How to Be Your Own Stylist

I firmly believe that any wearable item can look good if styled properly. OK, maybe not cloven-toed shoes or butt-cheek-exposing short-shorts, but pretty much everything else. Trendy items like jumpsuits, tricky items like ankle booties, even garments that fit imperfectly or hit your body at strange angles can all be strategically styled in ways that will make the items look natural and you look amazing.

And since I want you all to feel confident in exploring style as a means of self-expression, to try new things and branch out, to grow your skills at assembling amazing outfits, I thought I’d write up some instructions on how to cultivate a stylist’s skill set.

BUT. What I discovered as I wrote was that the cultivation part is enjoyable and fascinating … but the timeline is much, much longer than can really be captured in a blog post. And the process itself isn’t just long, it’s nebulous and changeable depending on your personality and priorities. Nevertheless, I’m going to plow ahead. Because learning what you love to wear and which items fit your personal figure flattery priorities constitutes the groundwork, but learning to make clothing a true artistic medium for self-expression is the end goal. And a worthy – if daunting – one at that.

Here are the basic steps you need to follow to become your own best stylist:

1. Practice

Nothing can replace experimentation as a means of understanding how your body and clothes will interact, and to be done right it must be done ON YOUR BOD. Practice doesn’t mean brainstorming possible outfits, or sketching ensembles, or shopping. It means standing in front of the mirror and examining how combinations of clothing, shoes, and accessories impact your figure, your complexion, your overall look. It means starting with an outfit that looks horrendous and changing and refining it until you are not just satisfied, but thrilled with the results.

2. Inspiration

No woman dresses in a vacuum. If you want to learn how to style yourself, you need to see how others style themselves. Not only will the choices of others influence your own choices, but an awareness of what is available and how it’s being worn will help you keep your look current. Does this mean “copy outfits from magazine editorials,” “buy entire ensembles as shown in ads,” or “become a slave to trends”? Certainly not. It means that consuming images of dressed women will grease your imaginative gears. A photo of a runway model shouldn’t make you think, “I could never wear that.” It should make you think, “What can I use from that?” Color combinations? Proportional play? Hairstyle? Accessory placement? Blogs, magazines, books, television, movies, and women who pass you on the street can all fill your internal inspiration folder.

3. Courage

Related to confidence, but perhaps a step beyond, dressing with courage means committing yourself to wearing clothing that makes you visible, defined, and interesting. This doesn’t mean that you have to wear something loud and showy every day, or that you cannot follow this path toward a sleek, minimalistic style. But it does mean that you must be willing to push yourself outside your comfort zone fairly regularly in the name of exploration and refinement, try a new garment, silhouette, or look in a public setting and gauge your own reactions and the reactions of others. If your interest is in learning to be a creative, effective self-stylist who can make any outfit sing, then sticking to tried-and-true formulas will just work against you. Be bold, take risks, fail. You’ll never get good if you don’t have a few spectacular mistakes to learn from.

4. Time

Sorry, folks, but no weekend-long course will transform you into a great stylist. You may be able to hone in on flattering colors and styles fairly quickly, but defining and crafting your personal style typically takes years. You’ve got to find out where your tastes and lifestyle intersect, explore which garments work in theory but not practice, allow yourself to change as you learn more, refine your wardrobe, adjust your grooming … I could go on. The process of cultivating personal style is long and slow. And learning to work with any garment – no matter how unusual or strangely-fitting – and slip it seamlessly into your now-refined personal style? Honestly, that takes even longer. Not to say it isn’t worth it! Just to say that you need to understand that you’re working on a long timeline.

5. Passion

Finally, and possibly most importantly, you’ve gotta want it bad. Learning to style yourself is related to learning to dress yourself, but as these steps have illustrated it takes substantially more time, energy, and effort. If you are totally passionate about clothing, experimentation, and remixing AND you’ve got the time and willingness to dedicate to this personal project, you can absolutely do it. And if you don’t, and your goal is to learn what works and craft a look that makes you feel fabulous but never push beyond to styling, you are still absolutely golden. Neither path is a better path.

Image is the venerable Rachel Zoe, via sociablenews.

Originally posted 2011-08-02 06:09:30.

