4 Casual Holiday Get-together Outfits: Hassle Free Looks for the Gents

Casual Get-together, Outfit 1. This versatile red sweater is a simple choice for a holiday gathering. Brooks Brothers easy fit and high quality – this cardigan is made of a soft cotton and cashmere blend – ensures comfort and a polished look. No detail is over-looked, like the button and zip closure that really elevates this sweater to something special. We’re showing you an outfit that gives it a bit of an upscale feel, perfect for your favorite restaurant or bar, but it can also be worn with jeans over a long sleeve t-shirt for a truly relaxed look, so this is a sweater you’ll reach for over and over.

When you want to give the featured sweater in this outfit a dapper finish, layer this blue check shirt from Thomas Dean under it. The pattern adds interest, but is subtle enough to still coordinate a festive tie (as we’re showing below) into this look. And, of course, what gent can’t use a great blue patterned shirt to wear all year round? Tomas Dean’s modern fit looks good on every gent and the quality will hold up for seasons to come.

While there are many pants options that work in this look, like charcoal wool trousers or dark jeans, these olive green flat front corduroys show some holiday spirit – and gents, we promise, it’s not over the top. Polo Ralph Lauren uses a deep, neutral shade that works with the rusty shade of red in the featured sweater – and any of the basic browns, greys, and blues you already have in your closet. The modern fit and slight stretch in the soft fabric ensure a comfortable wear.

While a tie might not be necessary for a casual gathering, Brooks Brothers’ black, red and blue tartan cotton tie is a timeless classic that we simply can’t resist to complete this outfit. The larger scale plaid works with the tight check pattern in the shirt and the colors bring the whole look together seamlessly.

Casual Get-together, Outfit 2. We often talk about the go-to navy wool blazer. For a relaxed look, a corduroy version really gets the job done. The rich texture has a casual wintery feel, and Brooks Brothers’ deep navy shade works with traditional holiday colors (red and green) as easily as it works with earthy tones and greys, so you’ll get plenty of use out of it. This jacket is made in the Brooks Brothers Fitzgerald fit, which offer a modern fit that is trimmer than traditional Brooks Brothers styles, but not skinny – the somewhat shorter length and narrower lapels create an updated look that’s not trendy.

For a little pop of holiday cheer, this rusty red sweater vest is a great layering piece under the featured corduroy sport coat. Peter Millar’s modern fit ensures it won’t be bulky under the jacket, and the lovely merino wool is soft and cozy without being overly warm. The zip neck is a sportier alternative to a V or crewneck to keep things casual. Add this blue check shirt underneath to coordinate with the sport coat and really let this piece stand out.

AG’s flat front pants, made of a luxe twill adds polish that works with the sport coat featured in this outfit. But they also retain a casual feel in their super soft finish and washed grey color (called Cosmopolitan Grey through the ‘shop it’ button) that works with the sweater vest and jacket look we're creating here. The modern fit is just right for most gents with a mid rise, plenty of room in the seat and thigh, and a updated leg that’s not too wide.

A pocket square always completes an outfit, and this navy paisley version from J.Crew certainly does it here. The red pattern and navy ground color is a smart finishing touch that keeps a casual look dapper and stylish. Keep the theme going by adding these navy plaid socks, too.

“Hometown” Visit, Outfit 1. This Billie Reid pullover is the perfect hybrid of a sweater and sweatshirt that will be your go-to whether you are hanging around the house or making your rounds to see the neighbors. The toned down oxblood red shows your holiday spirit in the most tasteful of ways – as does the knit detail and button closure on the shawl collar. The soft cotton material and contemporary fit ensure there will no shortage of comfort, though.

Sure, the shawl collar pullover we’re featuring in this outfit stands on its own, but if you’re venturing out of the house why not step it up by layering this sport coat over it? If you’re just heading from the house to the car and back inside, you can skip your puffer and show off a little sartorial know-how by making this your jacket, without sacrificing any casual comfort. This JKT NEW YORK blazer has a soft construction, giving it a relaxed look. And the blue windowpane pattern looks really sharp with the pullover’s oxblood red. Pop up the convertible shawl collar for a dapper finish.

Once you add the sport coat over the red pullover in this outfit, replace your basic t-shirt layer with this Hugo Boss blue patterned shirt. Soft and contemporary in fit, it brings the whole look together – and is a piece you can wear on its own, or under any jacket or sweater, so it’s a great shirt to pack for a trip.

You’ll never go wrong with a pair of flat front chinos – especially if they’re from Bonobos. They always deliver on style, with a quality that exceeds the price. Started as a pants line, they nail the fit, which is available in 4 options: Tailored (the trimmest, contemporary fit), Straight (a modern “everyman” fit that is still updated and current), and Slim (which is in between the two). The Boot is their most relaxed fit. Besides choosing your waist size, you can also choose an inseam length that is right for you. This dark blue (called Jet Blues through the ‘shop it’ button) is as versatile as your favorite jeans, so they’ll complete this outfit and get plenty of wear with all your other staples.

“Hometown” Visit, Outfit 2. We are seriously into this shawl collar cardigan from J.Crew. They use a fabulous dark green Donegal wool that has flecks of red, yellow and blue in it that is great all Winter long, but feels holiday-right this time of year. The lower patch and flap pockets add a casual feel to the sweater that is already all about style and ease. J.Crew’s modern fit is great for most any gent, and you can size up for a truly relaxed feel.

The cardigan featured in this outfit works over a t-shirt or thermal as easily as it does over a button down. And for the holidays, the grey and red plaid in this one from Vineyard Vines really pops. This is how we like to “match” the pieces in our outfit. The red and grey plaid has accents of green, blue, and yellow that subtly pull in the colors of the sweater. It’s not obvious and completely works.

AG’s sueded sateen fabric is the softest twill around – and don’t let the word “sateen” throw you, there’s no shine, only incredible comfort and a casual washed finish that rivals your favorite broken-in jeans with ease. So, this dark sulfur navy color works with this outfit in the same way those jeans would, too. The Graduate fit is one of their best sellers, with enough room in the seat and thigh for most gents and a slightly tapered leg that still works with boots for a casually updated look.

Gents, these Harris Tweed high top sneakers from Banana Republic add a fun finishing touch to this outfit that you will wear all Winter long. The blue and green tartan pattern coordinate perfectly with everything in this outfit and have a fabulous holiday touch. Yet, the dark colors and wool fabric make them the sneakers you can wear with most everything in the colder weather. These are not something you'd normally find at Banana Republic - they're part of a special collection that will be an instant conversation starter.