Thinking back on my jean collection three years ago still makes me cringe. Me, standing in front of my dresser in my too-small Portland apartment bedroom at 7: 30AM, clothesless and twenty minutes before I need to leave for work, facing a pile of jeans that all seemed to fit horribly in different ways. The skin-tight jeans from my early 20s that were now basically leggings (but not a cute, intentional pair of leggings).
The “vintage inspired” high-waisted jean from Urban Outfitters I bought two sizes too small on sale three years ago that constantly gave me the grossest wedgie. The wide-leg jeans that fit every influencer perfectly but were basically a tent on me. I ended up wearing a dress to work that day.
In February. In Oregon.
Because I literally could not for the life of me find a pair of jeans that didn’t make me want to rip them off in disgust every time I looked in the mirror.
It was around that day I realized I’d been doing jeans wrong my whole life. I never actually took the time to curate a “wardrobe” and instead just impulse purchased whatever looked cute or was on sale when shopping didn’t actually require trying things on. And as someone who could neither afford nor afforded to wear crazy jeans every day, my jeans shopping strategy wasn’t working.
I threw on my oversized sweater (also still not immune to buying trendy things I felt “meh” about when it came to clothing basics) and went jean shopping that weekend. And man, did I shop. Sarah still teases me about my “denim obsession phase.” But truthfully, after that embarrassing day living out of a dress?
I was determined to make sure I had the right jeans for every occasion. I spent the next few months trying on jean after jean after jean like it was my side hustle. And you know what?
It was worth it. I still only own about 5-7 pairs of jeans, but now? Three years later?
I love each and every one and wear them all regularly instead of having a closet full of pants I hate myself in. The thing about curating a denim wardrobe when you’re broke is that you really can’t afford to waste money. When you’re living paycheck to paycheck, you don’t have the luxury of buying all the jeans your heart desires and hoping something works out.
You have to be strategic about purchases, picking pieces that will stand the test of time and pairing with everything else you own. So let me take you through how I learned what works in denim, because trust me when I say I made every mistake first. Let’s start with the basics.
No jean wardrobe is complete without a pair of good, classic straight-leg jeans. Nothing too skinny, nothing too wide – just straight across. It took forever for me to actually commit to this basic because every time some other jean silhouette was trendy I got distracted.
But here’s the thing: straight-leg jeans don’t *go* out of style, and as versatile as they are, you can pair them with literally anything else in your closet. Finding your “basic” jean is kind of like dating. You try on pair after pair that look like *they* could be THE ONE but something is just off.
And then one day? Boom. You try on the perfect pair.
For me? It was Madewell’s mid-rise straight that I nearly skipped over because I was convinced that high-rise was the only way to go. And yet, my body type actually looks ridiculous in ultra high-rise jeans.
Because I have a longer torso than most, super-high-rise jeans make my legs look super short. The wash is also incredibly important. You want something classic and clean – think medium to dark blue with little to no fading or distressing.
Another mistake I made early on was going for this super trendy pair of Madewell jeans with pre-made holes and whiskering. They looked so cool in the store but I ended up feeling like I was wearing costume jeans outside the store. The jeans I landed on?
This gorgeous dark blue that is neutral enough to pair with everything but also adds some interest to an all-white shirt and sneakers kind of outfit. I even bought two of the same jean in different hem lengths because, again, these jeans are my everything. I keep one pair hemmed to wear with sneakers and my black flats, and the other pair I keep the original hem for booties and heels.
The cost-per-wear on these bad boys is probably around $.50 now because I wear a pair of these jeans at least 4 days a week. They really are my uniform. Top-raising tee and sneakers?
Perfect. Statement blouse and heels? Works.
Sweater and boots? Duo-ready. They’re the unicorn of my wardrobe.
But what about on the weekends? When you’re dressing to impress no one but yourself, what’s your go-to? Once I found the perfect jeans for weekdays, I knew I needed something to pair with my favorite sneakers and t-shirts on the weekends.
Enter: relaxed jeans, my darling. Not boyfriend jeans – those things never really worked for me for multiple reasons, but probably mostly because I kept buying men’s jeans and thinking “Oh these give me212 vibes..?” No, Annie. Relaxed jeans that are actually cut to be slightly off without trying too hard.
These “dad jeans” (yes, that’s what the brand actually calls them) from Madewell are so buttery soft and really flatter my figure. They’re relaxed through the hip/thigh but not overly baggy, straight through the leg, and made of 100% cotton so they actually get better with wear. Throw them over a band tee and you look put together.
Throw them with a cute top and you’re good for date night or brunch with friends. They’re my Saturday/Sunday go-to. These jeans were where I allowed myself to branch out with wash.
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I wanted something that still felt classic but had just enough fading to give it some dimension. Because they’re 100% cotton and not a stretch denim blend, they actually mold to your body after wearing them for a few times too. It’s like they’re custom-fit to you!
