The Compass  /  Style  /  How to Choose Your Clothes: Mastering Men’s Fashion From the Inside Out

How to Choose Your Clothes: Mastering Men’s Fashion From the Inside Out

man wearing a white dress shirt with the collar popped up and a black tie around his neck looking at a reflection of himself with text "the compass. mastering men's fashion from the inside out"

Because men’s fashion is built on tried and true foundation items (the suit, the blazer, the dress shirt, the tie etc.), mastering men’s fashion is less about how unique your pieces are and more about how creatively you put these pieces together.So why do some men seem to be able to put the pieces together so well? How can you put together outfits that really impress? The key to mastering men’s fashion is dressing in a way that showcases the best traits in your own appearance. So we’ll start with what’s inside–what’s under all the clothes–you. We call that dressing from the inside out, and here are the secrets to doing it right.

Stop Taking Selfies and Take a Look in the Mirror

We are a culture of seemingly selfie-obsessed narcissists. In fact, Sundar Pichai, Senior Vice President of Android, estimates that 93 million selfies are taken every day. Therefore, a quick swipe through your Instagram feed will undoubtedly reveal a collection of photos of the people who posted the photos.

Yet, with almost everyone looking at their own reflections on a regular basis, few of us know how we actually look. Sure, we could give a general description to the average person on the street with details like our height, weight, and hair color. But most guys can’t describe in any detail the specific color of their own eyes, the true shade of their skin tone, or the nuances of their own hair. It seems that, despite all the time we spend taking pictures of ourselves and posting them all over the interwebs, not many people are paying attention to what they really look like. We are half-assing our narcissism and our looks are paying the price.

The worst part about all of this is that we could look so much better by simply dressing better. At Black Lapel, we believe that when you dress better, you feel better and you become better. And since men’s fashion moves at a relatively slow pace, mastering it doesn’t require subscribing to 20 men’s fashion publications (though we do encourage you to sign up for this one since it’s free). Most of what you need to know to master men’s fashion is staring right back at you every time you look into a mirror.

Start by taking a good look at your face. What do you see? Note your eye color. What shade are they? Be specific. How about your hair? Your skin tone? Any distinguishing traits? What makes you you? A signature set of freckles? Is a thick beard your calling card? Whatever you see, this is what you’ve got to work with. The underlying goal of men’s fashion is not to show off your clothes, but to cast your face and body in the best light possible. After all it’s you wearing the clothes, not the clothes wearing you.

Once you’ve gotten a good handle on what you’re working with, it’s time to unlock the style secrets.

Men’s Fashion Secret 1: Match Your Ties to Your Eyes

Your eyes play a huge role in your overall look. While men fret over everything from calf size to…well…the size of other body parts, our eyes are one of most attractive and engaging parts of our appearance. No women dish with their girlfriends about how they met a guy who “had the most amazing calves.” And while they may compare notes on the aforementioned “other body parts” it’s likely they won’t bother to gather enough data on the subject to make a fair assessment unless they like your eyes. In short, if you want to look good, dress for your eyes.

“But my eyes are nothing special,” we hear some of you saying. Chances are, you don’t have the recessive gene that makes blue eyes blue or green eyes green (it is, after all, a recessive gene). All the more reason to accentuate the depth and complexity of your eyes by wearing colors that harmonize with your eyes.

There are a myriad of ways to do this, but perhaps the simplest, yet most effective ways to put the emphasis on your peepers is to wear ties from the same color family as your eyes.

chart of illustrated eyes and eye colors matched with different colored ties

Blue Eyes: Pair with Blue Striped Knit Ties. Blue Gray Eyes: Pair with Armstrong and Wilson’s Wheaton or Gray Tweed Tie. Green Eyes: Pair with the Forest Green Knit Tie or Turquoise MNT Tie. Brown Eyes: Pair with The Brown Knit Tie or Mr. Bronze Knit Tie by Armstrong and Wilson.

Men’s Fashion Secret 2: Always pair your jacket and your hair.

Notice that we didn’t say “match” your jacket and hair. We are not suggesting that men should only wear suits and blazers that match their hair color exactly. We are suggesting that men think of fabrics in the same color family as their hair as the foundation of their suit and blazer collection. Why? Because when you wear a jacket in colors that harmonize well with your hair, you frame your face while casting it in the best light. And the opposite is true as well. When light blond haired men wear black or extremely dark suits, it can throw off the balance of their look and wash them out.

