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.

Otto L Shih

I’m a sophomore in college, and while I’ve always had a decent eye for clothes, I’ve recently had a large amount of difficulty walking the fine line between an overly casual t-shirt and jeans and going way too far and going to class in a suit. In addition, I’ve recently gained about 30 pounds of muscle, so even finding clothes is hard. Any tips for a muscular guy looking to look good but not overdressed?
Brendan

The hardest thing about transitioning into the “real world” from college was figuring out what was appropriate for which situation. Everyone knows business casual but how do you keep from being boring day after day? I found that the khaki shorts and sneakers I wore in the summers while in college no longer work for me now that I’m in my late 20s. Add in the weight I’ve gained since college and it’s been tough to find practical clothes I’m happy with–although your site has helped me this far.
Stav365

Everything i have is too big, and i hope to be able to advance my personal style in an affordable, but modern way.
Larry S Fish

Converting clothes that are too big (see button downs) to slimmed down over time, just a matter of money, and finding items that fit. Shoes are tough, 8 4E. Pants are easy, always get them hemmed as long as i find the right waist – 28/29/30.
Michael Li

When I was younger, I used to be clueless about style and fashion, throwing on random bits and pieces on myself that never fitted right.

Since then, I have spent much time, energy and cash on reinventing my wardrobe. Now it is full of staples of classic menswear, and I have a huge range of choice in outfits for formal and semi-formal events.

In my obsession of classic, “grown up” men’s style, however, I have neglected the casual side of things. Now I am either the best (perhaps over-) dressed guy in the room with sports coat, crisp shirt and tie, and fine leather shoes, or the worst dressed, in my only pair of tattered sneakers and faded jeans.

I hope to achieve a more balanced wardrobe in the future, and now with all the canvased jackets and welted shoes out of the way, it’s time for me to focus on dressing well for the more laid back occasions. Hopefully a read of the GYS can give me some pointers in this regard
jason posey

Spent about 1 1/2 years losing about 150 lbs. I’ve had to get smaller clothes, but I still lean toward loose fitting attire. Don’t know if I’ll ever be comfortable in anything that is form fitting.
http://pulse.yahoo.com/_OOOFRVOOPLAO5GGA2HT5ANGZZM MAYITO

I look forward to changing the everyday look of my life. As a twenty-something in the ridiculously competitive finance landscape of NYC, you need every inch you can get over the competition. Sometimes, looking good is almost as beneficial as being good.
Jason Williams

If you want to clean up the world, you have to first clean up your backyard. Focusing on style, personality, and self confidence is something we are missing in our generation.
http://www.facebook.com/profile.php?id=1639650547 Dan Kennedy

Hey Barron.
I’ve been upping my style, now that I’m 18 and heading off to college soon, and I want to start off looking great, making the best first impressions on future peers and professors as possible.
Currently I have two or three favourite shirts I wear, usually under the same black v-neck sweater as always, jeans, and some old clunky dress shoes I wore for band four years ago. I usually wear these things under a weird old leather jacket I inherited from my grandfather, and sometimes with my only tie. I think I look good, but it’s just a notch above the average, and the few good-looking things I have don’t make up for a full wardrobe.
I noticed that there are definitely some dressier shoes out there, but I don’t know where to look, and I definitely can’t meet much more than $100 in price, and I’m hesitant to wear anything other than my jeans on my legs… I am unsure just what real pants should be like to look good. My options are limited because all the used and cheap clothes my family has got for me don’t tend to fit me, even if I wanted to wear them. I’m much thinner than what most shirts and pants that match my height will fit. I’m in need of assistance in terms of where to find good fit, what constitutes a good pair of pants, where to find shoes in the $100-$150 range (I couldn’t find those nice Mr. B’s you mentioned), and just what colours match with what. More than one colour kind of intimidates me.
I think your advice is really great, and I’m thinking that your Effortless Guide to Graduation Your Style could ensure that I am definitely looking the part of the effortless gent when I head off for post-secondary this year.
http://howellsdesign.com/ Paul Howells

