place in my life that could really use a more grown up wardrobe.

Things are really tight financially with my fiance and I right now as well. Any changes that I make in my wardrobe (which will be coming pretty slowly due to money) need to be smart changes. Honestly, I don’t even have a spare $26 dollars to buy the EG Guide right now. Winning one would be a very special thing to me.

I truly admire your work, and the insight that you give, and would love the chance to win one of the copies of your guide. I really feel it would give me tools and confidence to dress in a more grown up way. Having the insight and the information from your website consolidated into one place, with pictures to help guide the reader (I’m a very visual learner) would be fantastic. How you look is more than just clothes – it symbolizes your composure as a person. Moving forward professionally and in my personal life as a well put together individual is very important to me.

Whether I win one of these guides or not, I’ll still be reading the blog avidly and picking your mind for as much info as I can. Thanks for everything that you’re doing, Barron. Keep it up, and I’ll keep reading.

-Jon
Patrick Regan

More than anything else: Matching colors and patterns I’ve got a good handle on fit, what looks good on my body, what looks professional, etc, but matching colors and patterns is still really tricky for me (I don’t dare try and mix a patterned tie with a patterned shirt). I refuse to believe that it’s something I can’t learn, and hopefully GYS can help me wrap my head around the color wheel.
James B

I’ve recently had some significant weight loss and figured that it was time for me to graduate from the filipino gangster/hipster look i seem to evoke and upgrade my style and wardrobe. I’ve made some small changes like going from 501s and timbs to a slim straight cut and dessert chukkas and fitted shirts, but my main hangup is knowing what to purchase and how to put it together. I am always second guessing myself when I look in the mirror. Another issue is I’m on a budget. I’m hoping your guide can help me with figuring out my style, rather than me following fashion trends and hopefully give me more knowledge to develop a more classic/timeless type of style I can be comfortable and confident with.
http://www.facebook.com/vcipollone Vincent A. Cipollone

I have a tough time with the backs of my suits and shirts. I bought them custom at Indochino and they’re fantastic, but really tight in the back and don’t pass the hug test. I hope there is something regarding sizing in here.
Jonathan Estrabillo

Shoes. I need help evolving my sneaker-freak roots into something more timeless and age-appropriate.
Andy Boulton

I feel like I have pretty good instincts as to what will look good on me but it is hard to actually find things I like on a student’s budget.
Markus

I recently decided that I my wardrobe made me look younger than my actual age. I stopped wearing t-shirts all of the time and started to wear polo shirts and oxfords. I moved from away from the overly washed denim to dark denim. My biggest hangup is that I stick to the same type of wardrobe every day and was looking to change it up a bit. I hope to know how to have the same style but change it up every so often.
JY1

Hello Barron,

As a soon to be college graduate, I have definitely seen a change in my wardrobe both casually and professionally. I have updated many of my outfits to be more business and mature driven so that I can be presentable at all times. However, I do have a very strange build that makes it quite difficult to find clothing that fits properly (15.5 34/35 and 42R shoulders with a 29 inch waist). I’ve spent a lot of time and money on items that are “slim”, “tailored”, and “modern” but none seem to fit properly. I’ve gone to tailors at department stores, chain stores, etc and to this day – no avail. Because of having no older brothers and an immigrant father, my knowledge and resources for sartorial personal experiences are rather limiting. This book will provide me with a plethora of information as I am trying to limit my spending on items deemed “necessary” due to the fact that I am an in debt college student that does not have much money to learn this “guide to graduating your style” through trial and error. I hope that you can see I am attempting to revamp my image so that I can no longer be classified as another “immature college student” but do not quite have the resources readily available to do. This is no sob story in which I want sympathy or anything in that matter; but rather, a humble attempt to get outside help. Thank you for your time and I love your site!

-JY
http://profile.yahoo.com/UJHR7RVX6Z3WWD6SIKISV2BSDU Adam Ryan

I am hoping to learn more about matching different colour of shirts to different style of pants. I am trying to break away from my typical “frat boy” image.
Bchin415

I’m a college student as an athletic training student. Being the only undergraduate professional program my school, I’m required to wear khakis and a black polo 80% of the time. Outside of that.. I don’t know how to dress. It’s like I’ve forgotten. Hopefully with this book, I will be able to look better outside a pair of khakis while going from class to class and while wearing business casual during games.
http://www.nicholascrawford.com/ Nicholas Crawford

Moving to SF, my dilemma lately is figuring out what to wear since there’s a possibility I could run into Barron on the sidewalk. Terrifying, really.

