If you’d like the specifics on Kyle’s new date look, the button down shirt is by French Connection, it’s layered over my favorite better-than-basic-T-shirt by Diesel. The grey denim is Lord & Taylor’shouse brand, Black Brown. Belt by Levi’s. The sneakers are John Varvatos for Converse, and the vest is a traditional suiting piece I grabbed from the Ralph Lauren suit separates.

For more men’s casual style goodness check out the MANifesto.

All this repetition is making The Donald sleepy!

These guys should've switched ties in the limo.

Remember that like the gorgeous celebrities themselves, dressing too is all an illusion. While a bow-tie may be classic it’s not the best choice for guy with a shorter or stockier frame. A long silk tie is a better choice, as it helps to lengthen and thin the torso.

Returning from LA on the red-eye I was unable to sleep next to my snoring, drooling seat mate.  My mind drifted to thoughts about guys who mostly dress in functional clothes - Nike active wear or golf shirts, survival training cargo pants, Keens, and how challenging it is for them to find dressier clothes that don’t make them feel like small boys forced into their first suit for a visit to Grandma.  For this group of men, the primary qualifiers for clothing choices are typically functionality, practically and comfort. Dressing up to them is alien, they have the same fear as Spiderman did when he was absorbed by the black suit. Here are some key things to keep in mind and to identify to get comfortable dressier pieces. (Dare to dream!)

Firstly it’s about adjusting expectations to reality.

Men who want their dress clothes to have the same features as their urban jungle wear (tons of pockets, elastic waistband, made completely of ‘performance’ fibers) are like the guys who appear on the Millionaire Matchmaker because they want a girlfriend with the kind soul and generous, humble personality of an unattractive woman with the body of a super model. In order for them to find happiness they must realize they are harboring an unrealistic expectation and must accept reality by determining what it is they actually need.

Like different tools serve different purposes, so does different clothing.

You need the right tool for the job - A hammer can’t remove a drywall screw elegantly or neatly.  Similarly, a modern sport coat won’t serve the same purpose (nor feel like) a Patagonia safari vest. Chances are you won’t be able to stuff everything you (think you) need into the pockets to survive a zombie apocalypse and still have room for your iPhone*. But remember – right tool for the right job; you are not choosing dressier clothes for a zombie apocalypse, you are selecting those clothes to make a particular impression, something more important to you and your future than “guess which pocket holds my beef jerky and trail mix?”

Just because it isn’t featured in a tactical clothing catalog doesn’t mean it can’t be quite comfortable.

My guys always discover this shortly after their initial flail coming out of the fitting room. With the alien skin newly applied, they waive their arms in large circles and say, “Maybe it’s a little tight , I’m having a hard time doing THIS”, their mid-air butterfly stroke expanding wildly. I ask them how much flying around the room like a pterodactyl is required of them at meetings.  Then I ask them if they’re comfortable performing all the physical activities in that blazer that most likely would be required of them while wearing it. Like shaking hands, pointing to increased sales figures, sitting, etc., and voila! Within moments they realize that for those things the jacket they have on is actually quite comfortable. With expectations adjusted here are 3 other tips that will make getting comfortable dress clothes less challenging.

1. It doesn’t have to be a monkey suit. Men assume they have to stuff themselves into a stiff restrictive traditional suit to look dressed up or professional. Erase that assumption from your mind. It’s about mirroring the attributes of that professional clothing.  Miraculously, you will discover you can find more casual and creative versions of all business attire. The blazer above is made of brushed cotton with a bit of spandex so it doesn’t feel like a typical suit jacket. The shirt has contrasting fabric lined double point collar, more creative and distinct than a plain old dress shirt. The pants are soft chinos in a dark gray with a slim cut so that they resemble slacks but feel more like pajama jeans. Even the lace up oxfords look like a dress shoe on top but have a rubber sneaker sole.

2. Don’t settle. You have to feel confident after you’ve put it on. Seriously,if you don’t feel like one bada$$ motherf@#*,  don’t buy it. I don’t care if it’s on sale, you’ll regret it later.

3. It doesn’t have to be expensive. Thanks to Zara, the entire look above from head to toe, even with California being home to the highest taxes in the nation, totaled $220.

So next time you need to get some dressier pieces, keep in mind the intended purpose. Use that as your basis to judge suitability, while taking into account how much the item reflects your personality, and most importantly, and how confident you feel. And if the Zombie’s attack while you’re all dressed up and sans tactical gear, you’ll look so good that not only will you get saved, you’ll probably get elected de facto leader of the surviving humans. It’s all in your hands now.

*Scottevest makes the most city appropriate, concealed pocket clothing around, but currently have no Emmi Approved modern sport coats. If you carry a lot of stuff and need a daily casual sporty fleece, windbreaker, or a classic travel jacket, definitely check them out.

