Men's Fashion: Dressing For Success

Thanks to one of my managers I found myself in possession of a $25 gift certificate to amazon.com, which I used to buy two of the personal style-related books - Trinny and Susannah's "Trinny and Susannah Take on America" and Carson Cressley's "Off the Cuff". Naturally, I read "Take on America" first (let's face it, I am after all a girl). You may laugh all you want, my friends, but this book is the first work of what I would like to call psychology of fashion. It's not just a list of what to wear and what not to wear, it is a journey into what larger, more painful and serious issues might be lurking under someone's inability to enjoy dressing well and looking good. I absolutely recommend "Take on America" to everyone - of either gender, I can guarantee you will not regret reading it.

Sadly, there are not as many similar books for man, as I would like to see. So, following "What Not to Wear's" Trinny and Susannah's model, my husband and I have identified a group of male fashion disaster archetypes and provided a brief summary for each group. Obviously, some groups overlap and the ultimate solution to every style-related problem depends on the individual. However, we hope this would be helpful as a starting point for the sartorially challenged.

For some of the archetypes the remedy does include some extensive shopping. However, please keep in mind that what we are offering are ideas - if you can find similar items for less, good for you. Second, better quality clothes usually cost more, but last longer and wear better (keep their shape), so you'll be saving money in the long run. Third, think of all the money some of you saved over the year by either not buying anything new or buying only cheap clothes. Surely there is a wardrobe budget hiding in your bank account somewhere. Finally, looking better changes more than just your appearance - it changes your entire attitude and helps you achieve things you haven't thought about before. It's true! A hot date or a long-awaited promotion is well worth the trouble and the money.

1. Can't dress down
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The look: This guy is permanently stuck in a suit; if he is going somewhere casual after work, all he does is take off his tie and unbutton the top button of his shirt (which doesn't look casual - it looks like he...umm... took off his tie and unbuttoned the top button); if he switches to a casual work environment, he just wears suit pants and a white shirt, sometimes all he does is leave out his tie; he doesn't have an intermediate group of clothes between his endless grey suits and jeans.

Why: (1) He developed his attire when a guy was either working at a bank or working on his car. (2) He is afraid to screw it up - a suit is safe, because everything matches. (3) He feels bad casting off a closet full of really nice and expensive (but, unfortunately, really dated) suits. (4) Anything other than a white shirt just feels weird.

The remedy: Try mock turtle necks or crew necks in nice silk knit; for a less trendy look wear a button down collar oxford shirt in coarser fabric; wear your favorite suit to a men's store, like Men's Warehous and say, "I'd like to dress this down". For ideas, go to catalogues like Charles Tyrwhitt and Paul Fredrick to find examples of casual shirts. Then cut out your favorite pages and go shopping to less pricey places like S&K and Haggar's. If your job requires that you wear a suit and you are going someplace less formal after work, carry a silk knit mock turtleneck with you (it will easily fit into a briefcase), sneak into the restroom when it's time to run to your after work engagement, ditch the jacket, tie and shirt and replace with that mock turtleneck. Use color. Please.

Life tip: Being less dressy doesn't mean just being less dressed.

2. Nature child
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The look: thrift store stuff; drab ill-fitting natural fabric clothes (the natural part is admirable, the rest is not); carpenter pants; lots of baggy t-shirts; military surpluce stuff.

Why: He wants to do right by the world, but insists on buying cheap (this contributing to garbage, because his clothes fall apart at the seams every 3 months); think that unkempt look means getting closer to nature (it doesn't - it just means looking sloppy).

The remedy: Buy clothes in natural fibers and colors that are good quality and well-tailored. Run searches for "organic clothing for men" and "bamboo clothing for men" to find many, many available natural fiber options that look good and wear well. Ask around and find a good barber, who can give your hair some shape, even if you insist on keeping it long; if you wear a ponytail, you can still benefit from a good haircut, and if you want dreads, have them done professionally.

Life tips: (1) Find other ways to recycle if you feel guilty about your new wardrobe. Learn a new skill that appeals to your re-using, environmentally conscious nature: refurbish and sell (or donate) old furniture, turn your back yard into a nature preserve, grow your own herbs and veggies (it can be done in an appartment these days), adopt a homeless animal, start a "donate your car to a local NPR station and buy a hybrid" campaign among your friends and relatives - possibilities are endless. (2) One man's trash is not always another man's treasure - sometimes it's just trash. Recognize it and let it go.

3. "Why make the effort?" (slob)
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The look: missing buttons, torn pant hems, never-cleaned dry cleaning; everything wrinkled and thrown together at the last moment (because he can never find what to wear - everything is permanently in the laundry). Colors faded, whites are never white, because everything gets washed together in one big load once a month.

