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

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People love to talk about how much they love summer. And listen, I get it—the weather allows for pool days, beach vacations, and wearing dresses sans outerwear. But if I'm being honest, winter fashion is much more exciting to me. I love the challenge of styling outerwear, and to be frank, it's just easier to look polished when there are more layers involved.

While the first day of winter is not technically for a couple of weeks (mark your calendars for December 21, friends), I'm already getting my outfits in order with a little help from one of my go-to retailers, Moda Operandi. The site carries all of the best brands, from contemporary favorites like Proenza Schouler and Wardrobe NYC to luxury designers like Prada and Bottega Veneta. The best part about Moda Operandi is that it's partnered with Affirm,* so I have the option to buy my winter looks now and pay for them over time. I currently have these five chic outfits in my shopping cart, each of which I'll be relying on for upcoming occasions both big and small.

The Day-to-Night Outfit


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.

The New Year's Eve Outfit


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.

The Date-Night Outfit


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.

The At-Home Lounge Outfit


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.

The Ski-Trip Outfit


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.

*Rates from 0-30% APR. For example, an $800 purchase could be split into 12 monthly payments of $73 at 15% APR or 4 interest-free payments of $200 every two weeks. Payment options through Affirm are subject to an eligibility check, may not be available in all states, and are provided by these lending partners: Options depend on your purchase amount, and a down payment may be required. CA residents: Loans by Affirm Loan Services, LLC are made or arranged pursuant to a California Finance Lenders Law license.

Associate Fashion Director, Branded Content

Michaela Bushkin is the associate fashion director on the branded content team. She is based in Los Angeles and is going on her sixth year at Who What Wear. Michaela has always worked in the content world, previously at Whalerock and The Zoe Report. Her current role involves executing content, photo shoots, and events for fashion brands from retailers to luxury designers and everything in between. She spends her free time online shopping (or "researching" as she likes to call it), reading at the beach, and trying as many new restaurants in L.A. as possible.