Manfashion Interlude – Stepping Up Your Game

This Manfashion Interlude is in response to several reader requests for general style advice for men. Husband Mike, resident stylish man, graciously agreed to give his two cents.

dressing sharp

Ryan Gosling and Steve Carrell in “Crazy, Stupid, Love”

Most men don’t put a lot of thought into their clothes. So what? It’s their clothes, their body, their social interactions. I would guess that large segment of the male population just accepts that what they are wearing is good enough since looking any better would certainly require significant additional effort. This is not necessarily true. I’m going to point out a few easy ways that a man can step up his game, fashion-wise, without too much trouble.

Step One:  Wear clothes that fit correctly

For a guy, getting dressed up will probably mean wearing a button-down shirt. White or blue. Most button-down shirts are made either hipster slim or beer-belly boxy (at least in the USA). This means that most men will default to a shirt that is too roomy and this translates into sloppy. Even though I do not have an athletic bod personally, I will always seek out athletic fit button down shirts. These are the only ones that seem to fit me correctly when I have my shirt tucked in. Once you find a brand that you like, buy multiples and you will be all set. This means that the salad dressing stain than never came out will not result in you having to shop for another perfect shirt. Take the identical unworn shirt out of the back of the closet and you are ready to go for the next wedding/funeral/holiday party.

Keep in mind two things when buying a dress shirt:

  1. The top button needs to button so you can wear a tie.  If your weight fluctuates, get the same shirt in two different neck sizes, just in case.
  2. If your shirt gives you a spare tire when you tuck it in, this shirt does not fit you. Find a different size or even a different brand.  If you have a belly and/or otherwise find it impossible to find a shirt that fits you correctly, get as close as you can and focus your efforts elsewhere–a cool tie, a tailored jacket, for instance.

Next up, pants. Yours pants are too short and a bit out of date. I’m basically talking to myself here. I recently donated 12 pairs of jeans after cleaning out my closet and realizing that my pants were either too short or a bit dated. When buying pants, always try them on while wearing shoes. They must crease a bit at the top of the shoe and touch the top of  the heel, more or less, but not drag on the ground.  If you can see your shins when sitting down, your pants are too short. This is the most common fit problem I see from the average guy.

Remember that scene in “Crazy, Stupid, Love” when the Ryan Gosling character tells the Steve Carrell character to be “better than the Gap”?  You don’t need to be better then the Gap, in my opinion, but if you have not bought jeans in a number of years, try opting for a slimmer fit and a darker wash. This is a relatively easy way to step up your game without too much work.

Khakis.  If you don’t wear suits, there is a good chance you wear khakis.  You may even just call them, “Dockers.”  I got no problem with Dockers. They have served me well in a number of situations in which I needed to look nice, but not going-to-a-wedding nice. Dockers, a button-down shirt that fits well, an interesting tie, and I fit in just fine. Step up your game by choosing flat front over pleated pants. Flat front khakis say you are at least trying to be in style rather that just phoning it in. If you are going to a family function, this may be the one thing that sets you apart from your less-cool Dad. I stopped wearing tan khakis the day both my father and I showed up at a thing wearing the exact same shirt and pants. Black Dockers? He’ll never wear those. Flat front?  He’s never heard of such a thing so I’m good with either one. And this is a good place to remind you again: Don’t let your pants be too short or too baggy.  If you wash them and they shrink up an inch too much, never wear them again.  They will do you no favors.

Step Two: Shoes


Tsubo boot

If a woman has never complimented you on your shoes you are wearing the wrong shoes. Most women will notice your shoes so this is probably the easiest way to step up your game. The first thing I look for when evaluating shoes is whether or not the soles are sewn on or molded to the shoe. When the soles are sewn on, this is an indicator of a high quality. A good shoe should at least have the option of being re-soled, which you cannot do when the soles have been molded on. Also shoes with molded soles often trap pockets of air between the layers which leads to squeaks and shoe farts.

