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Hey gents,

I want to address the younger dudes right now. I’m talking to the guys who know better than I did when I was their age… the guys who are realizing the importance of a well-balanced wardrobe, and who want to nail it the first time around so they can skip the years of trial and error that most of us went through.

I wanted to pass along five useful tips that will help get you on the right path from the beginning. I’ve received a lot of emails saying how helpful EG is to a guy trying to fix his mistakes, but there’s no concise, step-by-step guide for the guy who wants to get it right the first time.

Not yet, anyway… more on that later.

Here are five general guidelines to set the groundwork for what needs to get done. Don’t write these off. As with any big reinvention, the planning and foundation-building process is just as important as the actual steps you take to progress.

And now, the tasty and useful morsels

1.) Read. A lot. And then read some more.

EG is a great place to start, but you want to glean as much info as possible from as many sources as possible. This will give you a better overall view, and gathering info from several places allows you to filter out the stuff that doesn’t ring true for you, and to apply the stuff that does.

Don’t get stuck on this step. Some people just read and look at photos, but don’t make any actual changes. You’re defeating the whole purpose if you do that. Read and then apply, read some more, readjust, reapply, etc. You get it.

Some sites (besides EG) to check out: Primer Magazine, Real Men Real Style, and Dappered, for starters. In fact, to make it easy, just check out the Purveyors of Style links I have down below in the footer. When you’re done reading this post, scroll all the way down and you’ll see it on the right.

Tumblr is also an excellent resource, especially for visual images of people doing it right. Just check out the #menswear tag.

Be warned though, if you’re a beginner, you may feel overwhelmed with some of the stuff these guys talk about. It’s advanced shit.

Just admire the pretty pictures, make note of what you like and don’t like, and move on. Don’t get too bogged down in Brunello and Boglioli and Bastian if you don’t even know what kind of denim you should be buying. Basics first!

2.) Be honest with yourself and what you have

Don’t try to pass off your ratty, billowy button-up hand-me-downs as decent dress shirts. Start over and buy new stuff. Save those old shirts for mowing the lawn, or something.

If you have a closet full of t-shirts, you’re essentially working with a blank slate. Now it’s time to add things so you can dress like a grown man.

3.) Don’t be afraid to eliminate / donate, and make sure to pick timeless classics

Fine, this is kind of a two-fer here, but they go hand in hand. You HAVE TO get rid of things, or at least be okay with the idea of it.

If you’re young and haven’t bought one grown-man outfit yet, you STILL will have to clear out space in that teenager closet of yours. You probably have a ton of stuff you haven’t worn since 6th grade. Get rid of it and make room for some real clothes.

When you’re ready to start buying things, keep in mind the classics. Something you can wear in ten years and not look dated. Things like a basic, slim fitting (not tight or snug) white dress shirt, another in light blue. A slim (not tight) charcoal gray or navy two-button, single breasted suit.

These items won’t ever go out of style; they’re standards that go beyond trends. Kinda like Sinatra’s greatest hits. When’s that guy ever gonna go out of style? (Probably never.)

4.) Take it a step at a time

This goes with step 3.  You don’t have to buy a whole wardrobe at once. In fact, you probably won’t be able to, since quality can cost money, and not everyone has the money to blow on a top-notch wardrobe in one hit.

My advice would be to tackle things one item at a time, or one group at a time. Think of it like building a collection; the fun part of collecting is gathering these coveted items one by one.

For example, when you have enough money, buy a few dress and sport shirts (start with 3-6) to start building your wardrobe. When you’re looking for the next piece in your collection, get a great pair of dark denim. Keep building slowly until you have a well-rounded wardrobe.

5.) You’ll always be refining

Keep in mind that even with classic pieces, your preferences may change. Maybe one day, you’ll realize you really like a certain sport shirt, but want more lavender instead of light blue… or after wearing straight legs, realize you prefer a slimmer cut of denim.

You will learn these things as you go, just make sure to stay open and realize you’ll change your mind now and then. As long as you’re in that realm of classic, timeless style, you can’t really go wrong.

