8 Holiday Season Outfits to Keep You Covered for Any Occasion

The holidays always present us with some sartorial challenges, and they will even more so this year, as we deal with the ongoing pandemic. Looking proper while working, perhaps working from home, lounging, decorating, cooking meals, opening gifts and socializing with family, requires a bit more thought than normal. Well, we're here to help and we make it easy. It starts with proper-fitting clothes in fact. For inspiration to look your best while staying ready for any and all occasions, look no further. These eight holiday outfits have you covered.


Outfit #1 Flannel and Jeans

An easy one to pull off, a simple Everyday Flannel paired with skinny fit jeans is comfortable and seamless. Flannel is the consummate fall fabric, taking you anywhere from afternoon strolls to evenings by the fire. For a little extra warmth, toss on a PMNYC Lightweight Down Jacket.

 

Outfit #2 Stripes

If plaid isn't your pattern, try stripes! And don't be afraid of the horizontal ones. If done properly, they're perfectly appropriate for our guys. Our new Cotton Quarter Zip Sweaters offer a simple design with everyday wearability. Pair them with a Chambray Shirt, Waxed Jacket, and Tan Kittredge Cords for another sharp yet casual look, incorporating more classic fall fabrics and colors.

 

Outfit #3 Navy Monochrome

One good indicator of a stylish man? One who can pull off the monochromatic outfit. Sounds easy, but is often butchered, because without the right shades of the same color, it can quickly go wrong. We like navy this season, and in this case, all you need are three basic pieces, and they're super versatile: a pair of dark wash jeans, a navy Crew Neck Sweater, and a navy Winter Parka. Add a pop of white with a white Everyday Shirt to finish the outfit off.

 

Outfit #4 Dressed-Up Without a Suit

We love that 'dressing up' no longer has to involve a suit (or even a sport coat). If dinner plans call for a more formal look, consider this outfit. Start with grey flannel Dress Pants and a white Easy Care Dress Shirt. Toss on a colorful tie (have some fun with it) and then a navy V-Neck Zegna Merino Wool Sweater. If venturing outside in chilly temps, top it off with a charcoal topcoat (see what we did there?).

 

Outfit #5 Dressed-Up With a Suit

Dress jacket and pants (or full suits) are still the easiest way to manage more formal holiday occasions. In this case, you can't go wrong with our perfect-straight-out-of-box navy pinstripe Essex Suit. Match it with a blue Easy Care Dress Shirt and a navy Winter Parka for another warm, monochromatic look that'll take you straight from freezing temperatures to a formal family function. Tie or no tie.

 

Outfit #6 Bundled-Up

For those that run cold, you'll appreciate this outfit. Navy pinstripe Essex Dress Pants and a grey Wool Shawl Collar Sweater provide a cozy and sophisticated base. A navy topcoat completes the outfit fairly well, but to really add some depth (and even more warmth), finish with our rust plaid Merino Wool Scarf, designed to be the perfect length and pattern for the Peter Manning man.

 

Outfit #7 With a Blazer

Blazers are a great way to quickly elevate an otherwise casual outfit. That makes this look perfect to transition from helping out in the kitchen to joining in for the holiday photos. Start with our grey flannel Essex Dress Pants (the ultimate fall pant), add a burgundy grey gingham Everyday Oxford and let the pattern poke out of a black Cotton Pullover. Finish the look with a perfect-fitting navy blazer.

 

Outfit #8 A Warm Weather Option

For those lucky enough to be enjoying the holidays in warmer climates, we are jealous, but have options for you too! Brown Everywhere Pants and a black watch plaid Everyday Oxford are a great pairing that works as is, or dressed up with a lightweight Unstructured Linen Jacket.

 

(Bonus!) Outfit #9 Early Morning Lounging

Too many of us have historically avoided PJs because they never fit properly, and man were we missing out! For those early mornings unwrapping gifts or just kicking back after a long day and a big meal, our grey plaid flannel Pajama Pants and white Vintage Crew T-Shirt are a cozy and comfy option. And they'll fit great - guaranteed!