White Dress Shirt Black Knit Tie Beige Print Pocket Square Brown Plaid Wool Blazer Black Wool Waistcoat Navy Chinos

For a casually elegant look, pair a brown plaid wool blazer with navy chinos — these two items go perfectly well together. When leaves turn yellow and red and fall takes over, you'll appreciate how great this look is for summer-to-fall weather.

White and Black Vertical Striped Dress Shirt Navy Plaid Wool Blazer Dark Brown Quilted Waistcoat Navy Chinos Tobacco Paisley Pocket Square Dark Brown Knit Tie

For an ensemble that's nothing less than incredibly stylish, try teaming a navy plaid wool blazer with Brooks Brothers men's Plain Front Vintage Chinos. Nothing like a killer look to cheer up a dull autumn day.

White Dress Shirt Navy Corduroy Blazer Navy and White Vertical Striped Tie Navy Chinos White Leather Tote Bag Mustard Leather Loafers

The combination of a navy corduroy blazer and navy chinos makes this a really well-executed look. Round off with mustard leather loafers and off you go looking smashing. You'll always look great even despite the sweltering heat if you keep this getup as your go-to formula.

Black Turtleneck Grey Plaid Wool Blazer Navy Chinos Black Suede Desert Boots

Pair a grey plaid wool blazer with Brooks Brothers Plain Front Vintage Chinos for a seriously stylish look. A pair of black suede desert boots looks very fitting here. Keep the autumn blues at bay in a sharp ensemble like this one.

Dark Brown Leather Brogues Navy Chinos White Long Sleeve Shirt Brown Scarf Black Cardigan

If you don't like getting too predictable with your ensembles, dress in a black cardigan and Brooks Brothers Plain Front Vintage Chinos. Complete your outfit with dark brown leather brogues. As you can guess, this is a neat pick when spring sets it.

Blue Seersucker Long Sleeve Shirt Dark Brown Tie Navy Crew-neck Sweater Navy Duffle Coat Dark Brown Leather Gloves Brown Leather Messenger Bag Navy Chinos Brown Leather Brogues

For an ensemble that's very simple but can be dressed up or down in a variety of different ways, wear a navy duffle coat and Brooks Brothers Plain Front Vintage Chinos. Consider brown leather brogues as the glue that will bring your look together. Needless to say, a look like this will keep you warm and stylish during the fall.

Navy Chambray Short Sleeve Shirt White Crew-neck Sweater Navy Chinos White Leather High Top Sneakers

For effortless style without the need to sacrifice on comfort, we love this combination of a white crew-neck sweater and navy chinos. Dress down this getup with white leather high top sneakers. This combo is a smart pick when spring arrives.

Navy Chinos Dark Brown Leather Belt Dark Brown Leather Watch Dark Brown Bracelet Navy Chambray Long Sleeve Shirt Olive Military Jacket Navy Cardigan

Pair an olive military jacket with Brooks Brothers men's Plain Front Vintage Chinos for a Sunday lunch with friends. You can bet this combo is the answer to all of your fall style problems.

White Dress Shirt Olive Cotton Waistcoat Beige Blazer Navy Chinos Olive Suede Tassel Loafers

If you're a fan of classic pairings, then you'll like this pairing of a beige blazer and Brooks Brothers Plain Front Vintage Chinos. Play down the casualness of your ensemble with olive suede tassel loafers. If you're already bored of your transitional weather fashion options, this getup just might be the inspiration you need.

White Crew-neck Sweater Gold Watch Black Pea Coat Navy Chinos Black Socks Dark Brown Suede Oxford Shoes

Make a fashionable entry anywhere you go in a black pea coat and Brooks Brothers Plain Front Vintage Chinos. Take a classic approach with the footwear and go for a pair of dark brown suede oxford shoes. An outfit like this is great for awkward transition weather.

White and Red Check Dress Shirt Navy Polka Dot Tie Red V-neck Sweater Grey Wool Blazer Navy Chinos Beige Socks Brown Leather Brogues

This smart casual pairing of a grey wool blazer and Brooks Brothers men's Plain Front Vintage Chinos takes on different moods. Brown leather brogues look awesome here. On not-so-bone-chilling afternoons, you can wear a variation of this summer-to-fall getup and look absolutely amazing.

Beige Baseball Cap Light Blue Dress Shirt Black Canvas Backpack Olive Raincoat Navy Chinos Black Socks Olive Camouflage High Top Sneakers

Opt for an olive raincoat and Brooks Brothers men's Plain Front Vintage Chinos for a Sunday lunch with friends. Break up your getup with more casual footwear, such as this pair of olive camouflage high top sneakers. Keep this combo in mind come warmer days, and we guarantee you'll save a lot of time getting ready on more than one morning.

Light Blue Houndstooth Dress Shirt Navy Cotton Blazer Dark Brown Leather Watch Brown Leather Belt Navy Chinos

This combination of a navy cotton blazer and navy chinos will set you apart effortlessly. You can bet this look will become your uniform when hot weather hits.

Pink V-neck T-shirt Navy Chinos White Leather Low Top Sneakers

Consider wearing a pink v-neck t-shirt and navy chinos for a casual level of dress. A pair of white leather low top sneakers will seamlessly integrate within a variety of outfits. We're loving that this outfit is great when hot weather hits.

Light Blue Dress Shirt Brown Sunglasses Dark Brown Woven Leather Belt Navy Chinos Brown Leather Double Monks

Perfect the smart casual look in a light blue dress shirt and Brooks Brothers men's Plain Front Vintage Chinos. For footwear, go down the classic route with brown leather double monks. This outfit is likely to become your summertime favorite.