Why: If he doesn't try to dress nice or generally make himself attractive to people, he can't fail. Tries to convince himself that people who might be attracted to his appearance (had he made an effort), are not worth meeting anyway because they are superficial.

The remedy: Admit to yourself that looks matter. If you know the meaning of words "ugly" and "beautiful" you already know it's true. If you are looking at two identical cars, but one with a nice paint job and one with a crappy one, you would be drawn to the one with nice paint job. So, why expect people to be drawn to you if you look like crap (regardless of your brilliant mind and heart of gold)?

To avoid ironing clothes, buy wrinkle-reducing fabric softener, take clothes out of the drier right away and hang or fold them immediately - this will get rid of 90% of the wrinkles. If clothes need repair, repair them (or have someone do it for you - any dry cleaning place usually offers alterations and can attach your missing buttons and falling pant hems), replace them or retire them.

Pick clothes that fit, update them every once in a while. If you keep wearing a t-shirt that's been your favorite for the last 5 years, it's time for a new favorite. Get a good haircut and buy a beard trimmer if you don't like to shave. Invest in clothes that are low maintenance (stain repellent, wrinkle-resistant, washable, etc.), but remember that even the lowest maintenance clothes still need to be washed. Learn to separate your laundry at least into whites, light colors and dark colors - your clothes will look a lot better longer.

Life tips: Get some exercise. You'll be in better shape and you'll be more motivated to dress your body well, when it no longer looks like the Michelin man.

4. Loud and proud
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The look: either really, really, really loud color clothes in the same colors (orange shirt, with yellow pants and jacket) or a mishmash of colors and patterns, where you can't see the person behind the clothes.

Why: There are several possible reasons or combinations thereof. (1) He wants attention. (2) Someone said he needed some color and he went overboard with it. (3) He thinks that loud clothes show off his personality. They don't. People will notice you, but not in a good way - these are the same people who pause to stare at a car wreck.

The remedy: Use one bright color at a time on one article of clothing. Find someone you know, whose dress sense you admire, and ask that person to help you pull together outfits that center around your favorites but don't look like circus came to town. Take two-three of your favorite articles (shirts, ties) to a men's store and ask what would work with them.

When you put an outfit together, add something funky or quirky that almost doesn't work but does. For example, my husband wears an earring (a diamond, onyx or sterling silver stud) with a full tux. It does make people do a double-take, because an earring with a tux looks odd, but it doesn't clash and somehow it works.

Life tips: (1) Get a magazine with clothes in the style you like (trendy, formal, casual, etc.) and peruse photos, including the ones in the articles (not just in the ads) and use them for ideas of what works. (2) Learn to shop (oh, the humanity! No, knowing how to shop for clothes for a man is not gay!). Look for something that stands out and almost makes you laugh, but not quite, and buy it.

5. "I hate dressing up!" (frequently preceded or followed by, "I hate wearing suits!")
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The look: perpetual jeans and t-shirt. He shows up at a wedding in a golf shirt and at a black-tie event in a blue button-down oxford shirt, khakis, maybe a jacket and definitely no tie.

Why: He is convinced that all dressy clothes are uncomfortable. He can't think of a good reason to dress nice (sometimes prompted by a dress-down job, like a mechanic, a builder, a farmer, etc.), and looking good and occasion-appropriate doesn't seem like a good enough excuse to go through all that trouble.

The remedy: Get some dress clothes that fit right and are right for your body style. Try things on - don't rely on measurements (I don't care if the measuring tape says your neck is 17", if a 17" collar shirt doesn't fit - it doesn't fit, try the next size). Look for nice crew neck silk knit shirts if you really hate collars.

Try on lots of dress shoes, experiment with different widths and sizes until you find what is comfortable. Nice shoes that are comfortable do exist - this is, after all, 21st century. Rubber soles are normally better than leather soles. Look in catalogues and stores that sell army and police surplus dress shoes - those are really comfortable (the black patent shoes my husband wore with his tux at our wedding were actually navy dress uniform shoes - nobody could tell the difference).

There are only two ways to do full formal: (1) a full tux; (2) monochromatic black, but it has to be extremely well cut and put together. However, if an invitation says "black tie" dressing in a tab collar shirt and khakis is just not an option, it's disrespectufl to the organizers of the event and you are begging to stick out like a sore thumb. Is that the kind of attention you really want or would you rather surprise everyone by showing up looking spiffy, classy and cool as a cat?

