In the summer of 2016, I decided that there was no reason I should morosely look at my reflection every morning and wish that I could have an outfit I actually liked, because as an adult with an actual full time job, I could now (literally) afford to make that change happen.
For a change, this post has no photos of me but just has some related comics. They’re mostly embedded Instagram posts which don’t show up in the email, so if you’re reading from the mailing list, click on over to the website.
While I certainly don’t claim to have reached Peak Personal Style in my own wardrobe, in recent months I’ve felt like things have been settling down (in a good way! I don’t want to be thinking about my wardrobe this intensely forever, though I also don’t think there’s such a thing a totally finished closet for anyone who loves fashion as a mode of creative expression). I thought I’d do a write-up collecting a bunch of things I’ve found helpful to think about when doing a wardrobe overhaul, similar to the inaugural post on this site that collected everything I could think of related to wardrobe tracking.
Most of these points have been said already by many people, but these are the things that I’ve particularly taken to heart or found useful, and would have liked to have seen all in one place back when I was starting out. I hope it can be useful to you, but since you’re not me, don’t feel like you absolutely must do everything I mention here.
The Curated Closet: This is THE wardrobe overhaul book. It provides not just lots of practical tips but a clear-cut process and examples. You can get a sample of a lot of the content of the book on Anuschka Rees’ blog archive: https://anuschkarees.com/blog
/r/femalefashionadvice wardrobe overhaul guide: similar content to The Curated Closet, but it’s always nice to get a summary or a slightly different take. If you’re just exploring the idea of an overhaul or are short on time to read a whole book, I most recommend reading through the thread I linked to. I could happily copy and paste that entire thread into here, but I’m going to try and bring some additional info so I’m not just completely rehashing one thing. If you search the subreddit for “wardrobe overhaul” or “wardrobe journey” this topic comes up periodically and you can get even more perspectives in the comments.
Spark Joy: An Illustrated Master Class in Tidying Up: A big part of any wardrobe overhaul is going to be letting go of some stuff. I don’t recommend going hard and fast with purging your clothes, I found that thinking a bit about the philosophy of minimalism can help with this aspect. I personally liked the companion guide to Tidying Up better because it had more practical tips. If that isn’t your style, you may also want to have a search into “Swedish Death Cleaning”.
Fashion vocabulary: learn what particular styles and details are called so that when you become infatuated with a sweater on the attributionless black hole that is Pinterest, you can more effectively find something like it by searching for “shawl collar cardigan with patch pockets” instead of just “cardigan”. I really like Zoe Hong‘s fashion illustration videos for learning more vocab, but just searching google images for things like “types of collars infographic” or “types of boots infographic” will turn up a lot of quick references. Things can have multiple names, or illustrations can be wrong, so take that as you go. Another simple thing you can do is read the descriptions for clothing in online shops.
GOOGLE (or your search engine of choice). You can google it. You’re not stuck in Pinterest. So much wardrobe overhaul talk is centered on Pinterest I would sometimes forget that I could just google for fresh sources.
Approach with Intention
Set out with specific things you want to achieve. If all you decide is that you want your outfits to look “better” or getting dressed for all occasions to be “easier” without defining what “better” or “easier” is, you’ll never get there.
There are a lot of ways you can take your wardrobe. I find it helpful to identify a few things that I want your outfits to ideally make you feel like as well as some more practical aspects. You don’t have to write a whole thesis declaring your exact intentions, but you should be clear about where you want to end up. Some common things I’ve heard people express wishes to achieve are looking more put-together or intentional, professional, on-trend, confident, or be able to express a particular aesthetic they like.
Example: I want outfits to feel put-together but not fussy, and express a grunge style with southwestern influences.
Example: I want to feel professional but approachable, and have a sleek and and relatively androgynous style.
What do you do with this vague list of adjectives? Over time, you can identify specific styling details in outfits that inch you closer or further away from these feelings. But having something to keep in mind every day that is slightly more specific than “better” but not so soulless as “get my wardrobe down to 100 items” (not that everyone needs to go full minimalism, it’s just the easiest quantitative example). For example, you can notice that wearing more structured items makes you feel tougher and more confident and then look into incorporating a piece of structured outerwear (e.g. a denim jacket or blazer).
