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. 

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.

You’d like to wear the sneakers, they’re comfortable, but visually on par with orthopedics.  And this summer you made a commitment to yourself (oh okay, I may be making it for you now)- no more dressing like a Floridian retiree.

For your warm weather enjoyment here are eight Emmi-Approved casual summer shoe options from two quality shoemakers.  Most of these are every bit as comfy as a sneaker yet without any of the unsavory side effects such as, loss of desirability, increased frumpiness, and sustained eyesores.

Cole Haan Boat Shoe - Perfect for shorts even when your yacht is in the shop.

Cole Haan Penny Loafer - Don't let the name keep you from trying this updated classic.

Johnston & Murphy Venetian - Similar to a loafer but with a cleaner vamp, that's the top of the shoe. Don't worry, knowing that now doesn't make you any less manly.

Cole Haan Slip-On - A multi-color shoe pairs exceptionally well with neutrals like khaki or white.

Cole Haan Driving Moc - Feels like a slipper on but their specially designed gripper sole makes them much better for lounging then extended walking.

Johnston & Murphy Canvas Lace-Up - These have a lot of cushion and make for exceptionally comfortable summer strolling.

Johnston & Murphy Sandal - Mandals can be tricky, it's key is to stay away from anything clunky.

Johnston & Murphy Flip-Flop - The added design detail on these makes them appropriate for casual and dressier summer looks.

So how about you? Which shoes do you find comfortable and stylish for summer wear?

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. 

Spring weather can be more fickle than your hot but crazy ex-girlfriend who broke up and reunited with you on a weekly basis.

A smart accessory that will help take you from chilly to warm in comfort and style is a lightweight (sometimes called spring-weight) scarf.  They come in a variety of fabrics from silk to muslin and in any color/print your heart desires.  You can tie lightweight scarves in the same traditional ways as your heavier winter ones.  Or, try this tucked alternative which looks chic under a jacket, vest, knit, or button down shirt. It’s easy and I promise that if you do it correctly, you will get compliments.  

Drape the scarf around your neck as you normally would, cross the ends to make a V shape across your chest and then tuck the ends underneath your top layer. Done.

If you choose to rock this look with a button down shirt rather than a jacket or vest, make sure the scarf is thin enough so it doesn’t look like you have a mountain of chest hair trying to break through your shirt (think: alien baby).

Maintaining good style in the face of a New England winter can seem akin to staying afloat in a dingy during the perfect storm, and nowhere is the struggle more evident than with men’s sweaters. 

When the mercury drops, too many men with perfectly good bodies don potato-sack-shaped woollen body bags in the name of warmth. You know, the kind made for hearty sheep farmers herding flock on windy Irish hillsides- perfectly charming in that context, but out of place in a metropolitan city setting, especially for business.  

Plus, bulking up is not where it’s at;  in fact you’ll stay warmer, more attractive, and comfortable through indoor/outdoor temperature changes by layering clothing that fits closer to the body.

While previous seasons were favoring thin knits like cashmere and silk, this season the focus is on thicker knits like Fair Isle and cable knit.  But not all thick knit sweaters are created equal, and the cut and size you choose can make all the difference between looking ruggedly handsome and looking like a man with too many cats who collects figurines.

Look at the example above: On the left we have the afore mentioned sack-shaped sweater, which is doing no favors for that man’s body.  On the right is an equally thick wool sweater, yet it still maintains the desired, masculine V-shape of his upper body.  How?

1. Since bulky knits generally run large rather than true to size, try a size smaller than you usually wear and you may find it fits much better.

2. It’s got a front zipper, so the vertical line lengthens and slims the torso.

3. Coordination: The V-shape is emphasized by unzipping the sweater to the mid-chest revealing a darker brown T-shirt underneath which features a graphic in the same color as the sweater. 

Add a scarf and you’ll be equally, if not warmer,  than in the blob+turtleneck combo, and guess which one will fit better under your coat?

Q:  For my girlfriend’s birthday I got her tickets to the symphony. I knew I’d have to go with her but I think I’ve been in denial, the show is this Sunday afternoon and I have no idea what’s appropriate to wear. I don’t own a tux or a suit. Help!

A:  Your sacrifice is commendable so don’t worry about dressing up too much, the last thing we’d want is for you to be bored and uncomfortable.  You’ll be happy to know that the symphony is rarely a black tie affair.  Formal attire is only expected on opening night and for the rest of the shows it’s suggested you wear something you’ll be comfortable sitting in for a couple of hours.  For a Sunday afternoon performance business casual dress is perfectly appropriate. Depending on how long the show lasts you may also want to take along the ultimate accessory, a full flask.