I was one of the lucky few to obtain a prerelease of the GYS, and after reading it beginning to end, I can easily say that it is incredible. Starting from the ground (er.. closet?) up, it guides you on what to wear, when to wear it, and any other wardrobe-related questions one could have. If you’re not one of the three winners here, but you still want to develop an understanding of how to look your best, you owe it to yourself to get a copy.
JIMMY HUANG

After browsing this site, SF, and AAAC, I have figured out my look. I mainly wear chinos and well worn raw denim. I’ve been wearing Sperry Top-siders, and L.L. Bean Signature shoes, but I’ve recently moved into Allen Edmonds! I’m still a high school student so I’m just a teeny bit overdressed. I wear a lot of OCBDs and am starting to wear polos now. I have some great outerwear from Club Monaco, and some huge wool sweaters, as well as some great Jcrew things of similar nature. From this site, I hope to learn more such as how to get a better fit, how to match certain things, and how to find high quality items without putting a huge dent in my wallet. So far, it has helped a lot and I hope to improve my wardrobe using your guides as I get more money from working during college. Currently, I need most help with my fit. My eyes aren’t good enough to tell when something fits impeccably (have yet to get anything tailored though most of my things seem to fit well). I’m also short (5′ 5″) and have a bit of trouble finding my size. Besides all this, I’m looking to get more into blazers, sportcoats, and suits as I slowly work my way towards professional settings. For now, I’ll stick to the Ivy Style and stick to this site to buy better things in the future!
Miles

I’m 34 and work downtown Toronto. I used to spend decent $$ on my wardrobe (never uber trendy, but fashionable) but as a new dad with an 11 month old baby girl, I fell into the trap of letting things slide.

I’m trying to get it back together, and have my bases at work covered I think, but I really struggle on the weekends, especially in the summer. No matter what I wear, I always feel like I’m 10yrs old, especially during the summer… and at 6’4″, you can imagine how odd this must be!!

I simply want to look like a mature and fashionable dad. Too much to ask!??
gmt4

I’m 20 and about to graduate from college. I dress fairly well and am happy with the basic components of my closet, but am having trouble finding the finesse for my post-grad life. At my college, most men wear a coat and tie to class, but we swear by some seriously rumpled casual style.

I am looking to streamline my wardrobe and develop some trim, clean looks for life as a young professional. I’m hoping your guide will help me to find the wardrobe I need for the real world. Learning how to develop more mature style will be a huge help as I venture into the real world.
Denny

I’m 26. About a year ago I became interesting in improving my personal style. I’ve been learning how to dress better and I’m trying to put together a classic looking, quality wardrobe. Most of the mistakes I’ve made have been buying clothes that don’t quite fit, usually because I got a good deal on them. I’ve yet to purchase my first suit as I’ve been hesitant to make such a large purchase. I’m not quite sure what I need in that regards. I still have trouble matching different patterns, and the ‘little things’ that tie everything together.
http://www.facebook.com/profile.php?id=1042950012 Cyril Boggs Serrano

I’m 25, been out of school for a couple years now and in the last year landed my dream career job. While the workplace is casual (we’re a tech start-up), I don’t want to be stuck in the same clothes I’ve been wearing all throughout my college days.

Hoping to not only upgrade my current wardrobe, but to also develop my own style as second nature – knowing intuitively what works and what doesn’t for me.
A_wall82

I’m 29, recently single with a new job. I have the pinstripe three piece suit and my standard blue jean with white tee/ maybe a sweater. I lack any style clue on anything blue, brown or anything varying from my norm. In fact, I just bought a pair of khakis and have nothing that I feel comfortable wearing with them. On top of all that, I’m 5’8″ and 120lbs. I need a lifestyle change, that starts with me.
http://twitter.com/richardfott Richard Fott

I’m 24 and am on the brink of changing my style and dressing in to adult hood.

Current hiccup:
My office is business casual, my Pinterest is more business than casual, but wardrobe is more casual than business. I’m finding it hard to make the transition from what I have to what I want. I run in to problems like:
- How do I go from untucked to tucked when it seems like all my button up shirts fit really well when untucked but aren’t long enough to be tucked?
- How do I go from Converse All-Stars or Boat shoes to dress shoes?
- How do I go from leather sport coat to blazer and tie?