Realistically, you don’t have to be young to take advantage of these guidelines. You can be any age, and if committed to reinventing your wardrobe, good stuff can happen. Take it slow and progress naturally, and soon enough you’ll have a killer starter wardrobe that will last you years.

What do you think?

  • Are there any other important pointers you may have for a younger gent trying to build his wardrobe right the first time?
  • Are you that younger dude, and you have questions?

Let’s hear em in the comments below.

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46 Responses

  1. Christopher Dravus on

    Great article Barron. Very helpful for the guys just getting their feet wet. Few things I might add as someone who just a few years ago was in this position. 

    1). Don’t be afraid. Your wardrobe is not going to look anything like it did before you began this venture. Its going to change. A lot. This is a good thing. You’re not losing part of yourself and nothing intrinsic to you is being lost. You’re growing up. Don’t fight it. You don’t hold on to the things you you wore as a toddler so why try and hold onto your high school style?

    2) Ask for help. Now is not the time to be arrogant. Be humble. There are a lot of people out there who know what they’re talking about. There are people out there who walked this path already. Ask. But learn to put the advice you get into context. Know its worth and know what to utilize and what to skip. I put up an article recent on my site, about how to ask for advice and what to do with it. Check it out if it helps. http://the-approach.org/2012/03/15/the-approach-to-taking-advice/  But just know that its hard to do alone and there is no reason you should have to.

    Good luck to anyone that’s embarking on a style change. Just know that you can do it… and that its worth the effort. 



  2. Chris Betterton on

    Definitely agree with Christopher’s advice on asking for help. I was lucky enough to work with some stylish women who had worked in business for a long time, and running ideas past them really helped give me the confidence to make the changes I needed to make.

    • Christopher Dravus on

      Thanks sir. 

      And not enough can be said for getting help from the ladies. Barron has an outstanding article talking about how men can learn a thing or two from the way women pair colors together. My current favorite thing on the internet is Style Girlfriend. Melissa from that site is doing a pretty unique thing over there, men’s fashion tips from a woman’s perspective. 

      I put a lot of value on the opinion of women. Typically they do it better than we do. 


    • Barron on

      Here’s the article he was referring to: http://www.effortlessgent.com/be-a-real-man-dress-like-a-girl/

      PS, the editor of Style Girlfriend is Megan, not Melissa 🙂

  3. Greg_S on

    I think #4 is extremely important. The more one reads, the quicker one will want to make these changes. However, you can read as much as you want and still not be 100% sure how to execute it. I think building up slowly as you get more familiar with your personal style and how to dress will save time and money long term. It avoids buying superfluous items you read about but won’t wear or the mistakes of buying several items at once before you’re completely sure of proper fit.

    • Barron on

      You’re bound to buy stuff at some point, where afterwards, you ask yourself, wth was I thinking? But that’s all a part of crafting a personal style of your own, so don’t be too hard on yourself if that does happen.

      Great point though, the more slowly and deliberately you buy, the easier it is to avoid doing that.

  4. Samuel Green on

    I’m ‘that young dude’ and I’m just starting out my wardrobe re-invention. I got 5 dress shirts tailored (in a variety of colors) and I think my next pickup will be some pants to go with them… all I have is a pair of black skinny jeans.

    I’m not sure if you can really help with this but I’ve put on my new shirts and I just don’t feel like I look good. Maybe I’m mentally stuck in my old wardrobe, or it’s just the fact I have no bottoms to go with my tops, but I just don’t feel comfortable in this stuff. Leaving the jeans behind is going to be an even bigger step than the t-shirts!

    I suppose if I read more, it will help out (since I see all those handsome models with their crazy non-jeans + t-shirt outfits), but I just don’t have time right now. I think re-inventing my style is the most difficult challenge I’ve had since my final exams at University!!

