Styled by Sydney Sadick



I must admit when I was asked to “interview” Sydney Sadick for the Costume Council of the Chicago History Museum event on December 8th, I immediately said yes—I’ve been involved with the CC since it’s beginning in many capacities. They sent me Sydney’s book, Aim High, and I became skeptical: What could a 26-year-old tell us about fashion other than through an “influencer’s eye” (nothing wrong with an “influencer’s eye” mind you, but…)?



A Zoom meeting was arranged, which didn’t work with her busy schedule, so we did a phone call instead. Still not impressed! That was until we talked—boy, was I wrong! The brief encounter made me a true believer in this dynamic, savvy young lady—someone I wanted to know more about. So much so I immediately asked her to do my nenasnotes blog post profile questionnaire.

What changed my mind? Many things. Sydney is a very confident, informed fashion follower. No pretense—nothing but a well-mannered, interesting person, one you want to get to know better. A sincere person who has done her research and is living the life she envisioned as a little girl: encouraged by her entrepreneurial mother, she jumped into her passion, fashion. My most favorite story in her book talks about her Bat Mitzvah (I’m not going to do a spoiler, you need to read it for yourself—delightfully charming and real!) But that is the entire book: real, fun, and informative. Great for a first book or any book for that matter.



For this piece, Classic Chicago was sent several topics to explore. I would rather give you my impression of someone you are going to hear a lot about in the coming years. I love the honesty of her backstories and advice but most of all the joie de vivre of a trendsetter. Her own look is a mix of classics with the “now” styles making the correct effect for her and what she advises: develop your own look and make it your own. How you style yourself is about who you are. Need help? Grab her book—it can become your guide. She may be young, but she gets that style is ageless, and you can incorporate the current trends into your lifestyle (this has always been my fashion philosophy!).

I’m so looking forward to introducing you to Sydney at the very special virtual luncheon event benefiting the Costume Council. See the invitation below to make your reservation. We have extended the deadline for Classic Chicago readers! Obviously, you won’t have the book for Tuesday’s event, but it will be sent to you.



In the meantime, here are Sydney’s 5 suggestions on how to style black leggings:

Have you forgotten how to dress for leaving the house? Growing far too comfortable wearing workout clothes exclusively? It’s okay, us too.

If your style is feeling stale going on month 8 of COVID/quarantine, we have tips from style expert and Aim High author, Sydney Sadick, to breathe new life into your old reliables, black leggings, of course!

“Black leggings are comfortable, look great on all women of any age and body type, and are the perfect canvas for dressing up or down,” shares Sydney. You don’t have to break your budget for online shopping. Reinvent your staples with these tips for every 2020 occasion.


5 Different Ways to Style Your LBL (Little Black Leggings)

Zoom Meetings 

Make a statement in the upper portion of your outfit, since this is where people will be seeing you. A puff-shoulder cardigan or blazer with a bodysuit/t-shirt underneath paired with a gold hoop and a bold lip will give your favorite bottoms a professional upgrade.



Socially-Distanced Lunch

 If you’re meeting a friend for a socially distanced outing, make sure you’re dressed warm! This is where layering comes into play. Pair leggings with a t-shirt below a chunky knit sweater in a fall-approved color (think burgundy, forest green) and a chic puffer coat. Leggings allow you to mix textures, colors, and patterns, so have fun with it!

Comfy and Cozy

Netflix-and-chill calls for leggings and hoodies. Tie-dye is here to stay but in fall colors. Throw on leggings and furry slippers, and you’ll still look put together even if you have no plans on moving.

Virtual Date

The dilemma: you don’t want to look like you tried too hard, but you still want to look put together. Luckily, leggings complement any top. Show off a little skin with an off the shoulder top paired with a chain choker necklace. It’s not too much but just enough.





At-Home Workout

Pair your leggings with a fun graphic t-shirt or colorful sports bra with a zip-up hoodie over it. The way you dress affects your mood, so bringing some color to your leggings will motivate you for that online workout class.


Classic Chicago Magazine readers wishing to attend the December 8th virtual program, please email Odette Barrientos at


Sydney Sadick is a TV correspondent concentrating on fashion and celebrity. She contributes to multiple television shows across the country to deliver runway and table-top segments, in addition to sitting on roundtables and covering red carpet events. She is regularly seen on the TODAY SHOW (Hoda & Jenna), E! Daily Pop, Inside Edition, NBC New York Live, and more, appearing in over 100 segments in just two years.

She is a former editor at the Daily Front Row, interviewing some of the world’s most coveted celebrities, designers, and stylists, among others, and covering New York Fashion Week, The Met Ball, and other top events.