Go Gore-Tex – You don’t have to be James Bond to benefit from some high tech action in your in footwear. Gore-Tex is a thin, man-made membrane that when used as a lining in shoes and boots makes them impenetrable by water yet allows for air to flow out. Since it’s so thin, this Fort Knox protection doesn’t come at the cost of destroying a sleek shoe’s line. Now this may not help you disarm a bomb or win at high stakes poker against a one-eyed villain, but it will ensure that your feet stay comfy and dry in the wettest weather without suffering a case of elephantiasis shoe. Brands like Ecco and Johnston & Murphy are a couple of the shoemakers that carry Gore-Tex lined footwear.

Water resistant vs. water proof – What’s the difference? Well if you live in a place known for torrential conditions it’s the difference between wet socks and dry socks. We could go into all the scientific mumbo-jumbo about how the two differ but instead you can think of Batman as waterproof and Robin as water resistant, when you get into deep water which of the two would trust more to get the job done?

Rubber soles with grip – It used to be that beautifully crafted men’s footwear always had a leather sole. Great in concept but once the streets start icing over you’ll be spending more time with your face on the pavement than you did during your last trip to Vegas. So if you like the idea of staying stylish and upright this winter, opt for shoes with a rubber sole instead. Cole Haan does a masterful job of blending classic and modern dress shoe uppers with streamlined, sturdy, and gripping rubber soles. It’s a winning union of form and function and a wonderful reminder that man no longer has to choose between style or comfort.

A – I get this question almost daily around the holidays and have come to realize that the confusion comes from a codependent set of common misconceptions 1: In order to be better dressed, one has to dress more formally, and 2. The only two options for social gatherings are either jeans and T-shirt or dress pants and button down shirt. Inside that rule set it’s nearly impossible to dress for a celebratory, casual dinner.

In reality men have infinitely more options for casual attire than ever before, but choices and uncertainty can make for a paralyzing combination. Here’s the secret – looking pulled together in ‘relaxed’ clothes is about mirroring the attributes of more formal dressing such as form flattering construction (emphasis on shoulders, not stomach), quality fabrics (cashmere/wool in lieu of pilled cotton), and making good use of layering and accessories. Try well constructed sweater or cardigan over a nice (not Hanes) T-shirt or simple button down and jeans or modern wool slacks. The sweater acts as the ‘finishing’ piece adding more substance to your look and cleverly hides any belly extension you’ll encounter after second helpings. When it comes to the footwear, just about anything will work with this, but you can also use the shoes to make your attire even more casual by pairing with some basic Chucks or dress it up with a half boot or lace up oxford. And don’t forget your most important accessory, a gorgeous bouquet for your girlfriend’s mom.

If a blue shirt & khakis is the boring uniform of business casual, its Luke Wilson off-hours equivalent is the untucked dress shirt & jeans.

Here’s how to take this casual pairing from “Eh.” to “Excuse me, is anyone sitting here?” with some easy adjustments.

Button down – An untucked traditional dress shirt, especially if it’s a standard fit can look sloppy, opt instead for an actual casual button down; these really do exist I swear, it’s not like the virgins waiting for you in heaven thing.  Typically casual button downs posses a fit and print better suited for ‘hanging out’.

Jeans – Even though the typical sartorial rules for pant breaks don’t apply to jeans, there is such a thing as too long (no TWSS jokes please). If the denim starts to to buckle and bunch up to the knee or higher, that jagged silhouette is a sign your jeans have gone too far, literally.

Layer – Layering is the casual man’s secret weapon, well that and ordering off the dollar menu. Even a simple, non logo emblazoned sporty zip up like the one above adds visual interest and can eliminate suspicions that you just rolled out of bed in your t-shirt.

Noggin - Men tend to update above the neck at an even slower clip than below. Exhibits A and B, glasses and hair style. If you’ve been wearing the same glasses for a few years now consider upgrading frames or getting contacts. Lastly, when it comes to your hair, even small changes can make a big difference like brushing your bangs to the side rather than having them lay limply across your entire forehead.

These gentlemen wanted to update their business casual look for an upcoming sales pitch meeting. They’re two intelligent and talented guys but their exsisitng look wasn’t showcasing them as such.

Now, business casual only works with modern, form flattering pieces; yet too many guys grab an old boxy blazer toss it over some dad jeans or dockers, and then for the final nail in the “don’t hire me” coffin, their old and busted 90′s squared toe lace ups or, trail shoes. Never wear footwear sold at REI to a business meeting, unless you and Richard Branson are talking merger while scaling a cliff face. Let’s take a look at the upgrades we made from head to toe during one quick shopping trip to Lord & Taylor. 

Sport Coat: Blobby blazers were switched out with better tailored sport coats in colors that are more flattering to their skin tones. Now while darker colors assert more ‘authority’, it’s August in Boston and their pitch meeting was happening on a 90 degree day, so a tan herringbone jacket was completely appropriate.