Realize that a decent pair of shoes may cost you over $100. Trust me that once you get a good pair of shoes you will not regret getting rid of the shiny $45 shoes you have been wearing so far. Look for shoes that have some interesting styling to them -leather soles, a toe that is a little pointy or a little square, some unique stitching, leather that is really soft. My favorite and most comfortable shoes are John Fluevog, John Varvatos, and Cydwoq.  Figure out what your European sizing is and start looking online for the deal. A lot of the really cool shoes are going to be European. Size 11 US is about a 45 in European sizing.

Some people will never be the sort to wear a pair of dress shoes. How can a guy step up his game when it comes to athletic shoes? One rule of thumb could be that if you would ever wear a particular shoe to play a particular sport, you should probably not wear that shoe if you are trying to step up your game. Like when picking out a dressier shoe, choose a style that has some interesting element – a cool futuristic sole, an interesting fabric, a lower profile. I don’t wear a lot of tennis shoes, but I have found a couple pairs from Tsubo and Simple that are pretty cool. It’s hard to go wrong with your Converse All-Stars or your Jack Purcells, but the New Balance with the grass stains? Leave them on the back porch.

Step Three: Accessories

Are you wearing a watch?  Ask yourself if there is anything distinctive about it. If there isn’t, this is an area where you can step up your game. I get a ton on compliments on a black Mossimo watch from Target.  It cost me $20, but it has an oversized face and is really shiny. There are four dials on it and only one of them moves. It doesn’t matter. The large face makes it unusual and stand out. I try to make my watch match what I am wearing. More casual clothes get the leather band (even the rubber band). Outfits where I am dressed a bit sharper get the watch with the metal band and the bright blue face. I’ve got an oversized square face watch with an unusual dial that I wear to arty events. I’ll even match my watch to my glasses. Watches don’t need to be expensive to make an impression, but if you are actually making an impression with your watch, you have stepped up your game.

Do you wear glasses?  Do you have more than one pair?  Once I figured out what frame size fits my head, I started buying glasses online at places like 39dollarglasses.com.  Since I can get glasses and lenses for less than $100 a pair, I have been more risky with my eyewear choices.  Again, when I chose frames that are distinctive in some way, I have just set myself apart from the majority of the guys out there who have held onto their frames for too long. I have some frames where the bows look like they are made from bobby pins. Awesome! I may have frames with a yellow accent which would look great with the watch with the black and yellow face. Coordinating these two things are ways to step up your game.

Do you have any rings? A cool belt buckle? How about a classy winter coat? If your only winter coat has a sports team logo on the back, you have just identified an area where you can step up your game. An easy place to start is an overcoat that goes past your butt. You’ll need something like this if you are wearing a sport coat to a wedding or something. Check out Marshall’s or TJMaxx and you are sure to find something. I have a brown overcoat that is more or less nondescript but there is a flap of fabric over the buttons so you can’t see them which makes it pretty sleek looking.

Take strides towards improving your wardrobe in any of these ways and people are sure to remark upon the changes, which means you will have stepped up your game. Congratulations!

And for your enjoyment, here is David Mitchell from “That Mitchell and Webb Look” to give his opinions on dressing unusually smart:

Next Post
Previous Post

  • St Pete Mom

    Good job Mike. I only wish my hubby would care about any one of these items. Oh well, that’s love I guess.

  • Just emailed this to my husband. He is a fledgling blogger, at http://www.thealternativegent.blogspot.com, and he is looking for new ways to “step up his game,” in Mike’s terms. Thanks so much for posting this! I enjoyed reading it and I know my hubs will, too.

  • Kathaleen

    Shoes! Thank you for saying this. It is true: women notice a man’s shoes and if we don’t compliment then, then there is usually something…er, wrong with them: old/out-of-date, scuffed/muddy/dirty, or inappropriate. I wish more men would think about their shoes.

    And “stepping up their game” is always a good thing. Too often I see a woman looking pretty and flattered by her clothing and then her male companion is there looking the total opposite. Erg.

