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.