Even though I’m the poster child of poor fashion sense and dressing down — jeans and Under Armour Heat Gear T-shirts make up the bulk of my wardrobe — I can tell when clothes look good on other people. And while I never think I look particularly good, I can tell when I’m wearing clothes that make me feel more confident, more relaxed, more… well, just more.

 

And I definitely know when the clothes I’m wearing make me feel insecure or self-conscious. Yet none of that knowledge helps me know how to pick the right clothes for me — whether in the store or in my closet. Until a Hollywood stylist showed me how simple it can be…

Leesa Evans is a film costume designer (BridesmaidsThis is 40NeighborsTrainwreck) and celebrity stylist. She’s hugely successful… and yet also able to relate to and give advice to someone as normal as me.

The process, she says, starts with answering one question: “Remember a time you wore something — it could be jeans, shirt, suit, whatever — and you put it on and you just felt great. What was it that made you feel great?”

As you’ll see, once you answer that question, you have all the information you need. Here’s Leesa’s easy-to-follow guide to choosing the right clothes for you:

Realize that what you wear makes a huge difference not just on how you’re perceived by others… but more important, on how you feel about yourself.

When you feel comfortable and confident, you feel happier in general. Feeling confident and happy impacts your business and your personal life… and it can come from something as simple as how you dress and go out into the world.

Yet much of the time choosing what to wear feels intimidating, uncomfortable, and awkward: we don’t know what to wear or how to wear it, and we definitely worry whether what we’re choosing is right for us.

That’s funny, if you think about it: in most aspects of our lives we have a really good sense of what we want and what suits us best. We just go to the store and choose. It’s not such a big decision.

But with clothing, somehow it’s different.

Where we get lost is when we think dressing well is more complicated than it really is. We think that looking good is an unattainable thing that only cool, skinny, tall people — models essentially — can really pull off…and the rest of us are left thinking, “Oh well.”

But that’s not true — at all.

Think of the clothes you see at fashion shows as art.

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What you see at fashion shows is designed to make an artistic statement. For the most part the clothes you wear should be used as a tool to increase your happiness and confidence and sense of well-being.

Start by separating those two ideas: there’s art, and there’s your daily “uniform,” the day-in, day-out clothes you wear that can sometimes be an expression of art if that is in your personality… but sometimes just is what it is: your daily uniform.

That’s step one. Separate art from everyday, and separate trying (and probably failing) to make an artistic statement from wearing clothes that make you feel empowered and at your best.

Remember a time when you wore something and felt great.

Maybe it was in college, maybe it was years ago, maybe it was last week… but at some point you felt great in something you wore.

When Leesa asked me to come up with an example, I said, “Last week. I have a pair of jeans that fit well but aren’t so skinny that they bunch up on my legs, and they’re really soft… and I like Under Armour T-shirts because they fit well but are soft and a little stretchy, so they’re really comfortable. I’m reasonably fit, so I like how that looks, but I’m also shy, so I like that it’s understated.”

“Just by hearing that,” Leesa said, “I already know how I would dress you.”

At first I didn’t believe her, but she was right. When you analyze why one thing works, it’s easy to replicate that premise.

Say I want to buy dressier pants. The fit and feel should still be similar to the jeans I love because that makes me feel comfortable and confident. Skinny jeans may be in… but if I’m not comfortable wearing them, who cares? (If miniskirts are trending, that doesn’t mean everyone can or should wear them.)

Never wear something just because other people are wearing it. Never wear something just because you think you should. Feeling hip will never outweigh feeling comfortable and confident — in fact, if hip is not right for you, you’ll actually feel insecure and self-conscious.

Your clothes should always empower you.

Extend that fit and feel into your broader wardrobe.

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Because I know how I like my jeans to fit, I now know how I want my suit pants to fit. Based on my shirt, I want a jacket with a slim line. I know how I want khakis to fit, and sweaters to fit, and I know I like soft fabrics, so I won’t buy anything else because that’s what feels good to me.

And I don’t have to worry about what is trendy or hip or will make a fashion statement, because what I care most about is how I feel in what I wear.

“I don’t know anyone, or any celebrity I’ve ever dressed,” Leesa says, “where the outfit was more important than how the person felt in that outfit. It just doesn’t work. You can take the best looking person ever and if they don’t feel good… it shows all over their face.​”

Another great outcome from staying focused on what makes you feel great is thatshopping is instantly easier. Choices create chaos — so when you know what you want, you don’t have to look at fifty different items.

The goal is to put together a fairly small collection of things that fit well and make you feel great. Once you get the fit right, it all looks good.

Then you can toss in something new or different once in a while, when you want to have a little fun with your wardrobe. But “different” should be the exception, not the rule, because while “different” may be occasionally exciting, on a daily basis what you want is to feel good about yourself so you can go out and be at your confident best.

Use color to create the desired tone of sophistication.

Let’s say I want to wear jeans and a fitted shirt. If I wear a white shirt and worn-in blue jeans, that’s a casual color combination.

If I wear a black shirt with dark jeans and a black belt, that’s a more sophisticated version of my jeans outfit. The actual items might each be the same; all that changed is the color.

And of course there are variations in between: I could choose charcoal gray instead of faded blue. I could choose medium-gray instead of black or navy.

Once you know the fit, use color to achieve the level of sophistication you need.

Find a solution, and stick to that solution.

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“I generally keep my colors to black, navy, camel, beige, and cream,” Leesa says. “And chocolate brown. That’s it. That way I pretty much always feel like myself.”

Finding a subtle color palette you like not only makes it easier to pick out clothes in the morning, it also ensures the attention is on you, not your clothes.

“A lot of men want to experiment with color,” Leesa says, “and they do it in a way that is too bold for them.” How do you avoid that? Look in the mirror: if your eyes are drawn to the color first and not your face… it’s too bold.

“Women love sexy heels,” Leesa continues, “but if you find it hard to walk, find a version of that shoe that you can walk in. I know the height I can wear comfortably, and I don’t go above it. If you feel awkward or uncomfortable in a pair of shoes, it doesn’t matter how great they might look.”

Above all, dress to empower yourself — impressing others is a secondary concern.

Hopefully someone will say you look great. And maybe they’ll say, “Hey, that’s a cool shirt.”

But compliments should be an afterthought. What you wear is really about you first. You want to feel confident, secure, empowered… that’s what matters. What others may think is far less important than how you feel.

Use that as your guide and you’ll always pick the right clothes, regardless of the setting.

And if you don’t have the right clothes in your closet… start putting together a better wardrobe, because now you know how easy it can be.

Let’s recap. Here’s the short version:

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Let us know what you think!