But enough about my everyday jeans, what about jeans you can actually dress up? If you’ve ever showed up to an event that says “business casual” wearing jeans only to realize that everyone else interpreted the dress code differently than you, THIS WILL BE YOUR JEANS. Pair of jeans so dark/black/blue that they can pass as not-jeans?
Gold. Mine are again, Madewell because come on guys I live in Portland – but these are their slim straight jeans in the darkest indigo they offer. They’re thick, sturdy denim that looks like they’ll last forever and shrink away any weird shadow/details that you’d find on more trendy jeans.
These jeans are my “church” jeans. They’re what I reach for when I need jeans that are dressier than my everyday straight but aren’t quite pants. I’ve worn them to client dinners, semi-fancy restaurants, and more than one work event where I was slightly underdressed but these jeans got me through.
I snagged these during one of their unusual-but-always-worth-it sales, but have had them for YEARS and they still look new. These are also the jeans I travel with for every work trip. They pair just as well with a blazer as they do a cute blouse.
You really can’t beat a solid pair of dark wash jeans. The whole point of these jeans is that they’re a darker wash than you would typically wear on the reg. Mine are slim-straight but I’ve seen wide-leg versions and bootcut versions that look incredible on friends.
Just make sure you pick a pair that fits you like a glove (literally – no weird gaps around your hips!) and steers clear of any “contrast stitching” or other details that give away their denim material. Wide-leg jeans were something I always swore I wouldn’t wear because every time I tried them I felt like I looked shorter and heavier. Which, newsflash: they KIND OF DO if you get the proportions wrong.
But my friend convinced me to try on a pair while shopping and oh.myl.gt I was converted. The right wide-leg jeans are absolute game changers, honestly. They eat up so much extra fabric in places you might worry (like your stomach and thighs) but still keep your silhouette sexy.
Promise. The biggest thing with these jeans is FIT. Your waist needs to fit perfectly – if you can cinch them more than halfway, they’re not gonna work.
Same goes for the rise – you want something that hits you at the highest, most flattering point (mine are mid-high rise, I do not own hiking boots aka ultra-high-rise jeans). As for the length, these either need to hit the ground when you’re wearing your intended shoe (flats! boots!) or be obviously cropped. If they look like you maybe could wear them longer?
They’re too long. I opted for a cream color for my first venture into wide-leg jeans because LORD knows I’ve had issues with lighter wash pants in the past. But the “barely white” color actually seems to be more forgiving than true white jeans, and have become a total staple for spring and summer events when I want to look put together but not over dressed.
Now we’re getting into the jeans (and jean-esque items) that round out my denim wardrobe. Things like denim shirts, skirts, and even (*gasp*) OVERALS. These aren’t things I need to survive my week, but they’ve become pieces I love to reinvent my jean game.
The denim shirt works as a lightweight jacket or layering piece. The denim skirt is more comfortable than an actual skirt in the summer. And the overalls were actually purchased as a gag, but now I legitimately love them and wear them for random projects on weekends.
These other denim items help break up your denim wardrobe when you’re wearing jeans multiple days a week. They also allow you to problem solve with your wardrobe. That denim shirt I mentioned?
Perfect for Portland nights when it’s too warm to wear a jacket, but you don’t want to look like you just threw on a T-shirt. That overalls set me in my own tiny garden plot or up painting furniture to spruce up my apartment. Try to stick to one color family with your denim pieces so you can mix and match without it being TOO matchy-matchy.
But that’s about where I draw the line on matching with these “accessory” denims. And honestly? I think following trends is kind of okay with these pieces.
They’re not the foundations of your wardrobe, so branch out with cut trends or colors that you know you’ll only wear for a season. You could always donate them come January when no one wants to see your denim pants anymore. Looking back, it probably took me two years to curate this collection.
I spent a small fortune and way too much time in jean fitting rooms trying to figure out what worked for me. But once I did everything about getting dressed changed. Instead of a giant pile of mediocre jeans I can’t wear, I have five I LOVE and reach for daily.
It was so worth the investment (and I don’t just mean money) to step back and really analyze what works for me in jeans. Here’s what I learned along the way: Know what you actually wear vs what you think you should wear. Look through all of your jeans and be honest with yourself about what you actually reach for and love vs what you bought and tried to make work.
What is it about your favorite pair that you love? Rise?
Waist?
Wash? Fit? Write this stuff down because when you go shopping again, you’ll forget all of this whatever advice you just read.
Good denim lasts. Mine dresses are four years old and look better now than when I bought them. Spend a little more on pieces that are well-constructed and designed to fit an actual human’s body, not just look cute on a model.
I have plenty of good jeans that came from brands known for higher pricing but also still cost under $100. Build a collection that works for you. Mine consists mainly of jeans because that’s what works for my lifestyle and needs.
You might not wear jeans as often and need more jeans thats stretchier materials, or maybe you’re a jean skirt kind of person. Don’t feel like you need to gravitate towards jeans just because thats what I reached for – think about what will work best for you!
