Call Me an Outfit Repeater, But These 5 'Fits Are All I Plan to Wear This Season

I can always count on a look that involves denim, loafers, and a blazer to take me from day to night. Whether I'm going straight to dinner after holiday shopping or to drinks with co-workers after a long workday, this combo never fails me. For a festive holiday spin, I'm choosing a blazer in a fun hue and layering it over a feather-sleeve Sleeper top. (FYI, the top is technically part of a pajama set.) And since embellished handbags are having a moment right now, it feels right to wear this blue crystal option for both a daytime and evening look.

This year, I'm all about holiday party outfits that really bring the sparkle. This Ciao Lucia silver metallic dress immediately caught my eye because it's the perfect style for NYE, a holiday party, or even a winter wedding. Personally, I'd wear it to all three because I'm not afraid of repeating outfits. For New Year's, I'm accessorizing with extra sparkles by way of crystal-embellished earrings, heels, and a handbag. The more shimmer and shine the better, right? I tend to err on the practical side with coats, especially when I'll take mine off upon entering an event, so this ultra-fuzzy teddy style is completing my look.

I like to wear a slip dress for a date night all year round, opting for a maxi version in a seasonal hue during the winter. If I lived somewhere really cold, I might choose a faux-fur coat, but in Los Angeles, this blazer will keep me feeling plenty warm (and looking plenty cool). I like the way these Khaite lace-up boots and this shoulder bag—which, by the way, I've been eyeing for months—add a slightly more casual vibe to the look than, say, pumps and a clutch would. As far as jewelry goes, I love anything that's gold and chunky, making this two-piece set a no-brainer.

Let's be real: We all spend a lot more time at home during the winter. I could easily stay indoors all day long watching holiday movies or reading a book by the fire and be very content. A matching cashmere set like this one from Lisa Yang is perfect for staying cozy while still looking put together. An oversize sweatshirt and Uggs are necessary for maximum comfort, and little, gold hoop earrings are necessary simply because I'd feel naked without any jewelry.

I may be a novice skier, but hey, I'm trying! I have a couple of trips to mountain towns coming up, where I plan to practice my skills in style—starting with this chic black and white jumpsuit from Cordova. If it's extra cold, I'll layer a bright turtleneck underneath and add this belted puffer on top. And since après-ski activities are most definitely my thing, I'll be packing some on-trend accessories to wear after hitting the slopes. These chic shearling boots and this chain-link Bottega bag are top contenders.