I have been dressing women for nearly 15 years and I have certainly been dressing myself for much longer than that.  So Imagine my surprise when I found a pair of pants I loved that I assumed would look awful on me.

I don’t own a lot of tailored pants.  For work I usually wear jeans, and when I did have times I needed to get dressed up I bought a dress.  However, I felt like I needed some variety and there were certainly times I wished I had some pants in my wardrobe that weren’t denim.  It was time to head out to the store.

I shop for myself like I shop for my clients.  It’s a trusted method of essentially being a numbers game.  The more you pull, the better your chances of finding something that works.  Let’s face it, there is nothing more dismal than loading up a dressing room and having to get dressed again to go get sizes or different styles.  I stopped by the Theory department and found myself intrigued by a pair of burgundy tailored pants.  Not wearing black, it can be challenging to find pants in shades I am interested in.  Yet, I became immediately disappointed when I discovered these burgundy pants had pleats.  Not only have I not worn pleated pants in nearly 20 years, I was sure they wouldn’t, couldn’t, be flattering on my body.  I have bulbous thighs and the idea of surrounding them with balloon-y pants just seemed like a sure fail.

I was so bummed, but, despite all this, for some reason I pulled them anyway.  I still don’t know why.  I guess I figured it wouldn’t do any harm.   If anything, I’d get a good laugh at the ridiculousness of how bad these pants would look.

I got into the dressing room, tried on a few other pants, and finally got to the Theory pair and almost didn’t bother.  As I slipped my legs in I heard myself say, “Okay, this is going to be interesting.”

Well, to say I was shocked is an understatement.  Not only was I pleasantly surprised by how these pants looked, I fell in love with them to the point that I didn’t care how much they cost.  They had to go home with me.

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After I brought my new favorite pants home, I thought about how I would have missed out had I not tried them because I was convinced they weren’t right for me just by looking at them.

If you have been passing items by on the hanger, ask yourself why?  No, really.  Why?  I can’t tell you how many times clients fall in love with something and tell me in a million years they wouldn’t have selected it for themselves.  Unless you can come up with a logical and justifiable reason why you can’t at least try something on, like you are allergic to the fabric, the color is wrong or you just flat out hate it, there is no point in resisting.  If it gives you pause, throw it in the dressing room.

Even if you have a good laugh at the disastrous outcome and wind up wasting all of five minutes of your life by trying on a tragedy, you will have learned something.  We don’t just learn from the wins, we learn from the losses.  Check out the color.  Is it flattering?  What is it about the cut that you don’t like, or do like?  What about how the sizing runs from a particular brand?  Take note of these things for future reference.

Yet, how do you know if taking a chance is right?  The short answer is you’ll know.  You’ll find yourself looking at someone in the mirror who you feels reflects who you are, shows off the style you want to express to others, and actually makes you happy.  It’s not so much a look as it is a feeling.  You might also notice that the price tag doesn’t matter as much.  Not to say that spending beyond your limits is advisable, but it’s hard to put a price on feeling fantastic.  You’ll be willing to put other things back when you find a gem.

What is also important to keep in mind is how this new, unexpected piece will acclimate to your new wardrobe.  While I loved these pants, I needed to make sure that spending full price on them was smart.  I hated the idea of taking them home and then staring at them.  So I came up with options in my head.  Below are three outfits I came up with using exact or similar pieces that exist in my wardrobe.

Outfit #1

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My original intent for these pants was to wear them to a speaking event I had scheduled.  I envisioned wearing pants instead of a dress.  Speaking to a group of women in finance, I knew I needed to look professional, but also didn’t think it was the right vibe to dress as corporate as they do in their profession.  It’s a tricky balance of looking like a fashion professional who understands a more corporate dress code.

For this outfit, I paired the Theory pants (that look much lighter in the outfit photo above than the rich burgundy they really are) with my favorite T Tahari Edie blouse in grey (which is what I was wearing in the dressing room photo) and layered a navy blazer on top and finished the outfit with my favorite Sam Edelman Telsa d’orsay pumps in oatmeal suede, a long Cole Haan pendant and a pair of hoop earrings from Swarovski that look similar to the Kate Spade style in the outfit above.  For what it’s worth, I didn’t wear the blazer closed.

Outfit #2

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I wish I could say my life was about high heels all the time, but it isn’t.  On most days I need to get around comfortably and with some sense of style.  I needed to make sure that these pants would work casually as well as professionally.  I tested them out with my super comfy silver Cole Haan pinch loafers in silver metallic that look similar to this pair from Louise et Cie.  On a casual day, I saw how these pants would even dress up a white t-shirt, like this one from J. Crew, a denim jacket and fun scarf.  I finished the outfit with a pair of earrings similar to this pair from Kendra Scott and bag in taupe from Sole Society.

Outfit #3

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This last look I styled super simply with a camel merino v-neck from Lord & Taylor that I own.  The pants, while basic, make a bit of a statement, so I liked the idea of keeping all the elements of the outfit low key.  I also love the way camel and burgundy look together.  For early spring, I added these super comfortable peep toe wedges from Cole Haan that are super similar to the Cole Haan Tali peep toe wedges I own.  I finished the outfit with a layered pendant from Vince Camuto, a bangle from Banana Republic and camel bag from Rebecca Minkoff.

Take it from me, someone who with tons of fashion experience and just got schooled, never pass up at least trying on something that catches your eye.  You might be surprised by the results.