The 7 Biggest Fashion Fears Stylists Are Seeing Now (And How To Fix Them)

The experts weigh in.

by Kendall Becker
Darrel Hunter
Darrel Hunter street style

Look, fashion can be confusing and, honestly, pretty hard to keep up with at times; are skinny jeans in or out? Ballet flats are cool again? It’s frustrating to navigate the sentiment of staying “on trend” ––and avoiding Gen-Z virally deeming what you once thought was cool as “cheugy” (read basic, overdone, outdated) on TikTok — while equally abiding by your own personal style. It’s no wonder that this creates a recipe for fashion fears.

With social calendars nearly back in full swing, these fashion nuances that once faded throughout a year in sweats have now returned – and it’s certainly cause for confusion. In reaction to lifestyle shifts, many dress codes have become more casual while the urge to dress up has certainly reignited (Fendi and Bottega to the bodega? Of course.). With many women reentering the dating scene, heading back into the office, or simply reconnecting with friends and family, showing up as your best self is a goal that’s likely top-of-mind.

But, let’s not forget that fashion is supposed to be fun! It’s a cliché, but it’s also true. With fashion rules being rewritten, now’s the time to bring out that dress you never had the opportunity to wear, take a risk on a new trend, and support unique, local brands, and boutiques who need a little extra love after the last year.

This is, undoubtedly, easier said than done, so it’s time to call upon the experts to guide you through this transition: professional stylists. From celebrity stylists in Los Angeles to personal stylists dressing the powerhouse women of New York, they’ve heard it all – and they’re offering up their need-to-know advice on showing up as your best and most confident self this year. Ahead, discover the most common questions and fashion fears from their celebrity and everyday clients just like you. Plus, their secrets on how exactly to combat them for guaranteed style success.

Doing Too Much

Jacqueline Zenere, stylist to trendsetters like Olivia Palermo and Ashley Benson says, “Is it too much?” is her most heard fear. “While it isn’t necessarily a complaint, I hear it about every fitting. After a quarantine [without] hard pants, we are all feeling weird about getting dressed up. My clients right now are most concerned with dressing accordingly during these trying times,” Zenere tells TZR.

As dress codes shift, this is the perfect time to rewrite the fashion rules. If you’re concerned about missing the mark, don’t be afraid to clarify with the host or check the location on Instagram for what others have worn recently; but, most importantly, wear an outfit you’ll feel confident in. As Zenere tells her client, “I always reinforce the idea that fashion can be uplifting and an extra source of beauty in the world right now. After all, many of the women I work with have an ethos as actresses that aim to beguile and entertain!”

Going No Bra

Tyler Minor, a Nashville-based stylist working with some of the coolest names in country music, understands the struggle of women on the go, whether they’re performing on stage or headed from desk to drinks, and that undergarment options don’t always suffice. “Women want the comfort of not wearing a bra but, unfortunately, support is needed for women who have larger busts,” he explains. “Sometimes, garments aren't very bra-friendly either. For example, a plunging neckline or a deep V.”

After a long (and welcomed) year of foregoing bras, re-figuring out how to make tricky tops work and finding a comfortable support solution may not be obvious. “My go-to solution is body tape,” Minor tells TZR. If you’re not familiar, body tape is an ultra-discreet solution used to help secure the edges of a garment and can be used to help create shape and provide extra support. Try it for yourself with one of Minor’s suggestions: “My favorite tape to keep in my kit is SKIMS body tape. It comes in a wide range of shades but it sells out FAST! I also really like Nue Breast Tape from Revolve. This product, too, comes in a wide range of shades, but the width of the tape is a little thinner,” he says.

Keeping Style Original

Allison Berlin, whose resumé includes stints at Bloomingdale’s and What Not to Wear as well as high-profile personal styling clients in New York, says that her clients frequently struggle with discovering how they can cultivate a unique personal style to ensure they don’t look like everyone else.

Her suggestion? Start by avoiding stores where you already know everyone else will be picking out pieces, too. “Fast fashion is not unique and far from sustainable; shop more locally and from smaller designers,” she says. While this can be an ideal solution if it’s within your means, you can achieve the same result by shopping vintage or thrifting one-of-a-kind pieces, whether they’re from Goodwill or Depop. If it is an investment, be deliberate — make sure it’s a piece you really love and see in your wardrobe rotation for years to come, and the price tag won’t seem so scary after all.

