Building Your Style Through Basics

Why you should build your wardrobe using classic and basic pieces.

Once upon a time, an online makeover client came to me feeling a bit lost. She’d been an adventurous dresser in college, experimenting with punky/alternative looks and really embracing her quirkier side, but had fallen into a self-described Ann Taylor rut in recent years. She was bored of looking in the mirror and feeling bored with her clothes.

So we corresponded a bit, and she sent me links to tons of TOTALLY FANTASTIC dresses from Modcloth and Trashy Diva that were inspiring her at the time. Stuff with fun silhouettes and retro flair, gorgeous prints and fantastic detailing. I drooled over these dresses and skirts myself, and was excited for her to try ’em all.

But as we started working with her existing wardrobe – a marvelous stable of flattering basics in great colors and classic styles – something occurred to me. The Trashy Diva and Modcloth stuff was all SO fun … but she should probably hold off on buying really distinctive pieces for the time being. She was in the process of redefining her style in a huge way, and she had such a great foundation of basics already. I suggested she focus on recombining pieces she already owned – adding some really eye-catching accessories here and there – and figuring out more of what she wanted to look like before buying lots of vintage-inspired or super-stylized pieces.

I told her once she’d built up some confidence in her ability to create awesome outfits from simple items and could describe her personal style easily in, say, ten words or less, then she’d be ready to start buying zany shoes and vintage frocks. I felt like a bit of a troll saying, “No! No darling dresses for you! Stick to cardigans and belts until you’re older and wiser.” But the thing is, if you force yourself to recombine classic, basic items into fun new configurations, you build a skill set. If you splash out on five fab frocks that can only be worn ONE WAY, you’re relying on these items to be your style for you.

Transitional style is tough. You want definition and surety, so you reach out for things that radiate definition and surety. But when you’re still defining your own look, it can be more effective to use what you’ve got, embellish it a bit, and focus on remixing and reworking.

Images both via Trashy Diva, a great resource for the distinctive AND the classic, as it turns out!

**Disclosure: Actions you take from the hyperlinks within this blog post may yield commissions for alreadypretty.com. See Already Pretty’s disclosure statement for more details. Sustainable options are either used, handmade, made in the U.S., artisan made in non-sweatshop conditions, or made using sustainable/fair trade practices.

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  • La Historiadora de Moda

    Hmmm…. This is an interesting question. I tend to agree that it's best to work with what you've got until you feel confident in how your personal style has evolved. No reason to spend tons of money only to realize that it's not a good fit for your closet pre or post style shift. I wonder, though, if maybe your client would be willing to do 80% of what you have suggested and 20% thrift store shopping for those items that would help break her out of her Ann Taylor style rut…. Once she has more clearly defined her style, she can start buying more ModCloth dresses — and let's face it. Who doesn't want to buy more ModCloth dresses?!?!?!

  • adressandabike

    I completely agree! Back when I was going through my style transition from summer of 2007 to spring of 2009, I bought a couple of statement dresses and skirts… and guess what, I only wore them with that specific cardigan or this cream top. My skillset for combining clothes was limited and I often found I didn't wear these dresses and skirts. However I also bought a black pencil skirt and learned how to mix tops and cardigans with skirts using that more classic item, and then bought the denim and print skirts. I also pulled my statement velvet skirt and navy skirt back out and now wear them the entire time.

  • Eliza

    I agree that learning how to work your closet to get the most out of it is a good skill to learn. However, a couple well thought out purchases can really help. I updated my shoes, handbag and everyday jacket before I started to buy/replace much actual clothing. These pieces get a lot more use than a statement dress, because I still wear them every day with all my old clothing.

  • Musing Around

    Nice post. "Transitional style" is a tough one. Undergrad to grad school was a tough on my closet. Also, ModCloth has a bunch of summer/spring dresses on sale for $15 right now!

