Dressing Up For Guys Who Hate That $h@*!

It was no mistake that I timed my LA styling trip for mid January. Escaping the cold to make men look hot?  Sign me up!  On my second to last day I met a lovely woman who, upon discovering that I'm a menswear stylist, asked me so nicely to take her husband shopping that I willingly traded in my solitary day off to veg on the beach (I would be returning to blizzard back in Boston) for a most excellent shopping adventure on Santa Monica's Promenade.  The mission: Transform a talented guy who hates dressing up comfortable with a look that is stylish and suitable for pitch meetings with LA advertising executives and venture capitalists.

makeover for men
makeover for men

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.

Clients 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.