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.

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.

Emmi Versus the Spiderman from Todd Randolph on Vimeo.

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.”

Mistake #1

Poorly Fitting, Dated Clothing -  Men tend to select clothing that is too large for their frame. If you combine that with newer garments cut with an emphasis on a tailored silhouette it’s a recipe for self sabotage. It will be instantly obvious from across the room who is wearing out-of-date clothing. The last thing you want is to give the impression that you or your skills are anything less than current.

The Fix:
Many brands now offer dress shirts in a slimmer cut, a welcome improvement over the traditional boxy fit for a lot of men. These more flattering styles are available from Calvin Klein, Perry Ellis, Geoffrey Beene, etc. The slimmer fit will be notated on the shirt’s tag using terms like City Fit, Modern Cut, and Tailored. It’s also a good idea to pair these tailored shirts with flat front pants – yes it is time to replace your pleated slacks and khakis (see previous post).

Traditional cut dress shirt: Note the excess fabric distorting the torso - Photo courtesy of GQ

Slim cut dress shirt - Photo courtesy of GQ

Mistake #2

Too Casual – You don’t have to wear a suit and tie to look professional. The key to looking professional without resorting to a suit is to wear a  dress shirt and pants that are clean and crisp, with attention paid to the details. Rolled up sleeves, wrinkled pants, and dress shirts in less than excellent condition do not portray a solid professional image.

The Fix
Use metal collar stays to ensure your collar won’t curl under and stays stiff. Select slacks that have a small amount of Lycra in the fabric, this will help them retain their shape throughout the day. If you aren’t going to wear a sport coat or suit add another distinguishing touch by wearing a french cuff dress shirt with cuff links.

Mistake #3 – Losing Your Distinction – Going business casual doesn’t mean reverting back to the college days. You want to avoid losing your identity in a sea of lackluster polos and khakis, but be careful not to confuse distinction with flash. Ironically the photo below is from a Fox News report titled “Dressing for Casual Fridays”, making me wonder if the reporter accidentally supplied us with the Fox News Back Office Intern Dress Code Manual.  Don’t expect to get a lot of respect from your superiors looking like a college kid going for beers with the buddies, even if it’s Friday.

Don't default to the lowest-common-denominator mentality when it comes to business casual

The Fix – Pick up updated versions of the business casual classics with subtle creative detailing. From a distance you’ll simply look well put together and up close there is even more to admire. For example not all khakis are created equal. You could replace the standard all cotton Dockers with a cotton/nylon khaki from Calvin Klein which, although similar to Dockers in the sense that they are also khakis, have a cool modern look with no hint of flash. Also consider a button down shirt with a patterned weave instead of a solid. It’s actually easier to set yourself apart as a business leader in business casual attire because the majority of your colleagues will be opting for the uninspired default polo - khaki uniform. If you do decide to don a polo remember,“stripes are not your friend” (see prior post).

I have found even more proof that pleats are passe. On a recent shopping adventure I searched the racks to find some pleated pants to photograph and found only a few available.  In their place were a wide range of flat front pants, even in the “grandpas only” section. Luckily the Polo department, permanently stocked with shirts and sweaters in every color of the rainbow except for those that actually look good on humans, was a sure bet for some pleat action.

For the “pleats versus flat front” photo I selected a pure silk pleated trouser which not only provides the glorious benefit of distorting the hips but also comes with the extra bonus of developing a static charge after only a couple of steps. The result is fabric that clings to the legs in the way that wet toilet paper clings to tree branches.

At the risk of stating the obvious the same man is wearing both of the outfits in the photo below. So now I could articulate with flowery prose all of the ways pleats dishonor the man who wears them but rather I’ll let the following picture say the thousand words. For those of you as yet unconvinced those words would be “pleats make you look fat”, on repeat.

Last night’s shopping trip with a client led to several men’s style “pearls of wisdom” I have to separate the experience into sections. He was generous enough to let me take some photos of him sporting men’s common fashion mistakes. Note that he did this in the interest of improving the lot of his fellow man, a truly noble motivation, and would normally not be caught dead looking like this. 

Let’s look closely at the photo above. Hideous eh? The pleated pants, worn too high above the natural waist are also an inch too short, as a public service, if you are reading this and work in any of what are commonly viewed as “highly technical” professions, I must ask you to look down to make sure you don’t have something similar going on. If you are similarly attired to be comfortable in high water then it is likely that people have been laughing at you. The good news is that it is not too late to get help. 

Now back to our ensemble of “no”. The ill-fitting pants play second fiddle to the rust - colored plaid tablecloth, um, shirt. What may not be evident in the photo is the shirt (okay perhaps tablecloth was too harsh, it could also pass as excess drapery fabric from your grandmother’s house) is made of 100% silk, appropriate perhaps for the limited category of metro sexual lumber jack. Please excuse the slight blurr of the photo, as I failed in my attempts to control my convulsive laughter. To top off what is an obvious fashion atrocity, this shirt retails for $128.00. If you have the desire to splurge  on an extravagant item of clothing while maintaining that KMart Blue Light Special aura then this is definitely the shirt for you.

The real magic happened when the store’s sales person entered the fitting room as I was snapping photos. Our eyes met and I opened my mouth to explain to her that this was a fashion “don’t” photo shoot  for my blog  but my words were lost in giggles. My inability to offer an intelligible sentence gave the sales associate time to render her opinion on the outfit. “Wow.” she said. Now my client and I thought for certain the words following that would be along the lines of courteous attempts to steer him off the path of certain social ostracism. Perhaps a polite “Interesting choice, let me find you something that doesn’t deplete your manhood just by touching your skin.” But, no, not even close. With a straight face and an extra ooze of sincerity she looked at my client and said “Wow, that’s a great shirt on you! I love the pattern and the color! You should DEFINITELY get that shirt!.” As she left the fitting room she yelled out a final “DEFINITELY!”. Slack jawed my client and I starred at each other amazed to realize that there was not even a hint of sarcasm in her tone.

Next time you go shopping solo and a sales associate tells you everything you try on looks great, take a step back and assess the motivation of that sales person. Recognize that it is the job of a sales associate to sell more clothing; it may be directly adverse to that interest to acknowledge there isn’t much in that particular store that is appropriate for you. Most sales people do not get paid to make sure you look your best and are getting value. Now before a horde of retail associates show up with torches and pitchforks at my front door  there is something I must first tell you – - I have dogs. The second thing is that obviously there are exceptions to the rule, there exist sales people whose first priority is the client, and not their corporate headquarters, but those noble souls are in the minority. So when it comes to listening to the sales staff about whether or not you should buy their goods, stop and think- and take another real good look in the mirror and above all, always remember the first rule of survival for a spy, trust no one.

Know your industry and the expectations. Walk into a downtown Boston law firm and a Cambridge bio-tech company on a Friday and it’s clear business casual means very different things to different employers. What do the respected senior managers at your company wear? Follow their lead. Even in industries where dressing down is the norm, you can be a cut above the rest without looking out of place.

A suit’s function is to make the wearer appear polished and on top of their game. This look can be achieved with less structured clothing by making sure each item looks new, clean, unwrinkled, fitted well to your body, and in colors that flatter you. If the garment has a pattern it should be more subtle rather than eye catching.

Add distinguishing accessories to your simple button down and flat front khaki slack like a saddle leather belt and modern lace up shoes. A dress shirt with a french cuff is no longer only for special occasions, combine it with distinctive cuff links and you elevate your appearance without looking stuffy.