    • Devon Jordan on

      I’m working on the same as you are, slowly reinventing my college –> grown man status. Best advice I can offer you is to just keep wearing your stuff. I felt awkward as hell the first time I wore some flat front chinos, a “slim” dress shirt, and a v neck sweater. But now, I rock this shit! HAHA.

      Comfortability (is that a word?) will come with time is my guess.

    • Barron on

      Why are you leaving denim behind? Do you mean just the skinny part?

      If you’re a slim dude, you can stick with slimmer cut denim, just buy the right kind: http://www.effortlessgent.com/the-endorsement-the-one-thing-every-man-must-have-in-his-closet/

      Also, why did you have to get your dress shirts tailored? I commend you on doing so, but was it really necessary? You can find dress shirts that are really slim nowadays (again, I’m assuming you’re slim) which wouldn’t really need any extra tailoring.

      Anyway, to address your concern (and Devon said this well): you don’t feel like you look good because you’re wearing clothes you aren’t used to. It’s hard to be confident when you’re wearing something out of the ordinary (to you). It’s a gradual thing, so just keep at it and eventually it will feel normal to you. 

      • Samuel Green on

        I got shirts tailored because I heard that was good! I also live in China, where you can get tailored shirts for less than off the peg. I’ve kinda got short arms and an athletic body so every time I try and wear shirts off the peg they just don’t look like they fit well.

        Thanks for the advice (Devon too), I think I’m going to enjoy summer more when I can get some crazy coloured Chinos. Unlike dress shirts, they’re something I’ve always wanted to wear but now I’m gonna have the balls to do it 😉

        • Barron on

          When you say “tailored”, do you mean custom made? That’s what it sounds like. If so, that’s great! Custom made is always a better option than off the rack if one can afford it.

  5. Will on

    I think number one and four were the most critical things for me.  Perhaps the more important thing I learned in reading–even more important than the inspiration– was basic sartorial knowledge.  I don’t think many guys realize how little they know about the basic of getting dressed.  That has proven to be more useful over the last couple of months as I’ve slowly been redoing my wardrobe.

    • Barron on

      Yeah this is a good point. Do you have a resource where you learned basic sartorial knowledge / rules of getting dressed? Or was it just a summary of what you’ve learned over the course of a few weeks / months of reading?

      • Will on

        The stuff I learned have been through reading this blog and a bunch of other ones, including the “Purveyors of Style” sites.  Some things just get mentioned in passing in articles, and a lot of the time I’m like, “Oh.  I had no idea.”  Or, “Uh oh, I should stop/start doing that.”

        • Barron on

          That’s pretty much how everyone learns, through tidbits said in passing. Glad you’re finding all this useful though 🙂

  6. Chris on

    I went to a tailor for the first time in my life two weeks ago and it has made a world of difference.  Baggy, too long dress pants and billowy shirts are slowly making their way out of my closet.  For what it’s worth – I paid around $22 to have my pants altered and $15 to have my shirts altered.  Well worth it.  If you have a decent piece that doesn’t fit quite, it may be worth having tailored before donating.  I’m a beginner and new reader and have a lot to learn, but this one step has helped me a lot.

    • Barron on

      That’s great to hear. It’s certainly a cost to consider since it isn’t cheap, but well worth it especially if it’s a piece you like.

      For shirts, darting is easy enough (stitching down the left and right centers to draw the shirt in around the waist) but for things like suit jackets, be careful, because if the shoulders don’t fit, no amount of tailoring would be worth it. It won’t ever look or fit right.

  7. Stabino on

    I think one more bit of advice for starting a grown-up collection is to actually keep track of your clothes. By this I mean have a notebook, or spread sheet, of some kind. It’s kind of geeky, but it does help when you’re flipping through and trying to see how many pairs of pants and shirts you have. Also good if you give your self a budget on your clothing spending. I look forward to the next set of tips. 

    • Barron on

      This is an interesting suggestion. I could see this being important if I had a huge walk in closet with a ton of stuff, but if you have a minimal wardrobe with only a few key pieces, wouldn’t it be easier to just survey your closet and see what you have? Or do you mean to have this list on you, so you know what you already have when you’re shopping?