On the more logistical end, you might also set the goal to happily wear every item you own at least twice a month (when seasonally appropriate), get your wardrobe to fit comfortably in your closet/dresser space, be able to have a totally frictionless time choosing an outfit for work in the morning, or give yourself a wider variety of silhouettes and styles of clothes to work with.
Obviously, set a budget. Not much to be elaborated on there.
You can’t reach your goals if you burn out. Set limits for not just your budget, but how much time you want to spend on this. Since you get dressed every day and wear clothes most of the time, it’s possible this can become an all-consuming cloud over your head. I recommend treating it like a hobby or project. E.g. spend an extra five minutes in the morning logging what you wore and how you felt about it, and spend 1-2 hours on the weekend on larger things like physical closet organization or developing style inspiration boards. However much time you want to commit, try and stick to it but also don’t go over it.
You can also decide to only work on one aspect of your wardrobe overhaul at a time. You could decide to start with paring down your excess activewear and pajamas to start out with some more closet space to breathe in, or learning to put together sharper business casual outfits if that’s a really clear cut part of your wardrobe. You could decide to not actually buy or purge anything from you wardrobe initially but spend 1-2 months exploring different styles online and trying things on in stores to get a better feel for what you even like. There’s so much stuff you could want to work on, but you don’t have to overwhelm yourself with it.
Photograph your outfits
Taking photos is the most helpful thing even if you don’t share them publicly. It’s so much easier to evaluate outfits when viewing them from a photo later than trying to remember how you felt. They don’t need to be magazine quality photos, just clear enough to get a sense of how the items work with each other and your body.
If you only have the bandwidth to really do one thing in your quest for wardrobe happiness, I would absolutely recommend taking an outfit photo as often as you can and noting what you like and don’t like about it. This can be as simple as sorting outfit photos into “liked” and “didn’t like” albums on your phone, or more be involved, like having a private Instagram account where you can take advantage of the interface and add captions describing how you felt and sort things into saved collections while also having easy access to fashion inspiration. (As much as I like traditional blogs, I will admit that having inspiration and creation interfaces in the same app is much more convenient.) From there you can later look back for patterns of silhouettes, colors, and styling details that you liked and didn’t like, and modify what you wear and how you style it from there.
But if you’re down for more notes, track purchases and donations/things you sold! Doesn’t have to be super fancy, but I find that the goal isn’t just the acquisition of the items but being able to tune shopping behavior and process so I can generally evaluate whether a particular item makes sense for me. I like to note why I bought something and what my hopes are for it. When I get rid of something, I think if it fits a pattern with other things I’ve gotten rid of as to why I didn’t wear it. e.g. it’s a an uncomfortable fabric, it was hard to clean and keep neat, had some hard to style embellishment, etc.
Creating a comprehensive inventory and tracking item wears can also be very helpful but tbh not as much as seeing everything in actual outfits on your own body. I have a separate giant post on wardrobe tracking if you’re interested in trying that and figuring out what method is right for you.
Growth and Exploration
While ideally we would like to get from point A to B in our wardrobe as efficiently as possible, don’t expect that to happen super neatly. Treat everything as a learning experience, and don’t be afraid to think about or try out styles that may be a bit out of your comfort zone or your original goals if they pique your interest.
Don’t overfit to your goal. In particular, be wary of swinging too hard in a uniform/bland direction if one of your main goals is having a more cohesive wardrobe. I’ve heard of a few people other than myself who mentioned when they first did a wardrobe overhaul, they ended up with an aesthetically minimal look. Once they were comfortable with that they ended up doing a second overhaul which landed them in a more distinct style that felt more like them than a blank canvas. At the end of the day, you’re a person and not a fashion company’s Instagram brand, so you don’t need everything to fit neatly into one box.