What are the key items that I need to buy first in order to accomplish this transition? Once all those questions are completed, how do I use the new wardrobe to dress down if I want to?
http://twitter.com/richardfott Richard Fott

I think if you’re buying your first suit you should go with the well fitted black suit. It’s always in style and can be worn a variety of ways.
Edwardjsiegel

My big problem is imaging how to keep in mind how different pieces of an outfit can work together when purchasing things. Its easy to know when you buy a blue blazer, chinos, or a white collared shirt that they will go with a lot of things. But I have a harder time with say, colored chinos, or certain ties,or whatever, that may look good as individual pieces, but dont know how to bring them together.
Brian

My current wardrobe consists of a large number of t-shirts, well-worn jeans, and some outdated dress shirts, of which many look like garbage bags over my thin frame. I’m 24 years old and starting off my professional career, which means I’m dressing up much more often. Because of this, my t-shirts, jeans, and baggy dress shirts aren’t cutting it anymore, so I’m looking to upgrade into something more fitting in my profession (dress pants, shirt, and tie). The most difficult part I’m finding is how to tie the outfit together with accessories. What can I add to the bland pant/shirt/tie combination to make it a style of my own rather than just another person dressed the same at the office.
BudiCW

I surely need this Baron, thank you for the chance to win it. I’ve been following effortlessgent & all the other sites you’ve recommended, & really helped me to improved my personal style, especially about style on a budget, so to have it all in one book will surely be a convenience, thanks. I hope I win
Akira Tamashiro

I recently graduated, and now I’m moving from a marketing trainee to a headhunter position. Wink wink, the outfits are absolutely different. I used to wear jeans, casual shirts, and sneakers – that won’t work when you need to interview CFOs. I always thought social dress code was boring, but now I see its true potential.

Love from Brazil!
Christopher Johnson

Since I graduated from college last year, I realized wearing tees and sweatshirts of my school’s football team doesn’t cut it outside of the campus bars. I’ve found I like to dress nicely, but as a bigger guy (I was a defensive end), I feel like some styles I like don’t particularly work well for me. To complicate matters further, I’m on tight budget, so I can splurge only once a month. Effortless Gent has really helped in this area. Thanks a lot!
Ethan

I’m 23 with a very athletic body type but am struggling with how clothes should fit. I typically wear conservative/Dad-like clothing that do not fit me very well. Ideally, I would like to shift to a wardrobe that is more youthful, lively, and more form-fitting, while still being office appropriate.
TenneZman

My problem is that my work is business way casual every day. Even most days when I wear wool pants and a dress shirt I am overdressed. I can remember wearing ties on my job interview and being told then I didn’t need to wear all that. Oh well, so many ties so few occasions.
http://twitter.com/DavSkies David Reyes

Hi Barron! This is great news! I mean it. I have been following effortlessgent for a while and always thought a guide like this, that compiles all good tips you have given out, was a must!.Like it or not, we all are judged by the image others have of us, what others THINK of us. I’m a 24 years old Business Analyst, this year is crucial for my professional growth and earning a promotion, but despite working hard and giving results, as my colleages are older people, I am faced with the need of projecting an image that says: “Yeah, I’m young, but I’m a professional, competent and reliable man that works hard to achieve his responsibilities” I think I have a young-formal-casual style. I’ve always liked good shirts, polos, sweaters, cardigans, good jeans, formal shirts, ties (my addiction), suits.. etc.I enjoy buying clothes and dressing up. But somehow (due to budget, being in a hurry, lack of imagination or color-coordination habilities…) I can’t seem to put it all together.. that’s my major problem.. It’s kind of frustrating. Sometimes I end up with things that look individually good but don’t know how to match them in order to create a good complete look (example: I have more than 5 ties that have never been used because of this). I end up repeating the same combinations and disapointed of my ‘style’.I really think I need GYS’s help. I expect to understand the ‘science’ behind those great outfits I see in this site and how to build my own personal image.. Effortlessget has already helped me understand the reasons why a good personal image is important and how to solve some issues such as how to choose the right fit, how to choose quality shoes, how to manage the basics.. but still have not been able to reach that complete look that shows how much I appreciate life and enjoy work.David R.
OutofSkool