  • Well done, Mike! “Slimmer fit, darker wash” would elevate the game for lots of guys, right there. Also cool glasses = win.

  • Lark

    So, I’m a butch queer person who wears a lot of men’s and men’s style clothes. And this post appeals to me, especially with the shoes.

    Some additional thoughts:
    1. If you spill something food stain-y onto a cotton shirt, as soon as you can do so you should take some dish detergent and dab it all over the stain so that the cloth is saturated. Then let it set until laundry day. This takes care of most oily or dark food stains, although it does not work on red wine very well.

    2. Color choice helps. For instance, I rarely buy things that aren’t olive, navy, light blue, grey or black (with some camel-colored shoes). Everything I own works together, pretty much. So I don’t wear out my one favorite blue shirt because I am wearing it all the time. Obviously, someone else could have a totally different range of colors.

    Also, if white dress shirts don’t look good on you (and as a pinkish white person, I have to say that they make me look like a reddish and and puffy white person), you don’t have to have them. (Unless you work in a really dressy profession or need to attend a very dressy wedding.) I get most of my shirts in various blues – light, medium, dark; stripes, checks, plaids, a novelty pattern with sailboats that is maybe just a little bit too much.

    In general, people don’t really notice if all your clothes are similar as long as they fit you and look decent – no one has ever remarked “hey, do you have any shirt that’s not blue?” or “why are all your pants identical except in slightly different colors?” This is especially true of men’s clothes.

    The bar is low, people – I have worn both men’s and women’s clothes and men’s are simpler, more comfortable and sturdier. I rarely iron anything, for example, because I pull my shirts out of the dryer and hang them up right away…and since I work in a place where most people wear shirt/tie/sportcoat/khakis rather than suits (and sometimes no sportcoat) ironing does not matter.

    3. Another tip for shoes: a good shoe will follow the shape of your foot. A bad shoe (except for certain athletic shoes) will look “puffy” and will make your foot look sort of like a potato. Bad shoes are constructed this way because it is cheaper, and usually the “puffy” shape indicates that there is a layer of cardboard/paper product/cheap foamy filling between the outside and inside of the shoe. This layer will deteriorate and become misshapen, making the shoe less comfortable and causing it to look worse over time. I myself prefer a canvas shoe that’s not ugly to a cheap leather shoe – especially since cheap leather is usually “corrected” grain, which means that it’s leather with a layer of plastic on top to conceal any cracks and flaws. If you are ever puzzled about how a leather shoe has cracked and deteriorated so quickly, that’s because it’s corrected grain. In general, cheap suede is better than cheap calf – it will be a bit fragile so use a weatherproofing spray, but it will show wear less.

    4. When you buy coats and hats and gloves and bags, think about how they work together. Mine are all natural materials that look natural – cotton, wool, leather – in blacks, greys or camels. Someone else might go for mostly sporty material that looks sporty – ski jacket, fleece gloves, bright colored wool hat, nylon backpack with a lot of bells and whistles.

    5. Think about your daily life. I bike commute all year ( a gentle ~5 mile ride, not some kind of giant sweaty ordeal) and I loathe changing my clothes at work. So all my clothes are bike-friendly – sturdy cottons, shoes with robust soles (even though I wear dress shoes regularly), fits that are easy to move in, layers so that I can stay warm or avoid getting gross, a bag that is comfortable to wear while biking. If I rode the bus and spent a lot of time outside waiting in the cold, I’d probably have more and warmer layers and accessories, and I would not have so many really lightweight summer shirts because I would not need to stay cool while riding. I might also own more fragile/dry-cleanable things.

    5. Extend the life of your shoes by going to the cobbler! If you get a snazzy pair of shoes that are either quite cheap or have leather soles, go to the cobbler and ask him to put a sole cover on. A rubber sole cover will dramatically extend the life of both cheap and fragile/dressy shoes. You can get very flat ones that don’t change the look of the shoe or more robust ones with traction for winter.

