DEVIL-DOG® Holiday Outfit Guide – DEVIL-DOG Dungarees
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2023 Holiday Outfit Guide

It's that time of year again. The holiday season is one of the most joyous stretches of months in the year. Family time. Gratitude. Enough eating to send you into a food coma for weeks. It's no wonder it is the most wonderful time of the year for many people. There also seems to be one event after another. Rarely does a week go by that you don't have to dress up and meet with family, friends, or work colleagues to celebrate. While that may cause all kinds of different stresses (you have to pretend to love your partner's boss all over again, after all), your attire shouldn't be one of them. 

No worries, DEVIL DOG has everything you need to get sorted for the lineup of special events. Here are our picks for the best looks for all your get-togethers coming up, casual and elevated. 

Office Holiday Party

Casual

If you have a more laid-back holiday party on the calendar, consider doubling up on some of the best denim up top and pairing it with our Comfort Jean. While the Military Chambray Shirt keeps it basic, the Raisin CPO Jacket adds a pop of color to the ensemble. The Rugged Tan Comfort Jeans feel like sweatpants pretending to be jeans, so you will remain comfortable all night.

Elevated 

If you have the kind of boss or event that calls for a little more of a dress-up outfit, here is a good rule of thumb: keep it darker. Blacks and grays will serve you well in a nighttime event, adding elegance to your look. The trick with most of these parties is layering. It's cold outside, but the events will be warm. So, throwing our Deep Black Everyday Henley over the Charcoal Feeder Stripe Polo keeps you elegant without sacrificing comfort. Pairing them with the Chimney Rock Chinos pulls the entire look together and is a masterclass in color-blocking.

Personal Holiday Party

Casual

Your personal holiday parties lose the pressure of the boss and the co-workers, but add the stress of family. No matter how much we love our brothers, sisters, parents, aunts, and uncles, there is always a sigh of relief once they go home. With that in mind, comfort is the name of the game. Your more casual look for your family get-together should always start with the Gates Athletic Jean. The color is striking and can pair with anything in your closet. We like to go with green as a nod to our military past, so we chose the Gambler Graphic Tee and the Olive Night CPO Jacket. You can opt for a pair of green or olive sneakers like the example on the right, or you can bend the rules a bit and wear white after Labor Day with a clean pair of white sneakers and the White Bulldog 5 Panel Adjustable Cap for flair.

Elevated

Ok, if your mom is the kind of gal who is going to want you to look your best at her house, you can do so without sacrificing comfort. Once again, go a little darker with the Carbon Stretch Corduroy. The slate gray hue will catch some attention, while the stretch is handy when your mom brings out the mashed potatoes. Pair the Coal CPO Jacket over the Ash Heather Everyday Henley, and you will look your best, feel your best, and have the stamina and peace of mind to stay out of the family drama and debates that are bound to kick off once the spiked egg nog is flowing.

Dinner Party

Casual

One thing is for sure: throughout the holiday season, you will spend ample time around the dinner table. While you are likely not trying to impress anyone at the holiday table, it doesn't hurt to look your best and keep the attention on your creativity and how put together you look instead of focusing on the resolutions you still need to fulfill. The Farmer Sage Feeder Stripe Polo is as soft as it is attractive and will stand alone if the temperature in the house rises. But putting the Crowders Workwear Shirt over the top doubles up on the collars and gives you a creative and fun look - whether buttoned or left open. Of course, you can't forget the Kangaroo Athletic Comfort Jean if you plan to put on the holiday weight and still look great

Elevated

We have said it twice, but we're going to repeat it in case you need to hear it again. If you need to elevate your look for something a little dressier, go darker in the color. If your dinner party requires a little more sophistication, opt for the essential Black Chino. It looks like a dress pant but wears like denim, giving you the best of both worlds. The Marion Western Shirt may not sound elegant or elevated like a dress shirt, but once you put it on and catch a look at yourself in the mirror, you will be sold on the image. Finish the ensemble off with our trendiest outerwear garment, the Barnes Creek Fashion Denim Jacket, and you will undoubtedly be the talk of the group. Comfortable and still the best-dressed guy in the room. If you are beginning to notice a pattern, it may be our design intent.

Date Night

Casual

Here is the thing: the holiday season can get overwhelmingly busy. You can spend so much time focusing on gifts, parties, friends, and family that you completely forget (or, let's say, overlook, you could never forget) your significant other. If you are dating, you want to maintain your social life through the holidays. If you are married, date night is even more critical. If you casually stroll through Christmas lights or pick out your first real tree for the house, the Khaki Stretch Corduroy will stick with you better than most pants in your closet. They are solid, durable, and still attractive. Pair them with the Vintage Gray Heather French Terry Crewneck, and you will be the picture of comfort while still looking put-together. Finish the look off with our Fortana Denim Trucker Jacket and the Navy Patch Trucker Hat, and your ensemble will have your date cuddling up next to you to steal your warmth.

Elevated

If you are going on a date, whether you have known the person for ten minutes or ten years, they deserve the best you have. Therefore, you should opt for an ensemble of three of our best items available. Starting with the Chimney Slim Jean, they will be the most comfortable and stylish of our denim, likely becoming your "dress jeans." Pairing it with another polo and henley combination, the Melange Navy Blue Feeder Stripe Polo will provide the elegance, while the Indigo Slub Henley will provide the warmth. We know we said you should go darker with the elevated looks, but let's be honest: every guy looks great in blue. And if you are going on a date, blue is always a good choice. If you want to make a statement, the white sneakers will pop while you walk your date back to her car. You are walking your date back to her car, right?

Outdoor Party

Casual

If you are lucky enough to live in a part of the world that isn't below freezing all through the holiday season, then you may have the distinct pleasure of having an outdoor party. While the rest of us grumble at your good fortune, you can look great in some fetching looks. It is possible that you will be recruited to pitch in for some of the party chores like building a fire, working the grill, or getting Grandma a chair. This casual look will prepare you for anything your guests throw your way. The Butterscotch Carpenter Pant is one of the most unique colors we have in our stock, and the Motorcycle Long Sleeve Graphic Tee will have all of us wishing the weather was still good enough for a ride. Just because it isn't freezing, though, doesn't mean it isn't going to get cold, so pick up the Elmwood Patch Jacket. You may have to start sharing links as your guests will wonder where they can get their own. Top it off with the 6-panel Outdoor Hat, and you will be ready to entertain your guests with stories or take them on a walk into the woods.

Elevated

Casual outdoor events often come with some bright days. And nothing is better on a sunny day than a bit of color. The Olive Slim Straight Jean will be one of your favorite go-to jeans all year round, but it will especially shine bright throughout the fall months. If you want to get daring with the color, pair it with this Raisin Everyday Henley. The purple and green play nicely together, allowing you to add the two colors softly without looking garish. Top it off with our Carroway Denim Trucker Jacket to keep the rest simple while adding depth and charm to the look. If you really want the look to be complete, pair them with some desert chukkas, and you will be the talk of the party. Just because it is casual doesn't mean you can't still dress with intention and have a little fun.  

There you have it: ten outfits that will elevate your wardrobe this holiday season. These items are comfortable and versatile, allowing you to repeat many of these looks all year round. While they will fit like a glove when you pick them up, we can't guarantee they will after the mashed potatoes; that is a choice you will have to make.

Written & Curated by Mark McKee