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.

http://twitter.com/tdouble_u A$AP Frolic.

I’m currently struggling with what to wear to the office day in and day out. Everyone around me dresses so low key and casual, so it’s very easy to get caught up in doing that…but I’d rather not!

Hopefully your book addresses that!
Flexobrau

I am graduating college, so I do not have much of a budget, and I need to make the wardrobe transition for my first full time office position.
aHarold7

I would really like to dress well, and I believe I do, but I don’t want to make myself stand out in my small-town, high school crowd.
Chris

I think I do ok with putting outfits together and dressing appropriately for the occasion. My issue right now is that I’ve added some pounds so I want to make sure the way I’m dressing is right for my weight (no man-muffin tops, etc.) as well as learn some ways to dress that accentuates the good and helps disguise the bad. I’m hoping GYS can help me with this, as well as just broaden and expand my knowledge. Thanks!
Joe D

I’m currently trying to expand my seasonal wear. I want to find out what fabrics and styles of clothing work best for various weather conditions.
positivecarry

Most of my clothes are button up shirts and pants for work, and I just wear long sleeve tees, t-shirts, jeans, sweatpants when I’m not at work. I’d like to find some new clothing combos.
Brian

I’m trying to up the work attire to match a new promotion. I need some help!
judeobscure

Work wear is funereally easy as I am suckishly limited to black shoes, black trousers, black suit jacket and any color shirt and tie I so desire. It’s the casual wear that I need the most help with although, I do know enough to avoid cargo shorts.
adiventure

I’ve been having trouble as I lost a lot of weight, and now have options I never had before but also clothes that are far too large.
Sdesai3

Trying to find the the right pant size for slim lanky guy like me. 30/30 or 30/32?!
Matt

Hi Barron. Love the blog. I have a bunch of problems, and want to dress well, but it never seems to work out. First off, I have no idea about sizing whatsoever. As far as shirts, M’s look skin-tight, but L’s look like I’m wearing my big brother’s stuff…short sleeves come down to the elbows. Whenever I find a shirt or sweater that seems to fit right, it’s short and comes up in the back when I sit. I’m a very normal size and shape, so I don’t get it. I also have problems with jeans and pants…either they look skin tight or baggy. I can never find the right fit. I think I have a good sense of what my personal style is, but I don’t live it. I always tell myself, “one day” I’ll dress the way I want. But it’s always “after I drop 10 lbs” or “after the holidays” or some other excuse. I’m thinking of finally taking the plunge, and your site has given me a ton of great advice.

I also own one suit, which I’ve had for years. The top looks fine, but the bottoms look like MC Hammer pants. I just recently discovered that I could get “athletic cut” suits. Meanwhile, I look like a boy in 1989 getting ready for his communion or bar mitzvah, with ill-fitting pants that envelop my shoes.

This is the tip of the iceberg. I hope to win a copy of your book because a.) I’m a disaster and could really use some more advice, and b.) I hope to take the plunge and buy some clothes soon.

Take care!
Rafal

Hi Barron. Mostly my style issue is that I do not know how to wear some of the pieces I already own. There are also probably vast holes in my wardrobe that need to be filled!
Azhrei

My biggest hang up is how to dress well but not look like an old man. To combat this, I’ve put colored laces on my leather shoes, but I can’t figure out the rest. I’ve also found it difficult to develop my own personal style. By reading your book, I’m really hoping to have a one stop resource to answer by basic style questions.
Vic Licciani

Because im a 40 year old virgin who dresses like a loser. still living at home ..need help from you barron to get my act together..
Smooth510

My current style is basically khakis and a polo shirt or some color shirt cuffed up. Not pleased with my physique so I still keep my shirts untuck.

Somehow found this site along with a few others and finally realized i was long overdue to dress more grown. Wore baggy jeans, Jordans and LRG tees or jerseys for way too long. Unused to hate it when my girl asked me to dress up for her family parties.