Structure can help you, but acknowledge when the overhead isn’t helpful anymore. I was extremely into keeping track of my item wear counts when I first started out. I didn’t really have a sense of what my actual closet staples were, so having a couple months of data really helped illuminate that so I could make more informed choices when paring things out of my closet or thinking about adding more pieces. But after I had been doing that for a while and basically internalized the reasons that resulted in those numbers, I didn’t need to comb through wear counts in every category every month.
Besides your original plan (e.g. taking daily outfit photos and sitting down once a month to update some personal styling notes and shopping lists), try the occasional curation exercise or wardrobe challenge. Things like 10×10 or 30×30 challenges can be great for identifying things you could let go of or which are your real outfit staples, or simply encourage you to try new outfit combinations. Make up your own activities! They can be small or big. Try and make a few monochrome outfits, an outfit without black (or another color you wear constantly), an outfit inspired by some movie or book, or a new outfit with a pair of shoes you always style the same way. Pile all your clothes out and pretend you’re literally shopping for a new wardrobe from scratch from your own closet. Whatever you think might be helpful.
Have fun with it! This is a great privilege to explore the world of dress-up as an adult. Try on some stuff that you wouldn’t think you could wear. It might be fun, you might find a new type of item or a pairing that you like. Worst case you can laugh at how silly something turned out.
Take a look at what people are actually wearing. This might be other people in your area, or looking at real outfit of the day photos on Instagram. Don’t just judge on whether someone is wearing something you’d wear, but observe styling choices like pant cuffs or shirt tucks, or how different color and texture combos work.
Don’t feel like you need to have just one totally cohesive aesthetic all the time.
And don’t feel like you need to have variety if you find you’re happy to wear a limited range of color, silhouette, etc.
It’s dangerous to go alone
This is a major long-term project. It will be a lot better if you have some help and some moral support. Personally I’ve really enjoyed being able to participate in reddit.com/r/femalefashionadvice (“ffa”) and the small sphere of fashion Instagram (mostly reddit-based, but with a couple of people from the thrifting communities). Knowing you’re in this hobby / project with other people can make it a lot more fun and motivating. Most of the actually-a-person outfit diary accounts that I follow on Instagram are from the #redditffa hashtag.
It’s also just helpful to get feedback. Even though it’s a bit tired for me now, ffa is still the best forum for feedback that I’ve seen. I’m not talking the repetitive angst-piles in the top level posts, but rather the Daily Questions + WAYWT threads. You can usually get some solid feedback on specific questions and outfits in those. Instagram followers can also help if you ask directly for constructive criticism on a specific thing, but I think it’s harder to get engagement for CC. Most people are on IG to see feel-good photos, not to help you, whereas it’s in the name for ffa – female fashion advice. (If you’re a dude or identify with that typical style more, there’s also an r/malefashionadvice.)
Participating in WAYWT really entrenched the idea that developing a personal style and being able to put together fun outfits is something you can practice and improve at because I would see the same people in it week to week. Either I’d see them iterating on stuff or see examples of a distinct personal style from a real wardrobe.
Instagram: Follow people whose style you like. Follow people whose style and interaction with fashion you respect even if their outfits are not something you’d personally wear. Don’t feel bad about unfollowing anyone if they aren’t bringing anything educational or inspirational to your feed. Ask questions, leave supportive comments.
Misc Organization Tips
If you like having photos of all your items for inventory or outfit planning purposes but don’t actually want to take and edit photos of them, try and find the stock photos. If it’s too old to have stock photos out, you can always find something close enough.
Think about how you’re storing things. is there something you can do to encourage yourself to wear more things? Keep EVERYTHING out? Keep out a small selection on an instagram-worthy clothing rack each week?
Specifically with respect to an overhaul. There is lots of advice you could take into account for how to shop for quality clothes, clothes on a budget, shopping on particular platforms like Poshmark or Etsy.
Try things on! No matter how many photos you have pinned, you can’t know if you like it on you unless you put it on your body. Go “shopping” with no intent to buy anything, just try things on. Consignment stores can be a fun option for this since they tend to have slightly more variety than whatever the mall brands have decided is the current hotness.
