The Only 5 Questions I Ask Before Buying Anything New

Building a wardrobe with intention

This letter is brought to you by Madewell.

Curating a closet that feels like you is a life’s work. And bringing pieces into our lives is just the beginning. How we care for them, the ways we style them, even the attention we put into how they’re stored all add up to tell the story of how exactly we get dressed every morning.

Design by Luke Griego

In a culture of newer/faster/more, it’s refreshing to think of honoring your personal style through thoughtful additions and consistent refinement. A lot of people get used to the cycle of overconsumption and then a massive closet purge once or twice a year, but my preferred approach is slowing down the acquisition phase with these 5 simple questions.

I’ve been thinking a lot about this lately—especially as someone who primarily shops secondhand. When I do buy new, I’ve developed a pretty ruthless filter. If the item in question passes this test, I feel a lot more confident making it a part of my personal collection.

And very importantly, you can shop a wonderful collection of preloved Madewell pieces here, on ThredUp! This is especially useful if you have a Madewell style you adore that you’d love to own in another color/a Madewell piece from a past collection.

Is there a true gap in my closet?

Attempting to move from “I love it” to “I need it.”

The best way to keep track of gaps as they arise and validate them later on is by keeping a note on your phone. You can consult this note when you’re thrifting or when your aunt asks for a birthday idea or when your favorite brand launches new arrivals. Shopping from a place of necessity is better than a feeling of frenetic desire—most of the time.

Striped Pullover Sweater in Alpaca Blend

I would consider not having a striped crewneck sweater in your closet a blind spot. It’s a layering magic trick and looks so cool tied over the shoulders of a jeans and tee look.

Frye Campus 14L Tall Boots

About as classic as classic gets—the Frye Campus boot! These are very expensive on the secondhand market, so buying them new, or even, making them your whole holiday wishlist, is a great option.

Have I purchased a version of this item before? What did I learn?

Past mistakes, or, identifying your impulses

Whenever I really survey the bags of clothes I’m donating, I’m struck by the trends I can’t seem to break in my purchase pattern. One in particular is button up shirts with any kind of detailing or feminine cut. I never end up wearing those, and always default to my custom or menswear styles. Another repeat offender in my life is midi skirts. I’m just a mini girl!

This can be a little tedious, but what stays in your closet after a cull is just as important as what you drop off to be donated. Use this data to inform your future purchases!

Suiting Mini Skirt in Plaid

A great example of my platonic ideal in a skirt. Go look at the outfits you have saved on Pinterest. Can you draw any throughlines? A lot of mine include plaid minis.

Suede Western Jacket

I’d opt for this instead of the three other suede-ish jackets I’ve acquired over the past few years.

What’s the material construction of this item?

Learn what works for you

This is very person-to-person. And easy to figure out! Pull out your most-worn pieces, check out the tag, usually internally on the collar or on the bottom left corner, and see what they’re made of. I love a 100% cotton moment, in fact, I kind of demand it in a lot of cases. It’s easy to dig a little deeper when you’re looking at a product page online in the consideration phase. For accessories, I stick with real leather, knowing it’s something that will wear well over time and last longer.

The Lexington Oversized Tote

Take this suede bag to your local cobbler to be treated right away and you’ll discover a whole new lease on life. Imagine slipping into a bench for a breakfast meeting with this bad boy.

Striped Polo Sweater in 100% Merino Wool

This is far and away THE sweater silhouette of the season. I adore a long-sleeve polo and have since 1st grade, so if you’re apprehensive about it, make an investment in one made of 100% wool and report back to me.

Can I trade in something I feel uninspired by to make space?

Make your new additions earn their spot

Out with the old! In with the new! I don’t abide by a specific “one in, one out” policy, but I do find it helpful to pull out every single item close to the piece I’m considering, lay them all on my bed, and start to get very picky about what works and what doesn’t. There’s usually a weak link or two a new addition can take the place of in the end.

I can still remember the first time I participated in Madewell’s Denim Trade Up program eleven years ago. It’s simple. Bring in any pair of denim to trade-in and you’ll receive $20 toward a new pair from Madewell. And from October 10-20, it’s $50! This program is part of the incredible, larger Do Well by Madewell initiative.

The Wide-Leg Jean

I swear I’ve seen this wide-leg jean multiple times in the city this week. Like all Madewell jeans, it comes in a ton of sizes and lengths.

The Pencil Jean

This is for the skinny leg curious. This jean + any boot = instant outfit. I’d wear with a massive cashmere sweater.

What are 3 outfits I can imagine integrating this piece into right now?

This is the fun part

Here’s where we pull out our outfit inspo screenshots and take to Pinterest. If this feels like a chore or a stretch, it’s likely the item in question isn’t going to spark enough joy to earn its place in your closet. This part should feel like play. If you’re scratching your head, unable to see how this piece has the potential to play nice with your current closet, it might not be a fit.

The Dakota Perfect Crewneck Tee

I speak from experience when I say this white tee is the puzzle piece your closet is missing. I wear mine with whatever pants still fit and feel the way I imagine a fresh cortado tastes. It’s vintage-y and washes really well.

The Meadow Whipstitched Driver

I’m daydreaming about pairing these with bright blue socks and vintage Levis for a road trip to Connecticut. Do NOT sleep on Madewell shoes…

These questions have saved me from countless impulse buys and helped me build a closet I actually love wearing. The goal isn’t to never shop—it’s to shop smarter.

Thank you for reading Long Live. It means so much to me. You can order my romance novel, Exit Lane, on Bookshop or Amazon. You can shop my favs here, follow along on Instagram + Tiktok, and shop my Notion template. Get matched at EV Salon. And if you want to partner on a future Long Live, email evan@communite.co x