Fixing “I have nothing to wear!” Having go-to outfits for every occasion

When starting out doing a wardrobe overhaul, one of the main exercises recommended by Anuschka Rees’ book The Curated Closet is to sit down and list out all the activities you do in a typical month and how often you do them, to figure out what proportion of clothes you should ideally have in each type of category. i.e., don’t buy a whole month’s worth of fun weekend clothes if you only go-out go out once a month and aren’t the type of person to wear a dress out for a grocery run.

I think a related exercise could be used to help reduce the number of “I have nothing to wear today!” days. Since most of the time if you start a wardrobe improvement kick you aren’t totally starting from scratch, attempting to create a set of bookmarked looks that you can pick from on days when you just can’t even in the morning can more concretely show you potential holes in your wardrobe or particular categories of clothing that are already well-stocked. The point here is to have a few outfits for each category, not just one (I’m assuming you’re not going for the “personal uniform” strategy if you’re reading this) because that will help you get a better sense of how your pieces can combine and work across outfits.

For example, you might be able to easily come up with a handful of outfits you like that suit a category, but then notice that all of them use the same top. What if that top is in the laundry because you spilled spaghetti on it yesterday? Do you have any other tops that you could swap in that you’d be equally happy to wear? If not, then it’s probably a good idea to spend some time coming up with and trying on outfits that could work for that niche with your other tops. Often you might find an underutilized piece that works wonderfully for this category. But if you conclude that you really do only have one top that works for that activity, then consider buying another piece. It doesn’t even have to be a totally different one if you’re happy to wear similar outfits!

Coming up with categories

If you do this, your category list might look different! These are the categories I decided to list outfits for:

  • office-friendly: I work in a tech startup without a dress code so my personal definition of this is just “some vague direction of modesty and put-together-ness and not dressing so loudly and distinctly that your outfits are louder than your work”. This is of course a whole can of worms and can be many discussion threads by itself,  but I don’t want to become known as “that { goth/punk/twee/1970s style } girl” or “that girl who always wears tulle skirts” even if there is no malice attached to such labels in anyone’s head.
  • casual weekend: Can be more slouchy and show more skin than office outfits
  • going out / feeling extra: stuff that’s a little louder than I’d wear for the office
  • formal: Not merely extra, but for something like going to watch a ballet or attending a wedding
  • feeling blah or sick: this is different from casual weekend in that comfort is the number one priority, and tends more towards things that won’t draw attention

One of the more thought-provoking threads I’ve read on /r/femalefashionadvice pointed out that a lot of the time, “I have nothing to wear today” is short for “I have nothing to wear for who I want to be today”. If you find you regularly like to wear fairly disparate styles, it can be worth adding aesthetic as a dimension in your category matrix.

For each category, I also make sure to include outfits that work in cooler weather and warmer weather. I work in SF and I live in the East Bay so weather isn’t much of an issue for me (the temperature is between 45F and 75F 90% of the year), but combos that work in sticky humid weather or snow should also be on your lists (in appropriate proportions) if you live in a true four-season climate. In my case, I’m going to add all-purpose activity but weather-specific categories for

  • rain
  • actually cold

because these types of weather don’t come up often enough that I think it makes sense to add them as a dimension to the activity-based categories, but I’d still like to make sure I have outfits for them. Otherwise, I’m just going to make sure that about half the outfits in any given category include boots. In SF, the typical strategy is to wear layers the whole year and the only real weather-spurred change is swapping from flats/sandals to boots (or maybe throwing on a thermal layer which doesn’t affect the visible outfit).

Please note, for TRULY ADVERSE weather, your priority should definitely be getting all the practical elements right and you should think of style within the range of what is suitable for surviving that weather. So “cute outfit” for -10F and windy should be an entirely different ballpark than cute for 30F. There’s a great guide on Not Freezing to Death on r/femalefashionadvice that I recommend if you’re going somewhere actually cold for the firs time and want some advice. It’s a little old, but the general principles still stand.

Sarah’s Scribbles comic

At this point if you’ve decided you have 4 activities, 3 types of weather, and 3 styles, and want to come up with 3 outfits for each, that’s 108 outfits! Which is kind of a ridiculous amount of outfits to come up with especially if you’re visual and want to include a photo or collage for each. To that end, I’d recommend keeping aesthetics in mind but not aiming to fill out each one. The whole “finding your aesthetic(s)” thing is a whole other set of posts so I won’t be going over that aspect much here.


