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As someone who has struggled to find the perfect pair of jeans, I am convinced that they don’t exist. But, I have come pretty close with a pair of black jeans that I found last year.

They’re 100% cotton and hold their shape really well. Plus, they fit me pretty much perfectly. But they’re 100% cotton, and if you’ve ever worn 100% cotton jeans, you know that while they are perfect when standing, sitting is a whole other story lol. But that doesn’t mean I’m not going to wear the heck out of them!

I may have given up on my fall capsule wardrobe, but I’m still determined to get as many wears out of my clothing as possible. Which brings me to today’s post…I’m going to style these jeans with the same black t-shirt into 5 outfits for 5 different occasions.

I’ve definitely fallen into the trap of wearing the same things in the same way over and over. I think that boredom with the items I already own is one of my biggest shopping triggers. So finding different ways to wear the same outfit, simply by changing the other outfit elements helps me to feel excited about the things that are already in my closet!

I’m not much of a gambler, but I’m willing to bet that you have a pair of black jeans (or pants) and a black t-shirt in your wardrobe, or some other simple outfit in your closet that you keep going back to over and over!

It’s the tried and true pieces that you know fit you well and make you feel comfortable. You reach for them when you can’t think of anything to wear because you know they work.

But you also get a little bored by them because you, too, have a tendency to wear them the same way each time.

And if you’re not a fan of black (hey, I can acknowledge that it’s not everyone’s favorite color), any monochrome outfit could serve as your base.

* denotes secondhand

The Base

A small white woman with shoulder length silver grey hair is wearing a black t-shirt tucked into black jeans with white converse sneakers. Her left hand is in her pocket and she is looking down towards her right.

The simple outfit that I’m styling is a thrifted black Guess black t-shirt that I’ve had since earlier this summer and a pair of black jeans from Agolde (similar here) that I bought from The Real Real sometime last year.

I love the fit of these 2 items together. They feel casual, chic and comfortable. And since both items are black, I know that the styling opportunities are endless.

Choosing monochromatic items for your base will definitely help you make more outfits…think black on black, white on white, white on black or vice versa, or 2 brown items, or red, etc.

I added my Converse Chuck Taylor sneakers to show you an outfit I would wear on warmer days. Consider this one a bonus 😉

Black Jeans Outfit #1 – Add a cozy cardigan + moto boots to run errands.

Simply add a cozy cardigan and a pair of comfortable moto boots for a casual rocker chic vibe. Grab a crossbody bag to keep your hands free to carry your grocery bags.

// Tradlands Shelter cardigan

// Frye moto boots (similar)

//Botkier handbag

Black Jeans Outfit #2 – add a patterned blazer and boots for the office.

Work doesn’t have to be boring, at least when you’re wearing a fun outfit…dress code approved of course.

Add a patterned blazer and some subtly printed boots. At the very least, add in a fun accessory such as a belt if you have a more strict dress code.

A small white woman with shoulder length silver grey hair is wearing a black t-shirt tucked into black jeans. She is wearing a black and white checkered blazer, a black belt with a silver belt buckle and silver snakeskin boots with a low heel.

// vintage Checkered blazer* & belt*

// J. Crew snakeskin print boots*

Black Jeans Outfit #3 – add a colorful quilted coat for soccer watching (ball optional).

I’m quite literally a soccer mom. And this is what I’ll be wearing on the sidelines…at least my kid can always find me!

// Vissla jacket*

Black Jeans Outfit #4 – add a denim duster and chunky boots for a weekend brunch.

My best friend would expect nothing less of me than to come stomping into brunch in my chunky boots. And I am not one to disappoint lol. I added a denim duster so that I can comfortably sit outside. Plus, it has huge pockets to hold my phone and wallet!

A small white woman with shoulder length silver grey hair is wearing a black t-shirt tucked into black jeans. The is wearing a long dark denim duster that hits just below her knees. She is wearing white platform boots with a thick black sole. She is looking down and has her 2 arms out the the side. Her hands are pulled up into the sleeves.
I promise I still have hands lol.

// Toman Maier dress/duster*

// Ganni boots*

Black Jeans Outfit #5 – add a colorful blazer and fun boots for date night.

A t-shirt and jeans doesn’t have to feel casual for date night with a colorful patterned blazer and fun boots. And maybe a little exposed skin!

I’m a pretty modest dresser but a trick that I use when I want to be a little sassy is to gather my shirt hem (fairly tightly) to the height I’d like and tie an elastic around it. Then I tuck the tail up underneath and it stays in place perfectly!

// vintage Silk blazer* via Page of Air

// Coach clutch

// J. Crew boots*

I’ll definitely be wearing each of these outfits throughout the fall. They all make me feel fun and confident and what more can I ask for when I get dressed each day.

How about you? What’s a base outfit that you reach for over and over? How will you be changing it up this fall?