Holiday parties mean photo documentation... I always feel good in bold lips, and an interesting but classic structural garment from a local shop like Una or Stand Up Comedy is sure to capture someone's Instagram feed, if that's the point for you. If at any point during the day I lack confidence or comfort because of what I'm wearing, the culprit is banished from my wardrobe.—Julia Barbee, designer, artist, perfumer,

I'm into monochromatic dressing—white on white on white is my favorite right now—right down to the shoes and jewelry. I'd love to see a lady in elbow-length leather gloves, too. [And] have you seen the arty shell headband thing that Holly Stalder made?!—Britt Howard, founder, Portland Garment Factory,

For the holidays I am trying to harness two looks: (1) over the top: sheer layers and oversized, previously loved furs paired with dark lips. (2) Minimalist: menswear-inspired, a fresh pair of blue jeans, crisp button up or clean white tee, oversized camel trench/jacket, statement shoes, bag, jewelry. Or, knock off all this layering and keep it simple. Sometimes you just have to throw on a statement necklace and red lipstick and make it work.—Sarah Vale Rapp, designer, Seaecho,

I love to be overdressed all the time, and the holidays are the perfect time to really push it. I can't decide between two extremes: either head-to-toe monochromatic metallic and/or sequins, or hyper-minimal. I'm not really fussy about makeup, but I do believe that the perfect lip color can really bring a look together. My go-tos this year are going to be red and a deep brownish-burgundy. And my holiday shoe of choice [is the Bowery in metallic silver by I Desire the Things That Will Destroy Me].—Anna Branch, creative lead, Solestruck,

I think it's very important to make your outfit less about showing skin and all about showing the silhouette. I think a woman who knows how to look sexy and confident while wearing a long-sleeved and/or long dress is a true style icon. I like simple looks with bold statement pieces. I also love a bold shoe [and] the holidays just scream a red lip to me—but keep your other makeup understated. And top your look off with a leather or fur jacket.—Heidi Lieberman, designer, Honeyfox Jewelry,

I don't dress up often, but I absolutely love dressing up for a good holiday party. There is a spirit about the season that makes you want to be extra festive, put your best foot forward, and shine just a little bit more. If you are going to a holiday party and don't know what to wear, err on the side of dressing up, not down. Holiday parties only happen once a year, so make it count. Unless you are specifically going to an ugly Christmas sweater party, leave your tacky, ironic sweater at home. Chances are your host will not appreciate you showing up in a light-up Rudolph sweater while everyone else is dressed to the nines. Instead, wear a tasteful sweater in a playful motif with a shirt and tie. Men: always wear a tie or bowtie. Ladies: usually velvet and sequins can feel like too much, but not now. Shine like a damn disco ball. Big jewelry? Hell yes. Fancy heels? Doy. However, even though I say go big, play by the rule of keeping taste in mind. If you have big crazy jewelry, keep the dress on the simple side, [and] if your dress is nuts, pare down the jewelry. I love cool tights with a clean, short, simple shift dress and a statement rhinestone necklace. Men, on mixing patterns: If you are ever going to experiment with mixing plaid with stripes with another plaid, now is the time to do it.—Brady Lange, designer,

Whenever I am having a model styled for a photo shoot and the stylist is doing hair and makeup, I always ask that she is a little tousled looking—like she just woke up from a nap or wrestled with her boyfriend. Better yet, ride your bike to the party so your cheeks are flushed when you arrive. I do not like things that look brand new or perfect. I think if you are going to wear something that is really expensive, the rest of the outfit should be free hand-me-downs so you don't look like a snob. Always wear and collect vintage! Confidence is really your best accessory, [and] the best-looking girls are the ones who are having the most fun at the party. Julia Barbee is one of my favorite style icons. I saw her once in the morning wearing a floor-length black beaded bias-cut skirt with one of her cut-up metal t-shirts. She could have been going to the opera, but I think she was just headed to work.—Holly Stalder, designer,

I'm all about layering prints on top of prints to create a bold statement—a graphic dress layered with graphic jacket and graphic pants or leggings, etc. Perhaps this is deep-rooted in my Japanese genes, but I believe that as long as you are mindful of the total color combinations, you can easily create some fun, festive outfits just by purposely layering and clashing prints. Frances May, Table of Contents, and Stand Up Comedy are some of my favorite boutiques in town that carry modern designer pieces, and Portland is filled with good vintage shops, but Yo Vintage! and Palace are two of my favorites, simply because they are so well curated. I always make sure to throw in some unexpected elements and try to make it my own.—Chiyo Takahashi, designer, Crazy Wind,

Dos: Right now I'm really into art deco colors like mustard, orchid, indigo, sea green, and tomato red. I think these colors paired with unexpected metal accents like bronze, gunmetal, and brushed nickel can make for a great nontraditional holiday combo. If it is important for you to stand out, play with gender lines. Ladies, look for ways to throw in hints of masculinity, and boys, pull out your inner dandy. Don'ts: No more ugly Christmas sweater parties! There has to be a better Christmas party theme!—Bryce Black, designer,