Nice work on the book! Good luck!
Ian

Fit is my biggest issue. Learning how to determine good fit would be my goal. Plus, I’m on a college student budget.
Matt W.

My biggest issue is how clothes fit. I didn’t know that clothes could fit so well until a few months ago! My parents bought my brothers and I clothes that were too big in anticipation of our growth, but we never stopped buying clothes this way even though we stopped growing. Now that I’m out of college and working at a financial institution, I need to do better than shirts that wear like tents and pants with quadruple break. I’m still learning how to buy clothes that fit my 5’8″ “skinny as hell” body. EG has been a great resource so far and I look forward to future articles.
Christopher Taylor

I’m in the process of going to school on the GI bill. I’ve always either worn uniforms, or clothes that I didn’t mind if they got destroyed to work. Now I’m gonna be wearing a suit and tie everyday. HELP ME!
Guessed

Recent graduate looking to develop a style of my own. My biggest concern is liking a style on paper, then going out and making some purchases and realizing its not for me. Rinse and repeat this a couple times and I’ve assembled a patchwork of items with no continuity and am pretty much at square one still minus a good amount of doll hairs, and hopefully not my hairs too.
Jonathan C. Chen

I have no idea what to wear in the summer and haven’t fully figured out where I stand on summer clothes. Hopefully by reading GYS, I’ll get a better sense of what my own style is.
http://profile.yahoo.com/FUX44SMNRO5QWJJ3VJGCORCXLE Justin

I recently left a doctoral program in clinical psychology in favor of applying to law school. Now, with law school on the fairly immediate horizon (this fall), I need some help “graduating” from blending in with a group of completely non-style-conscious academic types to standing out among a group of style-conscious peers in the legal profession.

I have some of my own ideas about this, but many of them were formed with the “help” of my hopelessly-stuck-in-1970 father (think pleated khakis, blousy oxfords — ONLY those with button-down collars – and heavily shoulder-padded suits).

Grad school didn’t require a suit or tie — ever. Law school (and the legal field) will require plenty of both. It’s high time I formed a comprehensive style plan, and this book is going to help me do it.
Stanny91

My main problem right now is blending everything I have into a nice personal style, and choosing clothes that can look nice walking to classes or longboarding around campus (I’m in college). Another problem is choosing shoes that look nice but won’t be completely worn through after a month of riding.
Stevenjpro

I’m working on building a lean–but still mean!–classic wardrobe of casual clothing. As an aspiring young professional, I’m slowly trying to replace my near-homeless college look with a more adult casual getup. I love the helpful tips from EG and love the simple help the site, and now the manual, offer to guys like me who need to start growing up and stop wearing flip flops.
docscot

I need the most help in implementing my style in a college setting. Too many of my undergrad peers are very lax in their appearance. I would appreciate developing looks that are casual enough not to stand out too much but also stylish enough to look sharp.
David Higdon

I have two issues at the moment. One, I’ve lost twenty pounds over the past year, but I have about twenty more to go — so I’m between sizes and don’t want to update my wardrobe just yet. Number two, I’m in a creative casual work environment — I’m an Art Director, but I’m having issues creating a personal style that doesn’t look either too stiff or too young (I’m 36.) You’re site has been a huge resource though, so thanks for that.
Matt

I’m on the young side, and my sartorial sense hasn’t really developed much. I’m hoping to get a sense of what goes with what.
Jberrysf

I have alot of trouble pulling off polo shirts. Im a big guy with a pretty strong muscle to gut ratio but I’ve had the usual pendulum swings, but no matter where I weigh in (190 to 205) the polo seems to be a style that leaves me looking flat and billboardish, round and jolly or somewhere in between. Help?
http://the-approach.org/ Christopher

I just wanted to jump in and say that I’ve seen the product, read it cover to cover and I can say it’s worth it. It’s a great tool to put yourself on the right path to a better style. It doesn’t muddle the task with advanced style concepts. It keeps it simple and thus makes it an attainable goal. You won’t be intimidated, you won’t feel like giving up and you’ll be able to follow the book easily because of the slick visuals and writing.