So, yes, framing your face with a jacket color that matches your hair is always a winning look and choosing a color that clashes with your hair is a critical mistake. But wearing a color that is across the color wheel from your hair color can also work wonders for your look. So think of pairing your hair color and jacket color like any other color combo. See below for examples.

chart of illustrated natural men's hair color matched with different suit jacket colors

Brown Hair: Pair with the Charcoal Brown with Blue Overcheck Custom Suit or the Light Charcoal Blue Custom Suit. Black Hair: Pair with the Charcoal with Lavender Pinstripe Custom Suit or the Carnegie Copper Windowpane Custom Suit. Blonde Hair: Pair with the Cool Gray Custom 3-Piece Suit or the Royal Blue Custom Suit. Red Hair: Pair with the Warm Gray Sharkskin Custom Suit or the Brownstone Brown Glen Plaid Custom Suit.

Men’s Fashion Secret 3: Fake it ‘til you make it

Many great artists start off by trying to copy their heroes. Over time they develop their own style. The same can be said of stylish men. There’s no shame in stealing ideas for what to wear from a particularly dapper dude.

But the secret to doing this is knowing what you have in common with said dapper dude. Just mimicking the outfits of the best-dressed men won’t make you a men’s fashion pro. Especially if he’s a trim movie star with thick wavy blond hair and piercing blue eyes while you’re about three bills with bushy brown hair and dark brown eyes.

…Male celebrities of all shapes and sizes, have been featured on the pages of GQ, Esquire and all over TV and movie screens looking fly. Find traits that you share with these gents and do a quick Pinterest search for their name and a keyword like “suit” or “style.”

We suggest finding a celebrity who can act as a style proxy. Why celebrities? Because they’re often dressed by stylists who know how to make them look good and photographed in settings that accentuate their best features. And not looking like a matinee idol is no excuse for skipping this style secret. Women may not be able to find any pictures of anyone over a size 2 in mainstream media, but male celebrities of all shapes and sizes, have been featured on the pages of GQ, Esquire and all over TV and movie screens looking fly. Find traits that you share with these gents and do a quick Pinterest search for their name and a keyword like “suit” or “style.” Take our example from above, the guy who weighs about 300 pounds, has bushy brown hair and dark brown eyes could take a lesson from stills of John Goodman in a dope three-piece suit in The Artist or photos of Goodman showing how a trim haircut can slim down your look while nailing his black tie look on the red carpet.

To get you started we’ve collected photos of celebrities of all stripes decked out in some stylish gear in a Pinterest Board. Here you’ll find a wide range of looks to borrow from. Even if you’re balding, Bruce Willis will show you how to wear it well. Use these photos and seek out more on your own. If you look carefully, you’re certain to find some well-dressed men who share features with you. Then you’ll have a reference for how clothes fit the body type that’s closest to yours, how a certain color or style might look on you, even how different hairstyles will work for you.

In time you’ll be a pro at stealing from the stylish. And if you follow the advice above, pretty soon you’ll have other people stealing ideas from you. That’s when you’ll know you’ve truly mastered men’s fashion.

Put these secrets to good use.

Browse the full collection of suits, blazers and accessories from Black Lapel. We’re sure there’s something that’ll work for you.

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38 thoughts on “How to Choose Your Clothes: Mastering Men’s Fashion From the Inside Out”

  1. Alla says:

    Great advice, but I’ve got a question. My son has “classic” East Indian features – darker skin, eyes dark brown to almost black, long straight jet black hair. He’s also about about 6’2″ and is into Greco-Roman wrestling, so during the season, he can look “over-muscled”. What on earth do I dress this child in for high school graduation? It’s not formal as in tux, but the gentlemen will be required to wear suit and tie. Any pointers, pictures, and advice will be greatly appreciated!

    1. Black Lapel says:

      Hello, Alla!

      First off, props to you for wanting to make sure your son is looking fresh-as-hell for graduation. Parent of the year? Maybe. Regardless, as far as your inquiry goes, we have some answers.

      First, to address his size, this isn’t too much of an issue if you buy the suit with the graduation date in mind. If his season is over prior to the graduation date, you may want to wait to buy your suit until after the season in case he “slims down”. If his season is over in conjunction with graduation, being muscular isn’t an issue, you just need to nail the fit. For this, you can either go with a custom-made suit (like ours, go figure) or just be very, very conscious of proper fit when buying off-the-rack. If you’re going with the latter and buying from a retail store that isn’t made-to-measure, this article on how a suit should fit will be very helpful for you to have on-hand.

      Second, the suit itself. You’re right, high school graduations do not call for tuxedos, that may make the yearbook for all the wrong reasons… Instead, a suit and tie as you said.