I’m 23 and started my first job out of college a few months ago. I’m used to wearing polos and jeans, but now that I’m in a business casual workplace (law firm), I feel a little sartorially challenged. I’m starting to develop my own style and replacing my loose fitting wardrobe with a sharper looking one. To that end, I hope the Effortless Gent can help me.
SouthernScholar

I’m eighteen years old, and about to graduate high school. I’ve spent the past thirteen years of my life focusing far more on the academic aspects of my life than the social – such decisions have served me well, as I will be attending my dream college next month, but with this new chapter in my life comes a new opportunity for growth. I want to show the world that this generation CAN be capable of chivalry and class. I have a bright future ahead of me, but my current wardrobe of jeans and graphic tees simply won’t cut it. The ultimate goal is law school, and I’ve been around long enough to know that impressions and appearances are half the battle where I”m headed. It’s hard for someone my age to try and adapt what is generally accepted as a grown mens’ world of style, but frankly I’ve grown weary of the old “teenage nonchalance” wardrobe. It’s time for a fresh start, and I’ve a strong feeling that this is as good a place as any to begin.
Michael Berwick

Hey Barron, I’m 20 years old and just finished my first year of college. I like trying to dress with style but I find it hard because of my summer job as a roofer. I wear old work clothes all day and can’t find the time or place to “dress up”. I would like to learn from the guide how to bring together my wardrobe so that I can wear formal outfits with a casual side to them (business casual I guess). The majority of my friends dress the same and I fall into that category. I hope to at least stand out as more fashionable than I use to and gain a more older look! I have found your website very helpful for starting to dress better (with people noticing already) and even if I don’t win the free copy I will be sure to purchase the GYS.
Kennmyers

It doesn’t matter what you do, who you are or how you dress, we can all use some great advise and an honest opinion at times. I lost 50 pounds a couple of years ago and have had the pleasure (?) of having to completely rebuild my wardrobe. The question I always struggle with is how to incorporate trends with an overall desire to achieve a classic and professional look. How far can one go without looking like a total douche bag? What is the line between fashionable, personal style and being too trendy? My budget (do to current economic circumstances) is very limited. Trendy clothes can be found everywhere at my budget, but how does one decide what the classic investment pieces should be? So many questions… I look forward to winning a copy of your book to read on my iPad, and have my questions answered.

Thanks!

kdm.
Ryan Ferrier

I can’t consistently pick out killer outfits. My game will be tight maybe 1 or 2 days the week. Then I get lazy. And I feel way less together and sharp when I’m dressed all sloppy.
Jesse

As I continue to build my foundational wardrobe it’s so helpful to get expert guidance.
Liam

I am stuck with blues and greys.
Ckiser7744

I live in the world of olive drab!
Garrbbage2

All I have is black blue and grey clothes. I need a change in my life!
Psych

I’m a graduate student transitioning from the carefree life of a young 20-something beach bum to that of a mid-20′s clinical professional. My style is in desperate need of an update, and fast. Not only am I working with a meager assistantship budget, but with my lady and I currently in a long distance relationship, I a) have no clue how to dress and b) would love to dress to impress (her) when we do get to see each other. Help me Effortless Gent, you’re my only hope.
Justin K

Hey, Barron. I’d appreciate one of the free copies of your style guide because I’ve just made a major life change. I’m 27, and I’ve been studying for the last five years as a graduate student, ready to join the world of oddly dressed English scholars. I would have fit right in. But after a recent change of heart, I’m abandoning the doctoral coursework I’ve now completed (and I’ve completed all of it) and opting for a career in the banking software industry–an environment I’m ill prepared for both psychologically and sartorially, I’m afraid. I read your blog and Dappered all the time now, and I’ve learned a lot, but a guide I can take with me anywhere would be of great help. I’m an intelligent guy, and this will be my first professional full-time job. Because of the nature of the work (I’ll be traveling, teaching our clients how to implement the banking software), I need to look sharp from day one. Hope you understand. Please help!
Jimmy T.

