A solid button-up is the most foolproof method to simply look good—it’s called a “dress shirt” for a reason. The collar, however, doesn’t necessitate being stiff, and the holidays in particular are one of the best times to experiment with material and pattern. While an oxford is always a safe bet, for those headed to more formal engagements try a bold pattern or a reflective material like satin or silk. The point is, even with a pair of black jeans, this is the easiest way to impress.

For those on a budget ($100 or less), we recommend a plain cloth oxford shirt by Brooks Brothers or [Gitman Vintage](https://www.grailed.com/designers/gitman-bros-vintage—you really cannot go wrong with either. If you’re looking for something more bold and are willing to splurge ($250 or less), a patterned Dries Van Noten spread collar is guaranteed to be a conversation starter. For those hoping to make a statement—and have the wallet to back it up ($400 or more)—a satin Saint Laurent dress shirt of fashion-forward silk iteration by Haider Ackermann will do the just the trick.

Recommended Brands
$: Brooks Brothers, Gitman Bros. Vintage
$$: Comme des Garçons SHIRT, Dries Van Noten
$$: Haider Ackermann, Saint Laurent

If a dress shirt just isn’t for you, the best alternative is a solid sweater. More than seasonally appropriate, a pullover or turtleneck is a sure way to look dignified without sacrificing comfort. That said, this is not your college ugly sweater party, and we find best to keep it simple, whether it be a raglan sleeve cashmere or a merino roll neck. Going for a turtleneck or roll neck also doubles as a high-key layering piece; if you’re stuck wearing a suit for your holiday gathering, it’s a great way to ditch the shirt and tie. For those interested in keeping things festive, fisherman cable knits or Fair Isle sweaters are both great ways to up the ante while simultaneously reminding your relatives and friends of a classic Hollywood heartthrob.

For those on a budget, few things are as good a deal as Uniqlo cashmere, particularly those from the Uniqlo U line by Grailed favorite Christophe Lemaire. If warmth is your principal concern, and you’re willing to spend a bit extra, Acne Studio’s raglan sleeve knitted sweaters—in Shetland and Merino—are a classic. Turtlenecks can be tricky, particularly if you are prone to scratching, but if you are willing to spend ($300 or less) Stone Island’s technical iterations are par none. If your primary concern is to flex ($400 or more), wilder prints by the likes of Wacko Maria, Needles and Visvim in lush textures—like mohair—will be the envy of the rest of the family.

Recommended Brands
$: Uniqlo
$$: Acne Studios, Stone Island
$$$: Needles, Visvim, Wacko Maria

Impressing that family member who loves to ask just one to many questions about “your fashion hobby” can be tough. Shut them down with a great pair of trousers. While charcoal or black trousers are a staple, the holidays are inherently celebratory and, as such, are the perfect time to experiment. Try out a striking plaid or a single-pleated trouser. Both bold, yet just daring enough to impress. Additionally, paired with either your best button up or shaggy sweater (see above)—or better yet, both—trousers are key to looking “dressed up” without donning a full suit. It’s a look both your parents and significant other will get behind.

For those on a budget ($125 or less), A.P.C. makes some of the most dependable trousers and chinos out there. In either navy, tan or black, they will work with just about everything in your closet, meaning lots of post-holiday wear. At the medium price point ($225 or less), Ami makes exceptional single-pleat wool trousers (in solid and plaid) that are both fashion forward as well as exceptional value. Insofar as comfort, you would be hard-pressed to find a better pair of trousers than those by Lemaire. With a dual-pleat, drawstrings and elasticated waist, the minimalist brand’s calling card is best in class, albeit comes at a price ($300 or less). Even for those interested in avant-garde fashion, a pair of Rick Owens’ classic knife trousers (without the gnarly drop crotch) is a perfect choice, however those will cost you ($400 or more).

Recommended Brands
$: A.P.C.
$$: Ami, Lemaire
$$$: Maison Margiela, Rick Owens

No doubt the most controversial, take-it-or-leave it part of this list, many guys today couldn’t be bothered to wear a blazer. While we are not by any means suggesting a full sartorial makeover, a simple unstructured lightweight blazer is a great compliment to any of the aforementioned items. For those with more formal obligations—office parties, dinner with the in-laws and so forth—a blazer is not only encouraged, but a great way to earn some much needed style points. If you want to dress to impress, there are a slew of casual, comfortable and affordable ways to do it. That said, for those seeking the center of attention, a bold dinner jacket will make an outfit.

For those on a budget ($200 or less), staff favorite Barena makes fully unstructured blazers that hit the sweet spot between jacket and cardigan. Available in a range of fabrics and colors, they are as informal as a blazer gets. While not known for its “traditional” tailoring, Dries Van Noten has an excellent selection of blazers at a fair price point ($300 or less). Still unstructured, slight canvassing in the shoulders allows for a more tailored look without sacrificing comfort. For a minimalist bend, a boxy, cropped cut by Jil Sander (either under the eye of Raf Simons or during today’s Luke and Lucie Meier-era) is more fashion forward ($400 or less). If flossing at the holiday party is your raison d'être, a dinner jacket by Dior Homme or Tom Ford comes at a price ($500 or more)... but so does being the evening’s best dressed.