      If this is his first suit, we would always recommend you go with a starter suit like navy (especially for young, growing men). The reason for this is the return on investment. If you buy him a starter suit that works for multiple occasions, he can use it for potential job interviews, dates or other formal occasions that may come up. If his first suit is more over-the-top, it won’t be useful down the road if he doesn’t already have a good foundation piece.

      That said, our recommendation for you is a classic navy suit. If you click the link, you will notice the model has a slightly darker complexion too. For some more reference, the model wearing this navy windowpane suit has a darker complexion and looks great in the navy — although we would not recommend the windowpane as a starter suit.

      If the suit being a foundation piece (a starter suit) isn’t as big of a deal to you, we would advise you still stick to blue, but you can explore different hues such as royal blue or indigo blue. Overall, any blue is a good choice, especially if the graduation is in May and the environment is more colorful.

      The remaining advice we give is going to be in the mindset that you choose one of the aforementioned blue suits (particularly the navy).
      To briefly touch on dress shirt choices, you’ll want to stick to a light color to create contrast — white or light blue shirts are good options.

      As far as ties go, this is also really simple. The easiest option is wearing a white dress shirt and a navy suit, the tie can simply be a different shade of blue (like this guy).

      There are way more options out there, though. The whole idea here is to create contrast, so if you have a light blue shirt and a navy suit on top of it, your tie needs to stand out amongst the two blues. That means going with a separate color such as gray, brown or even his school colors. Feel free to add a pattern as well since your suit will be solid.

      We hope this helped you, don’t hesitate to respond with more questions or clarifications!

  2. L says:

    You left out the silver foxes!

    1. Black Lapel says:

      You’re right! We’ll correct this oversight.

      The concept of pairing your jacket and your hair still holds up for guys with gray hair. Look for jackets in shades of gray that are in the vicinity of your hair. One caveat with lighter haired guys is that you can wear the same color family but slightly darker shades. So maybe your hair is as white as John Slattery’s but it doesn’t mean you have to only wear light gray suits, like he’s wearing in this photo. You can also wear darker shades of gray like he’s wearing in this photo. The trick is to tone down the contrast between the suit and accessories so that your outfit doesn’t draw attention away from your face. For a deeper look at how to make your coloring work with your clothes, check out our story on Picking Shirt Colors That Match You, Even If You Have No Eye For Matching.

  3. Rhys says:

    Heading to Vietnam for some backpacking, and will potentially be having some suits made for me their. Thank you for the tips!

    1. Rhys says:

      I meant to write “there,” of course. Did I mention that I teach English? 😉

    2. Black Lapel says:

      Ummm…okay. You know we make suits, right Rhys? They’re priced well and guaranteed to fit you flawlessly. Plus, you can order them one online so you don’t have to travel to Vietnam or even our headquarters in New York to get one.

      Thousands of guys have done it and had great experiences (see our 5 star Yelp Rating). Check us out at blacklapel.com.

  4. PIC says:

    Planning January 1 nuptials. Will be low-key (second marriages). I plan on wearing long skirt, cream top, wine color jacket. Fiance has white hair. We were thinking about his attire as such: Black jacket with Gray dress pants, White shirt with wine-colored tie to match my jacket. What do you think? Thank you so much!

    1. Black Lapel says:

      Congrats on the nuptials. We like what you’re thinking for your fiance’s outfit, but we’d suggest making one change: swap that black jacket out for a navy or darker gray jacket. Those colors are more cohesive together.

  5. Mark says:

    My daughter is getting Married the week before Christmas, My daughter is walking down the aisle with both her Moher and I, In a very $$$ Nice Princess wedding dress, All the Bridesmaids are wearing peach colored matching dress, The future son-in Law and all his Groomsmen are wearing Khaki pants, white long sleeve shirts, suspenders, and hats, pretty casual look, My wife is dressing to the nines, ocean blue Gown, I want to wear light grey Jacket, Black pants flat front, white shirt and a blue tie to match my wife’s dress and my eyes, No body wants me wear clothing to match the groomsmen not even me, Iam in my early 60’s and want to look sharp with my grey hair , What do you think

    1. Black Lapel says:

      Congratulations, to the proud papa. Sounds like a great celebration to come.

      The outfit sounds good. The only tweak we’d suggest is the pants. Instead of black, we recommend going with navy blue pants. They’ll still be dark and so you’ll get a similar look to what you’ve laid out, but the blue in the pants will coordinate with the blue of your tie and the blue in your eyes.

