Holiday Outfits for Men - What Taelor Stylists Say

Christmas Day is all about feeling cozy yet looking polished as you celebrate with loved ones. The right holiday outfits for men reflect this festive spirit. Whether you’re lounging at home or hosting a family feast, little touches of style can uplift your look and mood.

• Sweater Season: A soft cable-knit or cashmere sweater in festive hues like cranberry, forest green, or midnight blue paired with beige or navy chinos strikes the perfect balance of comfort and class.

•  Festive Layers: Add a blazer or wool cardigan for a more refined touch, especially if you’re hosting.

• Seasonal Accessories: A plaid scarf, textured socks, or a leather belt with subtle holiday tones adds warmth to your outfit.

From cheerful gatherings with friends to sparkling corporate events, holiday parties are where style meets fun. And holiday outfits for men that match the occasion let your personality shine through.

•  Casual Cheer: Pair a brushed flannel shirt with dark-wash denim and rugged leather boots. Add a quilted vest for a cozy outdoor vibe.

•  Semi-Formal Sparkle: Choose a sharp button-up shirt, slim-fit trousers, and a velvet blazer for an instant festive upgrade.

• Modern Sophistication: Choose a slim-fit dark suit in midnight blue or charcoal gray, paired with a well-pressed dress shirt in white or a subtle festive hue. Add a refined touch with a classic silk tie. Finish the look with sleek leather brogues or polished oxfords and a minimalist belt to keep it sharp yet understated.

The holidays often mean travel—whether it’s home for Christmas or exploring a new destination. The key to planning holiday outfits for men is aiming for comfort without compromising on style.

• Start with a knitted hoodie : Go for a textured, cozy hoodie that’s both simple and stylish. It’s perfect for layering and keeps you looking effortlessly put together.

•  Pair with comfy joggers or denim:  Choose joggers for a laid-back vibe or dark denim – both are comfortable and versatile for travel days.

• Finish with slip-on sneakers: They’re easy to get on and off, making them a security line lifesaver, and they pair perfectly with your outfit.

Christmas chic is the art of embracing festive spirit with understated elegance. Think timeless with a touch of sparkle.

• Statement Sweaters: A refined cashmere or fair isle sweater in bold yet classic colors paired with tailored trousers for a chic finish.

•  Festive Fabrics: Incorporate corduroy, or tweed into your blazers or pants for added texture and charm.

•  Finishing Touches: A subtle plaid pocket square, a sleek watch, or a statement tie completes the look with festive finesse.

Smart casual holiday outfits for men are where style meets ease. For a smart casual Christmas party, you want to strike the perfect balance between looking put-together and feeling comfortable.

• Start with a Dress shirt: A crisp white shirt is always a classic choice, but if you want to feel a bit more festive, try one in deep red, navy, or forest green.

•  Add a Deconstructed Blazer: A casual blazer keeps things sharp but relaxed – perfect for holiday vibes without being overly formal.

•  Pair with Chinos or Dark Denim: They’re versatile and easy to wear, and they’ll keep your look polished but not stiff.

Finish the look with loafers. A nice pair of loafers ties it all together – comfortable enough for mingling but sharp enough to impress.

This festive season, dressing up becomes part of the joy. With Taelor, it’s never been easier to look great for every moment—whether you’re unwrapping gifts, mingling at holiday parties, or catching a flight to your next adventure. Holiday outfits for men are a breeze when you have a Taelor menswear rental subscription which throws in the added benefit of personal styling.

Here’s to a season filled with style, warmth, and unforgettable memories. Happy holidays from all of us at Taelor!

Want some help finding clothes that will make you the best possible version this holiday season? Let Taelor help. Taelor is a menswear rental subscription service dedicated to helping men look their best when it matters most. Our styling service, powered by a human stylist and assisted by artificial intelligence, finds the clothes that help you win – at work, on a date, at a party, or wherever you spend your time.