How to Dress Up Jeans and T-Shirt Any Time Of The Year

Hi there! For as long as I can remember, I’ve always gravitated towards outfits with jeans. One of my favorite looks is jeans, a t-shirt or blouse, a blazer, and whatever shoes are in season. It’s an outfit that transcends time and trends. You can also wear this type of outfit throughout the year, which is important when you’re looking for real versatility. Anyway, a jeans and a t shirt outfit isn’t just for the weekend – I’m sharing a few of my styling tricks for elevating this type of look for different purposes!

How to Dress Up Jeans and T-Shirt

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Quick Tips For Elevating Your T Shirt and Jeans Outfit Ideas

There are so many ways to elevate your t-shirt and jeans outfits, but first, here are a couple of tips I’ve figured out over the years of wearing this look a lot!

  • I avoid distressed denim for the most part, and especially if you want to go with a so-called dressed up jeans and t-shirt look. While ripped denim comes and goes with being on-trend, it doesn’t give a timeless, classic vibe that you’re probably looking for if you want to elevate this type of outfit. In my opinion, raw hems are the one exception here, but I wouldn’t wear those to the office.
How to Dress Up Jeans and T-Shirt
  • Wear the style of jeans that looks the best on you, regardless of whether or not that style is considered “cool” at the moment. Everyone’s body is different, so jeans look different on all of us. It’s fun to find inspiration from bloggers and friends, but before I purchase anything, I always try to think, how would that look on me? Or, can I wear this with the jeans I love and already own? I’ve figured out that I love how straight leg and slim wide leg jeans look on me. I still have skinny jeans and actual wide leg jeans in my closet, but I definitely do not turn to them as much because the other styles fit me better! So, what style of jeans do you feel the best in?

  • Last, I do not shy away from having my jeans tailored in order to achieve the perfect fit. Jeans are notoriously difficult to find the perfect fit, and tailoring will help a lot!

Here’s What To Wear If You’re Wondering How to Dress Up Jeans and T-Shirt Looks

Choose Tailored Denim Or Denim Trousers Instead of Ripped Jeans

Like I mentioned, avoid ripped jeans if you want to elevate your jeans and a t shirt look. There are so many nice pairs of denim that look tailored! In fact, there is a huge trend right now for denim trousers. The pair I’m wearing are denim trousers, and they’re just gorgeous in person! I love the front pocket details. If you’re looking for more inspiration for what to wear with lighter denim like my pair, I wrote an entire blog post on what to wear with light blue jeans.

denim pants outfit idea

I linked multiple pairs of jeans I think have a tailored look, but they’re not all denim trousers – just to be clear! If you want to invest in a pair, I recommend also checking out Paige, as they have beautifully tailored denim that comes in a lot of colors, including blue denim, khaki, white, tan, etc.

Wear Elevated Accessories With A T-Shirt And Jeans

Okay, a lot of times when I hear elevated accessories, it sounds like code for something expensive. That is not what I mean here though! I just mean that adding pieces like a belt, jewelry, and sunglasses will take your t-shirt and jeans look to the next level! It never fails to surprise me how much better my outfits look when I remember to accessorize. For example, I wear a sterling silver birth flower necklace I was gifted by GLDN all the time! I love their dainty jewelry, but there are a lot of beautiful options. You can click here or use my code NATAMCLAUGHLIN for $10 off GLDN jewelry.

Go For Black Denim For A Business Casual Look

Black denim is often easier to elevate than other denim. I think it’s because black denim or even a dark blue denim more easily mimics work pants. An all black monochrome look will be super chic and also appropriate for a business casual dress code. If you’re getting dressed during the summer, opt for a linen top. If you’re wearing this look in cooler weather, go for a cashmere t-shirt.

Layer With A Sweater In Spring, Fall, and Winter

A sweater and a t-shirt go together just as nicely as a blazer and a t-shirt. I frequently layer my most comfortable t-shirts under any cardigan like I did below. But, I think one of my favorite ways to wear this combination is under a cashmere v-neck sweater like I did here. Cashmere sweaters are absolutely timeless, and layering a t-shirt under them gives you a little bit of an edgier look while keeping your entire outfit classic.

how to elevate jeans and t-shirt

Add A Seasonably Appropriate Blazer To Your T-Shirt And Jeans

Blazers are always in style – all year and every year! They’re pretty much made for layering over a t-shirt. Plus, I can’t think of a more classic piece that you can wear in so many different seasons and with different bottoms. I love this type of outfit all year. For spring and summer, I like to wear a simple white linen t-shirt under my lightweight linen blazer like I did below for dinner out with my family. I’m wearing mesh ballet flats, but can also wear sandals with this look.

How to Dress Up Jeans and T-Shirt Any Time Of The Year

When it’s still chilly outside, opt for a long sleeve t-shirt to layer under your blazer like I did in the photo below. I love this sweater blazer. It has the perfect amount of structure, so it gives your look a polished vibe. Anyway, this is an easy outfit to throw together but it always looks nice. Click here to read a blog post on how to style a navy blue sweater blazer. I’m wearing size small – it runs true to size.

Spring Layered Outfits

My jeans are the same cut but a slightly different wash (I own both and I actually can’t tell the difference), and the shoes are the most similar in the shade of beige that I could find!

Wear A Cashmere T-Shirt

Cashmere t-shirts are one of the few short sleeve sweaters I think are actually realistic to wear out in the world and not just on social media. Cashmere is super breathable, so it’s a nice fabric for spring and fall, and even early summer depending on where you live. Here in DC, I typically pack away any type of sweater in June – and sometimes even earlier. Anyway, this is an easy way to elevate your jeans and t-shirt look, especially for work or a dinner.

Pair With Ballet Flats

Okay, if you’ve read anything I’ve posted on my blog before, you might already know how much I love ballet flats and I always say they’re timeless. So, I’m sharing that sentiment again here! Ballet flats look nice with a lot of different outfits, but I think they look the best with denim. If you want an easy, effortless look that is definitely classic, pair your ballet flats with jeans and a t shirt! This look will never go out of style.

I love wearing neutral ballet flats, but a pop of color is also a lot of fun.

Pair With A Classic Bag Under $200

Just because you’re wearing jeans and a t-shirt, doesn’t mean you can’t carry a bag that feels luxurious! Yes, a designer bag looks nice with jeans and a t-shirt, but you don’t need a designer bag to help elevate your look. Understated luxury is also on-trend right now, so ditching flashy labels is not only cool but it also looks nice. For example, the plain suede bucket bag below will look stunning against blue denim. I also love the raffia or raffia-inspired options for warmer days with tan, beige, white, or ecru jeans.

I think each of these bags will help elevate a simple jeans and t-shirt outfit, and they’re all under $200.

You Don’t Have To Stick To Blue Denim

I love ecru, tan, beige, and brown denim all year. These colors dress up your look as they aren’t regular blue jeans. The first pair I’m wearing below are a really nice ecru, and the second pair are called oat, which perfectly describes the color! This type of option looks nice with sandals for warmer months, and I also love it with ballet flats, loafers, or boots when it’s cooler outside.

Wear A Striped T-Shirt

A striped t-shirt adds a nice dimension to your outfit, and stripes are always in style! I have a long sleeve navy and ecru striped t-shirt that I wear most of the year with jeans. In fact, I’m wearing it in the photo above under my black blazer. Anyway, it’s perfect to wear under a blazer, by itself, or under any type of lightweight jacket (I love it with my trench coat) when you pair it with jeans. There are some cute striped linen t-shirts out for spring and summer that would go perfectly with denim!

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