But thanks to this site, diapered and some others, im slowly but surely changing.
Thinning in SD

I’ve had some pretty big life changes the last two years having gone from a size 54 pant and 3 or 4XL shirts to a size 36 pant and large shirt (still want to lose 15 more pounds!). During that transformation I’ve also met the love of my life (who fell for me packing an extra 80lbs or so from where I am now) and makes me want to be the man she deserves. On top of that I’ve also been promoted to a management position at work, so I have people reporting to me as well as more interaction with executives at my Fortune 100 company. My office itself is business casual, so I want to look good and like I belong and be memorable, but without sticking out like a sore thumb and looking like I’m trying too hard or trying to show people up, especially since I’m about 20 years younger than my fellow managers.
Reggie V

My biggest style hang up is finding off-the-rack clothes that fit me well.

I am on the shorter side (5’6”), have a wide chest, slim around the waist, and have short arms. Until last year, I was unaware how badly my clothes fit me. They were simply too big for me. Then, I started reading a few style blogs and realized that almost everything in my closet was wrapping me like a blanket.

I started to throw out most of my old clothes, which was a pain because I had spent years and $$$ accumulating them. I decided that I will only buy stuff that fits me properly and not be tempted by discounts and new trends. The idea was to develop a small wardrobe in which everything would be a decent fit. Since I cannot afford bespoke clothing, I have been searching for off-the-rack brands that fit my particular frame well.

It has been a frustrating process. I have lost count of the number of times I have bought something and returned after trying it at home because the piece was too long, too loose or both. Specifically, the dress shirts seem to billow around the waist (even the slilm fit ones) and almost all of them have longer sleeves than my arms. The casual shirts and polos that I want to leave untucked are too long and look like I am wearing a dress. Some trouser fit me well around the waist but almost all are too long. I want to wear pants that have no break but I invariably end up with ones that have too much break.

The brands that have XS size does not fit around the chest and shoulders. If I move up to S size, these fit well around the chest and shoulders but tend to be loose everywhere else. I have found a couple of brands that fit decently, but only after some alteration by a local tailor. And spending $20-30 to alter a $50 trouser does not feel like a good use of money.

What I hope to get from GYS is a sense of how I can slowly eliminate the ill-fitting clothes from my closet (there are still a lot of them in there) and replace them with ones I truly like and fit well. I would be very interested in seeing specific recommendations similar to what is provided on the site often. I hope to be able to do all this without spending thousands of dollars!
Devyn Nelson

My biggest style hang-up is incorporating color into my wardrobe. I’ve always liked black, but it has been to the detriment of having color in my wardrobe, and while I am slowly changing that, I need some help going about it.
Dzimalrash

Oh yea I do have some wardobe hang ups.

I’m 24, just started my career as an engineer. So with lots of help from your blog, I managed to pretty much overhauled my wardobe, getting rid of the ‘college boy’ look.

But I find myself still fond of graphic tees, even though I hardly wear them anymore. Is there a good way to inject the ‘fun’ of graphic tees (think Pull & Bear, definitely not Ed Hardys) into my getup?

Keep up the good work with your book. I’m sure it will stand the test of time so don’t bother writing a sequel to it
Jake

As a college student on a very tight budget, it is quite difficult to be able to dress as well as I’d like to. Not only do I have to balance replacing my Hollister and Abercrombie with more mature clothes with being able to afford books, I have to do so in a way that I don’t come off as “that pretentious asshole that dresses as if he were meeting the President everyday”. Not an easy task, let me assure you.
NateR

The biggest hang up for my style currently is the tight budget I have to live on. I’m two years removed from college and still haven’t landed a decent job so my doing everything I can to make my meager income work for me. So as of right now, I have very little room in my budget for new fashion, but I’m also coming into a place where my style is changing and become more and more my own. Up until recently I was still receiving clothes from my family, and you can’t be as choosey with someone else’s money as you can with your own. But I’m working toward that goal and while it is a slow process, its definitely worthwhile.
Joe

I’m a big fan of your site and would love a copy of your new guide. I’m in my late 20s now and have finally figured out what I want most in my wardrobe. The most important issue I find is fit. I’m short, 5’5” and finding the right fit at most stores is difficult. I’m stuck somewhere between a size S and M. Experimenting with color can also be tricky. I do have some quality pieces in my wardrobe but I normally just throw on jeans and a T to save time. Help!
http://www.facebook.com/people/Mauro-Miguel-Morales-Mejia/548115721 Mauro Miguel Morales Mejia