And now to follow, what would be an embarrassing number of photos of myself if I hadn’t desensitized myself and fully embraced the instagram-everything life. It’s a lot of navel-gazing but that is the tagline of this blog. I’ve had most of these outfits tagged as “favorites” in my Airtable base for a while, but the impetus for this post was deciding to make a literal reference page with more specific categories so I don’t even need to scroll back and forth waffling through those on days when I don’t have time or have given up after exhausting my getting-ready energy trying to make a newer more experimental combo (something that’s happened a few times this week).

As always, these aren’t meant as an “ITEMS EVERY WOMAN SHOULD HAVE IN THEIR WARDROBE” type post, but as an example of seeing this done with an actual person’s wardrobe.

A lot of the outfits could definitely work in more than one category, and I’m not limiting myself to wear them only in those categories even if I felt they are a good example for one. I also obviously have a lot more outfits than shown which are suitable for each category, but I tried to pick some that I particularly like to wear but include some variety (again, for times when the favorite sweater or whatever is in the laundry).

I found it interesting to see which pieces popped up across multiple categories. This isn’t a how-to-shop-for-individual-pieces post, but at the end when thinking about pieces you might want to buy to fill holes, it’s definitely a good idea to consider filling those niches with fewer items that can work in multiple categories.

There is an inconsistency on captions being attached to photos because the WordPress editor is hot garbage and about half the time would crash when I attempted to add a caption


For any of these outfits that don’t include outerwear, I would usually wear these with a softshell or puffer jacket over for commuting. I just don’t have the closet space for a large coat wardrobe so I’ve made peace with mostly wearing the same dependable boring jackets for the 20 minutes I’m actually outside on weekdays. In the same vein, I always use a basic black laptop backpack and not a purse, though some of these photos were taken on weekends or days when I used a purse in the evening.

Like many people, I spend most of my waking time at an office. Most of my clothes fit into this category.

Not boots outfits:


Old Navy scoop neck tee
Uniqlo cotton-linen trousers
MIA clogs
Madewell purse


Old Navy cotton cable-knit cardigan (Goodwill)
Uniqlo cotton-linen trousers
Birkenstock Mayari sandals


Banana Republic trench coat (Goodwill, had the sleeves taken up)
Madewell “Perfect Vintage Jean”
MIA clogs
Madewell Zip Top Transport Crossbody purse

New Look petites pleather moto jacket, Old Navy rayon scoop neck tee, Uniqlo cotton linen pants (ebay), Birkenstock Mayari sandals, Madewell zip top transport crossbody bag

Boots outfits:

2019-06-13 and 2019-05-21 // Anthropologie square neck top, Topshop wide wale corduroy trousers, Marc Fisher patent leather lace-up boots


Uniqlo U cotton smock dress (consignment)
Amazon (Vero Monte) art deco fishnet tights
Marc Fisher patent leather lace-up boots
Topshop snake buckle purse


Madewell cotton blouson sleeve sweater
Forever 21 pleather A-line midi skirt
Steve Madden boots

Casual weekend



Uniqlo U fleece bomber jacket (ebay)
Athleta leggings
Dr Martens boots


College sweatshirt
Ralph Lauren coatigan (ebay)
Anthropologie embroidered joggers
Dr Martens boots
LL Bean hat



Anthropologie eyelet blouse
Madewell jeans
Birkenstock Mayari sandals


BP (Nordstrom brand) linen cami with rouleau buttons
H&M straw tote
Uniqlo x Ines de la Fressange cotton midi skirt
Birkenstock Mayari sandals


San Diego Hat Co straw hat
Urban Outfitters peter pan collar shirtdress
H&M tote
Birkenstock Mayari sandals

Going Out / Feeling Extra


(pile on more scarf, hat, thermal tights if it’s actually cold)


Forever 21 coat (knockoff of All Saints “Monument” Coat) with sleeves hemmed
Halogen (Nordstrom) cashmere blouson sleeve cardigan
Marc Fisher boots
ASOS petites jeans
Madewell velvet camisole


Again, sub out for thermal base layer if actually cold

Brixton beret
Everlane generic-ass sweater (consignment)
New Look petites pleather mini skirt (hemmed)
Amazon (Vero Monte) herringbone fishnet tights
Dr Martens x Hieronymus Bosch boots

I have a couple of variations on this outfit formula of tall boots + midi skirt. I’ll often start with the same base outfit I could wear to work but then bump up the accessories.


