These jeans–and the Union label in general–have been described as “modern,” “chic,” “raw,” “sexy,” “moody,” and yes, even “arousing.” If that description hasn’t sold you already, think about the fit: loose but not too loose, with a little fading around the front to give them a slightly worn-in feel. 100% cotton, button fly.  You can step into the Union Jeans Falcon Drake in Straight Classic for $158.

Mention Woolrich to most Americans and their heads fill with Norman Rockwell-style images of woodsmen in red plain hunting caps. But fabrics turned out by the 178-year-old woolen mill, America’s oldest, have withstood the test of time because not only are they very practical, but let’s face it, stylish. The Field Coat, with it’s elegant seven pocket design and leather-trimmed update is one example. By taking the traditional plaid overshirt and making it into a very comfortable and not so scratchy jacket, not only has Woolrich managed to keep their jackets updated, but has also made an article of clothing which should make you feel comfortable throughout your day.

Slippery shark skin-esque, this gray bomber jacket hearkens back to a time when Members Only was tops. It’s a no-brainer friend of jeans and sneakers, and the price tag isn’t scary when you consider 5 years of potential wear– and for multiple seasons, too. Slick and cool for city guys, and easily accessorized with a cap.

Buy: $400

While the 59fifty fitted cap has become ubiquitous in the world of streetwear, its not easy to find one in wool.  The 10 Deep Fall 2008 Wool Caps are available in light or dark gray wool with the official 10 Deep logo.  Personally, we’re a bit conservative when it comes to streetwear– we love to mix it in with casual gear, but tend to avoid anything overly loud.  This simple black “x” and brass knuckle crown is simple, reserved and well fitted toward the street fringe parts of your own wardrobe.  Tilt it just a bit, match it with a gun-metal watch and you’re looking good to go. [thanks highsnobiety]

Buy: $TBA

A streamlined item for the more metro among us, this bag is pretty darn unique. Like a contoured tote, it’s large enough to fit a man’s frame, but what makes it cool is the chain detail that skyrockets it to the next (designer) level. A zip closure reaches all the way down the side to fit your laptop and whatever else you need to stuff inside. Embossed logo detailing all over, 100% cotton.

Buy: $105

Daring, racy, and graphic to the max, this Money tee is available in either black or gray to give you decidedly different effects. Dark pops out and looks avant-garde, while gray is more on the everyday wear side. Take your pick or get both: they’re available in sizes S-XL and are a new autumn 2008 release.

Buy: $70

Here at GearCrave, we realize that everyone has a budget. There are some bags which are priced out-of-this-world, such as the Aria, and there are bags which are fairly inexpensive such as this Incase sleeve. Stylish, yet simple, this nylon sleeve is highlighted by a custom, lightweight, weather proof exterior with two pockets. Two internal mesh compartments and a breakaway accessory clip provide maximum durability, storage and organization for a bag designed for those who appreciate simplicity…

Buy: $59.00

Ray Ban wayfarer-inspired eyewear has definitely reached fever pitch, and I must admit, I might be right at my threshold for the look. I wouldn’t mind making allowances for this line of shades from Retro Super Future. Based in Italy (arguably the mecca of stylish sunglasses), the company’s Super sunglasses collection takes the classic Wayfarer shape and wipes it clean of all embellishments and distinguishable markings. It’s all about the geometry of the shades–like the body of a freshly carved soapbox derby car.

They come in several slick styles, but the most emblematic of the Super approach are the Basic (looks just like it sounds), the slyly unique Flat Top (again, just like sounds), and my personal favorite, the Ciccio (a thicker, bolder version of the Basic, also comes in a flat-top look).  All are available in a dizzying aray of colors, including two-tone and neon categories. The summer’s nearly over, but there’s still time for one last sunny-weather fashion statement, so make it count.

Buy: $116 to $181

Two selections for any man: black trousers and black jeans, one slightly more expensive than the other, but both with fantastic silhouettes. With Topman releasing a new site for American shoppers like us, it’s time to break in the credit card. True black jeans cost are under $50 for a trad 5-pocket style, and you can also branch out to a fabulous designer pair with an enviable shape (right). Awesome with chucks or any trainers, for that matter.

Buy: $140, $40