My look this year has gotten a bit like the opening credits of American Horror Story: Coven. I'm not a flashy person. I usually wear black, but try to find something with an interesting cut. I have a black House of 950 twist dress from Stand Up Comedy, so I'll probably wear that with some Hazel Cox pieces. Kim Namanny at WINDOWWALL has been cutting my hair forever. I have a bob right now, so she will just trim it up this week and I'll be good to go.—Heather Sielaff, perfumer, OLO Fragrance,

I'm seriously a purveyor of fancy, and love dressing up. (I actually don't own any pants—no lie.) I love all the bowties on gentlemen. For the ladies, I love metallics. There are a bunch of really fantastic dresses out there that have functional glitter, meaning fabrics that look great and you can totally wash and be comfortable in them. Dresses that come to mind are the Amelia dress (at Amelia) in silver sparkle, a Hubris tunic in gray and black stripes (at Union Rose), and a Veronica M LBD with tonal metallic black print (at Mabel & Zora). I'm also rethinking my aversion to velvet after seeing an amazing blue velvet dress at Folly the other week, [and] I'm loving all of the Reif turbans and turban hats.—Alyson Clair, designer, Clair Vintage Inspired,

Here's what I'm really into this holiday season: (1) bold, summery lip colors with a little black dress. Lipstick is such a great accessory, and as much as I love the dark, brooding lip colors that are popular this season, I think a bright lip is a great way to stand out. (2) I consider glitter, sequins, and animal prints to be neutral. I love the idea of a sequined pencil skirt with a chunky fisherman's sweater, for example. Because hey, it's cold outside, and you don't want to be one of those people who's pretending you're warm, wearing some tiny outfit when you're actually freezing. (3) Winter whites! I love cream and white together, and I think it would be a really fabulous holiday look.—Lindsey Reif, designer,

Long-sleeved dresses with an all-over print or texture are where it's at! I love the different ways to handle the balance of revealing and modest by using two extremes. Covering up completely, but the piece is skin-tight. Wearing a micro-mini, but it's long sleeved and a little baggy. Any of these pieces paired with chunky ankle boots, unexpected lipstick (hot pink or orange or Portland Black Lipstick Company in Chlorosis), and a simple piece of jewelry with a faux fur jacket make up my ideal holiday look: Art Deco Grunge.—Caitlin McCall, designer, Quick Study Clothing,

I like to go two routes: dressed up or dressed down. With the former, most guys, all they need is a proper two- or three-button wool jacket, a clean, trim-fitting poplin oxford, and trousers with proper footwear. [A] well-fitting modern suit with patterned Fair Isle socks and a clever piece of neckwear make all the difference. Guys in Portland tend to lean toward a bowtie or necktie, but I think the realness comes in the form of a wool throwover or, better yet, a punchy scarf. Just please, no Red Wings with your suit. For [a] dressed-down look, grab a chunky sweater and pair with a wool vest and a wool knit cap to keep the cold out, heavy-gauge corduroy pants, and once again, patterned, contrasting modern socks and some seriously chunky soled footwear. Keep in mind, you don't need to ball out on all these clothes, just try to take the time to find something that fits well. If you're gonna spend money on this stuff... please just make an investment in something that will last you many, many years. The other things... hair? Get a fresh cut the day of. It will make all the difference, and boost your confidence. Oh, and shave... I know it's Portland, but come on. Look the part.—Mike Andersen, marketing manager/lead buyer, Cascadian Fabrications, Inc.,

I am going to stick with a tried-and-true classic: sequins. My holiday uniform of choice will be pants, some sort of top, and a sequin coat. This will allow me to stay warm and hide any food/booze babies that might suddenly appear. I just found one at Red Light and will probably wear it to almost every social function this season. It is a little big, but as long I wear shoes with height it will balance nicely with my short frame.—Elizabeth Mollo, fashion show producer and Mercury contributor,

Right now I'm loving elements of Egyptian Revival fashion circa [the] 1920s. I always like the ongoing trends of sequins and shimmery fabrics for the holidays, and this is prevalent in a lot of fashion trends from the era. I also like how dramatic and festive this fashion movement was and how it is feminine yet architectural. Good shapes, too: oversized shawls, wraps, and capelets. I am a vintage junkie, and have recently seen some great dresses in Portland at Hattie's Vintage, a beautiful oversized shawl at Demimonde, and this '20s-inspired chiffon dress at Una. And of course, I am always in search of a '20s-inspired women's pantsuit. Paired with heels, that would be my dream outfit for the holidays.—Liza Rietz, designer,

This season I am loving all of the athletic details in even feminine silhouettes. It's a fresh take on party attire to throw together a flirty cocktail dress with socks, wedges, and a statement necklace. I just bought a fun little black-and-white '50s drop-waist dress that I will style up and down for various events. Menswear is really fun too. I feel like I can swap with my fashionisto friends: bowties from PINO, necklaces from Betsy & Iya or Tied Up and Tousled, and sweaters—even kicks, if the shoe fits! So many fun accessories! From cat-shaped purses to a full Nutcracker costume, I feel like nothing is off limits for 2013!!—Lavenda Memory, photographer,