Dark Brown Leather Loafers Navy Socks Dark Brown Dress Pants Green Cardigan Brown Plaid Wool Blazer Burgundy Wool Tie Tobacco Pocket Square Light Blue Denim Shirt

For a nothing less than incredibly stylish look, reach for a brown plaid wool blazer and dark brown dress pants. For footwear go down the casual route with Santoni men's Penny Loafer. Be sure this combo is great for fluctuating autumn weather.

Black Crew-neck Sweater Dark Brown Leather Watch White Crew-neck T-shirt Dark Green Chinos Dark Brown Leather Loafers

This combination of a black crew-neck sweater and dark green chinos is very easy to replicate and so comfortable to wear all day long as well! Dark brown leather loafers will add elegance to an otherwise simple look. Loving that this look is perfect come warmer weather.

Silver Watch Black Knit Blazer Navy Vertical Striped Denim Shirt Dark Brown Leather Belt Charcoal Dress Pants Dark Brown Leather Loafers

A modern man's sophisticated closet should always include such stylish essentials as a black knit blazer and charcoal dress pants. Opt for a pair of dark brown leather loafers to have some fun with things. A look like this is just what you need to get stylishly inspired this summer season.

Black Polo Dark Brown Leather Watch Olive Dress Pants Dark Brown Leather Loafers Olive Camouflage Leather Zip Pouch

Consider wearing a black polo and olive dress pants for drinks after work. A pair of dark brown leather loafers brings the dressed-down touch to the ensemble. This here is hard proof that you actually can survive the sweltering heat, all while looking fresh and breezy.

Navy Crew-neck Sweater Navy Puffer Coat Burgundy Leather Messenger Bag Khaki Chinos Dark Brown Leather Loafers

If you're facing a fashion situation where comfort is prized, try teaming a navy puffer coat with khaki chinos. A cool pair of Santoni men's Penny Loafer is an easy way to upgrade your outfit. There's no better way to cheer up a dull fall day than a dapper getup like this one. (Ok, maybe there are a couple.)

Black Sunglasses Light Violet Dress Shirt White Pocket Square Navy Suit Dark Brown Leather Loafers

Something as simple as opting for a navy suit and a light violet dress shirt can potentially set you apart from the crowd. Dress down this getup with Santoni men's Penny Loafer. As you can see, this is a neat option for summertime.

White Dress Shirt Dark Brown Leather Loafers Light Blue Pocket Square Brown Knit Tie Navy Vertical Striped Suit

A modern man's sophisticated closet should always include such stylish essentials as a navy vertical striped suit and a white dress shirt. Break up your outfit with more casual footwear, like this pair of dark brown leather loafers. Come summertime you're looking for a look to keep you cool and on-trend –– this look is great for this time.

Charcoal Scarf Tobacco Wool Bomber Jacket Grey Wool Dress Pants Black Socks Dark Brown Leather Loafers

Wear a tobacco wool bomber jacket with grey wool dress pants to ooze class and sophistication. Santoni Penny Loafer will add some edge to an otherwise classic look. These picks will keep you comfortable and stylish in transeasonal weather.

Light Blue Dress Shirt Navy and White Vertical Striped Tie Navy Double Breasted Blazer Navy Dress Pants Grey Socks Dark Brown Leather Loafers

A modern man's sophisticated closet should always include such stylish essentials as a navy double breasted blazer and navy dress pants. To break out of the mold a little, choose a pair of Santoni men's Penny Loafer. So if it's a warm summer day and you want to look seriously stylish without putting too much effort, this getup will do the job in seconds time.

Dark Brown Dress Shirt Dark Brown Leather Watch Dark Brown Woven Leather Belt Dark Brown Silk Pocket Square Beige Linen Blazer Beige Linen Dress Pants Dark Brown Leather Loafers

This combination of a beige linen blazer and beige linen dress pants is the picture of elegance. Dress down this getup with dark brown leather loafers. Clearly, you're looking at a smart choice for a hot day.

Black Sunglasses Gold Watch White Dress Shirt Red Silk Pocket Square Black Double Breasted Blazer Black Leather Watch Navy Skinny Jeans Dark Brown Leather Loafers

This combination of a black double breasted blazer and navy skinny jeans is the ideal balance between dressy and laid-back. Round off this look with dark brown leather loafers. Both stylish and summer-appropriate, you can work this outfit throughout the summer season.

Red Beanie Light Blue Denim Shirt Beige Raincoat White Crew-neck T-shirt Khaki Chinos Dark Brown Leather Loafers

If it's comfort and functionality that you're looking for in an outfit, make a beige raincoat and khaki chinos your outfit choice. Perk up your outfit with Santoni Penny Loafer. If you feel uninspired by your transitional season fashion options, this getup just might be the inspiration you need.

Dark Brown Leather Loafers Black Skinny Jeans White Dress Shirt Charcoal Crew-neck Sweater Brown Barn Jacket

This combination of a brown barn jacket and black skinny jeans combines comfort and efficiency and allows you to keep it simple yet current. Elevate this ensemble with dark brown leather loafers. On not-so-bone-chilling days, you can sport this transitional ensemble and look absolutely amazing.

Black Wool Hat White Dress Shirt Burgundy Tie Red Print Pocket Square Dark Brown Cardigan Light Blue Overcoat Gold Bracelet Grey Dress Pants Dark Brown Socks Dark Brown Leather Loafers

Make a light blue overcoat and grey dress pants your outfit choice for a sharp, fashionable look. Rock a pair of dark brown leather loafers to make the outfit more current. An outfit like this makes it easy to embrace weird transeasonal weather.

Tan Straw Hat Dark Brown Sunglasses White Short Sleeve Shirt Silver Watch Black and White Vertical Striped Chinos Dark Brown Leather Loafers

Try pairing a white short sleeve shirt with black and white vertical striped chinos for an easy to wear, everyday look. Santoni men's Penny Loafer will add elegance to an otherwise simple ensemble. So if it's a super hot hot weather afternoon and you want to look seriously stylish without putting in too much work, this outfit will do the job in seconds time.