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26 Responses to “How to Be Your Own Stylist”

  1. tiny junco

    all good, valid ideas! in my view, you’re basically educating your eye in this process, and there are ways to speed the process up (if you’re rabid to do so). any classes on design theory and practice (that cover proportion, color, line, etc.) will be invaluable. life drawing classes are great for being able to SEE the way the body interacts with clothing. art history classes are great for training the eye to look and the mind to think about visual information. any sewing classes that focus on fit will also help immensely to help you learn about how clothes work with or against the body (and forever disabuse you of the notion that your figure is at fault if clothes don’t fit!).

    ‘copycatting’ CAN be helpful and educational – if you take an inspiration look and then shop your closet to make an outfit you like along those lines. what attracts you about the original: proportion, line, texture, color? what have you accumulated that echoes what’s in your inspiration look, and what don’t you have? how do you end up tweeking the original look to make it ‘you’?

    i find it’s really important to look as closely as ‘i’d never wear that’ looks as ‘love at first sight’ outfits. that’s how you learn, how you expand your taste, how you don’t ossify. it’s funny, i’ve often found that people with very strong personal styles are more apt to love styles completely different to theirs than less individualistic types. i think they understand how hard it can be to pull off something that different from the herd : )

    lastly, it’s not just the clothes but HOW you wear them. tucking, belting, pushing up a sleeve – all these can make a big old difference!! Angie shows how true this is in a her latest look – she turned a black dress front to back to make it hers!

    speaking of which, the You Look Fab forum is an unique, supportive, creative place in which to discuss styling outfits. the women there are worth their weight in gold – definitely check it out if you’re interested in the topics discussed in this post!

    have fun, and remember – if you’re frustrated, it means you’re actually DOING something 😉 steph

  2. Kristen

    Interesting post. I think I am GETTING there….as in, I’ve stopped buying things that work for others but definitely not for me and have been very happy with the earthy/safari colors in my wardrobe. I’ve been branching out a bit with shoes and accessories, but still staying true to myself. I like the fact that I work in an extremely conservative environment, but still push the envelope enough.

  3. Blabla

    If think my biggest issue is time, but i’ll try the other points =)

  4. Stacy

    I think I am getting there, too. I don’t have a very deep closet, but I do tend to choose or make things that are flattering for me. I don’t think I choose a lot of “different” things, either. I’m very mindful of what I buy these days, in how I can deploy them with what I already have. I want to have a very wearable closet and I have been weeding out those things that just don’t get worn (too big, unflattering fit, etc.). It is definitely a work in process! 🙂

  5. Patti @ NotDeadYet Style

    Right now I’m working on the inspiration/courage pieces. I have the time and passion for sure. I’m actually cultivating a file now of some inspirational looks from fellow bloggers, and trying to adapt them to my lifestyle/aesthetic. It’s a lot of fun and a lot of work. But that’s true of all the good things in life, right?

  6. Jacqueline

    I love how thought out and step-by-step this article is. I think that I am almost there. I use everything in my closet and am big on accessorizing to perfection. But with this, I’m gonna be even better. Thanks for posting 🙂

  7. adriana

    my biggest challenge would be having courage. i tend to be more conservative when it comes to my wardrobe because i’m a big believer in first impressions and i meet new people everyday. it never seems worth it to be too risky. how does one build up courage with regard to fashion?

  8. Fab

    You’ve described my predicament perfectly…I’m on the ‘just starting out’ team. I’ve got loads of interest and definitely the time and the willingness, but I just get lost whenever I open my wardrobe! I collect pics from magazines, blogs etc. for inspiration, but translating the ideas from these into my personal style seems like a daunting task. I guess a certain inborn creativity plays a big role here.

  9. D

    I think it is a goal and a wish for me, and that it has been (perhaps subconsciously) for a long time. I’m definitely not there yet, but I am enjoying the learning process. I really only started to actually hone my skills in the last couple of years. I’m not sure that I’m at a point where I am comfortable with styling my 5 least worn garments yet, but I’m getting there. I could probably come up with some interesting, but not quite refined enough (in my eye) looks.

  10. Jill

    Is cultivating the ability to style any garment a goal? YES!

    I get stumped more often than not and constantly look to blogs and lookbooks for direction/inspiration. The conclusion is usually that I’m over-thinking it. So I scale back, start simple, and the details evolve from there.

    So flattered to be included in you recommendations!

  11. D

    …also, is it weird that I kind of like the cloven shoes? And derby makes me love me some booty shorts (with tights underneath…)

    • Katharine

      My only slightly off-topic contribution to this post’s excellent thoughts is that if I could afford them, I would LOVE a pair of Margiela split-toed boots — in the classic black leather, thank you, not the weird tan holey version — and would wear (or style, if you prefer) the heck out of them if they were mine. I’m a size 8, if anyone has a slightly worn pair they’d like to offload.

