Key: Pair it with color-coordinated, stylish, flattering pieces with elan, flair,and je ne sais quoi. (All these outfits are 100% from Goodwill except sunglasses)
"There are no ugly holiday sweaters, only ones that have not been styled correctly." (One of my students said I should start with this quote because it was intriguing. I'm not in favor of the concept of "correctness" but I think it makes a point.)
Now, sometimes we want to style a holiday sweater in a purposefully unfashionable manner for ironic effect (forgive me, I saw this phrase associated with sexy secretary sweaters and just couldn't forget it.) But if you want some tips for wearing a holiday sweater in a flattering way, read on!
1. Repeat the sweater colors in other items. This gives your outfit the all-important "I meant to do this" feel. Holiday sweaters can be chaotic. Repeating colors prevents the rest of your outfit from competing. Tip: if you want to wear a scarf but don't want to cover up your sweater, wrap the scarf around your neck an extra time and tuck the ends into the top of the sweater or knot them behind your neck.
2. Wear something that makes you feel stylish. Holiday sweaters often are have a vintage look that hasn't quite matured into cool. You, however, are cool, so insist on it!
3. Add flattering supporting players because holiday sweaters often are not - flattering, that is. (In my opinion, sweater shapes fell off a cliff in the 1980's.) And, since they're not super easy to find, you may have had to settle for one that doesn't fit quite right. This sweater was from Goodwill, and I couldn't resist an ice-skating bird with LED lights on the skates, but it's a bit too large. Skinny jeans offset the sweater's shapelessness.
4. Elan, flair, and je ne sais quoi are vital. It's easy to feel frumpy in an ill-fitting, shapeless, riotously colorful, overly earnest sweater (that doesn't know it's supposed to be ironic.) The secret to "pulling off" something like this is to feel great about how you look. So add another item that always, always makes you feel that way.
5. Bonus - try layering over a holiday sweater. In the first outfit, the faux Mongolian shearling vest gives shape to the sweater's boxy cut. As a note, I would would only do this wide-bottom pants like these flares to balance out the bulk of the vest. With skinny jeans or tight leggings, the outfit would look top-heavy to me (lollipop syndrome). Sleek, elegant boots contrast the country feel of the plaid scarf and jeans, but any boot would work well. I almost went with red cowboy until I discovered it was a golden-moment, non-rainy evening in Portland - time for a little extra winter style. So...
...pull out the most fabulous items in your closet to pair with that exciting holiday sweater. I'm all about the boots, but you could also try statement jewelry or an interesting hat or scarf. Away with "ugly holiday sweater"! How about "unique, eye-catching holiday sweater styled with creativity, flair, and a sense of humor"? You know Katharine Hepburn would have looked awesome in a holiday sweater because she would have been confident that she looked awesome. Just channel her, and you can't go wrong. Hope you have a great holiday season.