Red Gingham Long Sleeve Shirt Navy Denim Jacket Mint Parka Navy Jeans Brown Leather Chelsea Boots Charcoal Flat Cap

Go for a mint parka and navy jeans for a comfy-casual look. Opt for a pair of Cole Haan Lenox Hill Chelsea Shoes to take things up a notch. The start of real winter needn't mean you sacrifice on style, and this ensemble is a vivid example of exactly that.

Black and White Bandana White Polo Brown Leather Watch Navy Skinny Jeans Beige Overcoat Brown Leather Chelsea Boots

A beige overcoat and navy skinny jeans are great staples that will integrate perfectly within your current looks. Wearing a pair of Cole Haan Lenox Hill Chelsea Shoes is an easy way to add some flair to your look. It goes without saying that this one makes for a great, spring-ready outfit.

Navy Denim Shirt Navy Print Crew-neck Sweater Tan Shearling Jacket Tan Leather Belt Navy Jeans Brown Leather Chelsea Boots Olive Canvas Tote Bag

Make a tan shearling jacket and navy jeans your outfit choice to demonstrate you've got serious styling prowess. Rocking a pair of brown leather chelsea boots is an easy way to add extra flair to your ensemble. You see that just because it's below zero outside doesn't mean your getups should get any less stylish.

Beige Hat Black Sunglasses Charcoal Crew-neck T-shirt Black Leather Watch Black Canvas Messenger Bag Black Skinny Jeans Brown Leather Chelsea Boots

Make a charcoal crew-neck t-shirt and black skinny jeans your outfit choice for a casual-cool vibe. Got bored with this look? Enter brown leather chelsea boots to spice things up. What an obvious idea for hot weather!

Orange Crew-neck Sweater Beige Overcoat Beige Dress Pants Brown Leather Chelsea Boots

Consider teaming a beige overcoat with beige dress pants for a classic and refined silhouette. Throw in a pair of Cole Haan men's Lenox Hill Chelsea Shoes to make the look more current. Can you see how very easy it is to look dapper and stay warm come chillier days, thanks to this ensemble?

Beige Wool Turtleneck Charcoal Vertical Striped Dress Pants Brown Leather Chelsea Boots

This look clearly illustrates it pays to invest in such pieces as a beige wool turtleneck and charcoal vertical striped dress pants. Cole Haan Lenox Hill Chelsea Shoes are a smart choice to round off the look. A comfortable transition getup like this one makes it very easy to welcome the new season.

Black Sunglasses Orange Long Sleeve Shirt Black Leather Watch Beige Dress Pants Brown Leather Chelsea Boots

A modern man's sophisticated closet should always include such stylish essentials as an orange long sleeve shirt and beige dress pants. Brown leather chelsea boots are a smart choice to complement the look. This combination is also great if you're in search of warm weather wear to get through a tedious day in the office.

Black Crew-neck Sweater Black Print Pocket Square Grey Blazer Navy Jeans Brown Leather Chelsea Boots

A grey blazer looks especially elegant when paired with navy jeans. Tap into some David Gandy dapperness and complete your look with Cole Haan men's Lenox Hill Chelsea Shoes. A kick-ass look that transitions easily into fall like this one makes it very easy to welcome the new season.

Olive Crew-neck T-shirt Navy Zip Sweater Khaki Chinos Brown Leather Chelsea Boots

A navy zip sweater and khaki chinos is a wonderful combo to add to your casual lineup. Let's make a bit more effort now and opt for a pair of Cole Haan men's Lenox Hill Chelsea Shoes. When leaves are falling down and autumn is setting in, you'll appreciate how ideal this outfit is for in-between weather.

Burgundy Turtleneck Camel Overcoat Burgundy Chinos Brown Leather Chelsea Boots

Go for a sophisticated look in a camel overcoat and burgundy chinos. You could perhaps get a little creative when it comes to footwear and spruce up your look with brown leather chelsea boots. If it's one of those gloomy fall afternoons, what better to brighten it up than a stylish ensemble like this one?

Grey Crew-neck Sweater Grey Overcoat Dark Brown Leather Gloves Multi colored Plaid Scarf Black Chinos Brown Leather Chelsea Boots

A grey overcoat and black chinos are absolute essentials if you're piecing together a polished wardrobe that holds to the highest sartorial standards. Tap into some David Gandy dapperness and complete your look with Cole Haan Lenox Hill Chelsea Shoes. You can bet this combo is great when colder days are here.

Black Sunglasses White Crew-neck T-shirt Grey Henley Sweater Black Pea Coat Black Jeans Brown Leather Chelsea Boots

Consider pairing a black pea coat with black jeans for a work-approved look. Dress up your ensemble with brown leather chelsea boots. This look is the definition of perfect for when leaves turn yellow and red and autumn takes over.

Light Blue Long Sleeve Shirt Tan Scarf Grey Overcoat Navy Jeans Brown Leather Chelsea Boots

The combination of a grey overcoat and navy jeans makes this a really well-executed look. Up the cool of your outfit by finishing off with brown leather chelsea boots. As the weather is getting warmer, it's time to get rid of those bulky winter layers and choose something lighter, like this getup here.

Charcoal Turtleneck Grey Denim Jacket Dark Green Plaid Blazer Dark Brown Corduroy Jeans Brown Leather Chelsea Boots

Nail off-duty dressing with this pairing of a grey denim jacket and dark brown corduroy jeans. Bring a touch of sophistication to your look with brown leather chelsea boots. So when summer is over and autumn is settling in, you may find this outfit your favorite.

White Long Sleeve Shirt Charcoal Wool Waistcoat Navy Jeans Brown Leather Chelsea Boots

Tap into refined, elegant style with a charcoal wool waistcoat and navy jeans. When it comes to shoes, this ensemble pairs perfectly with Cole Haan Lenox Hill Chelsea Shoes. As you imagine, this is a knockout choice come warmer days.