You’ve won the lottery. Should you hire a stylist?

I love makeover shows. I used to love watching What Not to Wear as a teen: seeing unflattering secret camera footage, watching a woman’s entire wardrobe being trashed while the host stylists bombard her with sassy asides, and then shopping at glamorous boutiques in NYC. Occasionally I’d be confused by the outcome, because the women often seemed to end up looking more matronly by the end, but I mostly enjoyed seeing the huge, dramatic reveals.

Now I know better, though.

The whole point of these shows, which are just another variety of the American reality TV industrial complex, is to manufacture drama by putting people in extremely uncomfortable situations and capturing their reactions (remember those fun house mirrors where they had women show outfits they’d normally wear?). They have to make some kind of massive change happen so they can show the before and after videos. Who cares about the woman’s actual desires and practical concerns for lifestyle? Put her in bling and in white pants! Stilettos! Cut off all her hair and color it platinum blonde, who cares if she’s a busy mom who can’t dye her hair every two weeks!

Stylists are a crutch, and not even a particularly effectively one. They overstyle people into oblivion, put them in impractical outfits, haphazardly toss on unnecessary accessories, and pressure people into wearing uncomfortable heels. Makeup is piled on and hair is cut into often unflattering shapes, just to force some change. The result is people with deer-in-headlights who look like they’re wearing costumes that don’t reflect their personality.

Maybe outside the makeover reality show dimension, stylists can be helpful. Usually not, though. Read on to find out why they’re not the solution to style woes.


Why stylists are not the solution

Women are picky

It took me a long time to realize this, but almost all women are extremely picky about clothes and style. I know women who have a solid, well-executed sense of style, and I also know women don’t. I had figured that the latter women just didn’t care about looking stylish because it wasn’t a priority for them, which is fine. But it turns out I’m completely wrong.

Most every woman cares deeply about her clothes and her style, and each has very clear ideas about likes and dislikes. Once I start speaking about style with even not-so-stylish women, I usually quickly learn they actually think a lot about clothes and looking stylish. Often they’ve actually made a big effort into shopping. They just have a hard time finding pieces they like and look good on them, in part because they are very picky about what they wear.

Since clothes are something you wear on your body, women are completely right to be picky about clothes. Details like pant rise and how fabric feels are important, since getting it wrong might mean you have a wardrobe malfunction at work or you’re scratching yourself all day. There’s also visual preferences like how a top makes a woman’s chest look. Two women with the exact same body might feel very differently about how much skin they want to reveal. And it’s usually difficult for a woman to judge this without trying the top on.

Add to that a lot of women’s firmly held notions about what they should wear for their body shape (lengthen your body with v-necks! balance your wide hips with a flare leg pant!), which they’ve been indoctrinated with through fashion magazines. We have very confused women who have very hard-set ideas about the types of shapes they think they’re supposed to wear or avoid. As a result of the pickiness, most women aren’t going to like most of the clothes they try on. Some detail, even minor ones, will put them off. I constantly read online reviews by women who are picky about the most minute details, who often ultimately decide to return the item.

A stylist can’t take all of these things into account when she’s pulling pieces. All of these details are things only you know, or might not even realize until you’ve actually tried something on. Only you can decide whether something feels good on your own body, and a stylist can only help so much in picking pieces that you’ll love and wear regularly.


Stylists can’t read minds

It’s really difficult for other people to figure out a woman’s style preferences. A lot of the time, women only have an abstract sense of the style image they want to put forth–things like “professional but easygoing” or “understated chic without looking too try-hard.” These ideas don’t translate directly into “Alicia should wear shift dresses,” because maybe Alicia prefers shapes that are tighter on her body, or doesn’t like the preppiness that a shift dress might evoke (whether a particular shift actually looks preppy is a different matter).

There’s also considerations for Alicia’s lifestyle like her job and industry, office dress code, climate of her region, tolerance for heat/cold, preferred laundry methods, and other individual aspects of her life. It’s hard to figure these things out without taking a deep dive into Alicia’s lifestyle. It’s likely Alicia’s hasn’t even really thought through these things herself, and may not be able to articulate them quickly. I can’t say I’ve even thought through all these things, though they are in the back of my mind when I do shop.