  8. James T-S on

    The most important part of this process though, is to hold onto your sense of self, while updating your closet. If you’re the kind of person who wore tons of bright colors (like myself), don’t try to buy only plain shirts and ties, do some looking into brighter patterned shirts or a lighter suit. You won’t be wearing them all the time as sometimes you have to dress conservatively, but don’t sacrifice self for maturity.

    I started updating my wardrobe about 1.5 years ago, and some of my favorite shirts have bold colors, patterns, or accents. I also managed to find myself a bright green blazer and am in the process of finding great orange casual pants. They would never pair well all together but work as great accent pieces to an otherwise boring (IMHO) outfit.

    All that said, I have to agree with what several others have said so far. Get yourself to a tailor. Find someone good and develop a relationship. It might just be a shirt at a time until you have more cash, but you look better in something that actually fits you.

    • Barron on

      I definitely agree with holding onto your sense of self as you upgrade, and I never suggest to be someone you’re not (like if you hate bright colors, to outfit your closet with bright colors only… that just wouldn’t make sense).

      I do suggest for people to branch out though. I think it’s important to experiment, otherwise how else would we discover other things we may love?

      But yes, that’s a good piece of advice. You won’t be happy with your upgrade if you buy things that are uncharacteristic of your own true style.

  9. Fivefingerfool_98 on

    fresh crisp stonewash bootcuts is a great foundation then get some striped shirts. american eagle is a good start. im pretty young for this site lets just say. tryina keep some money so i can afford these things. stay cool! 🙂

    • Barron on

      Hmm, yeah, no. Assuming this isn’t a sarcastic joke comment, continue reading, and keep advice in comments to a minimum, my young Padawan. You have a lot to learn.

        • Barron on

          If we’re talking about a grown man wardrobe, there are other places to get clothing that would be much more worth your money / time. Plus there just isn’t much of a selection at a place like AE; they cater to a different, younger crowd and so their offerings are limited.

  10. M. Ambassador Bruny on

    Barron: Another great post.  I had my wardrobe moment about 2 years ago when a stylist friend from “The Brooklyn Circus.”  Set me straight.  I thought I knew something about dressing until this guy came through.  He taught me the importance of fit and developing a style of your own.

    I love what you are doing.  We should have a meet up at WDS.

    • Barron on

      Thanks Mike! Ah yeah, the dudes at Bkc are doin’ it. I have yet to visit their store here in SF. Love the story about how the brand got started too.

      Sadly I won’t be at WDS this year 🙁 Have some family trips scattered throughout the summer and didn’t have enough time. Next time though, for sure.

    • Christopher on

      Well, I can try.

      The first thing that I think is more relevant to you to know is that a great of what you do, and what any of us men do in general, is to be noticed and appreciated by women. It’s how we function. Also, guys your age haven’t totally figured out who or what they are or what they like yet. 

      What I mean is, your lives are going to be constantly in flux. High school will seem like a long time for you but its really just four years. I’ve been at a job that 50% of the time is soul crushing and I’ve been there seven and a half years. That’s long. In those four years youre going to be living life in extreme fast forward. 

      Fashion trends change in highschool roughly every semester. Sometimes quicker. What’s in style and what isn’t is very likely to shift rapidly and it sometimes focuses on key figures in the school too. Certain people set the trend within certain cliques. 

      The problem with suggesting to you classic timeless styles is that the people (read: high school girls) around you are likely to have not learned what actually looks good on guys yet. They have no real clue what they like yet either. Its one reason why the guy dressed in the stuff on the Hollister mannequin does so well with the ladies in HS. Because the outfit was put together by a store they likely shop at and it has all the things that the ads and cosmos have told her look good. 

      So, while  you could start aiming for timeless fashions you are going to hit some resistance from people (read: girls) because they don’t really understand what you’re doing yet.And if you aren’t careful you’ll end up being that guy in silk backed department store vest wearing a stingy fedora and wayfarers everywhere. 