Pants: Both guys wanted to wear jeans to the pitch rather than slacks so it was important to find jeans that had an even, dark wash with no embellishments, distressing, or whiskers (I swear I’m not making these terms up) and were cut like a trouser.

Shirt: We got button downs with tailored torso so they wouldn’t have flying squirrel side wings when they removed their jackets.

Shoes: Time and time again I hear from guys that they can’t wear better looking shoes because they have wide feet, or they’re on their feet all day. Both of these reasons accompanied us to the shoe department. Yet after fighting me that fugly was the only was to go, both men, in their new shoes stood proudly grining as content as a politician with an envelop of special interest money. Turns out both Born and Johnston & Murphy make shoes that are plenty wide, comfortable, and good looking on our guys.

Accessories: Don’t forget that your belt and socks count. They may not be visible all the time but at those moments when they are, a beat up belt or hole ridden sock won’t help your credibility.

We replaced each of their looks for under $300 and all of the pieces can be incorporated into an unending array of outfits bringing their cost per wear down to pennies. Now that’s good business cents. And, in case you’re curious, I got word that they ”killed it!” during their pitch meeting.

What Happens When Dress Shoes & Sneakers Meet?

Evolution in the shoe kingdom has produced a handsome hybrid offspring, the canvas oxford.  You’ll be seeing this relaxed take on the classic popping up at retailers everywhere this season.  A light neutral pair like these by Generic Surplus plays nicely with trouser (we’re not saying snake) shorts, light color denim, and khakis.  Easily categorized as casual chic they’re a nice option for the summer days and nights when you want to look more dapper than sporty.

So you’ve been invited to an event and the invitation reads “Dress To Impress”.  Hmmm, sometimes you’re impressed that you remembered pants that day, so does that count?

Here’s some helpful guidelines to dispel the mystery.  Starting with the shoes and working our way up, here’s what should (and shouldn’t) be on your body.

Shoes - Obviously no gym sneakers.  Sketchers, while ok for casual parties are a bit low brow for a stylin crowd.  That doesn’t mean you have to break out those uncomfortable dress shoes, plenty of in between options like a slip on, driving moc, or streamline street shoe.  Extra bonus points if you opt out of black.  Style isn’t about matching, it’s about coordinating- color shoes add excitement to traditional color schemes and look great with denim.  You don’t have to go out full technicolor either, a grey or color accented shoe can also step up your overall look. 

Pants – Most clubs and party venues now welcome jeans- not dad jeans, well cut, unripped (unless you’re with the band) modern wash jeans.  If you prefer a trouser, flat front only.  Again, go beyond black, like a taupe with subtle print of glen plaid or window pane can coordinate with almost anything.  Lightweight wool or linen for a summer event will keep you cool as the room fills up.  Keep the socks in line with the color of your pants, remember the ankle is an extension of the leg.  You can also go for a creative print, but avoid silly novelties like cartoon characters.

Shirting -  If you are only wearing a dress shirt make sure you nail the fit.  Being swallowed by your shirt doesn’t showcase you in a power position. French cuff shirts with links always add some elegance.  Wearing it without a tie? If you’re going to wear a undershirt, make sure it’s a V-neck so the collar doesn’t so the top doesn’t stick out from the unbuttoned collar, we may love accessories but an underachievers ascot is never where it’s at. 

If you prefer a T-shirt or a knit make sure these pieces are refined rather than loud.  Graphic Ts aka Jersey Shore are the fabric equivalent of jaundice, looks good on no one.  Unless your T-Shirt is hand crafted like a Murcielago, add some more interest to your look with another layer.  Tailored vest, lightweight cashmere v-neck or masculine (not Mr. Rogers) cardigan, or… 

Sport coat – A modern, Italian cut sport coat is the easiest, most instant way to dress up and dignifiy what you’re wearing.  Looks just as stellar over a well selected T or dress shirt, with jeans or with slacks.  And, provides you extra storage for your smart phone, wallet, and James Bond USB stick into poison dart key chain.  

Accessories – Accessories pull your look together and are the finishing elements that make women want to touch you, and guys secretly jealous that they didn’t think of wearing that too.  As with everything else on your body, only wear the accessories that you feel confident in.  A neatly folded pocket square in your sport coat pocket,  a well woven straw fedora, a tie or for some more youthful edge, embellished bow tie, are just a few accessory options. Remember your belt does not need match your shoes, as noted earlier, it’s about coordination not matching.

When it’s all put together your natural swagger should be as noticeable as a Vuvuzela in a library.  If all of this sounds scary and confusing, stop hyperventilating.  Show up, order a Kettle One martini, mingle, and be your most comfortable self.  Besides, confidence is the sexiest accessory.