2019-06-01 // New Look petites jacket, H&M off the shoulder blouse, Uniqlo x IDLF corduroy button-front midi skirt, Free People x Jeffrey Campbell “Joe” boots (Poshmark), Topshop snake buckle purse



San Diego Hat Co Hat
H&M peasant blouse
ASOS petites denim shorts
Dr Martens


All Saints “Mayur” top
ASOS petites trousers
Anthropologie purse
Birkenstock Mayari sandals

Feeling blah

I usually want to wear a comfortable and non-fussy sweater when I’m feeling sick or just really blah (difficult mental days, whatever that might mean for you). I’d probably always stick to jeans here if I had to go to work, but I do have two pairs of these light wash jeans (which I don’t usually wear every day) so the laundry thing isn’t an issue. If I am so ill that I can’t tolerate jeans, then I would probably just be home wearing pajamas. I’ve found that I do feel a little better knowing that I don’t look like a wreck even if I’m feeling like it if I have to go outside.

I didn’t own blue jeans for a few years but getting a style with a more on-trend cut and wash has been great for the “fuck it, just jeans and t-shirt/sweater today” days.


Athleta sweater
Madewell jeans
Birkenstocks (a staple shoe for me, clearly)


Sometimes you just embrace the stereotypical uniform.

vintage programming tee (Quotron, via ebay)
same jeans
New Balance sneakers


I made this a separate category from “feeling extra” because I historically have had trouble coming up with outfits that are Truly Fancy. I grew up in a family/town where people would wear flip flops anywhere and I didn’t really know how fabrics played a part in formality.

If you hardly ever go somewhere formal it’s totally fine to just have one outfit you always wear when the occasion does pop up! I like to have a few options here because I’ve somehow managed to work myself into a lifestyle where I watch multiple shows each season at the SF Ballet and I enjoy having different outfits for those, and a lot of pieces I could work into outfits that pass the local bar for “formal” I can wear at work or any old weekend.


I’m often overdressed for casual weekend errands and I would totally wear this top + bottom with clogs or boots to the grocery store, but formal accessories can bring it up a notch.

H&M skirt and top
Nine West sandals (these are terrible quality, the leather started peeling from the sole after two wears. I wouldn’t recommend them but they’re not so bad that I would throw them out myself yet)

Moto jackets are definitely not black-tie formal but it works for going to some artsy fancy event in SF


This lace-back godet dress could be my go-to for any formal (but not like, fundraiser gala floor length gown formal, but I don’t live that kind of life and would probably do rent the runway if I ever needed that) event. I don’t have a better photo with just the dress but it’s just a plain crew neck style on the top front.

ASOS petites dress
New Look petites faux leather moto jacket
Franco Sarto pumps


Same outfit as the Going Out section but upgrade the jeans to a skirt (Forever 21)


This is probably the weakest category for me. I’ve had a more aesthetically versatile (i.e. longer and not gray) raincoat on my wishlist for ages but I haven’t found the right one yet. It’s still not a huge priority though because rain is one of those things that’s just sort of changes my frame of reference for what’s cute in terms of outerwear. It rains often enough here and usually for several days in a row that I usually get sick of wearing docs with black jeans and a fitted top.

(pretend this outfit has the raincoat instead of the wool coat)

Uniqlo heattech extra warm thermal as a top // ASOS petite jeans // Dr Martens 1460 boots

This is basically my one Rainy but Make It Cute outfit.

Madewell sweater // Patagonia jacket // H&M x Morris&Co pants, Born boots

Actually Freezing

What I wear if I’m visiting Boston or NYC and it’s Actually Cold (i.e. below freezing) but not Deathly Cold (e.g. Antarctica; Deep Freeze Wisconsin). Since I don’t live there I find that I’m totally fine rotating through the same two white sweaters and black bottoms with 2-3 scarf and hat options.


This would have either a puffer or the wool coat below stuffed over it as well as gloves.

LL Bean sweater
Steve Madden scarf
LL Bean hat
Uniqlo pants (hemmed)
Marc Fisher boots
thermal shirt and leggings


Concluding Thoughts

I found that I had no trouble coming up with outfits for work or typical weekend activities. On that end, I spent some time thinking about what didn’t make an appearance in this collection of outfits because I could definitely see myself just repeating endless minor variations of everything here and being set for years. The two categories that stood out to me are the fancy docs that I recently dropped a lot of money on, and my collection of vintage graphic tees.

Traditionally I’ve just worn a nondescript fitted look with black docs or That Printed Pants Outfit every time it rains. I own three pairs of docs now and while they are newer, I think the reason they don’t appear much here is because they’re so busy that I find them easiest to style in outfits with tights and a shorter skirt or dress. (e.g. in the outfit with the fleece bomber jacket in the “Going Out” section. I’ve tried using them in outfits once or twice a week but I always end up going with other shoes with pants or longer skirts.) The only mini skirt I have doesn’t really work for the office, but I can see one or two slightly more modest denim or twill or corduroy mini allowing me to bring those into rotation and make some more colorful outfits.

