Black Leather Baseball Cap Grey Plaid Overcoat Black Socks Dark Brown Leather Boat Shoes Tobacco Dress Pants Black Crew-neck T-shirt Black Long Sleeve Shirt Black Leather Messenger Bag

Wear a grey plaid overcoat with tobacco dress pants for a classic and refined silhouette. Timberland men's Classic Boat Shoe will contrast beautifully against the rest of the look. On not-so-bone-chilling afternoons, rock this summer-to-fall look and look absolutely awesome.

Dark Brown Sunglasses Beige Long Sleeve Shirt Tan Raincoat Blue Crew-neck T-shirt Navy Jeans Black Socks Dark Brown Leather Boat Shoes

Consider pairing a tan raincoat with navy jeans to create a great weekend-ready look. Timberland Classic Boat Shoe will become an ideal companion to your style. A stylish summer-to-fall transition ensemble like this one makes it super easy to embrace the new season.

Navy Plaid Long Sleeve Shirt Beige Cotton Blazer Dark Brown Leather Belt Dark Brown Chinos Dark Brown Leather Boat Shoes

The combination of a beige cotton blazer and dark brown chinos makes this a really pulled together ensemble. A pair of Timberland men's Classic Boat Shoe brings the dressed-down touch to the ensemble. An outfit like this is just what you need to get in the mood for this summer fashion season.

Olive Crew-neck T-shirt Beige Bomber Jacket Silver Watch Black Chinos Dark Brown Leather Boat Shoes

Who said you can't make a style statement with a casual look? Draw the attention in a beige bomber jacket and black chinos. A pair of dark brown leather boat shoes looks very fitting here. On not-so-bone-chilling afternoons, you can work this easy-to-transition outfit and look absolutely awesome.

Light Blue Long Sleeve Shirt Brown Leather Belt White Ripped Jeans Dark Brown Leather Boat Shoes

If you're all about feeling relaxed when it comes to fashion, this combination of a light blue long sleeve shirt and white ripped jeans is just for you. Channel your inner Ryan Gosling and make Timberland Classic Boat Shoe your footwear choice to class up your outfit. Stick with this one if you're in search of a great summery getup.

White Long Sleeve Shirt Dark Brown Leather Belt Olive Shorts Black Canvas Holdall Dark Brown Leather Boat Shoes Black Sunglasses

Pairing a white long sleeve shirt with olive shorts is a comfortable option for running errands in the city. Balance this outfit with dark brown leather boat shoes. Come summer you want to feel comfy and seriously stylish –– this outfit is just the one you need.

Light Blue Long Sleeve Shirt Navy Polka Dot Pocket Square Grey Blazer Blue Jeans Dark Brown Leather Boat Shoes

Stand out among other stylish civilians in a grey blazer and blue jeans. To break out of the mold a little, make Timberland Classic Boat Shoe your footwear choice. This combination is a safe option if you're on a mission for a great, summer-ready getup.

Mint Long Sleeve Shirt White Crew-neck T-shirt Navy Bomber Jacket Navy Skinny Jeans Dark Brown Leather Boat Shoes

A navy bomber jacket and navy skinny jeans are great staples that will integrate perfectly within your current looks. Play down the casualness of your outfit with Timberland men's Classic Boat Shoe. You can bet this getup is great come colder days.

Black Sunglasses Brown Blazer Red and White Polka Dot Long Sleeve Shirt Dark Brown Leather Belt Navy Jeans Dark Brown Leather Boat Shoes

If you're a fan of classic pairings, then you'll like this pairing of a brown blazer and navy jeans. Make your ensemble more fun by finishing off with dark brown leather boat shoes. We can't get enough of this combo for summer days.

Brown Sunglasses Green Polka Dot Bow-tie Light Blue Dress Shirt Brown Woven Leather Belt Silver Watch Yellow Shorts Dark Brown Leather Boat Shoes

This smart casual pairing of a light blue dress shirt and yellow shorts takes on different moods. Take your look into a sportier direction with Timberland men's Classic Boat Shoe. This combination is basically a lesson in how to master the summer fashion.

Light Blue Long Sleeve Shirt Black Leather Watch Brown Leather Belt Yellow Chinos Dark Brown Leather Boat Shoes

Who said you can't make a style statement with a casual ensemble? Draw the attention in a light blue long sleeve shirt and yellow chinos. A pair of dark brown leather boat shoes will seamlessly integrate within a variety of ensembles. We're loving that this look is great come summer.

White and Navy Long Sleeve T-Shirt White Shorts Dark Brown Leather Boat Shoes Red and Navy Horizontal Striped Canvas Belt Beige Straw Hat

Busy days call for a simple yet stylish outfit, such as a white and navy long sleeve t-shirt and white shorts. For footwear, go down the classic route with Timberland Classic Boat Shoe. Clearly, it's easier to work through a summer afternoon in a fresh look like this.

Black Sunglasses Grey Long Sleeve Shirt Dark Brown Leather Belt Dark Brown Bracelet Dark Brown Chinos Dark Brown Leather Boat Shoes

Pair a grey long sleeve shirt with dark brown chinos for a casual level of dress. Complement this ensemble with Timberland Classic Boat Shoe. You can't go wrong with this one on a super hot afternoon.

Dark Brown Sunglasses Grey Polka Dot Long Sleeve Shirt Grey Crew-neck Sweater Dark Brown Leather Belt Silver Watch Pink Shorts Dark Brown Leather Boat Shoes

This combo of a grey crew-neck sweater and pink shorts spells comfort and style. Complement this outfit with Timberland Classic Boat Shoe. As we all know, the key to getting through the hottest time of year is sporting cool combos like this one.

Black Bow-tie Navy Print Pocket Square White Dress Shirt Grey Plaid Blazer Brown Leather Belt Navy Chinos Dark Brown Leather Boat Shoes

A grey plaid blazer and navy chinos are absolute essentials if you're picking out a polished wardrobe that matches up to the highest sartorial standards. For a more relaxed take, opt for a pair of Timberland men's Classic Boat Shoe. As warm summer weather settles in, it's time for light and breezy combos like this one.