Fashion Magazine

Why Women Have Trouble Figuring Out What to Wear

By Bridgetteraes @BridgetteRaes
trouble figuring out what to wear

With a client back in 2006

Being a personal stylist is tough work.  This is not a complaint (I love what I do), but a fact.  No, it’s not rocket science and nobody in this profession is making any huge strides towards the cure for cancer, but, even though being a stylist appears to be a glamorous profession, I assure you, it isn’t.

As a personal stylist I get hired by women to help them revamp their wardrobe, develop their personal style, learn to shop and get dressed, upgrade their image and feel more in control of the way they present themselves to the world.  I’ve been doing this for the past eleven years (prior to this I was a fashion designer for ten years) and am grateful that I’ve been able to sustain myself in this business all this time, even after the economy crashed and basically wiped me out.  To say that developing this type of business is tough is an understatement, especially now when everyone seems to want to be a “stylist” and that any Joe Blow could wake up tomorrow and call themselves one.  At this point I am quite accustomed to a salesperson walking up to me at a store and either try to hand me a resume, ask me how I started my business or want to know exactly how to be a successful stylist in the 30 seconds that I have to chat with them.  When this happens I just think to myself, “Oh, you have NO idea what this business is all about because if you did you would find something else to do with your life.”  Again, this is not me complaining about my profession, it’s just me being realistic and I simply question how many people actually have the stomach for it.

trouble figuring out what to wear

Styling a client

To describe what I do in simple terms: I am am basically a short order cook, marathon runner, psychologist and coach with two decades of fashion experience, a sick skill for color and a mind like a steel trap.  In the past eleven years I have experienced things like offering comfort to a client who sobbed uncontrollably over letting a pair of Chanel earrings go (true story that I will tell you about another time), have dealt with wool allergies, wide feet, narrow feet, clients with conservative religious restrictions, hoarder clients who have seen me as the devil for suggesting they part with clothing from the Bush administration (the first one), mom clients, professional clients, working moms, clients who don’t dry clean, clients who don’t wear heels, clients who only wear heels,  clients who are always cold, clients who are always hot and clients who are short, tall, plus-size, incredibly tiny, flat-chested, large-chested and who are convinced that they’ll lose 20lbs. over the course of a long weekend… to name just a few.  I need to be prepared for a call at any time from a client that includes, “Do you remember the yellow sweater with the things on it?  Do you think it will go with…” and then have to remember exactly what the yellow sweater with the things on it is.  I have to know when it’s okay to push a client and when it is smarter to pull back because they’re just not ready to be pushed, and I have to be incredibly perceptive, intuitive and I have to listen…very closely.  In addition, being a personal stylist is very physical.  The day after shopping with a client my arms are actually sore from lugging piles of clothing from the racks to the dressing room and it is normal to stand for five hours while with a client  before I actually sit.  I’ve bent, climbed, stretched and reached into more closets than you can possibly imagine and have probably zipped hundreds of clients into over a thousand dresses.

Trouble figuring out what to wear

A loving moment with a client.

I’m also incredibly dedicated to what I do which is why I’m not keen on how loosely the word stylist can be used by just about anyone who likes fashion and wants to make a career out of it.  My passion and respect for my profession and, more importantly, my clients is unyielding.  I do what I do not for the perks, the chances to go to fashion shows, the endless shopping hours I rack up, the so-called fabulous job title, or for the opportunity to stare at clothing all day.   I continue to do what I do because the satisfaction of watching clients transform is like a drug that I can’t get enough of, and every challenge and obstacle with a client that lays before with their own personal style challenges is like a puzzle that my brain is obsessed with tackling.  I’m also a visual person, it’s just how my brain works.  So, for me,  styling a client is the equivalent of a really pretty, well dressed math problem that I commit to solving like a dog with a bone.   Last night I actually had a dream that I was playing what seemed to be the stylist’s version of Candy Crush- I had to match three outfits together, not candies.  I’m serious.

With all my experience it is important to I express to you that if you have trouble figuring out what to wear it is with good reason.  I’ve never wanted to be an editorial stylist (stylists that work on photo shoots for magazines, advertisements, etc.) because I prefer to deal more in the realistic side of styling.  From the years I’ve spent styling real women with real lives, and managing the unique sets of challenges that every client presents to me, it is no wonder that most women stare blankly into their closets on most days.   Here’s the thing, when you look at a fashion editorial spread in a magazine, or peruse your favorite catalog, you are, first of all, looking at a model who is usually quite perfect in size and build…something that few of us are.  However, body issues aside, let’s talk about the fact that this model doesn’t have to be home by 2:30 to pick up the kids from school, doesn’t avoid light colors because she has a black dog that sheds profusely, doesn’t need to have the perfect outfit ready to give a presentation and work tomorrow  and isn’t allergic to wool.  Well, maybe she is, but we’d never know that from the way she is laid out on a chaise lounge wearing a $2,000 gown.  Fashion advertisements and editorials sell fantasy and few women’s lives are all that fantasy based.   While I’m not saying I’m for or against the way fashion sells its clothes, what I am saying is that if you have trouble figuring out what to wear you’ve got to cut yourself a little slack.  Where the heck are you getting your information for your own unique set of challenges, a magazine with a 5’11″ glamazon who just reached the legal voting age this year or the celebrity who has an endless budget and a team to make her look perfect?   Doubtful.

trouble figuring out what to wear
So I tell you my story to hopefully give you a little ease around the challenges you are facing in figuring out what to wear, finding it in a store and knowing how to style it, by assuring you that you are not alone, you are actually normal.  Your challenges are my typical workday.  While this may not solve your dilemma, I think comfort is often found when you realize your challenges are normal.  It’s quite funny when a new potential client calls me.  I ask them why they are seeking help and they tell me all their problems, like they’re the only ones in the world dealing with them.  As I listen I usually chuckle sympathetically and say, “This is not to in any way minimize your problems, but to assure that  you are not alone. I can finish all of your sentences because 99.999999% of the clients I have worked with have cited the same exact issues you are dealing with.”  After I say that I hear a pause, a sigh and a sense of relief on the other end of the phone.  For it is in that moment that they realize that the trouble figuring out what to wear is actually not their fault, that they are normal, not fashion inept and that, most importantly, their problem might finally get solved.   And then I start again.

Why Women Have Trouble Figuring Out What to Wear
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