Red Wing's Flying Away with It

When it comes to winter boots, again and again we turn to Red Wing.  For winter shoes you first need a shoe that will hold up.  After that you and only after quality can you look at style.  In the winter it doesn't matter how nice it looks, if the shoe isn't durable, water proof and warm, who cares.

Red Wing boots are a staple in quality boots and they look good, that means they are worth buying.  As with any good dress shoe, boots should hold up for years no matter what you put them through.  Red Wing boots will be good for years.  Drying them out after the snow and the rain, and wear them again and again.

Especially nice when they come in interesting options like blue leather or chukka boots.  Basically, if you don't have a pair, buy yourself some Red Wing boots.

Timberland Steps It Up

As an attempt to not miss the party, which is stylish and fashionable clothes, Timberland has decided to make some shoes that widen their appeal. Timberland under the brand name Timberland Boot Company has decided to make some shoes that not only standup to what any brand offers but actually surpass many.

Timberland has released an Oxford shoe and a Chukka Boot. While the Oxford has appeal, it is the chukka offering that stands out. Presented in a brown and black leather with a slightly distressed look the shoe looks like it has been worn for years. It delivers a refined look without being stuffy or pretentious. Exactly what we look for in a boot.

While his boot would be perfect for jeans, it could really set off a nice flannel or corduroy suit in the fall months.

Sprezzatura At Its Finest

Lapo Elkann exudes style. He makes bold statements with his outfits and always seems to own the looks with a cool confidence. I love the outfit captured here by the Sartorialist. Lapo wears a bold colored odd jacket that is impeccably tailored with a even bolder pink shirt. He adds a dark pink knit tie and linen pocket square for good measure. Elkann also adds some sprezzatura to the outfit by unbuttoning the cuffs on his sleeve, twisting his tie slightly and haphazardly wearing the pocket linen.

My favorite element of the outfit is the sartorial contradiction of the chunky motorcycle boots. The boots balance and ground the bright pink worn on top. They are interesting, have vintage appeal and anchor the look. It is the addition of the boots that really make the outfit memorable and manly.


This is an outfit that not all men have the confidence to pull off, but Lapo does it with a rebellious cool that makes us all wish we could.

Winter Boots: Warmth in Style

Utilitarian style is certainly a departure for the typical business man.  Aside from a trench coat or over coat to protect him from the elements, most modern men do not utilize utilitarian clothing on a regular basis. The suit and tie are certainly far from utilitarian and while a sweater adds warmth and style, it would be hard to call it utilitarian.

Yet some utilitarian pieces are so iconic, they themselves become stylish: motorcycle jackets save your hide in a fall and look great, Sperry Topsiders keep you on your feet while on a wet sailboat, and duck boots keep your feet warm and dry even in the heaviest rain or snow storm. The look of each of these items is designed to help facilitate the task in question. A motorcycle jacket is made from rugged thick leather, it has padding in all the right places and is streamlined so that nothing will catch in the wind.  Topsiders have rubber soles with wavy cuts in the sole to help prevent slips, they are designed to get wet, holding to the foot better as they get wet, since the feet are sure to get wet they are designed to be worn without socks, as no one enjoys wearing wet socks.

As for duck boots, the soles help provide traction in the snow. The rubber, water proof sole wraps from the bottom of the shoe upward to cover the vamp.  Halfway up the vamp the leather upper boot begins, covering the foot and leg in warmth and water protection. The boot is typically fur lined and has a water resistant lining. Sorel the maker of the infamous Caribou boot, a variation on the duck boot rates the boot for up to -44 degrees.  This boot will keep your feet warm and dry. In addition to the great utilitarian value the boot offers, it also is quite stylish. The iconic look of the duck boot means that you can stay out of the elements and look good while doing it. Nothing flashy or ostentatious, just plain old utilitarian style, a man always looks good like that.  In my opinion the best looking and most functional pair of duck boots is manufactured by Sorel.  There Caribou boots sell for $110 and may be on sale for a few bucks less. These are the pair I choose to cover my feet.

Good shoppers find good deals

Priding myself on being a good shopper is not always about finding sales on items at J Crew, Ben Silver and Nordstroms, but sometimes it is about finding the right piece at a discount store. Most of the clothes at discount stores do not fit right or are out of style, but sometimes they get it just right and for a really good price. My two favorite stores to watch for deals are Target & American Eagle Outfitters. Take a look at the items I found at American Eagle, really cool stuff for great prices.

American Eagle Trench Coat - $99 - It has the same style as all the top designers for considerably less. Most of the designer Trench Coats are between $800 - $200 a coat, this one for only $100 is a great deal.

American Eagle Brown Leather Oxfords - $54 - As any faithful reader of this blog knows these are not Oxfords but instead Bluchers. But whatever you call them they are a good shoe for casual wear. They are useful for a night at the bar or any sporting event, and considering the circumstance could be great for a date or a casual Friday at work. I think the silhouette on these shoes are very cool, chunky where it counts and slender everywhere else. I of course love the patina and distressing, which will only improve with time. Not to mention the great price for shoes that have a wooden sole.

