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The LYB Gal’s Guide to Dressing Up

three night outfits styled by Lisa Berry

Years ago in yoga teaching training, I received a piece of advice that has stayed with me about how we present ourselves to the world. We were discussing different teaching styles and were told that we would only develop into great teachers by channeling the best version of ourselves, not someone else. So, I decided to teach disco yoga (yep, you read that correctly!) because that’s just me. Trying to talk in an elevated, soothing voice to my students and chanting, not me. And you know what? I became a really successful yoga teacher with a following of high-energy students who dug tunes from the 70s and 80s!

So, what on earth does this have to do with the LYB gal’s guide to dressing up? Absolutely everything. Getting “dolled up” is the one area of style where I most frequently witness women deferring to a formula that either doesn’t really suit them, or simply doesn’t reflect their unique personality. It’s where women so often decide to just “play it safe.” I can remember attending a large black tie gala last year with hundreds of guests in attendance, and staring out into a sea of nothing but basic black dresses and matching pumps. Nothing wrong with basic black (I’m the queen of it!), but where had everyone’s individuality gone?

I have traditionally despised having to get dressed up. If you’ve been following me, you know that my daily uniform is usually some version of drawstring joggers and an 80’s-inspired off-the-shoulder top. Date night for me, if I can help it, usually boils down to yoga pants and heels (which I tend to ditch under the dinner table.) However, owning LYB and being our chief buyer has begun to revolutionize things for me: I’m coming to discover that dressing up really is a fun opportunity to play with unexpected ideas, contrasting textures, and strong accents—all key LYB styling principles. With the holidays upon us and great sales (like this week’s 40 percent off all dresses and jewelry) to boot, I thought it a perfect time to share with you some of my favorite ways to dress up:

  1. Pick one dressy piece: Pairing someone shiny with an overall casual concept really is the epitome of cool. For a holiday party that’s festive, but not black tie, I would choose my favorite pair of Parker Smith or Black Orchid skinny jeans and contrast them with a gorgeous silk blazer from Bailey 44. Scrunch up the sleeves and toss on a heavy metal bracelet from Jenny Bird, and the look is complete. It’s what we call “accidentally fabulous,” or the opposite of contrived. It’s effortless glamour.

  2. Pick one casual piece: This is another great way to play with contrast and tone down a look for an affair that isn’t black tie. One of my favorite pairings is a denim jacket with an otherwise dressy ensemble. Take a dressy Ella Moss, Velvet, or Bailey 44 number, accent it with a jeweled headband from Deepa Gurnani, and finish the look with denim atop. Now you have a look that can be “daytime” or “nighttime” in an instant.

  3. Choose boots over pumps. Traditional heels are great with rolled up boyfriend jeans (remember, we love irony!), but they’re way too predictable with a dressy outfit. I adore an elegant swingy dress, like the ones Ella Moss does so well, with a pair of heeled ankle booties. Don’t be afraid to show some skin even in winter! If you’re going to opt for a fitted number like some of our latest arrivals from Velvet and Bailey 44, look for a tall suede boot to complete the look. Whatever you do, have fun with your shoes and try to think outside the (shoe)box!

  4. Use jewelry to make the outfit. This is one of my favorite techniques for dressing up my look. I don’t like my clothes to feel “fussy,” so I am invariably unhappy when I end up in a complicated or over-patterned dressy outfit. I much prefer to keep my look clean and simple, and take it to the next level with one fabulous, show-stopping piece of jewelry. My favorite jewelry designers for evening looks are Jenny Bird, Deepa Gurnani, and Chan Luu. Each of these three designers has such a completely different style, so what I pick depends on both my outfit and my mood. When I want confident and sexy, I reach for Jenny Bird. Deep Gurnani allows me to show off creative and eclectic. Chan Luu—particularly the earrings—is for when I’m going for stunning elegance. And, please, whatever you do, don’t overdo! Pick one focal piece and leave the matching accouterments behind.

  5. Stand out with an elegant hat. This is a dressing-up opportunity often overlooked. Think of the benefits of adding a wide-rimmed hat to your look: it, along with jewelry, is the only accessory you need to transform a basic look; your hair doesn’t have to look perfect; and you’ll easily stand apart from the crowd and come across as both elegant and confident. Every time I’ve donned a hat for a dressed-up affair, I have received a sea of compliments and felt fabulous all evening. Please note, only integrate a hat into your evening look if the overall outfit is understated (e.g. a solid black, body-skimming dress.) You want the hat to look almost like an afterthought, not a paint-by-numbers, going-to-a-polo-match or English wedding situation.

The fun in life is discovering who you really are and finding ways to confidently share your uniqueness with the world. So, the next time you’re called upon to get dressed up, pause before reaching for the same tried-and-true formula that has gotten you through dressy events in the past. See if you can alter that look in one meaningful way that better expresses something that is unique to you, whether it be your personality or some defining physical feature. And, in the true spirit of LYB, make sure you are, above all, comfortable!


Lisa Berry

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