      But, if you have the emotional fortitude to get asked questions like “why are you dressed that way” every day you may be able to establish yourself as a really classic individual. 

      Otherwise, and there’s no shame in it, you can stick to the stores that offer your age range the best options for looking presentable. Think Hollister, Abercrombie, American Eagle, GAP and H&M (I hate H&M). Stores like Banana Republic and Express can add some savvy items to your closet but they have a much higher price point. Macys is a good middle ground between fashion and price. Specifically you may want to look at Macy’s INC and Sons of Intrigue line. They’re slightly on the clubby side for INC and Sons of Intrigue has this hipster ironic/classic/dandy thing happening. 

      Good luck man. High School sucks so the best thing you can do is use those four years to chisel out some hardy self esteem and really explore your tastes. 



    • christopherDravus on

      I wouldn’t mind taking a crack at this.

      Zemaken, I think the first thing you have to understand is that your world is a little different than ours. Don’t take anything I’m going to say as rude because it’s not meant that way. I’ve been out of high school for ten years now but I remember it very well.

      High School seems like forever when you’re there. It’s your entire world. But in reality it’s only four years. I’ve been at a job that eats my hopes and dreams for breakfast for the last seven and a half years. That’s a long time. 

      My point is, you live those four years in extreme fast forward. You get a lot of life squeezed into a short amount of time and that applies to everything including style. The styles in high school change very rapidly and our dependent on a lot of pop culture and school community factors You get these “flavor of the month” fads in High School and nothing tends to last more than a semester there. 

      A second very important point is to admit that you, like most of us men, do pretty much everything for the attention of women. It’s a major motivation and especially so in high school. And there in lies the problem with holding you to the standards that some of us have for clothes. And it’s not even your fault really. The girls in High School, just like you, haven’t really figured themselves out yet. They’re not entirely sure what they like and what they don’t because their life experiences are confined to one suburb and played out inside the walls of one school all while puppet stringed by parents and teachers. 

      The girls there, most likely, won’t appreciate classic timeless fashion approaches because they don’t understand that they’re classic yet. To them, its just dressy. And you’re going to end up getting frequently asked “Why are you so dressed up?” We get that question a lot too in our adult lives but the difference is having the self esteem and confidence to answer it the right way. In high school it’s hard to stand out. In Our adult lives its what we strive for. So you have to have the mental fortitude to endure constant affronts to your appearance.

      This is why certain guys do so well in high school. Because every girl there shops at Hollister  because Hollister markets well to their age group and those girls have no real time in their lives to develop a more independent set of likes and dislikes. Hollister has done it for them. (Or any of the other big teen retailers for that matter) Now them men see the women in their Hollister outfits, they wander the same malls, come from roughly the same incomes and all exist in the same school. So they pick up on where to shop now and boom, they’re in Hollister too. Now the girls can immediately pick up on who they think is well dressed just by looking at the clothes, because those clothes are found at the same place they shop. 

      Now figure in that you run a bit of a risk in aiming for classic styles. A lot of the younger kids I see trying it just end up in a shiny backed vested and wearing a stingy fedora and wayfarers with chuck taylors on. Basically you can easily make a few mistakes and wake up one morning to realize you’ve become a hipster douche-bag.

      That being said you can try it. You might succeed and develop a persona for yourself as being that fashion savvy dressed up guy. 

      Alternatively you can aim for the trending fashions that are happening in your school. You’ll likely want to have a look at Hollister, Ambercrombie, American Eagle, GAP and H&M (I hate H&M). If you’re willing to drop a little coin you can add some really sleek items to your closet from Banana Republic, Express and Macy’s. Macy’s is actually a really nice middle ground between affordable and stylish. Specifically look at their INC and Sons of Intrigue lines. They have some great casual blazers. 

      I wish you luck sir, High School sucks. Just remember, its only the least important four years of your life. You’ll do fine.


