the self-centered wardrobe

strategies for dressing + shopping for the long term

Fact: The New Look is oversized. The wide-leg and ultra voluminous wide-leg silhouette is everywhere, and many people (like yours truly) who came of age during the era of the skinny jean are a bit thrown for a loop.¹ As someone who’s neither model tall nor likes to get everything hemmed, I must admit that the decade-plus reign of the skinny jean has been good to me. So now that the hemline tides have changed, what’s a girl to do? Thankfully, there are adaptable options. Which brings me to the question du jour: how do I strategically update my wardrobe (with many pieces bought in the 2010s) to reflect the current version of me in 2024?

An of the moment look from The Frankie Shop

I should preface by saying I don’t particularly enjoy conventional retail shopping — I find it tedious and usually have about a 2 hour limit before I need to wrap up or at least take a long break. Vintage shopping, on the other hand, I love. So much more interesting and mentally engaging and (often) easier on the wallet. Either way, I like to do my homework and ideally buy well the first time so that the purchase will have real longevity in my wardrobe. (Everything costs even more now, so why let your hard-earned money go to waste?)

My personal style project over the past fifteen years or so has been to build a wardrobe primarily based on timeless foundation pieces and gradually edit and update as needed every year. Overall, I think this method has worked — I haven’t felt the need to do a massive wardrobe overhaul, and more importantly I still love and wear most of the seasonless pieces I bought over a decade ago. I should caveat this approach by saying everyone’s mileage may vary. A decade+ is a long time. Personal and lifestyle changes — switching from commuting to working remotely, body changes, just growing out of an aesthetic — can all organically necessitate wardrobe shifts of varying degrees. And that’s okay, it’s something to be embraced! Developing your personal style is not just about cultivating a wardrobe — it’s ultimately also about cultivating a relationship with yourself. It’s an imperfect work in progress; let’s give ourselves grace and empathy.

Currently, these are my working strategies for considering what to wear and how to think about what to buy:

• Set up a style theme and refer back to this throughout the year. My 2024 theme is elevated comfort. This is also my perennial travel capsule principle. What’s yours?

• Vet potential purchases with a style objective in mind. The best buys are usually really well designed and make your life better — a favorite blazer that fits just right and gives you that extra boost of confidence; an elegant flat that’s all-day comfortable; a tote that’s roomy but isn’t a bear to carry. Work backwards from your existing needs to identify what you want the purchase to do for you, then shop accordingly. (Example: I’m looking for a lightweight bag that I can pack on vacation and is comfortably hands-free for day trips and the airport … Therefore I’m probably looking to buy a crossbody bag in a fuss-free material with minimal hardware.²) I’ve referred back to this method numerous times over the last two months as part of my buy-filter process, and I think it really has helped steer me away from Fantasy Rationalization³, which is when you see something tempting and create an ad hoc theoretical narrative for why you should buy it.

• Think about getting dressed like starting with a ‘prompt’ (as writers often do to get drafting on a topic). One ‘prompt’ could be building a look based on the pant silhouette. Depending on the cut you choose, it will inform the proportions and fit of the rest of the outfit (e.g.: a boxier or more fitted shirt/sweater/blazer, tucked or untucked, etc). Or dress from the shoes up. Or work out an outfit based on mood. Pick a starting point and go from there. It’ll help prevent analysis paralysis and let the components of your outfit form a cohesive dialogue with one another.

• Go with what feels and looks good … on you. Not a platitude. Put on those metaphorical noise-cancelling headphones here. Regardless of what the Cool Girls are wearing, if you’re not comfortable with the fit/look then it doesn’t need to take up space in your closet or in your sense of self. I enjoy seeing how others are styling the ultra wide-leg pant, but I’m sitting out this look because it’s not flattering on me without some serious hemming and a certain type of shoe (an exaggerated pointy-toe high heel, for instance, a style that I usually find uncomfortable), and that makes the look a bit too high maintenance for my life.⁴ I am trying out some less exaggerated cropped iterations, however. Currently really loving how this vibe is styled in Apiece Apart’s latest collection.

Plus everyone’s wearing flats! Everyday wearable looks from Apiece Apart

At the end of the day, there will always be a reserved space in my closet for a simple classic like the skinny/straight leg jean because 1) it works well with my proportions, 2) it looks good with most of what I already own and 3) it still has foundational versatility in my wardrobe even though it’s not the trending look at the moment. A great wardrobe reflects your past as much as your present. And of course, everything always cycles back in fashion … eventually.

N.B.: If you think about getting dressed as starting with a reference point, then that’s a microcosmic example of the macro project of building a wardrobe. The ideal wardrobe is self-centered: you are the primary reference point, with various secondary and tertiary elements sprinkled throughout that sample what’s happening in the wider socio-cultural world.

This is how my mind works sometimes.

What’s inspiring you this season? Do you have a favorite outfit prompt?

1. Jonah Weiner did a great deep dive on oversized pants. I’m glad someone finally wrote a long form think piece about that vague sartorial WTFness that many of us have been feeling since we emerged from the pandemic.

2. I recently bought that very bag … it’s great! More in-depth thoughts on travel bags here.

3. When you talk yourself into buying something spontaneously based on random external factors (e.g.: a big sale discount, seeing it on a hot young celebrity, etc) and convince yourself that something is workable but it’s actually not. Basically Jedi mind tricking yourself into justifying an impulse purchase. It happens to all of us, don’t feel bad! But being aware can help you be more mindful going forward and hopefully prevent some mistaken buys.

4. Part of the fun of fashion is the people watching. I can appreciate an idea or a look from the runways, street style photos, etc that looks amazing on others but I know doesn’t work for me. And that’s perfectly fine!