Say it with me: THERE IS NO SUCH THING AS A COMPLETELY CLASSIC STYLE OR SILHOUETTE. Sure, with time and years of experience you may find your personal “classics”, but talking in the sense of “I want to buy something that will always be in style!” there is no such thing. There is a spectrum and some types of items will be slower to change, or rarely come off as ridiculous in the appropriate setting or a contemporary styling, but even things like basic crewneck t-shirt cuts and pants rises change. Don’t try to shop with the aim of having a future-proof style. Just go for stuff that you feel you like and will wear a lot now and could see yourself being into for at least a few years. Don’t try to predict whether people can still pry those high waisted jeggings / mom jeans / wide leg cropped pants out of your cold dead hands 20-30 years down the line. People are bad at this sort of planning generally. Don’t waste your effort and money. Have some fun now, but be reasonable about your consumption.
If it’s not a hell yes it’s a hell no. Do not let any new pieces into your precious personal space (and waste your money) if you aren’t even over the moon about them at the time you forked over the money for them. Exceptions can be made for cheap secondhand purchases made within budget for the purposes of experimenting with.
Don’t try to replace your whole wardrobe in a few weeks. You can’t know that it’s not a phase, it’s who I really am unless you’ve lived it for a while. Just because you’re infatuated with your mood board of 1940s femme fatales or streetwear gothninjas today doesn’t mean you still will be next season.
In a similar vein, strongly consider buying a trial version before an “investment” piece for non-replacement styles (except for certain designer pieces there is no such thing as a literal investment piece of clothing in the literal economic definition of the word). Adam Savage apparently has a philosophy about buying tools that I think works well with clothes too: buy the Harbor Freight version (it’s not garbage that will break after one use, but not an expertly-crafted-of-the-finest-materials-will-outlive-you sort of quality). If you find you use it enough that you actually wear out the tool, then you can get the best thing you can afford. If it’s the first time you’re trying to integrate a type of item into your wardrobe, especially if you’re new to having fashion as a hobby, it’s statistically not likely that this is indeed the keystone item for your wardrobe that you will wear to its death. You might find it doesn’t work as well down the line, or simply that you like wearing something else more. Don’t kick yourself later because you bought Jesse Kamm sailor pants or a Burberry trench coat but it turns out that you could never figure out how to wear it regularly.
Measure your favorite-fitting things to help with online shopping. Lots of stuff on ebay, poshmark, etsy lists flat measurements. If they didn’t specify, make sure to check whether the listed measurements mean “as measured flat” or “for someone with this size waist, but the actual measurement of the item has some extra clearance”
Keep an anti-wish list of details or types of items you know you should stay away from because you always end up regretting it. For example, tops with sleeves that can’t be pushed up, sweaters that need to be hand washed, unbreathable crepe fabric made of polyester, things that require a strapless bra to wear. Making a concrete and easily accessible list you can look at before checking out your cart can save you annoyance at yourself later.
Keep an “I wish” list, not just a wish list. As in, if you’re actually getting dressed and think “I wish I had thing. That would really make this outfit!”, write it down. It might be something as unglamorous as thicker socks for boots that are heavy or a hair too large, but if you find it popping up with some regularity that is probably a better candidate to actually get than something on your wish list that you came up with while brainstorming your ideal style but are not sure how you would actually style with your existing wardrobe.
Take photos and/or videos of everything before cutting the tag off. No exceptions! Try making multiple outfits with it. You might already try and think of a couple of items that the new thing would go with before you buy it, but it doesn’t always work out in practice! So check before cutting tags off.
That was quite the brain dump. I suppose I could sum it up with “Have a clear idea of what you want to get from the wardrobe overhaul, and then slowly and systematically work towards it. Personal fashion sense is a skill that can be learned. Don’t let it take over your life, and make sure you have some support from other people.” I’d love to hear your wardrobe overhaul stories or tips in the comments!