Aim High: How to Style Your Life and Achieve Your Goals

1.

FASHION 911

A woman is never sexier than when she is comfortable in her clothes.

—Vera Wang

I’ve always been comfortable and confident with my personal style and fashion choices, but let’s face it, it’s not this way for everyone. We all come in different shapes and sizes and have our own insecurities, but regardless, we strive to bring personal style out from within and present the best versions of ourselves to the world. While most people have some sort of an idea of how they want to look, making it a reality can be as challenging as overcoming your biggest fears. At a young age, I became the unofficial fashion EMT for my friends and family. No matter what the fashion 911 crises are, to this day they feel comfortable coming to me knowing I will solve their emergencies. That’s what on-call doctors are for, right?! Last minute Bumble date with nothing to wear? No problem—a quick FaceTime call later and I’m virtually in my friend’s closet and can assemble an outfit within minutes! She ends up looking effortless and fun, even though behind-the-scenes we just mad-dashed to create a great first impression. Going on a vacation and want to bring some new pieces but have a limited budget to spend? Easy! It’s all about creatively repurposing your pieces and adding a few pops of new in ways that most wouldn’t have the slightest clue how to nail.

Even after years of experience as that girl, never did I imagine I would be in a stranger’s closet in Buckstown, Pennsylvania, doing my thing surrounded by the crew of Hoda & Jenna from NBC’s Today Show.

Flashback to a boiling hot summer afternoon in late-August 2019. Tiptoeing around a lush flower garden surrounding a home in quaint Buckstown, Pennsylvania, I was terrified that sweat would ruin my makeup, camera-ready for the big surprise.

Today Show correspondent Donna Farizan led the way and I followed with a producer and two cameramen behind me. Her segment surprises selected viewers with a guest star visit to their home. The week prior, Mark Wahlberg visited an unsuspecting woman in Los Angeles. This week? Sydney Sadick on the opposite end of the country in Buckstown. This was my new reality, not a dream!

We were about to present Eileen, a die-hard Today Show fan, with a potentially life-changing gift. We hoped to solve her fashion emergency, which would potentially throw any woman into full-on panic mode: three weddings in multiple states within ONE WEEK! How is that even possible, you might be wondering, but it was very real for Eileen. And to make it even more of a challenge, each wedding was unique in location and dress code, requiring specific attention to make sure she was wearing something appropriate while still making a statement. Of course, you can imagine how expensive it would be to invest in three different looks within such a short period of time, especially when you’re only likely to wear the clothes just for the occasion. Everything had to be perfect and planned. I’m normally super calm, but as we approached Eileen’s front door, my heart started to race. I wanted to make sure I did everything right—for a woman I didn’t even know. It was completely different than all those years spent helping friends and family. If I could solve Eileen’s wardrobe dilemma and could help relieve her fashion financial burden, I would feel like I did my job. The financial piece was key, so she would still have money left over for wedding gifts and travel expenses. No easy task, for sure!

What?! Sydney! Donna! At my house?! Our cameras captured Eileen’s shock as she looked back and forth between Donna and me on her front doorstep. She hugged us both, nearly in tears. Petite with silver hair, Eileen is a sixty-one-year-old personal trainer, wife, and mother. She wore a charcoal-grey triathlon t-shirt, athletic shorts, and rectangular glasses, a typical daily outfit completely within her fashion comfort zone.

We heard through Sydney that you have three weddings to attend in one week, so we’re bringing you to New York City, and Sydney will style you! Donna said. These were magical words—a promise Eileen never expected to hear.

Eileen was speechless; she never believed that her wish would come true. Her usual day was going to work as a trainer in a basically calm environment. With that surprise, she was visibly thrilled and excited, especially because it was completely unexpected; hardly the day she’d planned.

Initially, Eileen reached out to me following my debut appearance on Hoda & Jenna in mid-July 2019. Impressed by my fashion ability, she went out of her comfort zone and wrote to me for help. She sent me an Instagram message with high hopes that I could help her with a fashion dilemma that made my mouth drop—and not much phases me.

The weddings included beachfront nuptials in Delaware; a winery wedding in Pennsylvania, followed by a reception in an outdoor pavilion; and a cocktail-attire wedding at the prestigious Franklin Institute Museum in Philadelphia. Eileen hoped to impress family and friends and wanted to look younger and stylish. She described a similar anxiety to what one feels before an upcoming high school reunion.

But this situation required knowledge of style and an assortment of clothing far beyond her experience or wallet. She didn’t even know where to start. The stores in her area were limited and buying online was too risky due to the unreliable fit. On top of it all, coordinating everything together was overwhelming, and understandably so!

My style is limited to t-shirts and gym shorts from the boy’s department, because girls’ sport shorts have no pockets, she wrote to me in an Instagram direct message. I attended school in a uniform and never developed a sense of style! I need YOU!

Eileen intuitively understood that I would try to help her. Whether or not the Today Show embarked on the project, it was my mission to assist. I assured Eileen that her multiple wedding dress emergency would be taken seriously. To our shared excitement, the Today Show agreed to document her wedding style journey, and before you knew it, we were rolling.

Eileen led our crew through her home and up to her closet. She graciously offered us drinks and even asked if she could take us to lunch. She exuded warmth. Few women open their closet to family, let alone strangers. A woman’s closet is typically very personal, but Eileen was far from guarded. She welcomed our cameras into her private world and willingly shared this doorway into her life with our viewers.

She laughingly disclosed that her husband had more clothing than she did. Her entire wardrobe fit on one small rod in the lower half of their shared closet. Her fashion world consisted primarily of the comfortable outfits she trained in: leggings, shorts, and a few t-shirts. Eveningwear was limited to one tuxedo dress with a permanent food stain and a dark pantsuit that was frankly dated. I told you, I’ve got nothing, she whispered.