Great work Barron and to all those on the fence, just take the plunge. You’ll come out of it a better dresser and with means to put your closet together. But that’s just my approach to Graduating Your Style. The choice is all in your hands.
http://the-approach.org/ Christopher

That’s a hell of introduction sir but thanks for sharing. I sympathize with you. There was a time in my life when I went with everything baggy and big and dark to avoid the attention. I wanted it, don’t get me wrong, I just didn’t feel like I knew what to do when I got the attention.

I talk pretty extensively on my site about confidence and style. It takes a lot to make the first step but once you do it gets easier. You need the determination to power through the first few snags that come your way when you start down the path to reinventing yourself. A lot of people lose steam after the first misstep. You can’t.

I don’t have the kids like you do but I’m close in age, 29, and I’m at a place in my life where I’m doing a lot of things as if i’d never done them before. My old ways weren’t working. Relearning how be a human being from scratch is how I always look at it.

The dating scene is the toughest but what I can say to you is this: work on you first. Get to a point where you’re confident, comfortable with attention and happy with your look. If you can’t be happy with yourself don’t expect strangers to be. Once you start walking around through life as a confident person you’ll find its a lot easier to deal with women. When you know your a worth while dude you can be choosey. People without confidence take everyone that comes along.

You got this my man, I know you do.
http://profiles.google.com/craigmurkar Craig Murkar

As I’ve recently graduated, and am attempting to make my way into a more professional world, I’m really trying to get a handle on dressing like a grown up. I’m getting there, but still flounder on the dressier side of things.
Vince

My problem is filling out my professional wardrobe while not becoming too “boring” but not too casual at the same time. Looking a little different but not enough to affect anything in a very conservative field a bad way is a hard line to ride.
Josh

I’ve recently joined the working class, purged my closet of old, ratty t-shirts and tennis shoes of my college year – leaving me with very little in the closet. Your book can provide me that blueprint to build my wardrobe from the ground up. I need to able to catch the eyes of my superiors at work, as well as those around me socially.
Talltexan10

Barron,

Howdy! I am just getting ready to start my career as an insurance agent. And being a big guy I would like to start developing my style as a young guy of 31. I’ve enjoyed your website and articles. My style consist of button down dress shirts and a few slacks with one blazer. I’d like to kick it up a notch and learn the correct way to build a wardrobe that can work for me.

Best,
Jerry
Z C

Lost about 35lbs, looking to renovate my wardrobe and improve from just polo shirt and chinos
Connor

My current attire(starting bottom up) is tan socks and shoes from
Clarks, grey chinos from Jcrew, a tan threaded belt from Clarocket square from Men’s
Warehouse, and a blue plaid bowtie from Men’s Warehouse

tl;dr I wear business casual, while following the rules(ex: belt match shoes)

I hope to learn new styles I can experimenks, a plain
white tee, a white with blue squares dress shirt from Jcrew, a Navy
blazer from Lord & Taylor, and a white pt with in my own style, as
well as new color schemes, and better wear for all seasons seperately
Connor

oh wow copy paste fail
Connor

Ill fix it
My current attire(starting bottom up) is tan socks and shoes from Clarks, grey chinos from Jcrew, a tan threaded belt from Clarks, a plain white tee, a white with blue squares dress shirt from Jcrew, a navy Blazer from Lord & Taylor, a pocket square from Men’s Warehouse, and a blue plaid bowtie from Men’s Warehouse

tl;dr I wear business casual, while following the rules(ex: belt match shoes)

I hope to learn new styles I can experiment within my own style, as well as new color schemes, and better attire for all seasons separately
Casey

I am 27 and require a much needed wardrobe change. I’m an engineer and work in an office building, where almost every day I wear a polo and khaki pants. My closet consists of mostly T-shirts from college, a large amount of polo shirts, some pants, and some dress shirts. I want to purge most, if not all, of my old clothes and make a change in my life. I really want to make this change so that I can feel more confident about myself and improve my life.
Alex

I love your site, and have been lurking for a little while!
I’m about to head off to college, and I figured it was time for a wardrobe change; I used to wear a graphic tee + jeans everyday to school, but now I’ve evolved into casual button ups, or just plain t shirts with chinos or dark denim (best advice, ever!) I’m just biding my time and slowly expanding my wardrobe until I have a closet I can truly feel proud of!