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    For many, this holiday season will be the first time in more than two years that they will be able to get together in person with family and friends to celebrate. So, if ever there is a time for glamming up, this is it.


    “I think people are excited to get to dress up this year,” says Chicago-based stylist and branding expert Brandy Penelope. “I think COVID gave us a higher appreciation for the ability to be social beings. We didn’t realize how much of a luxury it was before it was taken away from us.”


    The opportunity to step out in style over Thanksgiving, Christmas, Kwanzaa and New Year comes after two years of stay-home restrictions that saw many swap class for comfort, professional attire for pajamas. So WayMaker Journal turned to Penelope for some professional advice on how to dress well for the holidays.


    She got her love for style from her mother, who worked in high-end retail. Employee discounts enabled her to bring home topline threads that made her daughter stand out at school.


    Starting in chain store apparel retail, Penelope studied business and took a job in real estate before feeling drawn back to the fashion world. With fashion marketing and management training from Chicago’s Arts Institute, she began style consulting for Ralph Lauren and later Saks Fifth Avenue.

    People are excited to get to dress up this year.


    Four years ago, she went out on her own, primarily working in Chicago’s vibrant rap scene. Among her roster are artists such as G Herbo, Polo G and Calboy.


    Most clients have their day-to-day wear down—they’re used to working social media—but come looking for help for new release launches and special events.


    Penelope helps create a look for them by listening to the music and asking lots of questions. What’s the “story” they are wanting to tell? Whose look do they like? What are their favorite colors and fabrics?
    Those are the same kind of questions to ask yourself when you are getting ready to go out this holiday season, she says. Plus, ask yourself when you have felt most comfortable in your skin, recently—and what clothes were you in at the time?


    Penelope has some suggestions for helping you dress your best for four different holiday scenarios.
    Family. If you can be yourself anywhere, it’s here. “We have the luxury of just being ourselves,” says Penelope. You don’t have to think about dressing to impress—though you may want to bear in mind that there’s probably going to be plenty of photo-taking, whether that’s informal or group shots. Maybe consider a splash of color somewhere in your outfit.


    You should be comfortable with your family and comfortable in your clothes. Family gatherings usually mean lots of food, Penelope points out, so be sure that there’s plenty of room in your pants or you’re wearing something you can loosen. You may also want to get up to dance or get down on the floor to play with kids, remember.

    Friends. If family takes you as you are, good friends take you as you may want to be. Here’s a judgement-free space where you can be a bit playful and adventurous, trying out something new. This may be the best place to break out that ugly Christmas sweater or some crazy-loud piece because “they usually see your super fun side, right?”


    There’s less tradition here than in many family situations, because “we’re all growing together and evolving and becoming who we are,” Penelope says. “They understand who you are presently and don’t tie you back to when you were a child.”


    Functions. Working life has changed post-COVID, even for those who have returned to a workplace, but the new rules are still being worked out. The stay-home pandemic accelerated the move toward “business casual” that was already happening (in part driven by the development of relaxed fabrics), says Penelope.


    Chances are a work event could be held right after the end of the workday, so take something you can change into—maybe a button-down shirt to replace that polo, or heels instead of those day flats—or add to your outfit to brighten it up some. Match the evening vibe with a blazer.


    Accessories are a girl’s best friend, especially here. “Shoes, jewelry, a bag,” Penelope suggests. For guys, it could mean switching to a dressier watch or adding a pocket square, simple touches that “bring some flare to something you already had on the whole day.”


    Formals. If ever there was a season for special, dressy events, this is it. Church, concerts, galas, receptions and, of course, weddings. While you still want to be you, it’s about standing out while still fitting in. Most formal events have an express or expected dress code it’s important to honor—it’s about respect for the institution and the hosts.


    “The main thing is to be a polished version of yourself,” says Penelope. “They say cleanliness is next to godliness, right?” The rules don’t need to be restrictive. “Formal” allows for many styles and fabrics. “You don’t even have to wear a dress; a woman could wear slacks and a nice jacket.” This is also the time to break out the plaids, velvets and silks, the sequins and glitter. It’s all about “basically putting some effort in.”


    What about Christmas accessories, from that ugly sweater to the bauble earrings? Why not, she says? “The holidays are all about joy, laughter, fun, right? That’s what we should be focused on, not if someone is going to judge us. If you’re doing it wholeheartedly, how can you be corny?”


    And how about Penelope herself? What’s her plan this year? “I feel like at Christmas I get an excuse to wear all my sequins,” she says. “I love them. I’ve been collecting them for a long time, from thrift stores and all kinds of places. So, I’m going to wear something shiny for Christmas because that makes me feel good. I’ll probably pull some costume jewelry out and be all Diana Ross.”


    Style: your personal story

    When it comes to fashion, Brandy Penelope isn’t very big on rules. “You get to set the standard,” she says. “You can wake up tomorrow and be like, ‘I’m bored with that. I want to do something else.’” She does have one must, however: the clothes need to fit. Put it another way: are they flattering?


    There is a way to wear baggy or more form-fitting clothes well, but it’s about how they feel when they are on. You need to be comfortable in them, she says, because that comes through in how you carry yourself. It affects the rest of you.


    That’s why clothes are so important; they tell the world about you—both who you are and who you want to be. “Whatever we wear tells the story of us,” she says. “Clothes are probably my most comfortable way of self-expression, because I don’t have to say much,” says Penelope. “They kind of speak for me.” Everyone has a style; they just may not be aware of it, she says. It doesn’t have to mean being all look-at-me: take Mr. Rogers as an example. “He was fully committed to his cardigan and his little sneakers and his tie and shirt; that was his vibe,” she says. “It wasn’t about being loud, but he was still fashionable and that was his vibe.”


    The closest thing Penelope comes to a second rule for clothes is her strong dislike for people wearing things that are too small. “It probably comes out of respect for the fabric and the garment and respect for the design of the garment,” she says. “If you’re wearing something that does not fit well, then the design does not come across the way it is intended.”


    Take men’s jackets. “There’s a way that your shoulders are supposed to lay in the jacket,” she says. “The jacket should be smooth there. When you button one of the buttons, it should not be pulling; you should not see wrinkles in the back, under your arm.”


    While holiday styles don’t change as quickly as fashion for the rest of the year, Penelope observes some trends worth noting. Skinnier leg pants are on the way out, being replaced by straight to wide pants. Monochrome is increasingly popular, too.


    BRANDY PENELOPE: MY WAYMAKERS
    There’s my mom, because she showed me that you could have a kid—I have a 2-year-old—and still be successful. Otherwise, it’s been more of a tribe thing: the creatives I came up with in Chicago that liked fashion as much as I did, and we became friends. Then there are people I don’t know personally but who have inspired me, like Virgil Abloh [designer for Louis Vuitton, who passed in 2021]; knowing that he came from my city just made everything feel very possible. Even people that are trying and failing are inspiring, because they are the ones who are living fearlessly.

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