Eileen clearly needed a creative solution. We reassured her that she had nothing to worry about—Eileen’s problem was safely in my hands.

Think about her challenge: How to invest in affordable outfits for three equally important occasions within such a brief period—clothing she might never wear again. I’m sure you’ve faced similar fashion frustrations. My goal: To lift Eileen from her comfort zone, flatter her petite figure, and turn heads with affordable, reusable items.

An ordinary dress could be spiced up with different shoes, bags, and accessories, but at the end of the day, it would still be an ordinary dress. Then it came to me: What if one dress could be worn in multiple ways? It’s something one rarely hears about—hardly a trending style at New York Fashion Week or at fast-fashion stores like Zara. But given my fashion network and experience, I knew such a dress existed. I Googled diverse word combinations: one dress for all occasions; multipurpose dresses; one dress that fits all. You name it, I entered it. As fate would have it, I finally found the Convertible Wrap Dress.

Translation: One dress that can be transformed into over one hundred styles! Yes, you read that correctly—over a hundred different ways! The dress could be worn with sleeves, sleeveless, backless, strapless, on and on, and is available in just about every color of the rainbow: Pastels, brights, neutral, and deep hues. Once you select your color, you can instantly transform the silhouette.

Eileen could wrap and accessorize for a distinctive look during the week of weddings and beyond. The best part? The price! Retailing for sixty-nine dollars, this truly affordable solution provided a stylish foundation for any fashion-worthy occasion.

While the dress was available in a plethora of colors, choosing the right option was no easy task. Although black is typically the safest choice, it’s controversial for a wedding. I preferred a deeper fall tone because bright colors didn’t seem appropriate for the season. I finally selected navy blue to illuminate her stunning blue eyes. The dress fit Eileen like a glove, each version accessorized with shoes, handbags, light outerwear, and jewelry based on the wedding setting.

Here’s how I styled each look:

Beachfront: I wrapped the dress to its cap-sleeve silhouette, the most classic option, and paired it with transparent block-heeled sandals from Steve Madden—making it easier for Eileen to walk and socialize in the sand. I found a twenty-four dollar wooden-style bag from online retailer Boohoo, inspired by a high-end brand, which retails for hundreds of dollars. For the jewelry, I added dangling star earrings from Bauble Bar, my go-to destination for budget-friendly jewelry that surpasses expectations. The overall look was simple and fresh.

The Winery: To diversify the dress aesthetic, I transformed it into a halter neck silhouette. To allay Eileen’s concern about feeling cold at the outdoor reception, I paired the dress with a reasonably priced Karl Lagerfeld cardigan in matching navy blue with white pipping. For accessories: A classic black kitten heel sandal from Steve Madden, a marble box bag embellished with a pearl closure from Anthropologie, and statement white drop earrings from Bauble Bar. The overall look was classic and preppy.

The Franklin Institute: A more formal venue, Eileen could bring on the glam with sparkle, shine, and sequins! So I wrapped the dress into a one-shoulder style, paired it with a metallic silver peep-toe heel from Steve Madden, a matching micro-bag from Urban Outfitters, a statement silver sequin shawl from Betsy Johnson, and crystal hanging earrings from Macy’s.

The total cost of all the accessories for all three looks was under a hundred dollars, and they were sufficiently versatile to be comfortably used time and again.

This is all yours! I told Eileen after showing her my selections. The brands mentioned above, including the Convertible Wrap Dress, generously gifted their items to Eileen after hearing her story. The best part: Today Show viewers could quickly see how emergency fashion might be adapted to their needs. Of course, Eileen never imagined that it wouldn’t cost her a penny.

But it was more than just receiving stunning clothes and accessories. With tears dotting her cheeks, she thanked us for expanding her comfort zone and helping her tap into the self-confidence that she always knew she possessed, but that she needed a boost to let shine through.

Just a few weeks later, Eileen met me at 30 Rockefeller Plaza in New York City, the home of the Today Show. It was the day before our live broadcast—rehearsal time. She arrived with her yoga instructor, also named Donna, a source of guidance and comfort for Eileen. She loves Donna’s yoga class so much that she drives forty-five minutes weekly to attend. Donna reassured me that this was exactly what Eileen needed at this point in her life—she had faced many challenges and it was time for her to focus on herself.

To my delight, Eileen was already showing a new persona. Out of her athletic wear and into jeans paired with a plaid purple top, she proudly showed off her self-styled look. I bought this yesterday! It looks like the purple plaid suit you just wore to New York Fashion Week! Eileen exclaimed, referencing my outfit in an Instagram photo.

Eileen tried on the dress, and the wardrobe department examined how it functioned. This was critical because Eileen’s appearance was unlike any prior Today Show segment. Our producers created a portable dressing room directly on stage for the show. The wardrobe team would help change Eileen into each look—on LIVE television. Talk about pressure—for everyone!

Eileen, trusting and with newfound confidence, was game. She was definitely ready for her fifteen minutes of national television fame. Eileen was in camera-ready hair and makeup bright and early the following morning. Although a bit nervous backstage, she was also overjoyed. Eileen looked forward to meeting Hoda and guest host Meredith Viera, who was filling in for Jenna while she was out on maternity leave.

I told Eileen that if she felt nervous during the process, to just look at me. I had her back. She was not alone. We were in this together.

The segment opened with the Donna’s Door Knock video, featuring our surprise at Eileen’s home. Moments later, Eileen appeared on stage, proudly modeling the beach ensemble in front of millions of viewers across the nation. Her face glowed and she radiated confidence. She then returned to the make-shift mini dressing room behind a black curtain and changed into her winery wedding dress in less than two minutes. Eileen was now confident