Last spring, my husband and I were getting ready for a PTO fundraiser, and we found ourselves in a familiar situation of him not knowing what to wear for a semi-dressy occasion. “Does this blazer work?” “Are these jeans dressy enough?” “What socks though?” were questions we struggled with. He had his casual style down pat, and he owns a few classic suits for formal events like weddings, but that in-between style is where he often got stuck. I asked him how he felt about a little wardrobe refresh to round out his closet with men’s fashion essentials he could rely on time after time. To my surprise, he was on board for some closet upgrades and was ready to explore new outfit ideas for holiday events and beyond.
How to Upgrade His Wardrobe for the Holidays
There are a few pieces all men should have in their closets that make getting dressed much easier, and the holiday season is a great time to help him build out his wardrobe with quality classics. When planning a closet makeover for men, think about adding pieces that reflect his personality while enhancing his overall look. Fortunately, when it comes to men’s style, there are a few pieces that stand the test of time and you really can’t go wrong with. From tweed blazers to Chelsea boots, men’s style doesn’t change quite as often as women’s. If you’re unsure what color or pattern to select, stop overthinking it, and go with the classic earth tone option. Navy, muted blues, grey, khaki, greens, white—they universally look great on all men.
A wardrobe refresh for men can be a bit tricky—you want to help him elevate his style without making him feel like his current wardrobe choices aren’t cutting it. That’s where the joy of holiday gift giving comes in. If you’re wondering how to upgrade his wardrobe this holiday season, look no further. A few carefully chosen fashion gift ideas for men can make all the difference in his style game, helping him go from casual to polished with ease. From essential closet upgrades for men to timeless pieces he’ll wear on repeat, these 12 men’s style gifts will upgrade his wardrobe and ensure he’s always the best-dressed man in the room.
Whether it’s a versatile blazer, sleek dress shoes, or classic accessories, these wardrobe essentials for men are perfect for holiday style upgrades that he’ll love and actually use. Get ready to make this a Christmas gift he won’t forget!
1. Midweight Jacket
When I worked in retail, I learned the fashion styling rule of adding a third piece to complete a look. Adding a “third piece” or item in addition to the shirt and pants elevates and gives an outfit that “finished” look. A nice jacket is a great example of the third piece to layer on.
If you’re looking for a fashionable Christmas gift for your boyfriend, you cannot go wrong with anything from Sézane’s men’s collection, Octobre Éditions.
The Sezane Nelson Jacket is the perfect wardrobe upgrade in this category and essential for those in-between weather months. With its tailored fit, cozy texture, and earthy tone, it’s a versatile piece that pairs effortlessly with everything from sweaters to button-downs, bringing a polished touch to his wardrobe.
2. Nice Sneakers That Are Not Basketball Shoes
We know every dude in America has his favorite sneakers, but odds are they look more gym-ready than dressy. Kickstart his wardrobe refresh by upgrading his beat-up running shoes. These BKE Luke sneakers have the same cushioned footbed he loves for all-day comfort, but the leather finish gives them a polished look that works just as well for date night as it does for weekend errands, making them a men’s fashion essential.
If you’re looking for a stylish yet affordable men’s fashion gift under $100, these faux leather sneakers are the perfect choice—both trendy and practical, making them something he’ll wear and truly appreciate.
3. Classic Chinos or Trousers
A nice pair of Chinos in classic khaki or navy is the perfect go-to for a guy when he needs something nicer than jeans but not as dressy as a suit pant. As a timeless wardrobe essential, chinos pair well with a polo, blazer, or sweater, offering a look that’s polished and tailored without feeling stuffy. It’s truly a classic style gift for men that suits any occasion. If he’s a bit more fashion-forward style, get him a pair of relaxed pleated trousers, a style popping up at menswear stores everywhere this year. They’re a wonderful nod to dapper-looking men of the 1940s and earlier.
If the pleated trouser is a little too fashion-forward for your dude, the classic chino is timeless and fits the bill.
4. Upgrade His Denim
Most men have that pair of jeans they love and reliably throw on to run errands or clean out the garage. I’m not knocking it—we love a favorite pair of jeans. But that should not be the same denim he wears to date night, the friend’s engagement party, or Thanksgiving dinner.For some easy closet upgrades to boost his style, consider updating his denim collection with a more tailored fit in a darker wash—perfect for pairing with a blazer or sweater and loafers instead of his usual T-shirt and sneakers. Jeans can be tough to fit, but Banana Republic and Tailor Stitch both have a great assortment of styles, fits, and washes. This Slim Selvedge is a good example of this look.
5. A Nice Button Down That Is Not a Work Shirt
There’s something about a starched button-down that reads I am headed into my corporate meeting. If you’re looking for alternate shirt choices for dressing up that is less finance bro and more stylish bf, reach for one in a more relaxed fabric with no buttons on the collar. Tell him to leave the top button or two open. Pair with that nicer denim or relaxed chino and a loafer to complete the look of this wardrobe essential. Hello, handsome. One key to a successful closet makeover for men is choosing timeless pieces that can adapt to both casual and formal settings—and this piece does just that.