Hi right now I have no real style. I’m a very fresh guy who works from home so I normally wear jeans and some tee. I would really like to find a style that looks more professional but still keep my fresh attitude. I would love to win that copy!
Joefamous

I have a hugely varying sense of style. I have nice stuff from my days as a Nordstrom employee but my current job is a jeans and t-shirt gig that is polar opposite to my former wardrobe. I find that I randomly try to dress up just to prove to myself that I still know how. I mostly try buy things that are stylish but not trendy and have things in the regular rotation that are years old but still look good. I just try to make what I have look nice without looking like I spent an hour figuring out what to wear.
D4rkRXN

Over the past year or so I’ve been slowly been working on improving my wardrobe. However, I tend to still wear mostly jeans and a t-shirt, albeit well fitting ones. Though it’s a tremendous improvement from my old “uniform” of baggy cargo pants, clunky white new balance sneakers, and an oversized t-shirt. Now I’m at the stage where I’m really trying to upgrade my style and what I struggle with currently (and hope that GYS can help me with) is: knowing what a good fit is, how to wear colors that complement each other, and overall just expand my horizons in what I can wear and how to wear it.
amcdonald

Hi Barron, thanks for the giveaway! For me the biggest challenge is putting together a wardrobe systematically, so that quality and style are maximized, while $$$ and wasted items are minimized. If I could pop open my closet, see a handful of clothing items, and be able to quickly assemble a stylish and dress level appropriate outfit, I would be very happy indeed.
K301

Hi, I’m in college and my challenge is finding good stuff on a college budget, and knowing exactly what to look for.
http://www.facebook.com/zacharywenner Zachary Aaron Wenner

Hi, I’m a college student on a small budget. I recently realized how important it is to look sharp and how people view me differently when I dress nice. I shop at thrift stores and recently started saving and researching so I can get some base wardrobe clothing to upgrade my style. I’m still researching and trying to figure out what works and what doesn’t. Sometimes I’ll buy something (specifically at thrift stores) and realize later it doesn’t complement me at all or just doesn’t plain fit right. This guide would really help point me in the right direction. Thanks -Zach
Andrew

I have suits, shirts, ties and all sorts of formal wear. I have plaid and other comfortably casual things to wear. I can’t for the life of me find a good middle ground of casually classy. Furthermore, I love color but I can’t seem to find the right colors to make my wardrobe cohesive and still a little flashy, I know you wrote a post on it, but I imagine you wrote more in GYS so I want to take a crack at that.
Josh L.

I’m a new young professional, but here’s the problem – my company is super lax in dress code out here in California. Most people come to work in jeans and a t-shirt: a hoodie if it’s cold. That’s been my fall-back for years, and so while I want to graduate my style, my incentive is very small. I hope that this will give me a way to up my ante without going too over the top; a balance I can’t seem to find!
Rob

Ah, hahhaha. I’m likely a different kinda guy than most of your readers. I’m a transgender man (which means I lived as female for the first bunch of years of my life.) I’m just now living as the guy I’ve always felt I should have been, and oh, man! The clothes are fun! The clothes are confusing! I’m graduating my style in a really great big way.
Chasmang

I feel out of place sometimes when I try to dress nice at work because there isn’t much of a strict dress code at my office. Just wearing a nice pair of slacks or a button down makes me feel too formal, much less trying to incorporate more interesting colors into the mix. I manage most of that through my ever growing collection of awesome and colorful socks, but I’d love to be confident enough to wear some of the chinos I see advertised here. They look so cool, but I imagine I’d get them and just leave them in my closet, too embarassed to wear them in front of my co-workers.

Your site has helped me to start being more style-conscious and dress better, but I hope your book can give me the confidence to jump completely in.
Lou F.

I have no respect for tradition and no respect for
non-expert opinions. I guess that’s why
I worry about falling into the common fashion tropes I see every minute of
every day in my working class New England home.
My life is filled with Polo wearing ex-frat boys, older Dads with tired,
earth toned button down shirts, ironic T-Shirt wearing aging “gamers” and blue
jeans, blue jeans for every and all occasions.

