Looking Good, With Some Help: A Chat with the Woman you Ask for Fashion Help When You've Made a Mess of Your Closet

Some of us dress well, most of us don't. Usually we just throw on whatever's clean and in the closet, then head out the door, looking very much the same each day with little thought to our overarching sartorial decisions. Whether we'd like to admit it or not, we all could use some help. That's where someone like Kristen Kaleal comes in. She's a professional wardrobe stylist, and it doesn't matter if you're wearing the same ratty T-shirt every day or stockpiling your closet like a hoarder, she can help.

So, how the hell does someone end up in this line of work? You're on your own, and people pay you for fashion advice and shopping help.

I've been doing it for 10 full years. I used to live in Las Vegas, and while I was there, I would always notice and tell my friends that they looked great. Finally the jig was up, and I just asked them how they did it. Tell me what you know. Some of them had been taking classes from a lady who'd been a wardrobe stylist for TV shows back in the 1980s. L.A. is only a five-hour drive from Vegas, so I started making the trip to take classes with her a weekend a month. It changed my life.

Okay, so you have this TV lady giving you the goods. How do you return to Cleveland, which, ya know, isn't L.A., and make a job for yourself?

Well, first, I figured if it changed my life, it could change others' lives too. I joined an association, the Association of Image Consultants International, and got some training. That kind of set me on the right path to getting paying clients. I also do some corporate speaking on proper dress for the workplace and personal brands and company brands, but the real nuts and bolts of the job is working with individuals on their wardrobes, which is what I enjoy the most.

Is this a word-of-mouth thing? Like, you made me look great, now I'll tell my friend about it? Sadly, no, ha. This business is strange that way. If you look great, you don't want to admit that it's not you who's putting it together, because fashion is a very personal thing. I had a client the other day who told me I was going to be her secret weapon, which meant, 'I'm not going to tell my friends about you.'

When do you get the call from a client? Like, at what stage of fashion disaster do they admit they need professional help?

People come looking for me when they're at their wits' end with their clothes. Maybe they're overwhelmed. Like, how do you know what to pick out at the store? Or maybe they buy too much, which is what a lot of people do. They're drowning in clothes and they can't make sense of it all.

I saw you posted something recently on Facebook about a client who had 74 dresses. Seventy-four! That's insane.

Oh my god. That was before I got into her closet. It's a lot less now. I feel like there's psychological reasons for underbuying or overbuying, and I kind of have to get into that before I can help them. For a client who's a super shopper, someone who has unlimited means, that can be a problem because you just shop until you go crazy. With the 74 dresses lady, she wasn't editing her closet. I walked in and was like, 'This was from, like, 2005.'

Are they reticent to get rid of stuff? Do you have to really persuade them to pare down?

Sometimes. There's no ideal number, for example, for 74 dresses lady, or anyone. Everyone has different goals and lifestyles. If you're an accountant, for example, you're a numbers person and I can work with you methodically. If you're a creative person, we can work that way. Sometimes people need a softer touch.

Where do the clothes go?

Sometimes to a consignment shop. It depends on if they want to get something back for what they have. I literally bring garbage bags and tell them I'll take the stuff to Goodwill or the Salvation Army. As long as it's not going to the actual garbage.

Have you ever kept anything?

Ha, no.

What's your closet like?

Very, very organized. I definitely live what I preach.

Is 74 dresses lady among the crazier situations you've walked into?

In terms of number, sure. There are other situations that aren't overbuying though. I had one client who was terrified to shop. We went through her closet and she was feeling good. We were going to go shop the next week. Then that day comes and she calls me crying in the car. She had a breakdown because shopping made her so stressed. We calmed down and went and afterwards she felt great. She was literally skipping into the store the next time she went, she told me.

Why don't people know how to do this? Why do we dress like crap? At the bottom of it all, it's because no one teaches us. Our moms are there at the beginning, but with clothes, sometimes that's not good — moms can actually teach us some of the worst fashion habits. Sometimes it stems from our friends. Someone says we look like a piece of bubble gum and then we never wear pink again. Things stick with you. Bad advice sticks with you.

How do we learn? Do we pick up Vogue every month and scope it out?

I never tell clients to do that. I like InStyle — it's a bit more realistic. But you have to understand that you can't buy everything, and even if it's trendy now, for example, no one's going to want it in six months and look, it cost $800! I preach quality clothing and classic clothing. Sometimes the less you have, the better off you are. For some reason, a lot of my clients come in and just say they want to look age-appropriate, that they don't want to look like Brittney Spears. I don't know why that's the benchmark, but it is.

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