American Eagle Desert Shoes - $34 - These are exactly the same look as the desert shoes you will find made by Clarks, but a lot cheaper. We all know how important boots are this fall and these are a great deal on a classic shoe. Why pay more when you can get the same shoe for considerably less?

American Eagle Shawl Collar Sweater - $59 - I do like the sweaters at American Eagle quite a bit. This Shawl Collar sweater fits in with the current fall fashions and has a great accessory in the leather buttons. I would definitely think about adding this sweater to the collection.

American Eagle Woodsman Boots - $79 - These boots have a very similar look as the Red Wing boots made for J Crew, but are a lot less expensive. If you are buying boots because you need them to trudge through snow and rain and really test them in extreme conditions, go with the Red Wing boots, they are some of the best made. But if you are buying boots for fashion purposes, plus they are useful on a rainy day, these might be the boots for you. They are nearly $200 less expensive then the really nice Red Wing or Frye boots and they look pretty damn cool.

American Eagle Boat Shoes - $39 - Boat shoes never go out of style. The ones made by AE are very cool looking and significantly less than Sperry Topsiders. While I think everyman should eventually own a pair of Topsiders, these suede boat shoes are a great addition to the closet.
American Eagle College Cardigan - $49 - Cardigan's are great, they are versatile sweater that can be worn over a t-shirt or a button down, can be worn with a tie and slacks or jeans. This cardigan from AE has a cool accent of double stripes on the sleeve. It comes in Navy or Gray. For the price it is definitely worth picking up.

Always List - Boots

Every guy needs a pair of boots, a good pair of who-gives-a-damn-boots. The kind of boots that only look better the more wear and tear, or "character" they gain. The best boots can not be bought distressed but instead must earn the scrapes, scars and patina. Whether it be from riding on the chopper, doing yard work, or going to the bar, shit kicker boots are like a fine wine and a well dressed man, they only get better with time. A good pair of boots remind me of Marv, Mickey Rourke's character in Sin City, scars upon scars and each scar only improves his appearance. The kind of boots you need to feel comfortable saying, "This is blood for blood and by the gallon. These are the old days, the bad days, the all-or-nothing days. They're back! There's no choice left. And I'm ready for war." As Marv would tell you.

Frye Boots, Rogan Engineer 8 inch boots will work. Made well, classic style, good silhouette (sleek and full bodied), wooden heel with a rubber sole, rounded toe, high quality leather, no zipper. These boots can go from the board room to the bar to the motorcycle with ease.

Fall Essentials - Boots

Obviously, the change of weather in fall means that you must have shoes to handle the puddles, the mud, the ice and the snow. This means breaking out the boots. New or old, boots are an absolute essential in fall, and this season is no exception. In fact, more boots are popping up at more stores and by more designers than ever.

I am digging the round toed boot this season (square toes are so 2000). I also am a fan of buying brand new clean, non-distressed boots and breaking them in yourself. With as much as you will be wearing the boots this fall, don't worry soon they will have their own patina, their own scratches and wounds, their own individual wear and tear. They will be uniquely yours. The best way to break in a pair of boots is to wear them out one night to a crowded bar, that many drunks will be sure your boots are good and scuffed up. Also this season I am voting for brown boots, I just like the way brown boots get broken in. I like it better than black.

If you don't know how to wear brown boots, well try am with your favorite pair of jeans an oxford and a navy blue blazer. Or wear them with some tweed slacks, a dark shirt and tie and a matching leather jacket. You can also wear them with chinos and a cashmere sweater for a casual relaxed date look. Its the total cat's meow to wear a pair of chunky boots (scuffed or un-scuffed) with a heavy weight suit (make it a heavy wool, tweed or herringbone, the fabric needs gravitas for it to look right). Boots are the winters version of Chuck Taylors, they can be worn with almost anything and anytime and look damn good.

Fall Essentials - Denim Jacket

Fall Jeans Jacket by DandyFashioner featuring GAP

One of the great styles for fall is a Denim Jacket. It is a very simple and universal style, that looks great when dressed up. I like the look with a gray shirt and gray tie (gray is perfect for fall) and paired with big boots and a cool belt.

When buying a denim jacket, buy a it a size smaller than you would normally. You want it to have a snug fit. Try the dark blue Levi Trucker jacket that I have above. Wear it with jeans (of a different wash) or with chinos. Dress it up with a tie or dress it down with a t-shirt. Buy a clean dark wash, so that you can keep it versatile. If it is destroyed wash, then you won't be able to wear it with a tie on a Friday to work.

It can also look great with a white button down and a sweater of your favorite color. Throw it over for a casual, but trendy look for a date. It can be worn also any time you would normally wear a casual blazer.