    6. Also, extend the life of your leather shoes by getting wooden shoe trees! Shoe trees help your shoes dry out from foot sweat (ew!) and/or from rain and snow. They also help the shoes retain their shape. Now, I have far more shoes than shoe trees, so what I do is this: when I take off my shoes in the evening, I put in the shoe trees. I tend to alternate shoes rather than wear them day after day (which is good to do if possible) and so the next night, once my first pair of shoes has rested/dried, I remove the shoe trees and put them in the shoes I wore on the second day. (I once rescued a really sad, rained-upon and creased pair of leather shoes that I liked a lot and thought were ruined by putting shoe trees in and letting them dry for a couple of days. This converted me to shoe tree use.)

    7. Eventually, get a couple of nice belts. You’d be surprised.

    In general, I’ve found that now that I have sort of a “global” view of my clothes – everything works together, everything is easy to clean, everything is comfortable – I feel like I’m fairly well dressed most days and I don’t spend a lot of time thinking about it. I do spend a lot of time on shoes, but that’s different.

    • Sal

      (HM logged in as Sally) – Well said. i agree with all these things too. Everything I own can pretty much be worn with anything else, which is great since I dress in the dark by just reaching into the closet and grabbing what is next.

    • This post, and this comment, appeals to me personally very much, as a sensible tomboy-lady type. (I have had a bit of an identity crisis after 40, but I´m back on track now, after I found this great site!) I get loads of inspiration from men´s style magazines & sites. I find that men´s fashions are usually more classic and practical.

  • Anne

    Great advice Mike. I think my own hubs would add,”Find a woman who will get all these things for you and don’t give it another thought.” I would love it if my husband took more of an interest in how he dresses but we seem to have worked out an agreement over the years: I take care of how he dresses, he takes care of all my sports equipment. I guess the secret to a happy marriage is a good division of labor.

  • Oh, Husband Mike. I sure wish you would talk to my husband. I love him…LOVE HIM…but he looks like the Unabomber. Long gray hair, unkempt beard. Only wears black high top Nikes or combat boots. His idea of a suit is head to toe camo. Even his sunglasses are camo. His idea of wearing something nice to church, is a tee shirt with no rips, beer or mustard stains. When we walk through the parking lot at the grocery store, I hear people locking their doors. It’s sad. He’s a handsome guy, but cares NOTHING about how he looks and will not wear any of the clothes I buy him. So now I spend that money on shoes for me instead. It’s not a win-win, but it will have to do.

  • Heather Harrell

    Oh how I wish my husband would care about these things.
    We actually discussed this the other day and his approach is “I’m happily married, so I don’t care how I look!”
    Unfortunately that’s wrinkled and saggy…… and he won’t wear things I purchase for him.

    • I noticed that how I look affects how others subconsciously view me at work and generally what kind of treatment I get as I go about my day in the world. Looking nice isn’t just to attract a mate, it might give your husband more professional opportunities or better service. Maybe that will help you convert him? And instead of buying things for him, maybe you can convince him to go shopping with you and he can choose himself with your guidance?

  • Where I live, a guy would completely stick out like a sore thumb wearing fashiony watches and smart looking coats. I live in the land where new Carharrts = dress pants and fleece and down are the only winter coats anyone wears. Flat front black dockers? Ok, maybe to a job interview.
    Fortunately, the outdoorsy handyman-y look is (in my opinion) utterly adorable. So there you go.

    • Meshell

      Hey, one can be outdoorsy and slick at the same time! One can also be well dressed and sloppy. It’s all about finding clothes that fit. Flat front pants are more common in your out doors wear than one would think. It would be nice to hear on how to step up the game in your non city wear.