6. Heavyweight White Tee for Layering
White tees are a fashion staple I gift my husband every year because of the wear he puts on them throughout the year. And there’s a big difference between an old, thin, worn tee neckline popping out from under a sweater versus a crisp, thick cotton that pops. Last Christmas, I picked up this signature tee from Faherty for my husband, and he’s constantly reaching for it. The thicker material makes it not see-through, so it can be worn as a shirt under a blazer, as opposed to just layering it under sweaters, which he also does.
7. Sweater Polo
This past spring, when I helped my husband refresh his wardrobe, the sweater polo was the piece that took him furthest out of his style comfort zone. At first, he wasn’t totally on board with it, but I managed to convince him to keep it. Now, after wearing it on several occasions, it’s the item he gets the most compliments on. Sweater polos look fantastic—they’re a dressier, more stylish twist on the classic polo, instantly elevating any outfit and wearable year-round. In my opinion, having at least one sweater polo in a classic color is a must-have staple for men.
8. Chelsea Boots
If your dude doesn’t yet own a pair of Chelsea boots, I highly recommend gifting him this wardrobe upgrade that he will benefit from for years to come. It adds a polished edge to any outfit. Whether he’s pairing them with jeans or chinos, these dressier boots offer a versatile look that’s easy-going yet sophisticated—a tough balancing act. This timeless style is ideal for the man who wants a step up from sneakers but doesn’t want the commitment of dress shoes. It’s a great addition to his wardrobe refresh for the holidays, providing a comfortable yet refined footwear choice that’s effortlessly cool. You can do leather or suede; you really can’t go wrong.
9. Wool Topcoat
I don’t know what it is, but there is something about a man in a long wool overcoat that just screams handsome. If you’ve seen Peaky Blinders, you’ll know what I mean. This versatile coat is perfect for the colder months, bringing a touch of elegance to his everyday look. Whether he’s dressing for a formal event or simply layering over a sweater and jeans, a wool overcoat is a wardrobe must-have that never goes out of style. With options in classic colors like charcoal, navy, and camel, he’ll have a piece that’s both timeless and easy to pair with everything in his closet.
10. Knit Blazer
Similar to the chino pant vs. suit slacks debate, it’s good to have a more casual blazer option that isn’t a suit coat for when the occasion calls for it. My husband often throws on his knit blazer with jeans and a tee for nights out, and again, the compliments just roll in. He’s a pretty casual guy, so this simple step of adding a comfortable, casual knit blazer just dials it up a notch without sacrificing comfort.
11. Jogger Upgrade
If your man’s favorite sweats have seen better days, treat him to a little upgrade for his cozy wardrobe. I tell ya, you’ll appreciate seeing him in these as much as he’ll love wearing them. I’ve gotten my husband a pair of Vuori joggers for every occasion the last few years—Father’s Day, birthday, Christmas. They are so good. But now that his Vuori jogger collection has built up, this year I’m looking at this stylish Taylor Stitch. Quilted sweats? So handsome.
12. A Closet-Essential Sweater
Lastly, you can’t go wrong giving the gift of warmth and style this season with a classic wool sweater that’s as comfortable as it is versatile. Perfect for chilly days and winter outings, a well-made wool sweater instantly elevates his look, whether he’s dressing up for a holiday dinner or layering up for a casual day out. Look for neutral tones or earthy shades that seamlessly pair well with his new jeans and chinos. This cozy essential is not just a staple for his holiday wardrobe upgrade but a timeless piece he’ll reach for season after season.
If he’s a bit more fashion forward, you can opt for a cardigan. Thicker fabrics with unique buttons and structured collars make for an excellent choice and add style to any outfit.
Shop More Christmas Gifts for Him
- Gifts for Guys
- Gifts for Dads
- Stocking Stuffers for Men
- 40+ Practical Gifts They’ll Actually Use
- What to Buy Your Pickiest Loved Ones for the Holidays
Why You Can Count on Us
The Everygirl Media Group has published our beloved gift guides for 12+ years. Whether you’re shopping for a gift for your work wife, an insanely cool cousin, or your significant other’s dad (why are dads so hard?!), we have an idea they’ll love. The Everygirl editorial team is well-versed in sifting through thousands of products to curate a digestible and affordable list for you. We combine our own experience with in-depth research to bring you a selection that meets our high standards for both fashion and function.
Alaina Kaz, Chief Executive Officer
Alaina Kaz is the Chief Executive Officer, owner, and co-founder of The Everygirl and The Everymom. When she’s not leading her company, she’s sharing her passion for interior design, fashion, travel, and the journey of motherhood. Alaina is also a proud mom to two sons, Henry and Charlie.
This post contains a sponsored inclusion of Buckle and Sézane, but all of the opinions within are those of The Everygirl editorial board.