  • Second Skin

    As a full time thrifter, I know that having a closet of statement pieces can be very difficult if you don't have solid anchors: basics and classics. While the eye can be so drawn to and amused by prints and one of a kind shapes, what you say is true about only being able to wear them a certain way. So they sit for months at a time, waiting to be remixed for a new season. The items that get the most wear in my closet are my dark denim pencil skirts, classic coats, and plain scarves.

    I am very interested in this online makeover business. How long have you been doing it and how did you get started?

  • ranksubjugation

    Tough one. I agree that she can't go wild with the purchases until she has a better idea of what she wants to look like, but basics can only go so far. Without knowing HOW basic her wardrobe is, it's hard to say. Maybe she can start with inspiration boards of outfits she likes, attempt to recreate them, and make a note of any statement items that she feels really MAKE the look — a great vintage coat? Quirky shoes? Scarves? A cardi in retro colors? I know I couldn't create Modcloth-inspired looks without some quirky pieces.

  • issa

    ooh well i'd like to say i've always leaned towards more classic styles.. but lately in this fashion blogging realm it has really opened up my mind into trying lots of various trends.. but definitely spend the money on closet staples.. and spend way less on the trendy items

  • Sheila

    If you already have the basics, then yes, you need to know how to spark that outfit with accessories and such to make it "you". But if you've fallen into a rut with those basics and lost your inspiration along the way, then I think it's okay to grab a few dresses/skirts/vintage/retro items to spice up the mix.

    Maybe it's more of a combination, is what I'm saying. And both those dresses you've shown…wow, me want! And I could wear both of them tons of ways!

  • cwhf

    Interesting piece and philosophy. I admit I tend to find a great dress and build around it; a less creative approach granted but it works for me. If a dress fits me fabulously and looks great on, I tend to get it and work my style to it. It's harder to take a a more ordinary piece for me and make it exciting, but it is a challenge.

    I think I am going to take this piece as a challenge to work with my wardrobe basics. Definitely a good way to help you define your style I think. But a girl does love to shop.

    I have been drooling over trashy diva dresses for years. After I complete your challenge, maybe I'll treat myself.

  • Mardel

    Being in transition myself, I agree with you on this one. But an occasional statement piece is encouraging and helps. I'm doing this slowly, in bits and pieces, but you are completely right about learning how to use one's basics in new ways and then "graduating" on to new things.

  • futurelint

    Yeah, I guess accessories are the easiest way to punch up your style when you aren't sure what your style is… if she wants unique pieces, I would say to go thrifting! (disclaimer – I hate F21 and refuse to shop at all fast fashion places) Or go to a cheap place like that and hit up the clearance racks, they have all sorts of crazy patterned things and different shapes of garments she can try out without committing!

  • WendyB

    You definitely need basics. But you don't need all of them at once or in a row. You can mix in something more fabulous once in a while.

    I spent a lot of boring years in a sea of black thinking it was appropriate for everything. Sometimes it's more appropriate to stand out and be yourself instead of looking fungible.

  • Linda

    I have mixed feelings about this. On the one hand, learning to be more creative about combining and embellishing simple things is GREAT. On the other hand, falling in with fabulously creative dressers like you and Audi puts a certain amount of probably unnecessary pressure on a person, as much as I appreciate the inspiration. What you said about relying on inherently distinctive items to "be your style for you" reminds me of the complaint about Alice Waters's food, that it's "shopping, not cooking." But a delicious meal is a delicious meal, and a fabulous dress is a fabulous dress, and it's not so wrong to just wear it without further ado. Now I have lost my innocence and struggle with feeling guiltily lazy that I haven't thought of five things to do with it that the designer never imagined.

  • evanadine

    it sounds like she at least has an idea of the direction where she wants to go. given that, i think purchasing a few inexpensive statement pieces may be helpful for getting her creative juices flowing — provided she still follows your assignment to find new ways to reuse and incorporate the pieces she already has. sometimes you just need a little newness to get the initial spark going.

    for those who havent pinned down their style, though, spending more money doesnt seem like the right answer. you could buy a really fabulous dress that you decide in the end isnt the style youre striving for anyway. then it is a waste of money.

    thrifting helps me define and redefine my look on a regular basis. i dont think i have one singular personal style, and that can make shopping difficult for me. but by hitting the thrift stores, i can kill 2 birds with one stone: (1) find unique pieces that have some personality, and (2) not spend an arm and leg while "finding myself"

  • The Cake Decorator’s Daughter

    Really interesting post.