      • Cortney

        I’m totally with you Katharine! If anyone has a pair of them in size 6, I’d snap them up in a heartbeat!

        I tend to love those sort of statement pieces, especially in shoes. 🙂

  12. Kate K

    This is a fantastic post Sal–so helpful! I’m at the point in my style evolution where I’ve practiced a lot *and* I’ve become inspired by more and more people (both real life and in blog-land) *and* I’ve become courageous enough to try new things. It’s a really exciting combination.

    As an example, I bought this Target dress last night ( and even though it doesn’t work on its own for me (the fabric is just a bit too clingy), as I tried it on, I knew it would be perfect with a longer drapy cardigan over it, which is a bit of inspiration I picked up from one of the woman who works at a local art gallery.

    I got home, tried on the dress with the cardigan I had in mind and it was exactly how I imagined it and that was a first. A really really exciting first. It felt chic and effortless and comfortable and absolutely me.

  13. Mia

    I’m still pretty new to dressing my body for style instead of simply for coverage, so I’m learning about a lot of things. There are some things I’m pretty sure I have down–what silhouette I’m most comfortable with and that looks good on me (fitted top with full, knee-length skirt)–but there are a lot of items out there that I haven’t quite figured out yet, like pencil skirts. Can I wear them and not look off-balance? Can I wear looser tops without looking bulky and shapeless? Practice has helped, and I’m looking forward to figuring things out more in the future, especially with inspiration from all the personal style bloggers I follow!

  14. Kate

    Six months ago I didn’t care about style or fashion at all, and the thought of being my own stylist (or even having a stylist given to me), was something I would not entertain. Fast forward to now and while it isn’t my foremost priority, it is something that I find myself putting more energy and effort towards. Step one for me was actually getting the courage. The courage to break out of the style rut I have been in for the last 25 years and be willing to try something new. And frankly, it wasn’t easy, especially when others started noticing the changes I was making. I don’t like to draw a lot of attention to myself, so when others start noticing what I am doing, I tend to start panicking. I have worked really hard to get past this, and now that I have, I am starting to focus on the inspiration and practice aspects!

  15. Mary

    You always give great advice. I bought your mini makeover a while back & while I haven’t really finished it (I get easily distracted, lol) I feel like the tips are very helpful and I even managed to get rid of some stuff that I never wear.

  16. T.

    Love this post!
    I’m all for shopping the closet, so I challenged myself to style some more-or-less unworn things that have an awkward shape or that I think don’t suit me. Sometimes it worked, sometimes it didn’t.
    And you’re right, you have to try on an outfit to see if it works, not just imagine it.

  17. Meghan @ Life Refocused

    Love this post and appreciate the 5 points. I’ve been wanting to re-vamp my style and wear more clothes that I’m really drawn to but have previously thought I could never pull off.

  18. rb

    I do have a personal style and I don’t vary from it often. It would definitely not be the stuff of blogs, because I don’t wear a lot of color and I wear the same “classic” items over and over. But I do read style/fashion blogs like yours, because I’m interested in fashion as an observer. I can appreciate a look that would have no place in my wardrobe.

  19. Turophile

    I’ve been reading your blog for over a year now and have started following other fashion bloggers as well. I’m still not sure I understand what it means “to style”. When did this noun become a verb? I’m not being cheeky, but I still scratch my head at times when people say they’re going “to style” an outfit. Everyone has a style – it may be slovenly, it may be hip, but we all have style. Can you help me with this “style” verb please?

    • Sal

      Sure! I see style as a verb used like this: You build an outfit from building blocks. Shoes, skirt, shirt, cardigan. That’s dressing. Styling the outfit has to do with refining it, tweaking it, making it sing. So it involves both the choices for your building blocks – colors and textures and cuts for you your shoes, skirt, shirt, cardigan – and polishing it up with the appropriate accessories. Belts, scarves, brooches, earrings. The final level is hair, makeup, and overall grooming. Styling is what a stylist – like Rachel Zoe, pictured here – does professionally. Clothing is the medium, the stylist is the artist. Does that help?

  20. Lovers, Saints & Sailors

    What a brilliant post. I’ve been lucky enough to always be true to my personal style and in fact, work as a stylist. I am going to recommend this article to everyone that doubts whether they can be “that girl” that wears whatever she wants and gets away with it.
    Thanks so much Sal.