How to Wear Jeans and a T-Shirt

I wrote this post over five years ago, so I thought it was time for a reprise. You know I love jeans, and nothing is easier to pair with jeans than a t-shirt, but jeans and a t-shirt can look really sloppy if not done correctly so here are my best tips for rocking jeans and a t-shirt in style!

How to Wear Jeans and a T-Shirt and Look Stylish

How to Rock Jeans and a T-Shirt

1. Start with a great pair of jeans.

At the risk of stating the obvious, start with jeans that are on trend and look great on you. If they don’t fit you well, you’ll look sloppy and frumpy no matter how perfectly accessorized they are. Also make sure you’re wearing the style that works best for your body type.

Skinnies have been trending for a while now, but they’re not always your best look. If you’re more of a pear shape, you may prefer a straight or bootcut style. Experiment and try on different styles, and if you’re unsure what works best for you, I highly recommend Kelly Snyder’s Adore Your Wardrobe course. She teaches you how to dress for your body, and her jeans lesson is a game changer.

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2. Choose t-shirts with the best length, shape, and neckline for your body type.

The fit and style of your t-shirt is every bit as important as the fit and style of your jeans, and again, every woman’s body is different, so this may vary depending on your size and body type.

Learning what length of tee works best for you is another key to making jeans and a tee look chic and not sloppy. I always look for about a 25″ length in a classic tee. This Madwell tee, one of my favorites, actually comes in two different lengths, so I have to make sure to order the 25″ and not the 28″. If you’re taller than I am, or long-waisted, you may prefer the longer length, so it’s really a matter of trial and error to figure out what works best for you.

wearing: Madewell whisper soft tee (size medium) // Madewell high rise skinnies // Tory Burch travel flats

As far as shape goes, t-shirts these days are trending towards drapey and oversized, but these can be hard to pull off. I generally look for more of a classic cut, but there are ways to style a drapey tee and look good too.

The neckline of your shirt is also important, and once again, this will vary woman to woman. A crew-neck is looks better on smaller-chested women. Women who are more well-endowed should stay away from crew-neck tops; a v-neck or wide scoopneck is more becoming on us.

And finally, make sure your tee still fits and doesn’t look worn or tired. As we age, our sizes sometimes change, so if your t-shirts are getting tight, it may be time to update. You don’t want your t-shirt pulling too much across the chest area, and you don’t want it too be too low-cut or too baggy either. Like with any other article of clothing, fit is key to making a t-shirt look stylish and put together.

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3. Add interest with patterns, embellishments, and fun details.

I love a good solid tee, but don’t be afraid to try a pattern sometimes — stripes and florals are both trending right now, so there are lots of options.

This Caslon rounded v-neck is a great basic tee, and it comes in some fun striped prints this summer.

The cross-front tee in the picture at the top of this post is a fun way to elevate a basic tee, but it’s old and I’m having trouble finding links to current ones.

I’m also a fan of the knot front tees, a peplum tee is fun for a change, and don’t rule out graphic tees. Sure, they tend to read super casual, but there are ways to dress them up if you want to look more pulled together.

Details are important. Even a dolman sleeve or a cuffed sleeve adds interest and elevates a basic t-shirt to something a little more stylish and sophisticated.

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#4. Layering & Accessorizing

Elevate a basic t-shirt and jeans by layering or accessorizing (or both!) Throw on a blazer, utility jacket, cardigan, or hoodie to add interest and style.

And don’t forget to accessorize. This is where the jeans-and-tee outfits often fall short. Accessories are like the icing on the cake. You definitely want to make a great cake, but what’s a cake without icing? Likewise, you want to make sure you have great jeans that fit and a tee-shirt that is flattering and stylish, but without accessories, your outfit will still be pretty dull.

I always wear earrings and a bracelet and when I wear jeans and a t-shirt, and I often wear a necklace as well. Even consider adding a scarf to dress up the look a bit.

#5. Finally, consider your shoes and bag. 

Cute shoes or a bright colored handbag go a long way towards pulling an outfit together. Trade in your gym sneakers for a Converse or Superga. Ballet flats and loafers also work well with jeans and and a tee, and you can certainly wear wedge sandals or even stilettos if the event calls for it. For an edgier vibe, try wearing ankle boots with jeans and a tee for a fun transition look this fall.

wearing: Madewell whisper soft tee (size medium) // AG legging ankle skinnies // Ugg loafers (still on sale!) // red KSNY tote // necklace // bracelets

To tuck or untuck, that is the question.

I get sooo many questions about how to front-tuck a t-shirt, and it really no big secret. I just literally tuck the front of my tee into my jeans and then let the back hang out. Sometimes I futz with the sides a bit so they lay down if they’re flipped up funny, but usually I don’t have to. It does sometimes come untucked as I move around throughout the day, so just shove it back in as I’m walking along — no big deal.

I actually don’t love the look of the front tuck, but it seems to be a necessary evil with the way so many t-shirts are cut these days. It all comes down to proportion. Remember the rule of thirds — it applies to fashion as well as photography. If the shirt is too long or too boxy left untucked, then I try the front tuck to see if it looks better.

Because I’m short-waisted, front-tucking into low-rise jeans works okay, but I don’t like the look as much when I try it with high rise styles. I also think front-tucking looks better on smaller chested women, because it helps gives the illusion of more curves, while those of us who are more well-endowed may find it creates extra bulk we don’t need in that area.

Here’s an example of one I like to leave untucked. It has a curved hemline, and the length is on the shorter side, so I don’t feel a front tuck is necessary. Also, these jeans have a higher rise than the others pictured in this post, so front tucking would throw off my proportions.

wearing: stripe tee (old) // 7FAM skinnies // Ugg loafers (still on sale!) // Brahmin satchel // earrings

It also depends on how drapey the tee is. If the material is think and drapes well, I like a front-tuck better than when it’s stiffer, thicker material because that tends to bulge out more. If this still confounds you, take a look at my post on how to front tuck your shirt — I’ll try to update that soon with newer pictures.

I hope this post helps you rock your jeans and t-shirts with confidence! Just remember: good fitting pieces are key, little details pack a punch, and don’t forget to accessorize!


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