      Aside from adding cohesiveness to your outfit, navy blue pants give you more options for shoes (you can wear black, dark brown or oxblood shoes), as opposed to black pants, which force you to wear black shoes. And dark blue pants will still create contrast with your white shirt and light gray jacket but it won’t be so extreme that it looks jarring.

      Knock ’em dead, Mark!

  6. Gilbert says:

    I have a medium brown hair, typical Filipino Mestizo skin tone, and brown eyes with almost black accents.

    I have a charcoal grey suit which I pair with my powdered blue shirt and burgundy tie. As for the other suit that I’m getting in the future, I’ll have it in charcoal brown which has the same subtly-striped texture with my charcoal grey db suit, except it’s gonna be single breasted. I’m thinking of pairing it with a powdered yellow shirt(which I might as well wear with my charcoal grey suit while I save for the new one) and a bronze or dark brown tie.

    1. Black Lapel says:

      Hello again, Gilbert, you win the award for most active commenter this week! The prize for the winner: you’ll dress better next week!

      As for the yellow shirt, we’d caution you against it. We’ve just never seen yellow dress shirts pulled off well. Perhaps it can be done, perhaps you’re the pioneer to do it, but we’d hate to send you down the path of looking like Dwight Schrute from The Office.

      1. Gilbert says:

        I guess I’d just settle with my white and powdered blue shirt. how about a cream-colored shirt?

        1. Black Lapel says:

          Cream colored shirts can work as an alternative to stark white, but we prefer the sharpness of white to the wishy-washy look many cream colored shirts can have. And, as we said above, it’s all about how things look on you.

  7. cs:go says:

    Wow cuz this is great work! Congrats and keep it up

    1. Black Lapel says:

      Glad to be of service.

  8. Coniah Grimes says:

    Great article, guys. You covered things that are fairly hard to come across when learning about men’s style as they’re often not covered, but you did so with clear, concrete examples. Thanks for raising the bar and revitalizing men’s style knowledge.

    1. Black Lapel says:

      Glad we could help, Coniah. Keep coming back for more like this.

  9. Pat says:

    This is one of the best men’s fashion articles I’ve read (and I’ve read a lot :). All three points are spot-on. Thanks for this.

    I have medium-green eyes with brown in the center, and dark green rings at the edges. I definitely prefer green ties with darker accents or lines – now I know why.

    The jacket to hair color thing is something I hadn’t considered before. I like that a lot. I still struggle to figure out a good contrast… my skin tone and hair color look pretty similar to Brad Pitt (unfortunately, color is where the resemblance ends…) and I have those green eyes I described above. I think that puts me at a bit higher contrast than BP – his eyes are lighter than his skin, which is lighter than his hair. Whereas my eyes are darker than my skin.

    Guess I just have to play with colors a bit more and work out good contrast levels. If you’ve got any suggestions based on what I’ve said, let me have em! But in any case, thanks so much for this really helpful article.

    1. Black Lapel says:

      We’re glad this article helped, Pat. It can take a little getting used to and it’s definitely not an exact science (you don’t need to be precise, just in the ballpark of the colors and contrasts in your face and hair) but once you start seeing your clothes this way, you never see clothes the same way again. And, of course, things change. Skin tans and lightens seasonally, hair turns gray (and sometimes disappears) as we age, but now you’ve now got a system to use so you’re ready for anything!

  10. shawn says:

    im short, somewhat tanner skin and black hair with green eyes. could i look good in an off white suit like what leonardo di caprio wears in the great gatsby?

    1. Black Lapel says:

      Sure, assuming if fits well and is appropriate for the setting. If you wear an off-white suit that’s made for somebody three inches taller than you to, say, your grandmother’s funeral in Milwaukee, then no, it won’t be a good look. But if you wear one that’s made to your unique measurements (like this Khaki Linen Blend Custom Suit) to a summer wedding you’ll likely be the best dressed man at the event.

  11. adedoyin dohao says:

    Update for latest suits.

    1. Black Lapel says:

      We’re always working on updating our content—we have a pretty long list of to do’s, in fact. That being said, you can still apply the principles we outline for the suits included in this story. Read the context under the suits graphic and you’ll see that they are evergreen rules for mastering men’s fashion!

  12. Dave says:

    Although I am in my early 40’s, my hair has turned completely white and my eyes are blue. Any recommendations for a professional with white or silver hair?

    1. Black Lapel says:

      Don’t fret, you can still follow the rules we outlined above. Although your hair and eye coloring would pair excellently with a navy suit, you could also try matching your suit with your silver hair. A light gray suit like our Gray Windowpane with Shadowcheck would complement all the white/gray/silver tones in your hair. You’ll see the guy in this suit is wearing a black knit tie – you definitely should not wear a black tie. Our suggestion? Blue eyes = blue ties. Check out this heather blue tie from Armstrong & Wilson so you can get an idea for what we’re talking about.

