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By this we mean investment pieces and items that you’ll actually wear time and time again. Pants that work harder than you do, [__outerwear__](https://www.levi.com/US/en_US/clothing/women/outerwear/c/levi_clothing_women_outerwear) that you can wear season after season and totally transitional basics that you can wear all-hours without the extra trip home. You know, that magic combo that suits everything from an office work party to afterwork drinks with friends and a concert with your S.O., without so much as a shoe swap in between. Because, let's be real, nothing's more annoying than postponing a spontaneous rooftop rosé date to "go home and change really fast." So, in an effort to permanently nix that midday wardrobe swap, we teamed up with Hailey Bieber to make Holiday Outfit planning, for any kind of event, less of a chore. Never not on the move, the model and media personality swears by versatility and is probably lugging around an extra pair of kicks in her bag right now for any last-minute outfit switch-ups. We managed to squeeze ourselves into Hailey's busy schedule—meeting up with her to get a masterclass on all things holiday style. We picked her brain on her [’90's Outfits](https://www.levi.com/US/en_US/jeans-by-fit-number/women/jeans/501-90s-jeans/c/levi_jeans_by_fit_number_women_jeans_501_90s), her affinity for a killer pair of [__high-waisted jeans__](https://www.levi.com/US/en_US/jeans-by-fit-number/women/jeans/high-rise/c/levi_jeans_by_fit_number_women_jeans_high_rise) and her foolproof advice on crafting your own authentic style. (Hint: It's a lot easier than you think.) Get the full scoop, just below. - [SHOP HAILEY'S PICKS](https://www.levi.com/US/en_US/shop-the-edit/c/levi_clothing_email_favorites_1)  ## There’s something very sexy and cool about a woman who’s not afraid to lean into oversized silhouettes. ## RELAXED BUT NEVER SLOPPY One of our favorite things about Hailey’s style is how her ensembles always feel effortlessly pulled together and true to her covetable aesthetic. Since the holidays involve a little extra sartorial refresh (hello, virtual hang parties, nights out and New Year’s Eve), why not pick something that won’t stick out like a sore thumb when you recycle it in February? Our [__Math Club Slacks__](https://www.levi.com/US/en_US/search/math%20club%20slacks) are the ultimate wear-anywhere pants with a nerdy-chic fit, elastic waist and a subtle print thrown into the equation just for fun. We’re partial to pairing with a tonal crop top and loafers for a jazzed-up, tomboy-inspired vibe.  Since the look could err a little monochrome, give it a playful edge and add an eye-catching __[coat](https://www.levi.com/US/en_US/clothing/women/outerwear/c/levi_clothing_women_outerwear)__ boasting a statement print, unexpected texture and a roomier fit à la Hailey. “There’s something very sexy and cool about a woman who’s not afraid to lean into oversized silhouettes,” she says. Don't feel like you have to stick with color, black and white work just as well. Just top it off with a __[bucket hat](https://www.levi.com/US/en_US/accessories/unisex/c/levi_accessories_unisex/facets/colorgroup/black)__ or a ribbed [__beanie__](https://www.levi.com/US/en_US/accessories/unisex/c/levi_accessories_unisex/facets/feature-style/beanie), which are likely already in your winter arsenal.   ### THE DAY-TO-NIGHT LOOK Purchasing pieces that are suitable for both day and night is a sensible investment, especially now that the odd social engagement is back in the cards. And while head-to-toe sequins are generally an evening-wear favorite of the holidays, the denim part of the equation, thankfully, remains appropriate for nighttime—anytime, really. Hailey recommends building a look around your favorite [__jeans__](https://www.levi.com/US/en_US/clothing/women/jeans/c/levi_clothing_women_jeans) and pairing it with a [__cute top__](https://www.levi.com/US/en_US/clothing/women/shirts-blouses-tops/c/levi_clothing_women_shirts_blouses_tops) that can carry you “from day-to-night, dusk-to-dawn, sun-to-moon.” If there's one pair of shoes that works for any occasion, it's a pair of sleek black ankle boots. Just add some jewelry and a bold red lip to punctuate the whole thing.   ## “I love the ’70s High because they make me feel sexy, long and elevated.” Now that we've got our looks down, all we've gotta do is start making plans. Take a page from Hailey’s book on uncomplicated dressing and shop our new [__Math Club slacks__](https://www.levi.com/US/en_US/search/math%20club%20slacks) and [__high-waisted 70s jeans__](https://www.levi.com/US/en_US/clothing/women/jeans/c/levi_clothing_women_jeans/facets/feature-fit/70%27s%20high%20rise) online and in-store. Then, follow us on [__Instagram__](https://www.instagram.com/levis/) and tag [__@levis__](https://www.instagram.com/levis/) and #LiveInLevis to share your Levi’s® style with the world. Sign up for Levi's® Red Tab™ to start earning points on Levi's® purchases. Plus, new members get 100 points just for signing up! New email subscribers enjoy 15% off + free shipping on their first order. Every $1 you spend on qualifying purchases equals 1 point. 125 points earns a $5 reward. First Name* Last Name* Email* Send me news & offers from Levi's®. 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