I’ve also got a hard time understanding common social
queues. I’m
worried that by experimenting with new ways of dressing I’ll fall into an
existing stereotype that doesn’t describe me at all. So as a 30 year old I fall back into the way
I dressed in High School, cargoes, T-Shirts and Sneakers with an occasional,
stumbling foray into something more dignified.
At least I know what that style says about me, even if it’s not great.

I know what it feels like to dress well because I do so at
work but in the rest of my life I want to develop a style without falling into a
trope.
A. Wintervold

I am 17 years old so my current wardrobe consists of chinos, a pair of dark slim cut jeans, white t-shirts and oxford button down shirts.

I would like to get some tips on how to expand on this by adding more variety and especially ties as there has never been a place or time to wear them during my high school years.
http://twitter.com/BetterGuyX Brian Joyner

Love the concept! I like how you do what you do
http://twitter.com/ConnoisseurTT Modern Connoisseur

Hi, hailing you all the way from Trinidad. Dressing well in our tropical climate has always been an issue. What you all call “Summer fabrics” i.e. Seersucker, Mohair etc are very very expensive in this part of the world because of this as an aspiring gentleman at times I have no choice but wearing polos & t-shirts over dress shirts. Wearing a suit during the day is out of the question unless you’re in an air condition environment all day. Even at night it’s a challenge and layering is also out of the question. For evening events that arent formal I may wear caridgans or polos. I really like what you all are doing and any advice or knowledge I can gain to help me shape my wardrobe accordinly would be awesome! I definitely need to learn more ways to dress well while not feeling like I’m a walking sauna.
Jon

I’m in process of building and finalizing a wardrobe that can last for the rest of my lifetime (28 – working professional in socal) and would like to know the components and how to guide to do so, with minimal waste in spending and maximizing efficiency. I employ a conservative, classic, timeless style
Nate Gilbert

Shirts that fit right, Oh, and money. I try to do the best I can with what I have.
Spencer

About a year ago I embarked on the extremely long and arduous task of getting healthy and losing 140 (!!!) pounds (I’m half way there!). Obviously along the way, as the pounds fell off, my clothes, such as they were, started getting looser and looser. As I started to consider new wardrobe options, I realized that I actually cared about style, and that I no longer wanted to be a t-shirt and jeans schlub. About a month ago I started frequently EG, as well as a couple other style sites, to start getting an idea of how I should start rebuilding my wardrobe. As I still have a considerable amount of eight to lose, I cant jump right in and buy a new wardrobe, but I want to get a head start for the finish line and start developing better taste in clothes as I make the transition from “silly t-shirt guy” to “dashingly handsome gentleman”. I’ve recently picked up a few new clothing items as I just started a new job, and was amazed at how even little changes has done wonders for my confidence. I’m going to buy the guide either way (unfortunately I couldn’t get in on the prerelease for various reasons), but hell, I cant help but try and score a freebie!
Christian P.

Hey Barron, I’m a 20 year old college student studying to become a high school teacher. This semester, I started an internship at a local high school. Sometimes, I’m mistaken for a student! I mean, there are actually some students with great style. One time, a student and I were both wearing blue button downs, khakis, and sperrys. I can’t seem to find my own style and haven’t graduated from my teenage wardrobe of hoodies, oversized t-shirts, and jeans mixed with the polos and button down shirts I now buy. My wardrobe is in its awkward years and right now, I don’t know what clothes to buy or get rid of. I need a style overhaul. Your blog has helped a lot and I hope to read more about having my own affordable style in your book.
http://www.facebook.com/bill.speakman Bill Speakman

I’ve got a few challenges that require regular problem solving. For one, I’m a video journalist by trade. There’s not much of a dress code, but I’m a bit of a clothes horse, and like to look sharp under any circumstances. Here’s the trick… on any given day, I could be interviewing the Governor, covering a fire, or doing a feature story at the dog park, etc… . Since the news isn’t always planned, I have to be ready for anything, so balancing style and functionality can be tricky.
On the “build” side, there are challenges too: Broad shoulders, narrow waist, long torso, short and thin legs, but with size 12 feet. Its hard to find even casual clothes that don’t require tailoring.
I don’t care about “brands” but I tend to stick to the few things I know tend to work… Bonobos shorts, Fred Perry Polos, Levis jeans, and a few basics from H&M usually work… for the weekends. Where it gets sticky is staying sharp during the week in something I won’t mind being destroyed if my morning story with a room full of “suits” is followed by an afternoon of documenting flood damaged neighborhoods.
As I move through my mid 30s, I also want to stay age-appropriate without getting boring. I’m sure your book will have lots of helpful information.
Erik

