How many outfits do you wear in a day? It turns out that I’m liable to change up to 4 times on a regular day.

It starts in the morning when I take my kids to school — this is after the chaotic parade of getting them dressed and fed has taken place, with either an outfit I’d wear to go for a run (recently flare leggings and two layers of sweater with these running sneakers which I looped red laces into), or something that looks like pajamas but is not actually pajamas. It has a bit more point of view (this is by design):

This impulse is definitely inspired by What do Moms Really Wear veterans such as Paz Friedman and Nurit Quinters who look cool when they drop off their kids, and these outfits in partic — the ones I put on to wear for the very specific purpose of morning shuttling are some of my favorite.

I touched on this in last summer’s story on the concept of “in-between dressing” (that thing where you’re not dressed, not not dressed either) but the basic gist on why is that the outfits never become anything. They’re the same as “coffee clothes” (what you put on to go out and grab coffee, with the expectation that you want to convey something about your style, even then).

They never take on such a solid or rigid identity which makes the clothes that comprise the looks feel more fluid and there is a sort of freedom in that, less pressure or commitment, you know? Plus mornings with kids are hectic as they are, so there’s something here about what you turn to to wear when there’s limited room to think about it even though you do care what you look like.

After I get home most mornings (post-coffee, which I order to-stay at a shop across the street from their school), I either work from home until I have to leave again for mom stuff (so pick up or a quotidian errand) or work stuff (like a lunch meeting or showroom appointment or whatever). The guardrails of time are more flimsy for mom stuff — more buffers than they are fixed appointments, so I usually don’t change until the very last min, which is when I put on something I’d wear on a weekend:

It’s something so simple I don’t have to try it on to know if I like how it looks — like a trusted grey t-shirt and jeans, but with a personality coat (accent of whimsy).

Getting dressed is sort of like a moving meditation for me where I try things on and then take them off until all the elements feel right together, so it’s helpful when I don’t have to try it on because if I’m dressing for a weekend or an orchestra of events (quotidian errands) that precede another event (school pick-up); one that is solitary (with less urgent desire to convey point of view while errand-running) vs. one that is social (the moms are my peers!), I’m considering several settings I want to be dressed for this one outfit.

Such variables include questions like: Is this appropriate for the environments I’m dressing for? Do I feel confident in it?

Then the coat does all the lifting to make the broader-whole look interesting, more extraordinary than a grey tee and jeans. The one I’m wearing is, I think, the best thing I got this year, but if its impossible for you to consider, this one does, in its own less fanciful way, kind of come close.

You can achieve this with more flexibility even if you don’t have a dramatic coat by emphasizing flair in your cold-weather accessories (hat, sunglasses, bag, earrings etc).

If on the other hand I’m going to do something work-related, I look more capital-D-Dressed, but not that much more capital-D-Dressed, like this:

This basic formula with pants and a sweater is as simple as what motivates the look above but the actual variables have more going on. So it doesn’t take much more thought/moving meditating to combine a look like this, but there is def a bit more puzzle-piecing together with the prints and the materials and the colors and what kind of bag to include.

In this instance, I was playing off the snake print leather pants which I considered the anchor of the look and worked around it.

The easiest way to figure out how to be creative around a pair of pants like these is to consider them a neutral like jeans even though they’re not one. It gives you more creative license and confidence to pair unlikely counterparts, focusing on how to create subtle contrasts vs. those that are too slapstick.

(A example of slapstick would be like, a supple suede fringe jacket to clash with the rigid leather pants.) The printed blue sweater makes sense because of the grey knit patch on the cow. First thought with shoes here was: go soft, so I chose a pair in this glove-ish shape. Moccasins def work too.

Per the “glove shape” reference, shoes with a higher vamp (top of shoe) are good with pants that hit at the center of the top of the foot. Ballet flats can look a bit awkward if the vamp is too low and a classic loafer might be too obvious. A suede boot (same ones as the linked on sale here in black) could work too. So would sandals with socks if you dare.

To this point, one more pared back equivalent of the above outfit:

The pearls (wait, look at these too) and the bag say, “Trust me, I’m responsible,” while the slightly awkward shape on the pants and flimsiness of the cozy sweater are more like, “But to be clear, I make mistakes, I’m human” — which is a balance I actually aim to convey more often than I’m probably conscious of.

Now third time I change in a day depends on whether I’m going out, which I don’t do more than once or twice a week. The occasions under which I go out are either for work or for pure unadulterated girlfriend fun. For the former, something like this is common:

But with a jacket or sweater over it. The recipe for putting this together is something like: start with one everyday garment (neutral, utilitarian, basic — in this instance it was the corduroys) and work around them: offset the neutral color with an exciting accent like red tights (purple shoes optional) and then tie in the second item by trying to create a new dynamic.

In this instance, it meant responding to thick pants with a light tank. Pure function with delicate whimsy. With functional pants as your base (could be jeans, could be corduroys), you can do the same with a plain cotton tank (this one is very expensive but looks so good), or sequined tank/blouse or something velvet like this.

For pure unadulterated girlfriend fun:

Bathe in a tub of your self-hood. This occasion usually consists of dinner, either at a friends place so we’re sprawled across the living room floor (mini skirt allows for maximum floor comfort, tights for underwear concealment) or a restaurant, then over to some place we can dance. I start this recipe with an idea, knowing what I want to express.

Responsible adult who can let loose enough to suspend their obligations without completely forgoing them. So in my mind, it was more like: what two garments can I wear together that do and say different things but could work? I started with the crochet button down (also good for ventilation while dancing) because it is so specific and initially was going for a velvet tap shorts vibe but they were almost too simple, so I included the skirt which inspired the pearls (for a big boudoir energy).

Then I knew I’d want to wear tights, which made me want to style in a pair of gold shoes and these ones in partic are great for dancing because of the strap over the ankle (but not around it), making sure your foot stays fastened to the shoe with its very reasonable wedge.

These last two looks are probably good outfit ideas for the spirit of the holiday season too. I’ll have more on that next week but for now, have a great week!,

Leandra