      • Sal

        (HM logged in as Sally)
        -You’re going to need a non-city dude for that. I’m sure the guidelines to wear clothes that fit and to find items that have unique features works for non-city wear as well. I’m sure others would have some input, too. -HM

    • Halo

      Yeah, I live in Carharrtslandia, Wyoming. My ex-boyfriend claimed wearing clean Carharrts in navy with a sweater was formalwear. He did, however, buy funky glasses and a cool watch, and he gets approving comments from the other bearded hunters, but YMMV.

  • Thanks HM for this helpful post. My husband asks me for advice but I’m just not sure what the cool boys are wearing. Any suggestions for matching button-down shirts to ties, as far as colors and patterns? What if the jacket also has a pattern in it (herringbone, plaid, etc)? We’d also love an Insomniac shopping guest post on shoes, not on dress-up shoes or sneakers, but the casual shoe options in between, to wear with Dockers for dinners out or things like that. Thanks!

    • Kim B.

      “Thanks HM for this helpful post. My husband asks me for advice but I’m just not sure what the cool boys are wearing. Any suggestions for matching button-down shirts to ties, as far as colors and patterns? What if the jacket also has a pattern in it (herringbone, plaid, etc)? We’d also love an Insomniac shopping guest post on shoes, not on dress-up shoes or sneakers, but the casual shoe options in between, to wear with Dockers for dinners out or things like that. Thanks!”

      I totally second Debby’s post! Help!

  • We’ve really tried with my husband to find clothes that fit but it’s nearly impossible! He has very broad shoulders/larger upper chest so clothes that fit him there are ridiculously baggy everywhere else. IF we fit his midsection then he can’t move his arms anymore! Pants are also a tricky fit because he has a bit of a tummy but slim legs/small butt so once we fit his stomach they are very baggy everywhere else. I know he’d like to look more put together but without spending lots and lots of money on alterations it’s impossible.

    Shoes are one are I see many guys putting in effort. I know my husband takes good care of his shoes and he’s gotten complimented before on them by other guys. 🙂

    That being said, we do have to be careful about what accessories he wears due to safety concerns here in Brazil. He has some nice watches but can’t wear them for fear of getting robbed. 🙁

    • Sal

      (HM logged in as Sally)
      -Your husband might need to have a custom shirt made. There are online resources out there that might do the trick….

  • Yes! There’s nothing like a well-dressed man. I love menswear!

    Most mid to high-end menswear stores will offer simple alterations for free.

    My boyfriend has a large neck for his size, so he often ends up buying a shirt that is a little large through the body, but fits in the neck, and has the tailor add vertical darts in the back to take in the excess.

    Why don’t woman’s stores offer in-house tailoring?

  • Kate K

    Bravo Husband Mike! You definitely complement your fashionable wife, and I think this is just helpful information in general. As a single woman (i.e. as someone who checks out men on a pretty regular basis :D), I would agree that fit is important and that a good pair of shoes can do so much.

  • jii

    Those Tsubo boots are the most beautiful shoes I have ever seen. That said, the men in my life won’t wear them. I think a man who is relatively clean, relatively neat, wearing a light splash of a fine cologne (Sung, Blue from Gap) meets my standards. Sigh.

    • Linnet

      Yes, I didn’t realize I’d scrolled down in the same post, and thought this was the start of a new post about cool boots — I immediately thought, I want those! 🙁 Too bad they’re men’s (and no, my feet are too small for men’s sizes)

  • Meshell

    Thank you for this post, HM! This was sent to my bf. I really just didn’t have the words to explain what to look for in male dress, and because he sees me rambling about feminine clothing styling, he looks to me to dress him well. And I honestly have no clue on what to look for (I know what I like, I dunno what he should buy). This was very helpful.

  • Carol

    My husband recently decided to buy himself some new clothes and get out of the “denim or chambray everything” rut. I think it was my pointing out that all his clothes were blue that did it. He’s a good looking 70, tall and thin (well, a little belly, but I have one too), retired for 10 years, and likes woodworking and other manly pursuits. He doesn’t have occasion to dress up too much but has spiffed things up with some heavy work khakis, black or brown jeans, and many new (and not blue!) shirts. He is coordinating his outfits quite nicely, with no help from me, in fact I’m starting to feel kind of frumpy next to him. He’s always been one to keep his shoes polished, even his work boots. And when we go out to a nice restaurant, he looks great in a classic tweed jacket and tie, which he will wear without being asked. I guess his new look isn’t the height of fashion, but he looks appropriately well dressed with nice, well made clothing – and he’s my sweetie!