When the next "black tie" invitation lands at your door, don't kick and scream and tell your wife to go by herself. Instead, accept for you both, then head straight to Men's Wearhouse and ask them to put you into their black tie wardrobe package. Don't worry, they are very nice people and will listen to you if you tell them if something pinches or squeezes too much. Actually help your wife pick out her own outfit and show up in all your glory to stun everyone. If it's a wedding, you just might outshine the bride and the groom.

Life tips: Looks do matter. To be successful you must be able to match the situation by dressing up for dates, interviews, business and social functions.

6. "Look at me girls!"
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The look: Actually, this particular type consists of two groups. (1) A guy with great physique, who wears too-tight everything leaving nothing to imagination. (2) Someone who is stuck in the 70's and thinks that a shiny polyester shirt undone to the belly button is sexy.

Why: He thinks it attracts women but (a) it doesn't attract that many and (b) it hinders him elsewhere (like in his business dealings).

The remedy: Watch movies or check out screen shots from films where men dress well and look good, but do so unobtrusively. Pierce Brosnan's dressy and casual looks in "The Thomas Crown Affair" come to mind, as well as - strange as it may sound - Dylan Bruno's casual look from "Where the Heart Is". It's a girly girl movie, but this guy's casual wardrobe - during the part of the movie where his character's fortune favors him - is awesome! If you have a good figure (broad shoulders, narrow hips), look for shirts and jackets that are fitted around the waist.

Flat front pants will also work great for you (pleated front pants work on some people, but only on those who have perfectly flat stomach - this applies to men and woman. As soon as you have even a hint of tummy, the pleats bunch out and make you look pregnant - really awkward, especially on a man.) Tailored suits, fitted shirts and t-shirts are proof that clothes don't have to be extra-tight or unbuttoned to the navel to make you look sexy.

Life tips: (1) Spandex and leather have their time and place, but making them the foundation of your wardrobe may not be the best idea. (2) What sort of woman do you suppose you'll attract dressing like an aging playboy?

7. Struggling to be cool
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The look: He wears sunglasses in the building. His Bluetooth is permanently clipped to his ear. His belt is sagging under the weight of all the latest gadgets attached to it. He wears all black not because it looks good on him, but because he saw it on TV and thinks it's cool.

Why: "Insecurity" is the word. He is trying to attract attention to things about him - not himself.

The remedy: That Bluetooth does actually come off, you know. Even nurses, policement and firement don't wear their phones, walky-talkies and pagers all the time. Whatever you do - it can't possibly be more important than what they do. So take that thing off your ear and turn it off!

Your gadgets are not for show (at least they shouldn't be) - they are for use. So, make them less "showy". Put your phone in your shirt or pants pocket (Dockers makes pants with zippered pockets if you are afraid to lose it) and your Blackberry - in the inside pocket of your jacket.

Better yet, instead of a collection of the latest and greatest gadgets find one that does it all (or most of it) and sell the rest on eBay.

Wear color or break up your black with pattern and texture. There is nothing wrong with monochromatic black, but wearing it all the time? Even Johnny Cash didn't do that.

Life tips: (1) Electronics do not make you more interesting. (2) Use the money from selling off your gadgets to take a long weekend on the beach. Take no electronic devices with you. Bring a book.

8. The billboard man (logo/designer label slave)
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The look: always wears something with a huge designer logo on back, chest, butt, leg, shoulder, etc. At work wears a tie (and not the best quality tie either) with "Gucci", "Ralph Lauren", or "Tommy Hilfiger" emblazoned all over it.

Why: He thinks that a nice shirt without a logo cannot possibly say "status" like a t-shirt with a huge designer name on it. It's all about following the pack and stating it as loudly as possible.

The remedy: You are not a sign board. Designers are not paying you to be one. So don't do it. Sell your over-logoed duds on eBay (god knows, there are plenty of other label sheep out there, who will snatch them up) and use the money to buy a real wardrobe. There is nothing wrong with buying designer clothes, if you can afford them, if they suit you and you like the quality, but you don't have to announce to everyone, who made them. If you want to throw in some truly unique and interesting elements, look for vintage cufflinks, ties, sweaters, vests, etc.

And if you can afford it, have some of your clothes (like your business suits) custom made for you - that way you'll know nobody has anything quite like it. As a half-way option, Charles Tyrwhitt and Paul Fredrick both offer "build your own shirt" and suit separates, where you can pick out your favorite features to be incorporated into your shirt (collar type, cuffs, buttons or cufflinks, fit, etc.) and construct your suit from a set of jackets, vests and pants that are best for you.

Life tip: It's your look that matters - not the label.