  13. Griffin says:

    I am slightly below average height, have blue eyes with a hint of green, and dark brown hair. I am not what you would call slim, but I have broad shoulders which give me a more triangular body shape. Would you care to give me some basic guidelines?

    1. Black Lapel says:

      It sounds like you’re wondering more about dressing for your body type. From your description you might be considered an athletic build (the only way for us to know for sure would be to get out the measuring tape). In that case, check out our story on dressing for the athletic body type in our Flawless Fit series. The triangular body type you speak of is what makes someone an athletic fit. Don’t worry, this article will get you squared away (that’s a joke, Griffin, because you said you were triangular shaped and…(Hold up, why are we explaining it? Either you get it or you don’t (Wait, who are we talking to with all of these parenthetical asides?)))

  14. Claudio says:

    I liked this post, but here in South America, for example, most of the people is dark haired and with dark eyes.

    I assume these recommendations are not exclusive. Of course certain eye colour will match better with certain tie colour, but… If you have brown eyes, maybe it’s not that wrong to wear a light blue tie, for example.

    Great piece of advice, I always matched colours with the season (dark: winter, light: summer) or skin colour, never with eyes or hair.

    1. Black Lapel says:

      You got it Claudio. It is definitely not wrong to wear a light blue tie or any other colored tie, for that matter, if you have brown eyes. Also, it’s a flexible concept. You can wear patterned ties with brown in them, like ties with brown stripes or geometric patterns that include brown. As you know, these are not rules that must be obeyed, just techniques for creating harmony in your look.

      Now as for this whole, South America thing, we’d be glad to leave chilly New York and visit our friends in South America if you’re inviting us!

  15. peter says:

    you guys put up some solid content. with the renaissance of masculinity that’s burgeoning in cyberspace there are a number of helpful sites for aspiring gentlemen but yours puts out some of the most succinct and practicable information i’ve found to date. thanks for that.

    1. Black Lapel says:

      We’re happy to help guys dress better, Peter. Glad you find it helpful!

  16. Steve says:

    I understand the idea here but are you saying men with a certain eye color, hair, are limited to the recommendations above? For example, I have dark brown eyes, black hair and fair skin. Does that mean I can’t wear blue, green, or red ties or blue or grey suits? Or a blonde hair blue eye man cannot wear a black suit according to your other article on how to wear a black suit? Doesn’t this make our wardrobe somewhat limited and boring? Not trying to be difficult but really just want to learn about men’s fashion! Thanks!

    1. Black Lapel says:

      These are fair questions, Steve. Our answer is threefold:

      1. Treat these fashion secrets as guidelines for harmonizing your clothing and your look, not hard and fast rules. Nobody’s banning any colors, here, just suggesting that you work with the colors that are already present on your face when you get dressed.
      2. Remember, you can more than one color. In your case, Steve, you mentioned having dark brown eyes. That doesn’t mean all of your ties must be solid dark brown. That would be limited and boring. But if you had a dark brown stripe in your light blue ties, or a dark brown overcheck in your plaid ties, they would harmonize well with your eyes. If you look for ties with hints/flecks/dashes of brown in their patterns, you’ll find that, more often than not, you’ll like what you see when you put them on.
      3. Don’t get too hung up on exact color matches. Instead focus on shades. You’ve got black hair but we wouldn’t suggest you only wear black suits. (In fact, we wouldn’t suggest anyone outside of maybe a funeral director only wear black suits.) Wearing blue and gray suits that are on the dark side (like midnight or navy blue and charcoal gray) will harmonize well with your overall look.

      Hopefully that clarifies things a bit for you, Steve. The goal here is not to set out immutable laws of fashion, but to show you how to play with the cards you’ve been dealt, looks-wise.

  17. Paul says:

    How do you match a suit with someone with no hair?

    1. Black Lapel says:

      This is a great question, Paul. This secret is built on the theory of matching your contrasts. The more contrast between your skin and hair color, the more you can wear in your outfit.

      Guys who are bald have less contrast up top (though, don’t forget that your eyebrows and eyes create some contrast) and should wear less contrast from the neck down. Try pairing a jacket that is a shade or two darker than your skin tone and solid white or patterned shirts without too much contrast in them (i.e. black and white = NO WAY, but light blue and white patterned shirts are the way to go).

      You’ll be surprised at how much this contrast rule of thumb will improve your overall look.

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