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 trends, and it’s just so reliable. You can wear this type of outfit throughout the year with just a few changes, which is important when you’re looking for versatility in your closet. 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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You can shop my exact outfit above by clicking here.

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 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 Elevate Jeans and T-Shirt
  • Wear the style of jeans that looks the best on you, regardless of whether or not that style is considered on trend 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? 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?

  • Check the inseam measurements on jeans before purchasing them! Knowing how this number correlates to your height is basically part of a magic formula for jeans fitting you. I’m 5’4. So, I’m basically on the cusp of petite and regular jeans based on height. But, I typically go for regular length jeans. I know that any jeans with an inseam longer than 28.5 inches won’t work if I want to wear flats. A 27 inch inseam is my dream, but I own a lot of jeans that are 28 inch inseams and they look great!

  • I don’t shy away from having my jeans tailored in order to achieve the perfect fit. Jeans are notoriously difficult to find the perfect fit! Tailoring will help a lot if you find a pair you love.

  • My last tip is about the wash of jeans. If you want to wear jeans to work in a business casual dress code, go for jeans that are medium wash, dark wash, navy blue, or black. They tend to bring a level of polish to jeans that a lot of lighter jeans just don’t have.

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

Choose Denim Trousers For An Elevated Look For Work Or Date Night

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, which is what I’m wearing below. I linked this year’s version of my jeans. While I’m wearing these jeans for a weekend look, they’re perfect to wear to work with a blazer instead of a leather jacket. I had mine hemmed to fit with all of my winter boots that have a heel.

Black Leather Jacket Outfits

Choose Tailored Trousers For Any Lighter Jeans

Light denim can feel less formal and super casual compared to darker jeans, which is not a bad thing! But, if you want to elevate this type of outfit, I recommend going with a pair that are more tailored at the hem or have other details. I love the patch pocket and large hem of sailor jeans. And I wrote an entire blog post on what to wear with light blue jeans if you want more inspiration!

denim pants outfit idea

I recently wrote a blog post on how to style sailor pants, which are the type of jeans I’m wearing above.

Wear A Cardigan T-Shirt For A Classy Feel

I recently purchased a cardigan t-shirt, and it instantly makes a simple jeans and t-shirt outfit so much better. I love how they’re kind of a 90s vibe and back in style, but they don’t feel trendy. One of the reasons a jeans and t-shirt outfit is such a great option to keep in your closet is because it is so classic! You can see a video of how the cardigan shirt looks on me here.

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. My exact cashmere cardigan will instantly polish your jeans and t-shirt outfit! Be sure to size down one size unless you’re pregnant, which is when I bought mine.

elevated jeans and t-shirt look

Another one of my favorite ways to wear a t-shirt and jeans is to layer a t-shirt under a cashmere v-neck sweater like I did here. Cashmere sweaters are timeless. Layering a t-shirt under them gives you a little bit of an edgier look while keeping your entire outfit classic!

Wear A Wrap Coat

Who doesn’t love to hide underneath a cozy coat? This is one of the easiest things to wear in the fall, winter, and spring if you don’t need to take off your coat. This type of outfit is perfect for a coffee run or school run. While I love wearing a t-shirt under a topcoat, trench coat, or denim jacket, a wrap coat adds a touch of elegance to your outfit. Be sure to size down one size in my exact coat! it comes in other colors too.

Wrap Coat with jeans

Go For Black Denim Or Dark Denim For A Business Casual Look

Black denim and even a dark blue denim is often easier to elevate than other denim. These colors allow jeans to more easily mimic work pants. An all black monochrome look can even be appropriate for some business casual dress codes, especially if you add a blazer or other layer. If you’re getting dressed during the summer, opt for a linen or cotton top. If you’re wearing this look in cooler weather, go for a cashmere t-shirt. I always love to wear different textures when I wear the same color.

Wear A Suede Shirt Or Jacket

Suede shirt jackets like the one I’m wearing below are everywhere, and they make any outfit look so nice. They’re the perfect layer for fall and spring. I threw on this outfit to go out to dinner after a busy day, and I felt really put together. I love how my black and white striped t-shirt looks with this suede jacket. My suede jacket is definitely a go-to piece to dress up a simple outfit.

suede jacket with jeans

If you want to see the green suede jacket on me, click here and click here to see it in camel with my exact t-shirt above! The last option I linked is obviously a blazer and not a shirt jacket, but it’s really stunning. Click here to see it on me. I’ve tried it on a couple of times and it remains on my wishlist!

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. They also go with all types of jeans. 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. You can see that outfit below! I was going to dinner with my family. I’m wearing these mesh ballet flats, but you 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, go for a long sleeve t-shirt to layer under your blazer. You can shop my exact long sleeve t shirt here. 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. My exact sweater blazer is old, and this is the most similar I can find (use code YOUROCK for 20% off). You can also check out this one in crepe, which is a nice material to wear all year.

Spring Layered Outfits

Wear A Cashmere T-Shirt

Cashmere t-shirts are one of the few short sleeve sweaters that actually feel realistic to wear. Cashmere is super breathable, so it’s a nice fabric for spring and fall. It can also work for summer depending on where you live. Here in DC, I typically pack away cashmere sweaters in June. Anyway, this is an easy way to elevate your jeans and t-shirt look, especially for work or a dinner.

Use Accessories To Elevate A T-Shirt And Jeans Outfit

Accessories and shoes are the perfect way to dress up your jeans and t shirt outfit when it’s too warm to layer. 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. I’m wearing this birth flower necklace from GLDN, which I love and wear all the time. GLDN makes every delivery feel really special with the packaging and note inside – it’s a really nice gift. Click here to see my necklace up close!

classic white t-shirt and jeans outfit

I linked my exact bag, sunglasses, and belt along with some other accessories for other seasons. Although, I wear these sunglasses and the belt all year! My shoes are available in gold and lilac, or you can check out this similar pair also by Sezane.

Wear Your Jeans And T Shirt With Loafers

Shoes can do so much for an outfit! Loafers are my go-to shoe to dress up a casual outfit. First of all, they’re so comfortable. Second, they work for just about any season. I love how these loafers and accessories made my casual t shirt and jeans look so much nicer for a family brunch. My loafers are comfortable right out of the box, and I highly recommend them. They come in tons of colors!

loafers with jeans outfit

I also love these two tone loafers that I wear all the time, and I will definitely wear this spring and summer with a t shirt and jeans.

Pair With Ballet Flats

If you’ve read 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 classic, pair your ballet flats with jeans and a t shirt! This look will never go out of style.

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

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 easier than ever.

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

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. A similar striped top is perfect to wear with jeans, whether you’re wearing it by itself or under a jacket. I really love this striped top! I own it in the color called natural. I’ve just added the stripe version to my wishlist because I wear the other one so much.

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

Okay, if you made it this far, thank you so much for reading! I hope you found a few tips or outfits you love. Let me know what you think in the comments!

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