Published on January 10, 2018—  Leave a comment

5 Cute Jeans Outfits to Try Out in 2018

share this:

We don’t know about you, but we LIVE in our jeans (particularly our 501s). Sometimes we switch out of them when we go to work or when we go out at night, but we don’t really want to. So, we turned to our resident Style Challenge expert Hilary Pearson to see if we could realistically wear one pair of jeans all weekend long. To work on Friday, to the movies, even to a fancy night out. Turns out…well, see below!

Here, Hilary takes her favorite pair of blues everywhere she needs to go, in style.  


The search for the perfect pair of jeans is a long and arduous journey that most women are all too familiar with. Just when you are ready to give up, suddenly the stars align, the clouds part, and a serendipitous moment brings you the pair that was made for you.

My perfect pair happens to be a straight leg, mid-rise, non-stretch pair of vintage Levi’s 501s. I found them while browsing a vintage fashion fair in Alameda, California. At $15, they were the best bargain purchase I’ve ever made. The lighter wash is extremely versatile, allowing me to wear them with just about anything. This challenge pushed me to stretch my jeans beyond the neutral tones and simple pairings that have become routine.

As difficult as it is to find that perfect pair, once you do, the sartorial possibilities are endless.

Office Jeans Outfit

Gap sweater vest and linen blouse. St Agni mules.

Jeans are an everyday staple at the thredUP office. Office style alone is an excellent way to showcase how a pair of jeans can be dressed up or down. Over the years, I’ve grown quite fond of collared shirts, and one of my favorite ways to wear them is with a pair of jeans. Since it was a more active day in the office but it was still a bit chilly outside, I decided to layer an airy linen button-up under a tunic-style sweater vest, and paired it with my favorite pair of neutral mules. It was a polished look that helped me power through the day comfortably.

Jeans and Heels for Date Night

ShyVelvet silk cami. Heather fringe sweater. H&M heels.

You can’t go wrong with a classic silk cami, heels, and a great pair of jeans. It’s simple, comfortable, and chic without being too fussy. The added volume of the fuzzy sweater adds a playful element that’s also functional. Perfect for the chill that comes with the evening air.

Weekend Errands

Cotton On bodysuit. Renamed corduroy jacket. Dolce Vita for Target mules.

Corduroy is having a moment right now. If you’re like me, and not quite ready to take the plunge for a pair of corduroy pants, a simple jacket like this one is a great way to test the waters. It’s comfortable, casual, and perfect for running weekend errands. I added a simple white bodysuit to keep it clean cut and a pair of heeled mules to give the look a slightly elevated edge.

 Denim on Denim for Coffee Runs

Levi’s denim jacket. Theory turtleneck. Sam Edelman booties.

Stepping out for a coffee is one of my favorite ways to motivate myself when I have a long weekend to-do list. If a coffee alone won’t do the trick, I play dress-up, too. Today’s look was low-key, comfortable, and casual. Denim on denim is a favorite of mine. I like to mix washes to keep the look varied. Adding a simple black turtleneck and some red leather booties tied it all together without making it too loud.

Dress over Jeans for Sunday Brunch

Zara kimono. Tibi silk tank. Sam Edelman booties.

I used this morning as an opportunity to test a trend I’ve been seeing more frequently; wrap dresses over jeans. On this occasion, I let the beautiful print on the dress do the talking. The dress made the look flirty and fun, but pairing it with jeans made it 100% fuss-free and super comfortable. I paired it with my favorite booties and a silk cami to let the dress do the talking. I can’t wait to test this look with a pair of espadrilles come spring.

Tell us about your favorite pair of secondhand jeans and how you wear them in the comments below!