festive holiday outfits

From Casual to Classy: 14 Festive Holiday Looks for Men to Try This Year

From Casual to Classy: 14 Festive Holiday Looks for Men to Try This Year

The holiday season is just around the corner, bringing with it the excitement of Thanksgiving, Christmas, and all the festive celebrations along with we look forward to. It’s that time of year when everything feels a little more magical—and of course, we get the best sales on our favourite brands and festive holiday outfits.

And let’s be real: the best deals are always on holiday evening wear. After all, we all want to look our best for those holiday nights out, whether it’s a cosy gathering with friends or a lively night on the town.

In this blog, I've put together my top picks for holiday outfits 2024. If you're all about bold street swagger and rugged, statement-making styles, then these looks are definitely for you.

So let’s dive in! Here are 14 holiday outfits for men that are all about effortless style. These picks are designed to make you feel like the star of the season—without looking like you’re trying too hard to be cool.

Holiday Look #1: The Cozy Gentleman

Men's Jordan Underground Hoodie

Men's Jordan Underground Hoodie
Men's Bryant Logo Denim Jeans Pant

Men's Bryant Logo Denim Jeans Pant
New Balance Men's Shoes

New Balance Men's Shoes

Holiday Look #2: The Effortlessly Cool<

Roku Studio Men's Bad Habits Cropped Fleece Hoodie

Roku Studio Men's Bad Habits Cropped Fleece Hoodie
Jordan Craig Men's Dillinger Striped Denim Pants

Jordan Craig Men's Dillinger Striped Denim Pants
Adidas Anthony Edwards 1 Georgia Bulldogs Mid Basketball Shoes

Adidas Anthony Edwards 1 Georgia Bulldogs Mid Basketball Shoes

Holiday Look #3: The Rugged Outdoorsman

Jordan Craig Men's St. Cloud Work Jacket

Jordan Craig Men's St. Cloud Work Jacket
Jordan Craig Men's Meadowlands Denim Pant

Jordan Craig Men's Meadowlands Denim Pant
Timberland Men's Premium 6-Inch Lace-Up Waterproof Boot

Timberland Men's Premium 6-Inch Lace-Up Waterproof Boot

Holiday Look #4: The Modern Dapper

COOGI Brights Crew Neck Sweater

COOGI Brights Crew Neck Sweater
True Religion Mid Rise Camouflage Print Jeans

True Religion Mid Rise Camouflage Print Jeans
Timberland Euro Hiker Leather Boot

Timberland Euro Hiker Leather Boot

Holiday Look #5: The Street-Smart Layering

Pelle Pelle x TB Chitown Leather Jacket

Pelle Pelle x TB Chitown Leather Jacket
RTA Bryant R.I.P Skinny Denim Jeans

RTA Bryant R.I.P Skinny Denim Jeans
Adidas Predator 20.3 Shoes

Adidas Predator 20.3 Shoes

Holiday Look #6: The Minimalist Chic

RTA Men's Dion Rest in Peace Pullover Hoodie

RTA Men's Dion Rest in Peace Pullover Hoodie

RTA Men's Bryant R.I.P Skinny Denim Jeans
Converse Chuck Taylor All Star Ox Low Knit Shoes

Converse Chuck Taylor All-Star OX Low Knit

Holiday Look #7: The Urban Edge

Roberto Vino Men's Paris Pullover Hoodie

Roberto Vino Men's Paris Pullover Hoodie
G-Star Raw Men's D-Staq 3D Slim Jeans

G-Star Raw Men's D-Staq 3D Slim Jeans
Adidas Men's Originals Crazy BYW Shoes

Adidas Men's Originals Crazy BYW Shoes

Holiday Look #8: The Classic Cool

Godspeed Men's Rock Dreams T-Shirt

Godspeed Men's Rock Dreams T-Shirt
Jordan Craig Men's Aaron Apocalypse Denim Pant

Jordan Craig Men's Aaron Apocalypse Denim Pant
Nike Men's Dunk Low Retro SE Shoes

Nike Men's Dunk Low Retro SE Shoes

Holiday Look #9: Vintage Vibes

Hugo Boss Men's Crew Neck Sweatshirt

Hugo Boss Men's Crew Neck Sweatshirt
Jordan Craig Men's Shreds Denim Jeans

Jordan Craig Men's Shreds Denim Jeans
Nike Men's Air Foamposite One Shoes

Nike Men's Air Foamposite One Shoes

Holiday Look #10: Street-Savvy Layers

Pelle Pelle Men's Panther Leather Jacket

Pelle Pelle Men's Panther Leather Jacket
Breyers Leather Pattern Hat

Breyers Leather Pattern Hat
Nike Men's Ja 2 Nightmare Halloween Shoes

Nike Men's Ja 2 Nightmare Halloween Shoes

Holiday Look #11: Dapper Yet Casual

Embellish Men's Riot Denim Jacket

Embellish Men's Riot Denim Jacket
RTA Men's Bryant Jeans 3D Embroidery Patch Pant

RTA Men's Bryant Jeans 3D Embroidery Patch Pant
Nike Men's Air Force 1 '07 Panda Shoes

Nike Men's Air Force 1 '07 Panda Shoes

Holiday Look #12: The Urban Explorer

Timberland Men's Ribbed Cuff Beanie

Timberland Men's Ribbed Cuff Beanie
Timberland Men's Core Tree Logo Jogging Suit

Timberland Men's Core Tree Logo Jogging Suit
Timberland Men's Premium 6-Inch Lace-Up Waterproof Boot Shoes

Timberland Men's Premium 6-Inch Lace-Up Waterproof Boot Shoes

Holiday Look #13:The Weekend Warrior

Jordan Craig Men's Meadowlands Denim Trucker Jacket

Jordan Craig Men's Meadowlands Denim Trucker Jacket
Jordan Craig Men's Meadowlands Denim Pant

Jordan Craig Men's Meadowlands Denim Pant
Nike Men's Air Vapormax Plus Cool Grey Black Shoes

Nike Men's Air Vapormax Plus Cool Grey Black Shoes

Holiday Look #14: The Smart-Casual Combo

Men's Savar Ice Grey Slim Denim Jeans

Men's Savar Ice Grey Slim Denim Jeans
Smoke Rise Men's Regular Collar LS Overshirt

Smoke Rise Men's Regular Collar LS Overshirt
Meras Men's Short Sleeve T-shirt Classic

Meras Men's Short Sleeve T-shirt Classic

 

Note: Use Code “FALL10” to get an exciting 10 % off on all men’s holiday outfits listed here.

Mens Holiday Party Outfit Sale:

And that wraps up our top picks for men’s holiday outfits! Don’t forget to check out Tops & Bottoms for amazing sales on all things streetwear, partywear, and especially sneakers

We’re constantly updating our collections to make sure you’re always stepping out in the latest and greatest looks this winter 2024.

Final Thoughts:

I’d love to hear what you think of these 14 holiday outfit ideas for men—drop a comment below and let me know your favourites, or how you plan to rock the block this season!

Thanks for reading, and see you soon with more style inspiration!


About the Author:

Ryan ShykH

Fashion lover, street-savvy, and true sneakerhead. I know every color of the rainbow and love sharing my style tips as a writer and guide. 🌈 Get to know me better by following me on Twitter! @RynAhmed47



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