      • Otateral on

        Very good post, christopher. I’m 30 now and your description brought back memories. I’ve been in t-shirts & jeans my whole life, and highschool was no different. One thing I’ve learned lately is dressing to the occasion. Putting on a 3 piece suit to go to highschool isn’t appropriate. But dressing well and wearing clothes that fit well is appropriate.

        Dress well, not up.

        • christopherDravus on

          Thanks sir. I remember High School too and the guy I used to be back then. It’s so far removed from who I am now that it’s hard for me to imagine trying to plan out my wardrobe likes and dislikes back then. 

      • tbirdandkoolaid on

        huh…I did not read all of that

        Just because he’s in high school doesn’t mean he shouldn’t wear button downs, nice shoes, throw a blazer on every now and then, to keep them guessing.

        Young buck, wear what makes you comfortable. You don’t need to go out and buy some AE just yet…

        Start at goodwill and thrift shops. Chinos. Button downs. Nice shoes.

        Find your STYLE and run with it.

        As for the girls not appreciating your style, i think different. If you stand out from the crowd and your comfortable invest in a bat because you’lll need it to beat them off of you..aha

        Wow just noticed this is an old post.

      • wildejamey on

        Interesting. But girls grow out of high school too – and even faster than boys. What I’d add is that it seems studying wardrobe is almost a full-time activity in itself and you have to fit it in with other professional and other commitments but I see it as an investment in my future career.

  11. Infantryman on

    I have a unique scenario and I’m looking for some advice.

    I’m a pretty skinny guy who joined the military a few months ago and will be leaving for basic training and AIT in May. I am in desperate need of a new wardrobe as it is, but I will likely gain weight while I am away, growing out of the few decent things I do have. How can I start building a wardrobe on a few hundred bucks when I get back without wearing the same things over and over?

    • Jon Helmkamp on

      Hey man, congrats on joining the military. What branch? By the name “infantry man” I’m going to say Army or Marines. My advice would be to wait until you get back from basic. Different people change in different ways at boot, so there’s really no way to predict how you will look and what will and won’t fit when you get back. You should have a little more than a few hundred bucks when you get back from basic, and will be making decent money in the military.

      Start with some essentials – dark denim, a pair of nice shoes (like a desert boot or suede oxford or something versatile like that), some button downs… I’m re-working my wardrobe right now too, and I’m realizing the best way is to just get one nice quality piece at a time. With your military money, you’ll be fine!

  12. Reginald on

    Along with revamping your wardrobe, you must take care of your clothes, i.e., folding and hanging up your clothes. Keep the shoes clean as well.

  13. BradChicagoLoop on

    Hello, I have a shoe question.

    I building my first basic wardrobe. I think I found a good dark brown Cole Haan cap toe. I’d like for it to be a shoe that I can dress down for drinks or a date. The top edge if the shoe is wider and has more pronounced “ribbing” along the seem.

    Does this make the shoe a less better choice for dressing down?

  14. beardedman on

    Barron, I admire what you’re doing here and I’m enjoying your advice and fresh approach. Just have one small issue to mention, and that’s your occasional choice of language. All your great articles are about dressing like a grown man, and we know one way to show the world (as well as convincing ourselves) we are grown men is by our grown up dress. (I’m 56 but still don’t always think of myself as a grown up.) But all of that gets somewhat undone when you curse casually in print like a kid. Speaking a four-letter-word is a matter of judgement based on your present company. You can usually tell if it is appropriate for your audience. Cursing in print is always unprofessional and widely frowned upon. You say it’s “you” and you have to be yourself, but frankly that is a rather juvenile way of justifying something that is widely considered inappropriate. You’re doing great things here. Up your game with a cleaner vocabulary and I think it will help get your message across.

  15. wildejamey on

    Is 23 (24 in September) grown up? Sorry, but who’s Sinatra? (haha just joking). Great advice. I’m having problems finding jeans that are slim but not grungy or especially slim straight (does anyone sell them?). Also shoes are a bugbear. On the upside I’m doing well with chucking junk.