The Holiday Lookbook: 4 Outfits from Casual to Dressy

Thanksgiving Ready.
Why is it a Find? Ledbury’s super soft merino wool sweater is the perfect shade of sage green for Thanksgiving – so earthy and warm. And since it’s not too heavy, you’ll be comfortable all day long. The button neck styling gives it a fresh and modern feel that looks great dressed up or down, so you can wear it no matter how formal or casual your day is.
Wear it with: Dress it up with a button up shirt and tie - you can even wear a navy or grey tweed blazer to make it a great work option all winter long. In the outfit we’re showing here, we’re giving it a more casual feel, pairing it with corduroys. Jeans and a t-shirt layered beneath it works, too.
Fit Tip: The fit is modern, and not too trim. Size up if you prefer an easier, gentleman’s fit.
Alternatives: There are a few other great color options through the ‘shop it’ button, too.

Why is it a Find? The purple and olive color combination in this David Donahue shirt looks so fresh with the green Ledbury sweater featured in this outfit. The small check pattern is modern, offering a lot of versatility.
Wear it with: Besides the outfit we’re showing here, you’ll get plenty of wears out of this shirt. It is great with a dark navy solid knit tie for a polished look that is office ready with khakis or jeans.
Fit Tip: The fit is modern with enough room for most gents in your normal size.
Alternatives: If you prefer a more body-conscious, contemporary fit, you’ll like this Vineyard Vines shirt.

Why is it a Find? Instead of your everyday jeans, pair the shirt and sweater in this outfit with these dark grey Vineyard Vines corduroys. The super soft cotton fabric has a touch of stretch for added comfort (a necessity on Thanksgiving, let’s face it) that also helps keep the pants looking good all day long.
Wear it with: The color is a great neutral that works with the look we’re showing here, and most eveything in your closet. Wear them with sweaters, button up shirts and even sport coats. A nice alternative to dark jeans, they are great for a casual day at the office, too.
Fit Tip: The fit is modern with enough room in the seat and thigh for most gents.
Alternatives: If you prefer a trimmer, contemporary fit, these Vince pants are a stylish alternative.

Why is it a Find? These Cole Haan’s are a cool cross between dressier oxfords and comfortable sneakers. With a modern perforated design in the leather upper and a thick ivory rubber sole that gives them an athletic edge, they stand up to any polished casual look.
Wear it with: The dark brown is such a perfect neutral, so they look good with the colors in the outfit here, and most anything you already own. From jeans to work-ready flat fronts, these will take you from the office to a casual night out with ease.
Fit Tip: These run true to size.

Every & Any Casual Holiday Gathering.
Why is it a Find? What’s the fun of the holidays without a little splash of holiday color? Robert Talbott’s cotton and cashmere crewneck sweater does just that, without being too bold. The knit is soft and lightweight so you can comfortably get through a day - and night - of celebrating without overheating.
Wear it with: As we’re showing in the outfit here, we love pairing this holiday pop of color with simple neutral pieces, keeping the look stylish and subtle. The light fabric blend also makes it great for layering under a sport coat, so you can dress it up with wool trousers, and a solid navy knit tie for a dressier look.
Fit Tip: This sweater is a classic, gentleman’s fit for ease and comfort. Size down for a trimmer fit.
Alternatives: It’s available in a lot of amazing colors through the ‘shop it’ button, and it’s a great basic to have in your arsenal.

Why is it a Find? A great white button up shirt makes any holiday look so much easier to put together. White not only goes with everything, it is a perfect foil for the reds, greens and blues of the holiday season. This white self-jacquard print shirt from Thomas Dean layered under the red sweater featured in this outfit - or any other holiday sweater – is just what we mean. The jacquard pattern makes it a little more special than a basic white shirt, another reason it’s so awesome for the season.
Wear it with: The spread collar lays just right when you leave it unbuttoned and add a sweater over it. But it looks just as good buttoned up with a tie and sport coat, so you’ll get wear out of it all year long.
Fit Tip: The fit is modern with enough room in the shoulders and sides for most every gent.
Alternatives: : If you prefer a trimmer, contemporary fit, this Jared Lang shirt is another dapper white option.

Why is it a Find? Dark wash jeans are an easy and always appropriate option for any casual holiday party, all season long. And a gent can’t have too many. These Joe’s Jeans are one of our favorite Finds. The indigo wash is nice and dark, with just the slightest whiskering for a modern look, and the dark self-colored stitch gives them a really clean look.
Wear it with: These are great “go to” jeans that are so deep and neutral, they work with everything – including the red sweater in this outfit. Fit Tip: The 2% stretch in the denim adds comfort, without giving them a fitted look. These are cut in Joe’s classic fit, so they have plenty of room in the seat and thigh, with a straight leg that is modern and not too skinny.
Alternatives: If you prefer a trimmer, contemporary fit, you’ll love these these 7 For All Mankind jeans.

Why is it a Find? As we’ve been talking about this season, the influence of the athletic look has really taken men’s footwear to a whole new level. And we couldn’t be happier. These Cole Haan chukka boots have a modern, athletic-inspired, white sneaker-like sole that makes them the ideal finishing touch any day of the week, and really completes the look we’re showing here. The black vachetta leather upper has the polished look of a boot, providing perfect balance to the sporty sole.
Wear it with: For a casual party, dinner, or day at the office, the black and white combination goes with simply everything.
Fit Tip: They run true to size.
Alternatives: There are also a few other neutral color combinations through the ‘shop it’ button that are just as handsome.

