How I Finally Built a Denim Collection That Actually Works (After Years of Terrible Choices)

God, I still cringe thinking about my denim collection from three years ago. Picture this: me, standing in my tiny Portland apartment bedroom at 7:30 AM, already running late for work, staring at a pile of jeans that somehow all felt wrong. There were the super skinny ones from my early twenties that now looked like leggings (and not in a good way). The “vintage-inspired” high-waisted pair I’d bought on sale at Urban Outfitters that gave me the world’s most unflattering wedgie. Those trendy wide-leg jeans that looked amazing on the Instagram influencer but made me look like I was playing dress-up in someone else’s clothes.

I ended up wearing a dress to work that day – in February, in Oregon, because I literally couldn’t find a single pair of jeans that didn’t make me hate my reflection. That’s when I realized I’d been doing denim completely wrong for years. Instead of building an actual wardrobe, I’d been impulse buying whatever was on sale or looked cool on other people, without any thought to what actually worked for my body or my actual life.

That embarrassing morning (I was twenty minutes late to a client meeting, by the way) started what my friend Sarah now calls my “denim obsession phase.” Which is probably fair – I did spend the next few months trying on jeans like it was my part-time job. But you know what? It worked. Three years later, I have five pairs of jeans that I actually love and wear regularly, instead of fifteen pairs that made me feel bad about myself.

The thing about building a good denim collection when you’re broke is that you can’t afford to make mistakes. Every purchase has to count. You can’t just buy whatever’s trending and hope it works out – you need pieces that’ll last years and work with everything else you own. So here’s what I learned about creating a denim wardrobe that actually functions, from someone who made every possible mistake first.

The foundation of any good denim collection is one perfect pair of straight-leg jeans. Not skinny, not wide, just straight. This took me forever to figure out because I kept getting distracted by whatever silhouette was having a moment on social media. But trends come and go – straight-leg jeans work with everything and never look dated.

Finding the right straight-leg jean is like dating, honestly. You’re going to try on a bunch that seem promising but feel wrong, and then suddenly you’ll find the one that just fits. For me, it was a mid-rise pair from Madewell that I almost didn’t try on because I was convinced I needed ultra-high-waisted everything. Turns out, when you have a longer torso like I do, super high-rise jeans can look kind of ridiculous.

The wash matters so much more than I realized. You want something clean and classic – a medium to dark blue without weird fading or distressing. I learned this the hard way after buying a pair with pre-made holes and whiskering that looked cool in the store but felt costume-y in real life. My perfect straight-leg jeans are this beautiful dark indigo that works with literally everything in my closet.

I actually have two pairs of the same jeans now, which sounds excessive but hear me out – one is hemmed for sneakers and flats, the other is longer for boots and heels. The cost-per-wear on these jeans is probably about fifty cents at this point because I wear one of these pairs at least four days a week. They’re my uniform. T-shirt and sneakers? Great. Blouse and heels? Also great. Oversized sweater and boots? Perfect. They’re the Swiss Army knife of my wardrobe.

Once you have your perfect everyday jeans sorted, you need something for weekends. This is where I discovered the magic of well-cut relaxed jeans. Not boyfriend jeans – those never worked on me, probably because I was buying actual men’s jeans and calling it fashion – but jeans designed to be relaxed while still looking intentional.

The pair I love are technically called “dad jeans” by the brand, which should be horrifying but actually they’re amazing. They’re loose through the hip and thigh but not baggy, straight through the leg, and made from 100% cotton so they actually get better with wear. I can throw them on with an old band t-shirt and somehow look like I made an effort, or wear them with a nice top for casual dinner plans.

These weekend jeans are where I let myself have a little more personality with the wash. Mine have the tiniest bit of natural-looking fading that adds character without looking overdone. And because they’re 100% cotton instead of stretch denim, they actually mold to my body over time. It’s like having custom-fitted jeans for the price of regular ones.

