NBA superstar Dwight Howard talks about enjoying life and staying true to his roots. He rocks a true original in the Adidas Samoa.

Howe PJ Tech Cotton Blazer, Obey Revolution Nubby Tank, Obey Recon Cargo Shorts, Steve Madden Lande sneakers, Goorin Brothers Hammond, Ray-Ban New Wayfarer

He’s ahead of the curve, trend-savvy and not afraid to take style risks. The Trendster is always on the lookout for the coolest style pieces and coming up with interesting ways to wear them.

Our stylists put this particular Trendster outfit with fresh urban style in mind. The fashion-forward combo of a blazer, graphic tank and camo shorts are punctuated with sleek high top sneakers. Throwing on a cool fedora and classic Wayfarers rounds out this neo-urban look perfectly.

To see even more outfits for your specific style, check out our new and improved Shop by Personality page.

TV personality Billy Bush raved about his favorite go-to shoes, the Olukai Moloa while guest-hosting on the TODAY Show alongside Kathie Lee last week. During their "Favorite Things" segment, Billy showed off the comfy Moloa slip-on loafer and how the back folds down to transform it into a slipper.

We think they're the perfect all-around casual shoe, and perfect for guys of all ages. Get yours today with our fast and free shipping, and you'll be slipping into these comfy bad boys in no time!

Reef Umbrella Drink Tee, O'Neill Hudson Walkshorts , DC Block Spartan High sneakers, L-R-G Core Collection Tree New Era ® hat

He lives to ride and loves the laid-back life. Whether he’s in SoCal, the Midwest or the East Coast, his style is uncompromisingly chill.

Today’s outfit was put together by our stylists with the board-riding dude in mind. The beach-inspired tee, comfy shorts and high-top skate shoes are all about California style, no matter where you may be.

Cruise into the new and improved Shop by Personality pages for even more men’s outfits to make shopping fun and easy.

Lightweight and well-balanced, the Ghost 4 by Brooks follows in the Ghost 3’s footsteps as it was recently voted “Editor’s Choice” in Runner’s World Fall 2011 Shoe Guide. 

Runner’s World described the Ghost 4 as "a lightweight shoe with a snug fit", noting that "the Ghost has a fast feel and a surprisingly springy midsole that supplies just a bit of stability." 

Whether you are going for distance or speed, the Ghost 4 will make you a believer.

Fred Perry Cotton V-Neck Sweater, Ben Sherman Shoreditch Collar Shirt , Ben Sherman Garment Dye Hampton khaki pants, Clarks Desert Boots, Lacoste chronograph watch

The Classic Man is timeless, polished and refined. He’s all about more tailored styles when he’s dressed up and clean basics when he’s dressed down.

Our stylists put together this handsome business-casual attire that suits the Classic Man’s impeccably timeless taste. A simple V-neck sweater over a plaid button-down shirt and crisp khaki pants equal a great ensemble for a lunch date or business meeting.

To check out more Classic Man outfits and other style personalities, visit our new Shop By Personality page!

We thought we’d give the boys some love in today’s edition of Fresh Picks with some of the coolest high-tops around. High-top sneakers are a great way to transition into fall and back-to-school season. Paired with skinny or straight-leg jeans, this old school-meets-new school style is eternally cool.

Check out some of our current favorites:

1. Clae Russel: Simple yet understated, these comfortable sneakers will have you feeling so fly. 

2. Gourmet Sedici C: The clean design lends a modern look to these cool sneakers.

3. DC Village Hi: This is a great minimalist approach to the classic high-top.

4. PF Flyers Center Hi-Tailored: These retro-inspired sneakers are a true classic in every way.

5. Creative Recreation Cesario XVI: A nice dose of Euro style gives these sneakers a modern-meets-classic look.

6.  Supra Vaider: The sleek urban design makes these perfect for the city dweller who appreciates great style.

Sebago Waterbury

Part  of the Stash for Sebago Footwear Collection, the Waterbury is a slick chukka-mocassin hybrid that’s steeped with cool details inspired by the legendary NYC graffiti artist.

We especially love the unique speckled design on the Tan Suede colorway! These are limited edition, so we highly suggest picking up a pair before they’re gone.

Make sure to check back on the Sebago page for even more collaboration styles coming in!