I think that would also help me wear more of my vintage t-shirts. Most of them are a very oversized fit on me so I found that I feel pretty schlubby when I wear them just with jeans. I had a Stranger Things inspired look I did recently that made me realize a mini skirt and jacket and docs or sneakers+socks is an outfit formula I particularly like with tees. So getting 1-2 mini skirts would help glue these items into regular rotation. I can certainly wear them now, but if it’s always easier to reach for one of the looks here, then in practice I don’t wear anything else as much as I could/should.

It’s not a “Camp Know Where” shirt but it is (as far as I can tell anyway) an actual 1980s computer nerd kid shirt. Getting this skirt hemmed made me like it aesthetically a lot more with casual rounder shoes, but the flip side is that it is now too short for the office.

But overall I guess I’m pretty set. There’s always some weirdly specific occasion that will be perplexing to make an outfit for, but I think my current wardrobe does a pretty good job covering all my bases. Anecdotally, unless I’m trying to figure out a new-to-me type of item, I can pretty much always make an outfit that feels like me and is appropriate for whatever the day is throwing at me. The last frustration I have with my wardrobe has been not wearing my stuff equally easily, and going through this exercise helped get my sartorial analysis brain juices going.

What activities or weather do you find it difficult to make outfits for? Do you have any neglected categories of items?


  1. Love the rain and cold outfits!!

    Neglected items: shoes. Well, rather, I own many but strictly wear the same old pair of trainers. But I’m not wearing my wall hangings out, either, which is how I rationalise it. Some art is static. It only appears to be several items of unworn shoes, but it’s not. Sometimes you gotta have something to look at that’s beautiful.

    Liked by 1 person

    1. There are a lot of shoes that could definitely qualify as art! I love open shoe displays because it feels like a shoe art gallery, but since you can see everything it also can remind you to wear things more often. I’ve been trying to put my shoes back on the shelves facing outwards because it’s nicer to look at. But I’m also coming to the realization that I probably shouldn’t buy any more heeled shoes because in recent months I’ve been neglecting half my shoe collection because my calves are always sore from something or another.


  2. I have mostly the same categories with the exception of never having been anywhere below freezing, so just ‘work/casual/casual extra/actually fancy/rain/cold-to-me.’ Casual and casual extra used to be challenging to me, but I upped my casual game and changed the styling on some work pieces to make them feel more casual-friendly.

    Rain is also my weakest section because a number of my shoes have leather soles, are light-colored leather, or otherwise inappropriate for rain, so I have an extremely limited shoe selection in the rain. My palette is very dark – black, navy, maybe a colorful top. I avoid light colors because I don’t want undergarments showing through if I get soaked. I’m really over it but I’m not wearing light linen pants on a rainy day.

    I’ve been thinking any shoes I want to buy in the future must be wearable in the rain, because I am sick of rotating between rain boots and rain sneakers. It rains often enough that I should have more than two pairs of waterproof shoes, but I am a sucker for lighter leathers and most rain shoes are uncomfortable and don’t fit my high-volume feet. I grew up in a culture where people didn’t wear rain boots, so I spent years not prioritizing them.

    I tried embracing a techwear thing in the rain with like, DWR pants and DWR shirts and a rain jacket that doesn’t look awful, but techwear gets expensive quick and wearing the same black coat with the same navy pants and same black shoes really put me in the fashion doldrums. The pants and shirts are frankly just my vanity and me enjoying stunting on people by walking in the rain and having water bead off, but the shoes are a real problem because twice I have worn non-rain shoes in the rain (with umbrella) and gotten them totally soaked. Non-black rain shoes that are comfortable will probably be on next year’s extremely limited shoe list.

    Liked by 1 person

    1. Rain is so tough! I feel like it seems even harder than snow, because since it isn’t as extreme it feels like you ought to be able to come up with outfits suitable for it more easily. 🙈 Since I write this post I actually ended up getting rid of the pair of taupe boots I’m wearing in the one cute rain outfit here. I’m hoping to get my louder docs into heavier rotation in the next rainy season so at least I’m not stuck with solid black.

      The full-on techwear sounds pretty sick, but I can see that getting boring after a while. A few people at my office who bike just straight up bring a whole change of clothes and have beater shoes for a rain commute.


  3. I know this is an old post but as fall is approaching…I recommend Sorrel waterproof boots for rain. I have two pairs of Moto boots and they are very comfortable and warm, and so far (only one year) dry. A lot of people also like Blondo, though I didn’t think the quality was as good. Aquatalia is great if you can find it for a reasonable price. TJ Maxx has a bunch of waterproof boots right now, and you can find some good deals on amazon if you make sure you get free returns.

    Love your styles.


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