1. The Basic Staple – Cole Haan Adrian Chelsea

Served with – Clean lines, versatility and classic styling.

Delicious paired alongside  - Straight or slim cut chinos, denim of any wash, or wool slacks.

2. The Rocker – Harely Davidson Hustin Waterproof

Served with – Metal hardware, side zip for easy pull on/off, and a side of badass.

Delicious paired alongside – Dark wash and distressed denim.

Allergy warning - Do not wear with sport themed clothing, windbreakers, or dad jeans.

3. The Techie Trainer – Asolo Asimut Gore-Tex Suede

Served with – Plenty of heal cushion and casual comfort.

Delicious paired alongside – Well cut chinos, lighter and medium wash denim.

Allergy warning – Pleated khakis, gym socks, dress pants.

4. The Executive – Cole Haan Air Winslow Cap Toe

Served with – Traditional business stylings, classic cap toe, extra tread to stay upright when slippery (or running from angry shareholders).

Delicious paired alongside – Suiting or dress slacks.

Allergy warning – Do not wear with casual denim.

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.

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: Kudos for knowing not to wear athletic sneakers to a conference.  Barring a medical reason, bulky sneakers instantly deplete your coolness factor by 97%, tough to recover from.  Plus, there’s an entire category of men’s shoes called comfort footwear.  Makers include Johnston & Murphy, Børn, Patagonia, Keen, Merrell and Dansko, to name a few. Comfort styles range from rugged (not good for professional wear) to business casual and it’s key to select the styles that work with your level of attire formality.  Since shoes that have been pimped out comfort wise are usually not labeled as such, here are the qualities to look for in shoes you’re considering bringing/buying for the conference.

1. Sole – Feel the rubber (resisting the low brow humor here with all my might…) sole.  If it’s rock solid the shoe will be very stiff on your foot, if the sole has some give when you bend it, the shoe will be much more comfortable.

 2. Versatility – SXSW or any conference can be a personal and professional networking mecca, so select shoes that will style up a relaxed look and can be worn with the most professional attire you are taking, like a sport coat.  Your feet (and shoes) will thank you if you take two pairs and switch them out daily.

 3. Cushion quality – Don’t scrimp when it comes to your shoes.  Cheaper brands that sell by price point or trend rarely have good support or shock absorbency.  If you solely (Ha! Sorry.) choose by looks or price, after 11 hours on your feet in cheap shoes, you’ll be kicking yourself for not spending the extra $30 to prevent your suffering in the first place.