9. Stuck in sweats (the next evolutionary stage of the suit hater)
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The look: Sweats, sweats, sweats... Sweatshirt with baggy jeans in winter. T-shirt with sweatpants in spring. T-shirt with big ugly carpenter shorts in summer and then we are back to sweats.

Why: He either (1) doesn't think he can look good in anything, or (2) doesn't think it matters what he looks like or (3) too comfortable to change.

The remedy: You might become a self-fulfilling prophecy - if you continue looking like a shapeless, stretched-out saggy blob of grey or navy blue, nobody will want to look at you anyway and then it really won't matter what you look like. We've said this already and we'll say it again - this is 21st century, "nice clothes" no longer equals "uncomfortable". We are all for comfort, which is why we favor places like Travel Smith and Duluth Trading so much. Peruse their web sites and catalogues and find clothes that are comfortable but are not shapeless and saggy. Challenge yourself to find good walking shoes that are not sneakers. They do exist!

Life tips: (1) Sweats are for the gym. Keep them there. Even athletes don't walk around in sweats anymore.You might as well walk around in pajamas. (2) Like it or not, but humans are cisual beings - we make our initial judgement of someone based on his looks. Sweats do not spell "success", "intelligence" or "industrious spirit" - they spell "sloppy", "mushy" and "slow".

10. Shoe that never fits
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The look: There is nothing wrong with the way this guy is dressed, until you look at his feet. Knee-length socks with shorts. Sandals or sneakers with a business suit. White socks with dark pants and shoes. Loafers with tux. Argh!

Why: Most likely, he just doesn't know any better or thinks that as long as the rest of his outfit is ok, he can get away with the wrong shoe.

The remedy: Print out the following and memorize it.

(1) Sneakers belong at the gym.

(2) When in doubt, wear nicer shoes than the situation calls for.

(3) Match your belt to your shoes or, with khakis and jeans, wear a colorful belt (like midwestern woven belts).

(4) In general, the shade of your shoes should be as dark as or darker than your pants. Shoes that are much lighter than your pants will make your feet look like canoes attached to your ankles.

(5) Not wearing socks is acceptable with jeans, khakis or shorts in the summer in non-business situation. Socks worn with shorts should be short.

(6) In general, your socks should match the color of your pants but slightly darker. A little pattern on the sock goes a long way. Sophisticated dressers know how to choose socks where the dot or the stripe in the pattern picks up the color of the shirt or the tie. If you don't think you can handle a patterned sock, wear a plain one.

(7) Wear pants that drape slightly over the top of your shoe when you stand. That way, if you cross your legs when you sit down, your pants won't ride up so high as to show your leg hair sticking out of the top of your socks. Person who invented tapered pants should be shot - just don't wear these things, they make everyone look bad - men, women, children, everyone (I mean, I saw a photograph of a Newport News model who looked bad in tapered pants - so what chance do the rest of us, mortals, have of looking good wearing those things?). Same goes for cropped pants - even Mr. Universe in the legs division shouldn't wear them, they make you look like your legs have been chopped off at the ankles.

(8) Wear appropriate shoes with a tux. If you can't affor tuxedo shoes, navy or army dress uniform shoes will work just as well and can be purchased at the fraction of the price. Wear appropriate dress socks.

Accessory summary
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You are dressed, shod and ready to go, right? Well, almost. There are a few finishing touches we need to mention before we let you out the door - accessories. Accessories for men do exist, believe it or not - spicing up one's outfit or tying it all together with a unique element is a privilege that is no longer reserved just for women. Here are some basic tips to guide you through the accessory labyrinth:

(1) No more digital watches! Please! An ugly plastic watch will always look cheap and can become an eyesore regardless of how impeccably you are dressed otherwise.

(2) No more multiple shiny chains (necklaces, bracelets, etc.) - it is tacky. If you enjoy wearing jewelry, that is perfectly fine, but look for subdued and tasteful. There are tons of places that cary men's bracelets and necklaces, including leather cuffs that can look killer sexy with a simple white shirt and jeans as can a silver cuff (think Clint Eastwood in "Bridges of Madison County" - I loved that silver bracelet he wore, it fit in very well with the rest of his look and was very masculine).

(3) If your briefcase is really dated, scuffed and battered (some styles aren't even made anymore - and haven't been in the last five-ten years), replace it either with another briefcase or with something different altogether. Check out Levenger.com for some really high-quality non-traditional work, out-and-about and one-night travel bags.

(4) To make your outfit more trendy, classy or dressed-up wear a dressier belt than you think is necessary. Do not wear dress belts with jeans - there is such a thing as nice casual belts. For clues on good-looking casual belts, watch guys playing golf.