  • J.

    I'm definitely in a transition, slowly parsing out my jeans – but since she likes dresses, perhaps she should buy maybe one or two dresses that she can actually mix up?

    For example, I actually realized that I didn't own many dresses or skirts in my closet, but I wasn't quite sure how to get a more sophisticated look with the few that I already did. I invested in a lovely navy blue Ann Taylor dress that I've been playing with. So far, I've tucked it into my jeans to make it blousy, put a cardigan and belt over it, put a cardigan and scarf over it, put a t-shirt and scarf over it, etc.

  • Christina F.

    Very interesting post! I'm also in a fashion transition period and I think the advice you gave your client made sense. I have lots of basics and I take outfits to the next level primarily with accessories. It's too easy to go in a new direction and then regret it later, if you're still trying to figure out what style works for you. Some time ago I followed your advice and started a "look book" (binder). I have a section for styles that I'd like to try. Mulling it over for a bit is easier on the budget vs. jumping right in, at least for me. I haven't thrifted since high school and I hate buying inexpensive (disposable?) clothing — even accessories — but I do think it's possible to shop at off-price stores such as TJ Maxx to experiment on different looks and often the styles are current, and the quality is good, if not great.

  • Diana

    I agree with you. I think it's best to spend time defining a personal style first. Otherwise, one might shell out for some gorgeous dresses only to realize that they don't fit in with one's aesthetic. Thrifting can be a good way to experiment with new looks without investing a lot, so maybe your client could try that.

  • Laine & Jesse

    Sometimes, a statement piece can get you through a blah day. Transitioning can be overwhelming but having a couple of pieces that you can count on to be easy and make you feel good seems likely to do more good than harm. -Is someone in transition mode up to remixing and reworking every single day? A break to be able to put something awesome on without having to invest too much effort can instill that confidence needed to continue experimenting with and developing personal style. I think it is a great idea to make a couple of purchases in the early stages because they set the tone that change and new thinking are underway. I definitely would limit early purchases but I think they are necessary for one to see instant results that will help inspire further growth.

  • A-C

    I agree with your advice. As someone who is essentially in a year long transition, I have to tackle the transition between law school and lawyer. In order to do this I've been extra creative trying to figure out whats conservative/dressy enough for work and what's not. Figuring out boundaries with your already existing wardrobe is a great way to start. Once you know where you are, then you'll be able to define where you're going.

  • A-C

    Also, I really want that black dress. GORGEOUS!

  • The Closet of Kim (ShopKim)

    I think it's absolutely important to be able to work with what you have. Like you say, it's about learning a skill and figuring out more what kind of style she wants to have. Once that becomes more clear, then any money she will spend on additional pieces will make a lot more sense. Of course to really start changing your style you do need to spend some money on getting a few new pieces. It's hard to completely work with what you have and come up with all new ideas. One or new pieces every so often can really ramp up the creativity.

  • orchidsinbuttonholes

    This is such a great post that speaks to me.

    I feel like I'm at the tail end of transition, which is why I'm not shopping right now because I want to really think about what I already have and what I don't have and how it all goes together (or doesn't). I think, when I return, I will infuse my closet (which is still basic/classic-heavy) with a few interesting pieces that really speak to me, and I believe more of these will be vintage than not.

    So I agree with your advice, and I think, too, that if your client decides to buy some things to mix it up, she might want to do so sparingly, to see how even a small dose of creativity and individualism goes a long, long way in a closet full of classics and basics. It'll save her time and money in the long run, and also might give her much more confidence in what she already has.

