The One Styling Tip That'll Make Dressing Up Fun

There are a lot of wardrobe styling tips and tricks out there. So many, in fact, that it gets to be a little overwhelming. Which should you subscribe to? Ms. Chanel advises that before you walk out the door every day, you should take one thing off. A classic woman doesn’t overdo it. But if Iris Apfel had her way, she’d tell you to put one more thing on. Mr. Lagerfeld swears that one is never overdressed or underdressed in a little black dress. Dior preaches that the real proof of an elegant woman is on her feet. With so many rules to consider and memorize, it’s no wonder some of us approach a store with nothing less than stress sweat. Finding a new dress makes you wring your hands, and thinking of hunting down pants that don’t bunch may or may not give you a nervous face spasm. All you’re certain of is that the whole affair is a complete ordeal.

And that’s such a terrible way to approach style! You’re jipping yourself the pleasure of creating a story for yourself in the form of sleeves and hems, laughing colors, and tumbling patterns. Expressing yourself through style to others should be nothing short of fun, but I can understand how the rules can put a dark cloud over things.

So if I can add to the turmoil for just one moment, I’d like to offer my own piece of sage advice. While I’m not trying to discredit any demi-god named de la Renta or Dior, I’d say scrap their ideas and just listen to me instead. I’ve concerned myself with fashion ever since I was old enough to know how to con my mom into buying me Vogue with puppy dog eyes and sweet chubby cheeks. I’ve been pouring over silhouettes and dress sweeps since I was 14 and I’ve tried just about every trend and style personality out there. And the one thing that I’ve found most important, above all, was this: Dress for the life you have now, and not the one you wish you had.

It’s simple and has nothing to do with waistlines or hem lengths, but if you follow it you’ll see all the difference in your style experience. Your tastes will constantly change: You’ll crave to be minimal on a Monday and then want to go tomboy on a Wednesday, and round off the week in a floral A-line come Saturday. You’ll wear what pleases you at the moment, but one thing that stays fairly constant is the state of your life.

Think of it: When was the last time you changed roles in your life, like becoming a mom or getting a whole team to report to you? When was the last time you lost your job, upgraded to a pent house, decided to become a vagabond, or traded it all and moved from the city to become a small town girl á la Zoe Hart? Things don’t change too quickly, right?

So why would you buy clothes for a life you think you’re going to have in, what you hope, is just two short weeks? You know what I’m talking about. It’s those skinny jeans you bought for "when you lose those five pounds," or that leather jacket you got in case you become a cool city kid next month.

To shed some more light on the topic, let’s delve into some examples. Are you not too confident with how your legs look like in shorts? Then stop buying yourself mini dresses that’ll only make you feel down on yourself when you zip into them. You know you won’t be happy wearing that short hem, and you’ll just end up fretting over the fact that you ate that cheesecake all by yourself last weekend (though, if you’re being honest, it was totally worth it and you’d do it again, because there's no reason not to). Don’t give yourself opportunities to be mean to yourself, and don’t give yourself chances to feel bad about things that you shouldn't have to change in the first place. Buy dresses that’ll make you love your figure until you actually do love it.

Maybe you're a new mom and not quite ready to give up your old life of dry-clean only tags and pieces that zip, button, and snap. You love dressing sharply and with an enviable amount of style, but that might only make you unhappy as you're struggling to cuddle, lift, burp, unhook bras, chase, and feed cute little monsters. Wouldn't being happy and comfortable be better than forcing an old chapter of life to extend just a little bit longer?

Or maybe you’re a homebody who feels like herself the most in canvas Keds and clean lined sweatshirts. So don’t spend your money on flashy dresses and bold prints that you’d feel completely uncomfortable wearing. We usually buy something trendy because we feel like we should like it, and because we saw women with completely different personalities and tastes pulling it off beautifully. But we know deep down it’s completely wrong for us, and you’d have to get a lion-amount of courage to wear it out onto the subway come Monday. Which is a tall order. So the end result is that it just hangs in your closet, biding its time till you toss it into a collection bin two years later.

Whatever your situation, embrace it. Be honest with yourself and don’t buy things just because you saw other women wearing them or think they’re on trend and you need them. Forget everyone else but you. Dress for the life you have now, and be all the happier when you open your closet doors in the morning.

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