It’s kind of like how architects should know what will happen in a building and how the building will be used, in order to effectively design a space that works smoothly for the users. There’s a passage in the book Where’d You Go, Bernadette about this. Bernadette, while an architecture student at Princeton, is at a presentation for the design of a buildingĀ meant for use by Japanese people. She asks about where users will put their shoes while in the building, since Japanese people take their shoes off before entering indoor spaces. No one else in the room, including the architect, has thought of this, even though it’s an important aspect of the entryway of the building.

This kind of thoughtfulness and attention to detail regarding a user is really important in anything design related, including clothing and style. Unfortunately, it’s a quality often lacking in stylists (and probably people in general). And even if a stylist tried to figure these things out, she might be unsuccessful because a client might not be able to speak to these things herself, as she probably hasn’t thought them through.


You can’t figure out your style in a single day

I once worked with a stylist when I was trying to build a wardrobe to transition out of college. She came over to my house to look through my clothes and see what could be salvaged, then we spent a day at Bloomingdale’s and H&M. She pulled a bunch of pieces for me to try on–loose, flowy, unstructured pieces from Free People and the like, along with skinny jeans–and this was July in NYC, when it is 90% humidity every day. I bought a bunch of clothes but ended up returning much of it later, because I couldn’t see myself wearing most of it.

It’s not entirely her fault. I had such an underdeveloped sense of what I wanted to look like, that I haphazardly tried on whatever she brought me and didn’t have much feedback on if I liked it or not. And to her credit, she asked me what celebrity I wanted to look like. Back then I had zero interest in celebrity style, so I had no answer, though if asked today I’d readily give Sofia Coppola as my style inspo. But we had nothing to start from, no images of what I wanted to look like that could be distilled down to actual pieces. So she just pulled a bunch of pieces she thought was appropriate for my life, I guess, and it wasn’t a very successful experience.

Years later, after experimenting on my own, I figured out I prefer structured pieces and straight legged jeans that don’t cling to my legs, along with other preferences like simple shifts and loafer flats. It took work on my part trying things on and also being inspired by well-dressed people I saw in real life. People watching around Soho was an education, since it’s full of cool girls who aren’t models but dress well for their body. I acquired pieces slowly and over a few years built a wardrobe I’m pretty happy with. More recently, I’ve even gotten away with not shopping in close to a year other than replacing some t-shirts that got holes.

A big part of the reason it takes a long time to first build a good wardrobe is because of what I discussed earlier, where women only have an abstract idea of what image they want to put forth, without understanding how that relates to actual physical clothes – what shapes, styles, colors work for them. A stylist could probably teach you about the shapes that look best on your body, but probably anyone can do that for you by seeing you in a particular style. You can even do it on your own by taking photos of yourself in various pieces.

Also, you’re not going to like everything that looks good on you–that was something I learned through trial and error, that certain shapes that might look good on me are something I actually don’t like wearing. For example, I look great in pencil skirts, but I don’t like how uncomfortable they are, twist around when I walk and force me to take smaller steps, and show off my bum a little too well for a work setting. It takes time and experimentation to have these realizations about what makes you feel best, and will probably take more than the few days a stylist might be able to devote to you.

This is probably why a lot of well dressed people have some kind of uniform they stick with. I’ve discussed mine before: silk blouses with straight leg jeans/pants. And if all of my clothes were lost today, I could replace the core of it pretty quickly, because I already know what looks good on me and where to shop for those pieces. I’d get a few Equipment shirts, Theory trousers, Old Navy jeans and sweatshirt, some kind of plain jacket, and that would tide me over as I slowly rebuilt the rest of my wardrobe (skirts, dresses, and other pieces that I don’t wear as often). This is possible because I already have a strong sense of what I like, developed over years of experimentation.

A stylist can’t be there with you at every step of this process; it’s something you have to do on your own, probably over months or even years. And then you’ll probably have to keep doing again as your lifestyle changes: a move to a different industry, becoming a mother, moving somewhere with a different climate, going from city to country, etc. You can’t rely on someone to make these kinds of decisions for you because they are such intimately personal preferences that might be changing constantly.