  • Julie

    Thank you for this….I've been trying to transition for months between Younger Punky Wild College Coed and Grownup Sexy Basic College Coed and usually I just find myself SO frustrated that I want to leave the house naked.

    So, thank you for this. Really.

  • a cat of impossible colour

    I'd probably give the same advice if I was helping someone else … but I also love this quote from Madame Dariaux's book, 'Elegance', and find that it applies to me.

    " Each time that I have bought something because it was a sensible purchase, I have worn it very little; whereas my irresistible impulses, which seemed sheer folly at the time, have usually been amortized very rapidly."

  • rb

    I agree on the limited usefulness of these distinctive pieces, but maybe one per season is OK. (I count two seasons per year but I guess it depends on where you live.)

  • jesse.anne.o

    I just wrote a response and the stupid word verification pop-up wiped it. Hello annoying!

    Anyway, I do remember when I was transitioning out of very basic, boring work-appropriate stuff I'd purchased for a business-y job. While I was able to pull that stuff back into my wardrobe eventually, I really needed the distance from it in order to get creative with it.

    I really hated that stuff and being forced to "reimage" it without injecting any new life/inspiration to keep on truckin' would have been hard.

  • Jingle Bella

    I agree with Laine & Jesse that sometimes a statement piece can make you feel all pulled-together and stylish and confident. Sure, buying 10 statement dresses is probably a bad idea, and definitely, learning to work with what you've got is great.

    But being able to pull on something amazing that makes your heart sing – even if you always wear it exactly the same way with the same black boots and the same jacket – that can help you keep from being discouraged by having to put lots of work into planning every outfit.

    Remixing is neat, but it doesn't always work out the way you thought it would in your head, and I think it's a wonderful thing to have a couple of outfits that you just know look fabulous and make a statement and you can go to if that's what you want.

    (Also: I love the first dress in the picture. And if I owned them both I would get more wear out of the leopard print one, for sure. The black may be dressy and versatile, but it's just not me (and wouldn't work with my figure so well) whereas the leopard one calls to me …)

  • akabini

    Two thoughts on this:
    1) I found a 'vision board' to be deeply helpful as I transition from Frumpy-Fleecy-Pseudo-Hippie to Sleek-and-Stylish-Fashion-Maven! My personal vision board pointed out some things I hadn't been conscious of, namely that I really really need a big orange knit scarf, and that deep down I want to be a brunette.
    (Latter accomplished; former being knit as we speak.)

    2) The other context for transitional wardrobes is, of course, weight loss or general body shift. I took a page from a friend who recently dropped a lot of weight: shop for fun, transitional items in thrift!

    So perhaps one way to work out your wardrobe transition jones could be to grab an image of what you'd love from the boutiques, and see if you can't thrift it? So if it doesn't become a wardrobe workhorse, you're not weeping over your bank statement?

    My green velvet blazer and orange cowboy boots salute you all and the voyage to new fashion horizons!

  • lisa

    I think you've given a sound piece of advice, Sal. Experimenting with basics and quirkier accessories before taking the plunge and buying statement dresses is a wise decision. I find that when I buy unique dresses, these garments prove to be double-edged swords: they're so fabulous that they stand well on their own and are easy to throw on, but unless I try to style them differently they'll look the same every time I wear them. And then it's back to square one, albeit in a different sort of rut this time. 😛

  • Imogen Lamport, AICI CIP

    I like to have a few distincitive pieces, but things that will work with the basics. So rather than a dress, which is an outfit in itself, a distinctive jacket, that can be worn with jeans, or pants or a skirt.

    A fun skirt that you can put your more basic tops with.

    Great shoes that make an otherwise basic outfit sing.

    Gorgeous unique jewellery.

  • Charlotte

    Oh Wendy B., "fungible" is a word that isn't used half often enough, but it's so right.
    Sal, your advice makes a lot of sense. Make sure she also sees your video on using a dress on top of other items–this way she'll come to see it more as another "separate" than as some poor little isolated piece that has to stay home while everyone else gets to mix it up and party.