I’m 22, a week and a half from graduating, and then I start my work as a professional consultant early in June. My wardrobe right now is in its adolescence – this past year I’ve worked on transitioning from worn-out jeans and t-shirts to dark denim and button-downs. With this guide, I hope to literally, and figuratively, graduate my style. I need to start preparing myself to dress for the world of business appropriate – where some days I’ll need to be wearing a suit and others I’ll be fine in a collared shirt and nice slacks. I’m looking for that je-ne-sais-quoi that can take me from the level of collegian to college-graduate/pseudo-professional, and I believe your style guide might just be it.
michael y

I’m 23 and I have recently realized my style and wardrobe are very much in need of an upgrade. Soon I will be entering the office world (currently working in construction) and I’ll need to make some clothing purchases. the biggest hangup for me is money. I don’t have much of it so I need to make the best purchases I can! I realize that it takes time, but I am trying to learn all I can so that I can step into a new wardrobe as efficiently as possible!
Chris L.

I’m a 23 year old new graduate finally getting a fashion sense. I’m pretty naive about how to build my wardrobe (from ties and shirts to shoes) for the different seasons – what materials are for winter, spring, etc. I’m also on a very limited budget so I really have to pick and choose what I’m going to buy every couple months. I’m sort of between sizes too so a lot of times I have trouble deciding to go with sizes with what fits. Finally, I’m also interested in learning about proportioning my clothing – getting ties, shirt and collar size, and lapel width all in proportion in my outfits. Making the right decisions on seasonality, proportion, and price are all things I hope I can improve on by reading GYS – and maybe I’ll notice more looks both in and outside of the office.
http://danvalenza.tumblr.com/ Daniel Valenza

I have my professional daily work style pretty well in place. it does what it needs to and is easy enough to put together each day.
I also have my most relaxy, lazy sunday bbq done and done.
Where I need work in my wardrobe is the in-between. Whether I am going to a bar with some friends, out on a casual date, or just around town, I need to work on the effortless yet adult and well put together look a few levels above a t-shirt and few levels below a shirt and tie.
EB

I’m 23 and needing to prove myself at work and with clients. Dressing appropriately is critical for my future success.
Craig

I’m a 20 year old Junior in college and I’m just starting to revamp my style. I’m slowly trying to graduate from all the American Eagle button ups that I wore in high school in order to have a more sophisticated yet simple look. I’d love to know what things are worth spending on (seeing as how I’m a college student with not much money), and where to shop for good affordable clothing.
Daniel Vedamuthu

What do you need help with most?
I’m a 35 year old. I’ve been implementing many of the ideas I’ve found on EG. Some I did unknowingly. I’ve been working on losing weight; it doesn’t make much sense to upgrade my wardrobe if it’s going to not fit in a few months! What I need help with the most RIGHT NOW is whatI can do to keep some type of style while I’m transitioning. Another Big Issue for me is finding footwear that can survive a Minnesota Winter. Even the independent shoe store that provides that high quality service and products carries mostly rubber soles because of our winters. I also have wide feet and it makes canvas or fabric dock shoes or sneakers look strange (or if I get something to fit the width of my shoes, they are so long they look like clown shoes!)

What would you like to improve upon most?
I want to improve the efficiency of my closet and dresser. That is, I don’t want it to be bursting at the seams (ha ha?) with stuff just because, but to have a very modular wardrobe that is high quality. It also has to work through Minnesota winters and Minnesota summers.

What kind of outcome would you like?
I want a wardrobe that is stylish for work, but that can adapt to also be comfortable so I can still be stylish when sitting on the couch or playing with the dog.
Snoboardp

My wardrobe consists of mainly v-neck tees for casual wear, with dark denim. Dressier nights will include a button up (i favor checkered designs) with a sweater.

Hope to get a better sense of what style works best for me, and some more versatility in the wardrobe without breaking the bank. No one wants to look the same everyday.
john

I need help with fit! I only just realized over the past year or so that I’ve been buying size large all my life because that’s what I thought I was when I’m really more of a medium.
hotdogwater

matching colors – eg ties to dress shirts
AndersLS

I’m 24 and looking to improve my professional wardrobe.
Joseph W.

I’d like to figure out what kind of shoes to be wearing in the summer when I’m wearing shorts and a polo.
G.

I am changing jobs and need to purchase some professional clothes, my previous job had a uniform and my wardrobe consists of old things I’ve had since college and gifts.