Recommended Brands
$: Barena
$$: Dries Van Noten, Jil Sander
$$$: Dior Homme, Tom Ford

Bottom line: everyone needs a formal-facing coat. Even though your Palace puffer is practical—and inarguably cool—this is neither the time nor the place. This season, invest in a topcoat, as classic a menswear staple as any. Guaranteed to stay in style—particularly given our current fashion trajectory and the surprising resurgence of “Ivy Style”—a classic three-button in camel, black or gray will look just as good over your hoodie collection as paired with anything else on this list. Although the luxury options are great, there are a slew of topcoats available at both the entry-level and mid-tier price point that are just as good. Supreme even makes one with Loro Piana wool! No matter your niche, there’s an option for you.

For those on a budget ($250 or less), Club Monaco is a steal. Although celebrated designer Aaron Levine has taken his talents to Abercrombie, his design ethos still runs through the brand’s DNA, and his camel coats helped shape and set an industry standard. Our Legacy, while at a higher price point ($450 or less) offers a car coat that’s the perfect blend of traditional luxury (in lush Cilium wool) and contemporary menswear (oversized, hidden placket, etc.). The aforementioned Supreme Loro Piana topcoats come at a similar cost, however considering the quality of the fabric, it’s one of the streetwear labels most coveted pieces of outerwear. At the higher price points ($500 and up), there are countless great options, but Loro Piana, Ralph Lauren Purple Label and Mackintosh serve as a great start. Few remember, but Raf Simons actually began his career focused on tailoring, and to this day his wool coats are best in class. If budget is no concern ($750 or more), Simons’ outerwear is the perfect synthesis of minimalist fashion and luxury tailoring.

Recommended Brands
$: Abercrombie & Fitch, Club Monaco
$$: Our Legacy, Supreme
$$$: Mackintosh, Raf Simons, Ralph Lauren Purple Label

For those whose family members have more conservative tastes, sneakers are likely a no-go at dressed-up holiday events. While we are as big a proponent of luxury sneakers as any, all of us eventually have to go to a wedding, and having a pair of formal shoes will inevitably come in handy. That said, for those uninitiated the options can be daunting. We recommend loafers, chelsea boots or classic oxfords as a starting point. Even from there, the range of styles at every price point is considerable. Today, even your favorite streetwear brands—Noah, Palace—make classic loafers. Thankfully, we’re here to help.

If you’re itching for a pair of Gucci Horsebit loafers, but can’t stomach the price ($400 and up), there are in fact tons of vintage options by both Gucci and Prada for considerably less ($250 or less). If you plan on dressing more muted for the big get together, an embossed loafer is a great subtle flex, and Palace’s snakeskin mid-tops are quite honestly a grail ($500 and up). As for chelseas, Represent makes a great pair for cheap ($200 or less), but even those fawned over Common Projects in suede are attainable ($300 or less). Of course, if you’re looking for a more formal option, Saint Laurent Paris makes some of the best boots in the business ($500 and up). Oxfords are tricky, but either stick with the classics such as Alden and Church’s ($300 or less), or really go for it with a pair of fashion forward thick-soled Prada’s ($400 or less).

Recommended Brands
$: Common Projects, (Vintage) Prada
$$: Palace
$$$: Church’s, Gucci, Saint Laurent Paris

With the above, we’ve laid out a piece-by-piece, brand-by-brand ensemble that should give you the general shape to nail whatever you’re scheming up for… well, any kind of holiday party this season. But there’s one element that our friends down south or out west might be asking: What happens if you live in a warmer climate?

We know that states like California or Texas still receive their fair share of winter weather, but we also understand that this is closer to fall or spring, than a true Nor’easter winter season. As such, the broad strokes are as simple as following the tenets of autumnal style. While the mercury may be a little higher that other parts of the world, keep in mind that it’s still the holiday season.

Starting at the top, we’d recommend keeping things simple—either a clean button-up shirt (without a blazer) or a light sweater (we’d recommend a cardigan for maximum temperature flexibility, but a light crewneck pullover works too). Even a plain white T-shirt works under the right sweater, so wearing a knit doesn’t have to mean feeling stuffy. If nothing else (and if there’s not a hard rule on the dress code) then take the “Christmas Island” approach and opt for an Aloha shirt from brands like Stussy (or, if the budget is open) Saint Laurent.

As for bottoms, the advice above on trousers would apply here as well, with preference to lighter-weight canvas and chinos in place of thicker wools or chunky plaids. As mentioned above, anything from A.P.C. to Maison Margiela or Ermenegildo Zegna should fit the bill; we recommend a leg shape that’s might leave your coworkers impressed with your eye for tailoring (but still roomy enough to dance in).

For footwear, the warmer climate doesn’t mean that things instantly become more casual, but we recommend going sockless if the thermometer allows. For an excellent middle ground when it comes to footwear that can be both formal and playfully casual? A clean pair of black loafers—be it Bass Weejuns or Gucci Horsebit loafers—should look smart in any scenario.