In addition, she advises altering how you use Instagram. “Don't copy what's trending on the 'Gram,” she suggests. “Scroll for inspiration but change up an element to make something your own; even a layering piece or accessory from a small designer can make all the difference.”

Instagram may spark ideas on trends or styling cues to try out for yourself, but the secret lies in making it your own. If you fall in love with a dress your favorite influencer is wearing, may it be on a vacation or to an upscale event, make it your own for every day by pairing it back to sneakers or throwing an oversized blazer over top for a more wearable approach. Or, take inspiration from the color, for example, and find the hue in a piece you’ll actually get notable wear from.

Simply Going Shopping

“Most of my clients are not into the whole shopping experience,” explains Tiffany Briseno, who has worked with Schitt’s Creek’s Catherine O’Hara and Shawn Mendes. “It can seem overwhelming.”

Walking into a store packed with both clothes and people can be stressful, even to the most well-versed fashion girl. Briseno says, “I find that you will have a more positive shopping experience when you have a plan of action in mind. Make a list of what shapes or trends you are after and when in-store, only look for those items. Once you have found at least one of those items, you will have this sense of accomplishment and find the rest of your time more enjoyable.” Let’s say your shopping list consists of finding the perfect menswear blazer for fall; once you score the essential, move onto the just-for-fun extras. This strategy sets you up for styling success.

Taking A Risk

Los Angeles-based stylist Mickey Freeman has worked with Keke Palmer and Azealia Banks, stars who know a thing or two about making a fashion risk work. One common complaint that I frequently hear from clients is their reluctance or fear of taking risks with their style,” he says. “They all have expressed at one point or another being fearful of exploring style ideas that are outside of those comfort zones than what they’re used to or known for.”

But what’s fashion without a bit of experimentation? “There are many methods I use which depend on the individual, but the one thing I make certain to do is to try my best to connect with the client on a genuine level,” Freeman says. “Provoking the imagination and invoking one’s inner confidence will always be in. As a result, there are many risks that my clientele are willing to take these days, some of which work and others that don’t.”

A great takeaway anyone can apply: Find sources you trust, whether that’s an editorial outlet you love, an influencer who offers great advice, or that friend who’s just a bit too honest– everyone has one. Plus, Freeman recommends “play dress up as often as possible” to help get comfortable with taking risks. “Try on different pieces and color combinations. That’s a great way to rediscover your wardrobe and inform future style decisions.”

Showing Off Too Much Skin

Ari Stark, a VIP stylist based in New York, says that many clients have concerns over showing too much skin — and arms can be a common pain point when it comes to dresses for special occasions. “It's the body part they feel most self-conscious about,” he says. “Growing up, I was surrounded by stylish women who prefer to dress modestly, so I picked up clever hacks from them.”

Ari suggests to his clients, “Start with a great dress. Don't limit yourself to options with sleeves and look for something that really excites you and work around it.” Finding a garment you feel confident in is key; from there you can layer to your comfort level and depending on the occasion.

“I love to pair a great menswear blazer with more feminine dresses — it gives them a striking attitude,” he explains. “For every day, you can also pair a long-sleeve knit under a slip dress in summer and wear the same dress with a chunky cardigan as the weather gets cooler. This kind of layering will increase the wearability and the longevity of the pieces in your wardrobe.” And most importantly, leave you feeling comfortable and confident in your own skin.

Wearing Painful Shoes

Whether you’re a celeb about to hit the red carpet or just have a slight shoe shopping addiction (no shame here), celeb stylist Amanda Lim’s common complaint is one all women know too well: new shoes often aren’t broken in enough to be wearable. After a year in slippers and sneakers, pinchy heels or stiff leather shoes are the things of nightmares.

While for last-minute red carpet emergencies, Lim has Progressive Shoe Shop in Beverly Hills on standby, she also has a go-to anyone can use. The stylist to actresses like Madeline Brewer and Bailee Madison recommends Pre-Heels Spray from Barefoot Scientist. She says, “It's vegan, hypoallergenic, and cruelty-free. It really does prevent the foot from getting blisters, even in the highest of heels – I swear by this stuff!”