Here’s something I wish someone had told me earlier: you need at least one pair of really dark, clean jeans that can pass for not-jeans in certain situations. I learned this at a work event where the dress code was “smart casual” and I showed up in what I thought were my nice jeans, only to realize everyone else looked way more polished than me.

Dark indigo jeans with no distressing, no contrast stitching, no weird details – they’re like the little black dress of denim. I can wear mine to client dinners, nice restaurants, even certain work events, and they read as significantly more formal than regular jeans. They bridge that gap between casual and dressy that’s so hard to navigate sometimes.

The cut doesn’t matter as much here – what matters is that uniform dark color and clean finish. Mine are slim straight because that’s what I’m comfortable in, but I’ve seen people look amazing in dark bootcut or wide-leg versions too. The key is finding a pair that fits you perfectly and doesn’t have any obvious “jean” details that scream casual.

These are the jeans I pack for every work trip because they’re so versatile. Day meetings with a blazer, dinner with a nice top, even drinks after work – they handle everything. And honestly? I’ve gotten into a few restaurants with “no jeans” policies wearing these, though I probably shouldn’t admit that.

Now, wide-leg jeans. I resisted these for so long because I was convinced they’d make me look shorter and wider. But my friend convinced me to try a pair during a shopping trip, and oh my god, the right wide-leg jeans are like magic. They completely change your silhouette and make even the most basic outfit look intentional and sophisticated.

The key is getting the proportions right. The waist needs to fit perfectly – if it’s too loose, the whole thing falls apart. The rise should hit you at the most flattering point (for me, that’s mid-to-high rise, not ultra-high). And the length is crucial – they should either elegantly brush the floor when you’re wearing your intended shoes, or be obviously cropped so they don’t look like you’ve grown out of them.

I went with a cream-colored pair for my first wide-legs, which terrified me because I have a long history of disasters with light-colored pants. But the slightly off-white shade is actually more forgiving than pure white, and they’ve become my go-to for summer events when I want to look put-together but not overdressed.

Beyond the essential jeans, I’ve added a few denim pieces that round out the collection. A slightly oversized denim shirt that works as a light jacket or layering piece. A knee-length denim skirt that’s more comfortable than traditional skirts in hot weather. And yes, overalls – which I bought as a joke and now unironically love for weekend projects and casual hangouts.

These alternative pieces keep your denim from feeling monotonous and solve specific wardrobe problems. The denim shirt is perfect for those Portland evenings when it’s too warm for a jacket but too cool for just a t-shirt. The overalls make me feel like a cooler version of myself when I’m working in my tiny garden or painting furniture for my apartment.

I try to keep all my denim pieces in a similar color family so they can work together without looking like a Canadian tuxedo situation. And here’s where I think it’s okay to follow trends more closely – these supplementary pieces aren’t the foundation of your wardrobe, so you can experiment with more current silhouettes without the same long-term commitment.

The whole process of building this collection took about two years and way more fitting room time than I care to admit. But it completely changed how I get dressed. Instead of standing in front of a pile of jeans that don’t work, I reach for one of five pairs that I know fit well and make me feel good. The initial investment – both money and time – has paid off in easier mornings and actually liking what I see in the mirror.

If you’re dealing with your own denim overwhelm, start by being honest about what you actually wear versus what’s taking up space in your closet. Look at the jeans you reach for repeatedly and figure out why they work – is it the rise, the cut, the wash, the fabric? Use that information to guide future purchases instead of getting distracted by whatever’s trending on TikTok.

Remember that good denim should last for years. My oldest pair in current rotation is four years old and looks better now than when I bought them. Quality doesn’t always mean expensive – some of my favorites were under $100 – but it does usually mean better construction and cuts that work on actual human bodies instead of just looking good on hangers.

Your perfect denim collection will probably look different from mine depending on your lifestyle, body, and personal style. But the principle is the same: fewer, better pieces that actually serve your life will always beat a closet full of trendy options that make you feel bad about yourself. Trust me on this one.