White Dress Shirt Dark Green Paisley Tie Burgundy Pocket Square Grey Herringbone Wool Blazer Red Cardigan Navy Jeans

For an everyday outfit that is full of character and personality try pairing a grey herringbone wool blazer with GUESS Desmond Adversary Wash Relaxed Jeans. So as you can see, this combination is a really savvy choice, especially for unpredictable fall weather, when the temperature is dipping.

Brown Herringbone Wool Waistcoat Red and White Polka Dot Pocket Square Dark Brown Herringbone Wool Blazer Dark Brown Leather Belt Navy Jeans Blue Floral Denim Shirt

This combo of a dark brown herringbone wool blazer and GUESS men's Desmond Adversary Wash Relaxed Jeans exudes comfort and functionality and allows you to keep it simple yet contemporary. As the mercury dives into single digits, you'll find that an outfit like this is great for the season.

Light Blue Dress Shirt Red and Navy Vertical Striped Tie Tan Cardigan Tan Suede Bomber Jacket Brown Leather Belt Navy Jeans

This combination of a tan suede bomber jacket and navy jeans will enable you to keep your off-duty style clean and simple. Undoubtedly, an outfit like this will keep you warm and stylish, rain or shine.

Light Blue Denim Shirt Navy Silk Pocket Square Navy Tie Tan Wool Waistcoat Navy Jeans Grey Houndstooth Wool Blazer

Make a grey houndstooth wool blazer and GUESS men's Desmond Adversary Wash Relaxed Jeans your outfit choice to get a laid-back yet stylish look. On not-so-bone-chilling days, work this summer-to-fall look and look absolutely amazing.

White and Red and Navy Plaid Long Sleeve Shirt Brown Trenchcoat Dark Brown Leather Belt Navy Jeans Dark Brown Leather High Top Sneakers

For an outfit that's nothing less than incredibly stylish, try pairing a brown trenchcoat with GUESS men's Desmond Adversary Wash Relaxed Jeans. Why not add dark brown leather high top sneakers to the mix for a more relaxed feel? We promise this outfit is the perfect antidote to gloomy fall weather.

White Leather Low Top Sneakers Navy Jeans Beige Wool Gloves Navy V-neck Sweater White and Navy Gingham Long Sleeve Shirt Black Puffer Coat

Busy days call for a simple yet stylish outfit, such as a black puffer coat and navy jeans. White leather low top sneakers look awesome here. When it's one of those dull fall days, what better to brighten it up than a dapper outfit like this one?

Blue Plaid Long Sleeve Shirt Grey Knit Shawl Cardigan Navy Jeans

The versatility of a grey knit shawl cardigan and GUESS Desmond Adversary Wash Relaxed Jeans makes them investment-worthy pieces. You can bet this combo is great when fall arrives.

Dark Brown Sunglasses Beige Raincoat Black Leather Backpack Navy Jeans Olive Suede Desert Boots

A beige raincoat and navy jeans feel perfectly suited for weekend activities of all kinds. Up the cool of your outfit by rounding it off with olive suede desert boots. As you can see here, it's very easy to look sharp and stay comfortable come chillier days, thanks to this outfit.

Dark Brown Leather Watch Black Print Sweatshirt Blue Denim Shirt Beige Bomber Jacket Navy Jeans Brown Leather Boat Shoes

This pairing of a beige bomber jacket and GUESS men's Desmond Adversary Wash Relaxed Jeans spells comfort and cool. Brown leather boat shoes will become an ideal companion to your style. An outfit like this makes it easy to embrace weird transitional season.

Black Turtleneck Grey Check Scarf Navy Plaid Overcoat Navy Jeans Dark Brown Leather Derby Shoes

Perfect the smart casual look in a navy plaid overcoat and GUESS men's Desmond Adversary Wash Relaxed Jeans. Dark brown leather derby shoes will bring a classic aesthetic to the look. This combo is perfect for in-between weather.

Multi colored Plaid Scarf Grey Overcoat Navy V-neck Sweater White and Navy Gingham Dress Shirt Navy Jeans Orange Socks Beige Suede Desert Boots

Wear a grey overcoat with navy jeans for a dapper casual get-up. Feeling brave? Complete your look with beige suede desert boots. We suggest this one if you're in search of an ultra-warm ensemble that's as stylish as it is practical.

Red Wool Hat White Dress Shirt Navy Denim Jacket Navy Jeans Burgundy Leather Casual Boots

If you don't like being too serious with your outfits, consider wearing a navy denim jacket and GUESS Desmond Adversary Wash Relaxed Jeans. Take a classic approach with the footwear and go for a pair of burgundy leather casual boots. We're loving that this combination is great come warmer days.

Beige Print Scarf Olive Military Jacket Brown Leather Backpack Blue Plaid Long Sleeve Shirt Dark Brown Leather Belt Navy Jeans Tobacco Leather High Top Sneakers

If it's comfort and practicality that you're searching for in an outfit, make an olive military jacket and navy jeans your outfit choice. Opt for a pair of tobacco leather high top sneakers for a more relaxed aesthetic. We love that this ensemble is great come fall.

Black Turtleneck Dark Green Cable Sweater Black Leather Bomber Jacket Dark Green Beanie Navy Jeans Navy Suede Brogue Boots

A black leather bomber jacket and GUESS men's Desmond Adversary Wash Relaxed Jeans is a savvy pairing to add to your styling repertoire. Take a classic approach with the footwear and throw in a pair of navy suede brogue boots. You can bet this ensemble is great come fall.

Brown Leather Bomber Jacket Navy Jeans Brown Knee High Boots

A brown leather bomber jacket and GUESS men's Desmond Adversary Wash Relaxed Jeans are absolute staples if you're piecing together an off-duty wardrobe that matches up to the highest sartorial standards. Rocking a pair of brown knee high boots is an easy way to add some flair to your look. As you can see, this look is a really great option, especially for unpredictable fall weather, when the temps are dropping.