I believe I’ve gotten a decent start on overhauling my wardrobe, but I still have quite a few details to fill in. I’m 22 years old, live in a temperate climate, but I love taking the opportunity to travel to other (often colder) climates and wear some of the pieces I’ve acquired so far. Because of my limited budget, a fair amount of my recent wardrobe has come from ebay, consignment stores, and thrift stores. A guide that would help me best allocate my funds would be very much appreciated though, because I’ve been told and come to realize through experience that the most expensive pieces in your closet are the ones you don’t wear. Thanks for the giveaway!
RTulk

Hey Barron,
I’m currently in the military (stationed in California), so my work clothes are not about to change. I need quite a bit of help when it comes to the off time though. I’ve been wearing jeans (and sometimes cargo shorts) and t-shirts for as long as I can remember. A few weeks back I was looking through some of the higher end outlet stores in Cabazon, and I realized my wardrobe was severely lacking and need improvement. I’ve been logging in several hours of research on websites like yours to fix that.

My biggest hang ups (besides starting from square one) would be using color and stepping away from only wearing t-shirts. I have a little trouble with my color vision, and when I go looking for clothes I rely a lot on my wife. She likes to suggest black, grey, and white, and very few colors outside of that (except when it comes to ties.) As for stepping away from tees, almost everybody here on base walks around in their Afliction, Metal Mulisha, and other ridiculous graphic tees, and I want to be close to the polar opposite. I’m just a little iffy on where to start.

I hope GYS will help me build a solid foundation for developing my own style. Then I can step away from the teenage clothes and dress like I should have been dressing for some time now. I also hope to accomplish this without taking hard hits to my finances.
CSweet

I live in Bangkok and I am just starting to get into style. My biggest problem here is that the heat and humidity in this city is INSANE! Layering with coats/jackets is not an option. I am looking to upgrade my style for this tropical climate, but still look killer weather I be outside in the heat, or at a University nightclub chasing Thai girls in the AC.
http://adventure-some.com/ Matthew

I just finished the transition from labor jobs to college to an office job. Now I need to upgrade my wardrobe to fit. After doing some research (here and on some of sites that you’ve recommended) I recently purchased some new shirts and am slowly building my wardrobe.
The hardest part for me is that I ride a motorcycle as my main transportation. So I have to stay safe (jeans, boots, and the heavy leather jacket) while commuting and am still figuring out how to make that look ok.

Ultimately, I want to create a personal style that is subtly but distinctly my own. I am picturing jeans, perhaps french cuff shirts (I’ve got the cuff links, might as well use them), and possibly a vest. (You may be shaking your head as you read this…)
Dave

Having survive the last several years as an unfunded PhD candidate, my wardrobe was my absolute last priority. Now that I’m in the write-up phase and working professionally in NYC, I’ve had to quickly adapt and try to get my clothes and wardrobe up to snuff. My hang-up, jeans and a fitted shirt have been my primary outfit for the last few years and now I’ve to be able to look respectable in the pubic and professional arenas.
My hope would be that GYS can help me learn the foundations for my personal style and can help me gain the knowledge necessary to develop a wardrobe that will fit with the branding and professional image I am trying to create as a non-academia based scholar and consultant.
http://www.facebook.com/profile.php?id=1628677817 Brian Schiele

I am a Veteran, and a National Guard retiree. For eight years I was full time with the National Guard, which included a four year mobilization working with wounded Soldiers. So for eight years I wore the uniform and didn’t have to worry about what to wear to work and all that..
Since retiring I have struggled with trying to figure out what to wear to work, so I am always looking for information about dressing for work.
Brian
Adam Luo

I’m starting graduate school in a new city in the fall, and my hope is that GYS will help me in … every area.
http://twitter.com/BadForecast William Haygood

I’ve learned an incredible amount from the site over the last year. I’m looking very forward to this.
yabbs

I’m struggling with getting over my penny pinching ways and actually spend some money on quality. Then there’s the “office style” at my workplace is much more casual than I would like.