Office Party Appropriate.
Why is it a Find? Cardigan sweaters are the laid-back alternative to a sport coat, so they are a great solution on the day of the office party, if it’s not dressy. J.Crew’s navy cardigan is made of luxurious Italian cashmere, which instantly gives it a more sophisticated seasonal look, and the color is so easy to accessorize.
Wear it with: For a holiday event, just add some festive color, as we’re doing in this outfit. Any other day, anything goes – grey wool trousers or casual jeans, easily work with it.
Fit Tip: In J.Crew’s typically modern fit, it looks great on most every gent in your normal size.
Alternatives: There is a truly fabulous holiday green and a perfect neutral grey through the ‘shop it’ button, too.

Why is it a Find? Since we’re adding some holiday cheer in the tie and pants below to complete this look, Brooks Brothers’ light blue indigo dyed shirt is a really nice neutral layer under the navy cashmere sweater. From their Italian Indigo Collection, the soft fabric is really beautiful, and will hold up for years to come.
Wear it with: Just like a great pair of jeans, this shirt will go with anything. Layer it under any sweater or sport coat, and pair it wool pants, corduroys, khakis, or yes, jeans (just make sure the wash is darker than the shirt’s color).
Fit Tip: The Regent fit is more tailored than what was typical Brooks Brothers in the past. But it is not skinny, so it’s a solid fit that works on most every gent.
Alternatives: If you do prefer a trimmer, contemporary fit, this J.Crew shirt is a nice alternative.

Why is it a Find? Red pants make a holiday statement, and the deep wine tone of these Bonobos cotton twill ones do it in subtle style. It is an easy shade of red to also coordinate with lots of shirts and sweaters all winter long. The all-cotton fabric has a seriously soft peach twill finish that is just made for comfort.
Wear it with: Let these pants be the statement color of the outfit. They are great with the navy cardigan shown or a navy blazer. They also pair nicely with navy, grey or olive button up shirts and sweaters.
Fit Tip: The fit is modern but not skinny, with an updated straight leg – a great fit for most every gent, and they come in 3 lengths.
Alternatives: These pants come in a ton of colors through the ‘shop it’ button, so you can go for a neutral or another pop color, too. If you prefer a trimmer, contemporary fit, we suggest this Brooks Brothers alternative.

Why is it a Find? This classic navy/green tartan wool tie from Polo Ralph Lauren has a toned-down holiday feel that, quite frankly, we’re pretty obsessed with it.
Wear it with: It is the perfect finish to the holiday party look we have here, and the soft wool plaid fabric has a great wintery feel, so you can wear it all season long with navy, grey, burgundy, or dark green sweaters and blazers. While it’s easy with a blue or white button up shirt, it can also be worn with a small gingham check or narrow stripe shirt.
Fit Tip: The 3” width is just right for a modern, but not skinny, look.
Alternatives: Another alternative to typical red plaid, Ted Baker’s tartan plaid tie uses a rich, deep pink that is truly stylish.

Your Holiday Finest.
Why is it a Find? There is nothing as downright dapper as a velvet blazer for a dressier holiday event. And J.Crew ensures you don’t have to break the bank to do it – though it looks like you did. The shawl collar and luxurious feeling cotton velvet offers style and versatility that makes it a holiday favorite Find of ours.
Wear it with: . The cotton velvet fabric and shawl collar styling gives it a a dressy, but not TOO dressy, look that makes it an easy choice for lots of party dress codes: for a formal party, with tuxedo pants; for a cocktail party, with charcoal grey wool pants; and with jeans, for a stylishly casual look. Add a spread collar white or blue button up shirt and optional bow tie to complete the outfit, as we’re doing here.
Fit Tip: The fit is contemporary, meant for a sleek finish that’s not oversized.
Alternatives: While we love the forest green featured, it also comes in black and navy through the ‘shop it’ button, so you can go with something more neutral, too.

Why is it a Find? The tonal self-textured stripe fabric of this Hugo Boss shirt takes it up a notch from a basic white shirt for a festive, holiday party look. The spread collar looks good with or without a tie, and the French cuffs provide an opportunity to add a pop of color with holiday cuff links.
Wear it with: Just because it’s a “tuxedo” shirt, doesn’t mean it’s only meant for tuxedos. It holds up beautifully to the velvet blazer featured in this look.
Fit Tip: The fit is contemporary, meant for a trim look that will lay smoothly under a blazer.
Alternatives: If you prefer an easier fit, this David Donahue tuxedo shirt is a great alternative.

Why is it a Find? These black chino tux pants from J.Crew are a great companion to the featured velvet blazer, and a fabulous alternative to traditional tux pants made of wool. The crisp Italian cotton still has the formal side stripe of traditional tuxedo pants so they look really polished, yet they add a bit more casual and comfortable touch to your holiday look.
Wear it with: Wear them with a velvet blazer (even a black one) for the dapper holiday look we’ve put together here. They can also dress up a holiday sweater or even be worn with just a dressy white button up shirt.
Fit Tip: The fit is contemporary, to complete the trim and polished outfit we’re showing, and come in 3 lengths.
Alternatives: If you prefer wool tux pants in an easier fit, these Bonobos pants are a great alternative.

Why is it a Find? David Donahue’s silk bow tie has a festive look in its tartan pattern, and we love how it plays with some untraditional colors. Bow ties are so chic now, you don’t need to wait for a black tie affair and traditional tuxedo to wear one. The 2 ½” width provides the perfect modern look.
Wear it with: The colors in the plaid work really well with the green velvet jacket in this outfit – and beautifully pop against any black or navy blazer or sweater, adding instant holiday style to basics you already have in your closet.
Fit Tip: Fits up to an 18 “ neck size.
Alternatives: This red tartan pattern bow tie will ensure you look your holiday best.