  • Audi

    I'd say your advice was sound; I went through a phase many years ago where I bought a bunch of stuff that I ended up not knowing what to do with, and sadly I got rid of some of it before I'd really worked it out. I'd say that when she does add new stuff, she should start with a few things that are fun but also have potential to work with her existing wardrobe. It's no fun buying a fantastic new dress if you don't even have one pair of shoes to go with it.

  • dandra

    I agree Sal. Basics are great to build on. Styling and accessorizing are key to making those basics your own.

  • Beatrice

    I have this exact LBD by Trashy Diva; I bought when it first came out, and I am in love with it! I did not even need anything like Spanx underneath because the fabric is a thick construction and it has a slight stretch. Oh, and here is what sealed the deal: The figure it gives me!!! It makes me look like I just stepped out of the film La Dolce Vita! Definately a head-turner dress. My husband calls it the aaa-OOOgah! dress.

  • Cedar

    I feel like this post is especially appropriate for me as I go through a style revision. I'm trying not to thirft two skirts and a pair of pants yesterday, but that's it), but I have been buying more accessories lately, including belts, a scarf, some jewelry and the like, which I feel like have been a big help, and even helped me wear some things in my closet that I haven't worn before.

    I'm also buying more shoes. I don't really own that many (and I own too many that don't fit–they have been purged!), and I feel like my shoe collection was keeping me from wearing certain items. For example, I have two brown skirts, and a brown dress, but never wore them because I didn't really have any shoes that looked appropriate with them.

  • Anonymous

    There's a lot to be said for playing with your existing wardrobe, but I think adding somethinng new ups the excitement level and helps to put familiar old clothes in a completely different light.
    I'm expanding my wardrobe right now as a prelude to possibly discovering my style. I didn't have much to begin with that wasn't old and ratty so I started simply by adding a few classic pieces plus some camisoles in neutral colours, tights, boots and a couple of print dresses. Then I got some much more adventurous handbags (COLOURS!) and scarfs (MORE COLOURS), some statement jewellery (necklaces, rings) and began to really experiment.
    The basic clothes have given me a comfort base to start with and lots of mixing options, and the new accessories have allowed me to play with new styles and colours that I'm attracted to without getting in over my head. I love this combo so much that I'm beginning to think this might just be my look: classic neutrals with great accessories.

  • Jen

    Put your resources toward accessories and shoes and bags that you think reflect the look you're going for and pair them with your basics for now. Then, you can branch out into clothes once you know what you want.

  • Vix

    I tend to fall into the "please god not the 'ONLY accessorize the same plain old basics'" camp as long as the person in question is either:

    –adding low-cost items
    –good-to-go as far as understanding how she wants to dress her particular body shape and what colors are good-to-amazing on her

    In other words if budget is an issue I don't think one should run around purchasing non-basics that appeal but don't flatter. Yes, I'm a killjoy.

    I also don't think it's an either/or. Granted, a dress may be less useful. Not that I'm against buying one just for the pullled-together-and-feel-fabulous aspect, and Trashy Diva items can certainly make a women feel that way!

    But as others have mentioned–and if she has any sense of what appeals to her, which the client in question does–why not up the classics by adding a separate with some real impact and flair? Most women have at least a few style personalities, so even if the piece ends up not being her dominant style she can probably integrate it.

    I mean I started moving away from the funeral-appropriate look by adding bold jewelry vs bolder clothing, but that's because I'm a wuss.

    This year I did yet MORE navel-gazing and took a small plunge into color-color plus texture and/or pattern, and I'm amazed by how much happiness 5 still-relatively-low-key items can bring, ha. So it makes me kind of sad to think of the client being kept apart from Li'l Leopard.

    ps And I still wear all the jewelry, because it was bought out of lust vs a desperate hope it would help things.

  • Rebekah

    That redhead on the Trashy Diva site is my little sister! Totally different faces and bodies, but definitely the same gene pool.

    Had to tell someone. =)

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