  • sigourney

    This holds a lot of promise as a regular feature in some form! Nicely done, HM.

    As a sartorial addition I’d say a guy should have a scarf in his eyecolour, maybe a little lighter or darker. That definitely makes attractive.

  • Jen F

    Actually, for the advanced masculine fashion-person, I’ve been seeing a lot of short-ish slim pants. They stop just at the ankle. With cool socks and shoes, they look really nice.

    • Shaye

      It takes a certain kind of man to rock the hipster/Blaine from Glee look, and most men who need help in the fashion department are just not that kind of man. Unless his wardrobe also includes a bowtie and a pork pie hat, I’d say HM’S advice that most men’s pants are too short is (hilarious and) spot on!

  • Wonderful post, and perfect timing–my fiance is going to buy his outfit for the wedding in the next few weeks and had no idea where to even start (he works in a super casual office, where non-ripped jeans and something other than a hoodie is dressed up!).

  • I noticed “Husband Mike” used the phrase “step up your game” like 10 different times. I thought that was funny.

  • Shaye

    I don’t have a man in my life to help fashion, but I loved this post! It was funny and charming and so accurate, based on what I’ve seen. I do love a well-dressed man. Funny to think that at one time, men were the ones with complicated grooming and fashion routines and all women needed was a comb and some soap!

  • Thursday

    Great post HM, and also loved the comments from Lark above. I think a number of these principles are great regardless of your gender/dress style. Particularly love Lark’s suggestion of creating unity in your accessories by focusing on the materials.
    This is particularly helpful as my own partner often looks to me for dressing advice. He has some great instincts and taste already, but often wants reassurance on choices or advice on how to step up his game. I want to be able to help him follow those instincts, and explain what works in ways that will stick with him – and this post has hit a number of those things on the head. At least he knows fit – even if he has trouble finding it. In Australia at least, so many suit cuts these days have what we call “display pants” – they lift and separate!

  • kentucky

    This is great advice! I am a musician in a genre that’s not known for it’s uh…fashionable-ness. I have thought about starting a style consultant service for said male musicians. When I’ve offered my services for free to friends (so I can use them to promote it), they have had a funny reaction: they get excited at first. Then I tell them, “We’ll start with a haircut, and then some jeans that fit better.” They always chicken out–I think most men I know just don’t want to put work into it. They want to look better, but not enough to try.

    But, great advice, nonetheless.

  • One website that, as a woman, I think does a good job explaining various versions of male fashion is http://www.dappered.com. One of my favorite features is when they ask, “I’m going to a [casual date, outdoor wedding, etc.], what do I wear?” Then they show pictures of possible outfits and describe the reasoning behind the choices so that at the end a person can think about what is in his wardrobe and come up with something appropriate.

  • Meg

    I just wanted to add a note about pleated vs. flat-front pants. I was finally able to get my (25 year old) partner to try a pair of PLEATED pants, because he too believed that pleats were out of style. But the thing is, pleats allow for some extra room in certain places; and when it comes down to it, the “right” pants are all about the right fit! They were the first pair of pants that ever fit his entire bottom half (waist, bum, thighs, length), and they’re the best looking pants he’s ever worn. He ended up getting them in 3 colors!

    So, I wouldn’t completely rule out pleats. They will fit better on certain body types, especially those who can’t afford to size up for a roomier bum-area in flat fronts, and then have a tailor adjust a too-big waist. If pants the whole body well, they will look modern.

    • Sal

      (HM logged in as Sal) -I write from a place of having very little bum, so I am glad pleats worked for your S.O. -HM