Be your own stylist

The only way to become stylish is to learn to become your own stylist. Most stylists seem to just dress you in what they think you should wear, instead of taking time to figure out what you like. And if you don’t already know what your preferences are in a way you can communicate easily, that’s an impossible task. It can take a long time to learn what you feel comfortable in and looks good on you, and it may just require trying on a lot of clothes and seeing how you and others react to them.

I don’t think there are any secret or shortcuts to this process. You really just have to try on pieces in a lot of different shapes and colors and see how you personally feel in them. One way to think about this is to pretend you’re on Say Yes to the Dress, a show I love. When I need a pick-me-up I watch this Youtube clip of a British bride who picks out a super see-through, sexy gown, whose friend tells her she looks like a stripper. It’s so fun.

Anyways on the show, brides try on various dresses until they have an emotional moment when they realize, “This is the dress!” Apparently the show actually works where a lot of (all?) the brides already have the dress picked out by the time filming happens, but it’s still great fun to watch especially when you can see the bride clearly light up in a particular gown. And while I’ve never been bridal dress shopping, in my normal shopping I’ve definitely had moments where I’ve tried on clothes and thought “Oh this is so me, I must have it.” I’ve bet you’ve also had that feeling, too, while shopping before. Before you make the purchase, you should still make considerations for whether the piece is actually practical for your lifestyle, but that’s after the fact of already figuring out what you like on yourself.

In this process you can definitely get inspiration from style blogs and TV show characters. But a big danger might be just being drawn to clothes worn by attractive people because they look good/cool in them, not because it’s something that would work on you or would fit your lifestyle. While Olivia Pope looks striking in white pantsuits, it’s not practical for most women in real life, who have to take public transportation or don’t want to dry clean a suit every time it’s worn. It would also be a little unusual in most office settings.


How to use a stylist

One area where stylists can be useful is just helping with logistics–where they have a clear understanding of what types of shapes, colors and styles work on you in your usual sizes. Then they can pull pieces for you that you’d pick out yourself, and they already fit you or can be easily tailored. They act more in a support role to help realize your vision, not as someone who tells you what to wear.

If I were to hire a stylist, I’d ask her to shop for items with the below qualities, which I already know I like and look good on me:

  • colorblock
  • navy
  • jewel tones
  • structured
  • jackets in fun patterns/colors
  • silk blouses
  • shifts
  • straight legs
  • high waist

She’d be able to run with the above and look for pieces I liked in my usual size. I’d also provide a list of my go-to brands she could shop at, and she might give suggestions for other similar brands. I guess you could say she’s more of a personal shopper than a stylist, so maybe my take to just not use a stylist stands.

This whole essay/rant was inspired by a piece Sofia Coppola recently wrote in W Magazine. It’s about actresses being dressed by celebrity stylists, a relatively recent Hollywood phenomenon. It was hilarious how she described such stylists as failed New York fashion editors who made up celebrity styling as a career. I’d never really thought about them, so it was interesting to think about briefly. She also described how it was too bad that there was no personality shown in red carpet outfits anymore. It is odd, too, because modern American celebrity is a cult of personality, requiring extensive social media engagement and playing silly games on late night shows, all to convince people to follow and like you and buy tickets to your stuff. You’d think it’s important to show personality in your clothes, too, but everyone dresses the same.


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5 thoughts on “You’ve won the lottery. Should you hire a stylist?

  1. Something you didn’t mention, but I tried Stitch Fix because I liked the idea of the magical fairy godmother stylist, but for all the reasons you DID mention above (plus the fact that services like SF are more generic/data-driven than truly personal) it really, really didn’t work for me.

    • Ah, yeah, I think that’s exactly the problem, that personal style has so many variables that it’s really difficult to break it down into data. I’m sorry it didn’t work out, though. Services like that definitely build up anticipation, which I suppose is part of the value, but must be such a letdown.

  2. I love your blog! You have such a thoughtful, funny, informative writing style. Your approach is also wonderfully practical and not dogmatic. Please keep writing lots and lots. šŸ˜‰

    I’d like to read about your year without buying clothes (except replacing the t-shirts) that you mention above. I have seen some other bloggers talking about not buying clothes for a while (I like this one:, but I bet you’d have a fresh and interesting take.

    • Aw thank you! It wasn’t a conscious decision at first, but I realized I was doing it after I read a NYT column about a year of no shopping by Ann Patchett. I’ll make sure to write about it!

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