5 Street Style Tips to Follow, According to a Stylist

In our Ask a Stylist series, we're tapping a new expert each month to weigh in with all of their style insights. Return each week for a professional's perspective on what to know in fashion.


(Image credit: @ciara; Getty Images/MEGA; Splash News)

"Hailey [Bieber] found me on Instagram five and a half years ago. She was 18 or 19 at the time, and we've been working together ever since," superstylist Maeve Reilly tells me over the phone from L.A. "We've really built this whole thing together. I would say that she and her friends were really the originators of this sort of street style movement—not that we did that on purpose."

Reilly is defining a new era of celebrity street style, a movement that grew organically from working on everyday outfits and red carpet looks with her mega celeb clients, including Hailey Bieber, Ciara, and Megan Fox. Her influence on fashion today is undeniable, and the looks she's putting together have likely inspired how you've been getting dressed. Reilly is a master of the elevated casual outfits pairing pieces like baggy jeans and crop tops with oversize blazers that have gone viral on Instagram, and she is an early adopter of the latest accessories, like pointy-toe heels, that emerge as the new cult fashion buy—all things that have certainly influenced how I've been getting dressed recently.

Speaking with Reilly, it's clear that she has an innate sense of what works for her celebrity clients and their looks, but she also has insight to share. Here, Reilly shares her five street style tips to adopt when you're getting dressed.

Look for Unique Pieces


(Image credit: Getty Images/MEGA)

"Not every blazer is created equal—you know what I mean?" Reilly says. "It's [about] looking for pieces that have really beautiful structure or some sort of unique detail or something that just sets it apart from everything else."

Pay Attention to Proportions


(Image credit: @ciara)

When it comes to getting dressed, one key thing to pay attention to is proportions. "It's just putting stuff on and seeing the proportions and seeing if it's the right vibe," Reilly explains.

Keep it Fresh


(Image credit: @lala)

For her clients who have been snapped wearing so many things, Reilly always questions the uniqueness of any new pieces. "It's like, 'Okay, is this cooler than the last thing we did? Is this different, or is it too similar?'" she says. "It's keeping it fresh."

Understand Your Body Type


(Image credit: Splash News)

Every body type is different, and so is every wardrobe. "I think what works well with my girls is you understand what their body type is. All my clients have very different shapes, and it's really about getting good at dressing someone's body type, and then I think the outfit sort of flows from there," she says. "I've been really blessed to have such different women in my roster, and I love that. It is not a cookie cutter—everyone's not the same, and it's important to always remember."

Go Outside Your Comfort Zone


(Image credit: Backgrid)

Reilly recommends trying on pieces that go outside of your comfort zone to see if they'll work for you. When styling Dixie D'Amelio for the MTV Awards, Reilly challenged her client to try a piece that she didn't gravitate to at first sight. "She wouldn't try it on, and then I basically begged her. I said, 'Can you please just try it? Just do it for me. Just try it for me, please.'" she explains. "It was the first dress she ended up trying on, and of course, it ended up being the dress she wore."

Next, read the Who What Wear summer 2021 swim report.

Associate Director, Special Projects

Kristen Nichols is the Associate Director, Special Projects at Who What Wear with over a decade of experience in fashion, editorial, and publishing. She oversees luxury content and wedding features, and covers fashion within the luxury market, runway reporting, shopping features, trends, and interviews with leading industry experts. She also contributes to podcast recordings, social media, and branded content initiatives. Kristen has worked with brands including Prada, Chanel, MyTheresa, and Luisa Via Roma, and rising designers such as Refine and Tove, and her style has been featured in publications including Vogue.com, Vogue France, WWD, and the CFDA. Before Who What Wear, Kristen began her career at Rodarte, where she worked on assistant styling, photo shoots, and runway shows, and at Allure, where she moved into print and digital editorial. She graduated from the University of Southern California, where she studied art history and business, and currently lives in New York.