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.

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.

A lot of men, especially-pressed-for-time fathers, tend to think items like a jacket and shoes in the purely functional sense unless they’re specifically dressing up for an event.  While that’s understandable it’s also almost always to their detriment, making them appear older and frumpier.  One of my clients this weekend had just that dilemma. 

He spends all day on his feet, and like many men before him, thought that there’s no way a good looking shoe could be as comfortable as his hiking boot.  He was also a little leery of giving up his windbreaker since he needs lots of pockets and thought a more stylish jacket would not give him as much ‘mobile storage’.  

We outfitted him in Johnston & Murphy shoes that were so comfortable he was grinning from the moment he tried them on and a Zara cotton military jacket with more pockets than his windbreaker.  Best of all, by switching out just those two items in his lineup he looks 10 years younger and infinitely cooler.   

So, in case you haven’t heard me say this a million times yet: Gentlemen, you no longer have to settle, no more choosing between comfort and style, they can now be commonly found sharing the same point in space and time. 

Trend #1: No Rules.

It used to be the case that specific clothing items were “in” or “out” of fashion with everything supposed to be worn a particular way, and being in style meant following those rules.  Some men prefer easy-to-follow rules, sensing that fashion freedom will create too much room for error (incidentally, that’s where an image consultant comes in handy).  But now fashion, especially casual menswear, has gone the way of the individual - just like a BK Whopper, you can have it your way.  Now, this doesn’t mean you’ll suddenly look good in anything and everything (very few men actually look good in pleated pants), and there are still dated items, like the super square toe dress shoe of the 90′s. However, the old rules of not wearing black with brown, no white after Labor Day, matchy-matchy belt and shoes combinations, etc. are gone baby gone.  This embracing of individuality means that when you make choices about clothes, pay the most attention to how you feel wearing them and whether or not they flatter your physique and are appropriate for your lifestyle, and least about what is ”in”.

Trend #2: No Excuses.

“But they’re comfortable!”  The 3 words men most frequently utter while I’m clearing their closet of Dad jeans and over-sized freebie T-shirts (and they wonder why the spark in their marriage or dating life is gone).  Back in the day, it used to be that comfort and style were elements rarely combined in the same garment. Let’s use men’s shoes as an example. Think of the countless men opting for bulky athletic sneakers to wear with their jeans because they think it’s the only casual comfortable shoe available to them.  But designers have known for some time now that people want both form and function; just because we’re not at the office doesn’t mean we have to devolve into frumpy, undesirable blobs.  Now, no matter what the activity – professional, social, or sporty – there is an easily attainable, attractive option to the purely functional and fugly predecessor.  Even L.L. Bean, king of plaid flannel cabin wear, is launching a stylish, casual clothing line: reinforcing that other than laziness, there is no excuse to look like a schleb.

If there’s one thing retailer H&M does exceptionally well, it’s quickly bring spot-on trends to market at affordable price points (albeit dubious quality, but therein lies the eternal trifecta conundrum - you can have it cheap, fast, or good. Pick two).

This is why I’m very curious to see H&M debut a new menswear collection from famed high end women’s shoemaker Jimmy Choo.  If you’re thinking “Jimmy who?”, then ask any well dressed woman near you but be ready to endure moderate screeching and frantic eye darting while she examines you to make sure you aren’t holding a pair behind your back.

The Jimmy Choo menswear line hits H&M stores in select states on Nov. 14th hoping to wardrobe the boyfriends and husbands of their shoe loving clientele.  The collection will include suiting separates, knits, jeans, jackets, and shoes; with a focus on simple lines and subtle detailing.  So, best case scenario, you’ll effortlessly look like a rock star.  Worst case scenario, you’ll have new pick line, “Hey baby, I’m wearing my Jimmy Choo shoes too.”

When I was interviewed for Radio Boston on National Public Radio about being a novice biker,  the producer rode his bicycle over to meet me and I was really impressed with his stylish, professional and yet functional attire.  Looking at what he was wearing I would have never guessed he had biked over had I not seen him riding.

As you’ll see, layering is one of the keys to biking comfortably and fashionably so as your body’s temperature changes you can remove or add a layer.

Adam is wearing a black cotton blazer with a light tan stripe by Hugo Boss, purchased on his honeymoon in Italy (light circles on his lapel are Obama pins).  The blazer’s softly tailored construction makes it easy to wear while riding.

Banana Republic makes these jeans. Shoes are from Johnston & Murphy. Socks sold at Sock It To Me.

The under layers: red thermal long sleeve T by American Appeal, black T shirt from Banana Republic.  Bag is made by Alchemy, details below.

This bag by Alchemy is awesome, made from 100% recycled materials it’s waterproof, very sturdy, and has reflectors on the back.

Here a couple of Emmi Award worthy fall coats that will last you for seasons to come.

This Gap basic black waist length jacket is sporty yet classic. It works for casual to business casual; wear it with your jeans, khakis, or dress slacks, but do not layer over a sport coat or suit. It’s reversible, water resistant nylon on one side and snuggly wool on the other. Available at The Gap for $118.

 For a fall jacket that looks great with jeans or a suit, check out this brown low contrast plaid trench. This coat adds more distinction to your look than a plain black jacket and it’s in a neutral tone so you can wear it with just about any color. Water resistant too. Available at Banana Republic for $250.