12 Expert Tips on Looking Effortlessly Stylish

Have you walked into a room and felt totally underdressed? It’s been the story of my life!

The truth is, there are a few simple fashion tricks that anyone can master. It’s not about following every trend on the planet but about understanding what works for you and your personal style.

Don’t wait around. We talked to leading experts to help us understand the ever-evolving fashion world. Refine your wardrobe and exude confidence with these 12 expert tips on how to look effortlessly stylish!

Everyone is Capable of Achieving This Look

Before you start thinking of all the excuses why you can’t be stylish — that you don’t have enough money or time, that you’re too old, or that you are not at your ideal weight — listen up.

“As an etiquette consultant, part of my M.O. is teaching people how to master personal, ‘effortless’ style,” Jo Hayes, a world-leading etiquette consultant and founder of EtiquetteExpert.org, begins.

“The classic, stylish, elegant look is not just for ‘those who can afford it.’ Anyone can master this — in fact, it’s far easier and simpler than most people think,” she adds.

Keep It Simple, Sweetheart

“First things first — the KISS rule applies — Keep It Simple, Sweetheart,” Hayes says. “A simple, streamlined ‘classic capsule wardrobe’ is the key to effortless style. A simple selection of good quality, classic pieces that will last for years.”

“Think, the staples at Ralph Lauren. Think [about] what locals wear — summer, fall, winter, spring — at Cape Cod. This is not ‘fast fashion’. This is the classic look that looks effortlessly stylish, and it really is effortless once you’ve mastered it, year in, year out,” she adds.

You Need the Essentials

So what should our wardrobe look like? Let’s start with the clothes that always stay in style.

Hayes gives us the lowdown. “The essentials: blue denim jeans; navy, white, or denim shorts/skirt; white tee (long and short sleeve); white long sleeve, collared shirt, nautical striped long-sleeve tee; neutral toned knit/sweater (grey, white, camel or navy); trench coat; white sneakers/tennis shoes; navy pointed heels; black strappy heels. Earrings: pearls, small gold hoops.”

The essentials can be worn as is, or alternatively, Hayes recommends adding “an on-trend piece to modify the look.”

Invest in Good Quality Pieces

“I advise clients to always buy the best quality they can afford,” Hayes says. “Not only do high-quality, high-end pieces (natural, durable fibers such as cotton, linen, silk, wool) look, fit, and feel better, but they last far longer than cheaper, chain-store options.”

It’s important to note that you don’t need to buy these items brand new. Who doesn’t want to help the planet — and their bank accounts — along the way?

“There are plenty of amazing high-end pieces available, second-hand, on Facebook Marketplace, at a fraction of the retail price,” Hayes added.

Update Your Wardrobe by Season

Sahra Brandt, the personal stylist behind Shop the City, the Bay Area's leading wardrobe consultant and trend forecaster, weighs in on tips to look effortlessly stylish: “Buy [about] 5 trend-forward pieces per season to integrate into your wardrobe.”

“I recommend one pair of trending shoes, one-to-two trending bottoms — jeans, skirt, [and so forth] — one to two trending tops, and a trend-forward sweater.”

Find a Stylish Jacket To Upgrade Your Look

Instead of hauling many jackets, a favorite shopping item of mine, Brandt keeps expectations reasonable for those living in the Golden State: “You can upgrade your jacket about once every year or two to something modern and stylish.”

If you live in a colder climate, Brandt recommends: “It's great to have a solid parka that’s updated every 5 or so years for those extra bitter cold days, but I do still feel you should upgrade at least one jacket in your wardrobe to a seasonally trending style. Right now, that could be a long camel wool coat, a denim trench, or a more classic trench.”

Monochrome Outfits for a Chic Look

Monochrome fashion is the art of one-color dressing. While people may have different approaches to the concept, it is quite common to see one color broken up into an assortment of shades to achieve the look.

“When in doubt, monochrome it out. Wearing a look of all similarly tonal colors always looks instantly chic and effortless,” Brandt shares.

Don’t Blindly Follow Fashion Trends

Someone with “style” is defined as being fashionable and elegant. While you might think of fashion as keeping up with the current trends, it doesn’t necessarily mean you have to blindly follow it.

April Grow, a mom of six who helps women find their personal style, captures this perfectly in her blog post: “Wearing the right trends can help you feel and look modern, as long as you don’t disappear.”

Instead of focusing on what is on trend right now, she looks beyond that and instead creates her own signature style, and I have to say, she looks glowing.

Accessorize, Accessorize, Accessorize

Dominique Croft, the founder of Elk & Bloom, an award-winning jewelry brand, shares her tips on looking effortlessly stylish. “Accessorising your look is the best way to upgrade an outfit — adding a pair of chunky hoops or a bold gold chain is the perfect way to add a bit of sparkle to your look,” she says.

Brandt also emphasizes the importance of accessories, “Focus on accessories. You can wear the most basic outfit — jeans and a tee — but what will really make you look effortlessly stylish is the right accessories. Right now, my favorite is either layered dainty necklaces or a chunky charm statement necklace.”

Be Confident

We might think wearing the right outfit will help give us confidence, and while that might be true for some of us, Croft gives us permission to think about it the other way around. “I’ve always felt that if you feel more confident, you’re going to immediately look more stylish, just from the vibe you give out.”

So, it’s not just all about the outfit. It’s also about your own belief and faith in yourself. My partner, whose sister is a former model, insists, “If you have confidence, you can pull off any outfit.”

Wear Something Meaningful to You

Wear what you love and be true to yourself. Croft shares that your outfit should hold meaning to you.

“Style is all about expressing yourself and wearing jewelry, or fashion, that means something to you. That is the only way your style can be individual and unique to yourself,” Croft says.

Jewelry Is More Than Just an Accessory

Croft reiterates the power of jewelry when crafting your outfit. “I think that jewelry is perfect for [looking stylish] because it is more than just an accessory; it has the power to invoke an emotion or bring back a memory, and more than that, it becomes an extension of who we are and how we feel—something that we keep on, no matter what.”