How To Style Your Clothes (Starting In Your Closet)

Stylist How-TosGuidesThe Foundational WardrobeWomenMen

Feb 12

three people in modern casual clothes style

Styling your clothes doesn’t have to be a stressful, daily drama. It can be a fun and creative process—when you know a few tricks of the trade.

Learning to style clothes is a skill that anyone can get better at -- and once you do, getting dressed in the morning won’t just be easier, it’ll be empowering and life-changing.

1. Dress More Stylishly Trying With What's in Your Closet

How to Dress Yourself Like a Stylist Would!

Stylists always take a look at what’s already in your wardrobe before recommending new pieces.

At least the good ones do…

Try this:

Put on one item (a pair of pants, shirt, or shoes) that is a favorite piece in your wardrobe.
Then looking at your most frequently looked-over items, see what new combinations you can create.
It’s helpful to start with one item you have always liked but don’t wear often—attempt to create a head-to-toe look with that one item plus your go-to you already grabbed.
Repeat the same process with that favorite item as a base for multiple outfits but always include pieces YOU DO NOT WEAR OFTEN.
The process is pointless if you don’t experiment with your least-worn styles.

Along the way, you’ll find new inspiration and start pruning the extra uselessness that is sucking up valuable closet space.

A great stylist understands it’s about maximizing what’s already in your closet and mixing new combinations.

And that can be you too!

Before you rush off to do anything else, take a good, honest look at your closet.

Want help in your closet? We've got a free guide to help make it easier.

2. How to Mix and Match Clothing to Make More Outfits

Stylists love to mix high and low, casual and formal, quirky and classic, to create unexpected looks with a lot of visual interest.

Try picking out pieces you’ve never worn together—like that oversized sweater you always pair with jeans—can you style it with a skirt (mini or long) for a different vibe?

Think Like a Stylist: Add contrast in texture, shape, and color by making sure you have different fabrics and textures.

For example: Combine lace with leather, cotton with cashmere, or suede with denim.

Wearing items in unexpected ways will shake you out of outfit boredom.

3. Dress More Stylishly Using Accessories

Accessories help personalize your look.

The beauty is that they make experimentation much easier and are more forgiving when you decide to change the look. (No getting naked to change a necklace, right?)

Think Like a Stylist: Take the five extra minutes to put on your accessories.

Instead of overlooking accessories and keeping things simple, try adding on way more than you’d normally wear.

They don’t have to all go to the same place! You can:

Layer necklaces
Add a bunch of rings
Use a pretty hair clip
Tie a scarf around your bag handle

And do one per day or all of these in a single outfit!

Other ideas:

Toss on a classic fedora
A large cuff bracelet
Try patterned tights

Any of these can become your go-to for making a favorite outfit feel more interesting and unique to you.

Make it stick: next time you get dressed, add one accessory you don’t normally wear and walk out the door in it. You’ll either fall in love with the item or remember why you never wear it. Win-win!

4. Tailoring is Everything

The secret to looking polished isn’t about wearing certain clothes—it’s about wearing clothes that fit fantastic.

Even a simple T-shirt and jeans can look like trash if they fit poorly.

Tailors are a stylist’s best friend.

If something you love doesn’t fit quite right—whether it’s too long, too loose, or just not hitting quite the way you want—don’t toss it, take it to a tailor.

Think Like a Stylist: Professional stylists always consider tailoring as part of the styling process. It’s one of the biggest differences between “wearing” clothes and a look becoming yours.

As much as you’d love for things to fit straight off the clothing rack, most clothes won’t fit perfectly as is, for the majority of people.

I swear! Every personal styling client I’ve ever had has needed to get some things tailored.

Have that blazer nipped in at the waist or hem those wide-leg pants to your perfect length. Think of tailoring as the final polish on a great outfit—details like this will set you apart.

5. Stay Stylishly Long-Term By Trusting Your Own Taste and Personal Style

Styling is not about following trends. (Yes, it helps to be aware of them, but I swear you don’t need to follow them to look fabulous.)

It’s about discovering your personal style and trusting when something fits into it and when something doesn’t.

Trends come and go, but great taste is timeless. And that is the key difference.

When you love something plus it’s well-made, it’ll last in your closet for a long time.

It doesn’t matter if you love boho, luxury, or you can’t live without bold colors and patterns.

Whatever it is, figure out what makes you feel like your best self and lean into it. That’s how you develop a signature look and stay in love with it.

Think Like a Stylist: Stylists help clients define their unique style, often by asking, “What is your vision and who is your style icon”?

Is your look classic, bold, and modern? Or more bohemian, casual, and effortless? Once you nail down your “Vision” use it to guide your choices.

6. Confidence is Key

Here’s the truth—no matter what you wear, the most important thing you want when you put on clothes is confidence.

Confidence transforms a simple outfit. It’s not just about the clothes, it’s about how you feel wearing them. Your outfit will reflect that.

Think Like a Stylist: Stylists always pay attention to how their clients feel in an outfit, not just how they look. Wear clothes that make you feel strong and comfortable in your choices.

If you feel good, that will radiate from the inside out. Confidence is amped up with a good outfit, but when you feel good in what you’re wearing regardless of what fashion says, it amplifies everything else.