How to Style Oversized Shirts

The oversized shirt is a wardrobe classic that’s so timeless, versatile and can be styled a zillion different ways. If you don’t have one in your closet, take this as a sign it’s time to invest! Whether you’re wearing a classic white oxford shirt, a blue button up, denim shirt or a striped shirt, this will be one you wear now and for years to come.

As a mom, comfort and style are top priorities for me when I get dressed and I wear these all the time. They’re easy to throw on and look classy while letting me do my mom thing—running errands, meeting friends, cooking dinners—all the fun stuff, haha! I love that this fashion trend is currently very popular again, though honestly, I don’t think it’s ever gone out of style. It’s certainly having a moment right now.

Best Oversized Shirts

When it comes to this shirt, you can opt to buy a regular size shirt in a size or two larger than normal, or you can buy a shirt that’s designed to be oversized. There are so many shirt options for this oversized style, here are a few favorites at different price points. In this post, I’m wearing this denim shirt and this white linen shirt, both in a size medium, one size up from what I normally wear.

How to Style Oversized Shirts

Oversized shirts are a versatile and essential addition to any wardrobe for their classic appeal. They provide comfort, style, and a trendy look that can be dressed up or down for any occasion.

It’s a classic silhouette that may change a little bit over the years, but ultimately remains the same. Whether you pair it with denim shorts for a casual daytime look or layered with wide-leg pants for a more fashion-forward outfit, oversized shirts are a must-have item IMO! In this guide, I’ll show you how to style oversized shirts to give you the confidence to rock this timeless piece with ease.

Now for some oversized shirt outfits to inspire you!

Tuck It In

While tucking in your shirt isn’t required, I often find that tucking it can prevent you from looking like you’re wearing a disheveled baggy shirt. It feels more styled, intentional & sleek. There are several different ways you can tuck in a shirt for different looks.

One of my favorite button down shirt outfits is simply pairing it with jeans and tucking it in.

French Tuck

The French tuck is one you’re probably familiar with and have likely used! It involves tucking just the front part of your shirt into your pants while leaving the back untucked. This simple trick helps create a more polished and put-together look by defining the waistline and adding structure to the outfit.

When pairing an oversized shirt with the French tuck, it works well with a variety of pant styles. Some options include high-waisted trousers, skinny jeans, straight-leg pants, or even wide-leg trousers.

The key is to find a balance between the loose, oversized top and the more fitted bottom to create a flattering silhouette. Experiment with different pant styles to see what works best for your body shape and personal style.

Full Tuck

Fully tucking in an oversized shirt is a classic styling technique that instantly adds a touch of sophistication to any outfit. For whatever reason this look feels so elevated and simple, but elegant.

By tucking in the shirt completely, you create a clean and structured silhouette that is both polished and chic. This look works well with high-waisted bottoms, such as jeans, trousers, or skirts, as it accentuates the waist and elongates the legs.

Whether you’re dressing up for a casual day out or a more formal occasion, fully tucking in an oversized shirt is a timeless styling choice that honestly never fails.

Half Tuck

Half tucking an oversized shirt is a stylish and modern way to elevate a casual outfit. I’ve been seeing this more and more, and I love the trend. Instead of tucking in the entire front, just tuck in one side. This creates a relaxed yet put-together look.

This styling trick adds a touch of effortlessness to your outfit while still maintaining a polished appearance. Whether you’re running errands or meeting friends for brunch, half tucking an oversized shirt is a simple yet effective way to stay on-trend and comfortable as well.

It’s a more casual look, but keeps you from looking overwhelmed with extra fabric.

Layer with a Sweater Vest

I have a feeling we’re going to see this baggy outfit a lot this fall and winter. Layer a sweater vest over an oversized shirt for a slightly preppy, yet cool outfit. I’d stick with colors that complement each other, like earth tones or neutrals, and pair with dark pants and ankle boots for a stylish & fashion-forward outfit.

Keeping it to neutrals instantly elevates this look. Just imagine if my vest was hot pink… not as chic in my opinion.

Denim on Denim

To pair an oversized denim shirt with jeans, consider balancing the proportions by opting for regular-fit jeans to complement the oversized top. Choose contrasting colors or washes for a modern and eye-catching aesthetic, or go for a monochromatic look for a sleek Canadian tuxedo look.

Consider layering the denim shirt with a denim jacket for added dimension and style.

Button Down Shirt with Denim Shorts

For summer, you can easily wear a classic button-down with shorts for a cool, breezy look. Pair a cotton shirt with denim shorts and sandals for an casual look for everyday wear or for a backyard BBQ.

Or style with tailored shorts and tuck it in for a more polished look. I love this with strappy sandals, a few buttons undone and some layered necklaces.

Pair your Shirt with Leggings

While normally I don’t like to wear leggings except to pilates or yoga, I do think an untucked oversized shirt with leggings can actually look really chic.

In fall, pair this with tall or over the knee boots and a jacket. For spring and summer, throw on your favorite sneakers or sandals for a casual look that feels a touch more polished than a regular oversized t-shirt.

Style with Trousers

To style an oversized shirt with trousers, opt for a sleek and polished look by pairing the shirt with tailored trousers in a neutral color. Again I find that keeping things neutral instantly elevates your outfit.

Tuck the oversized shirt partially or fully into the trousers for a more defined waistline, and add a statement belt for added flair. Complete the look with a pair of classic loafers, heels or sandals for warmer months.

This combination strikes the perfect balance between casual and chic, making it versatile for both work and social events.

Knot It In the Front

Styling an oversized shirt with a knot is a great way to add a casual and stylish touch to your outfit. By knotting the shirt at the waist, you can create a more fitted silhouette while still maintaining the comfort and relaxed look of an oversized top.

This styling technique is perfect for a laid-back and effortless vibe, whether you’re running errands, hanging out with friends, or simply lounging at home. Knotting the shirt also adds a playful and trendy element to your overall look but is definitely a little more casual.

Wear It As a Light Layer

Styling an oversized shirt as a light layer can add a cool and relaxed vibe to any outfit. Try pairing it with a fitted tank top, graphic tee or a crop top for a stylish contrast in silhouette.

This combination allows you to show off the oversized shirt while also adding a touch of structure to the overall look. Don’t be afraid to play with different textures and colors to create a unique and eye-catching outfit. Adding a colorful shirt is a fun way to bring a little pop of color into a more neutral look.

Pair with a Midi Skirt

Styling an oversized shirt with a midi skirt can create a chic and effortless look. Pairing a flowy oversized shirt with a structured midi skirt can balance out the proportions for a flattering silhouette.

Opt for a monochromatic color palette and accessorize to add interest and color based on your own personal style.

Perfect Swim Coverup

To style an classic buton-down as a swimsuit coverup for the beach or pool, simply slip on the shirt over your swimsuit. My mom ALWAYS wore an oversized men’s shirt as her coverup and it stuck with me. It was so simple, but so chic and effortless.

You can leave it unbuttoned for a relaxed look or tie the ends at the waist for a more fitted silhouette. Pair it with some sandals, a wide-brim hat, and sunglasses to complete the beach-ready ensemble. If you need something on bottom, try some comfy beach-ready wide-leg trousers or shorts.

Oversized Shirt Dress

Okay so technically this is not a shirt, but I felt like this oversized dress deserved a spot here because it’s another classic silhouette that I love.

For the spring season, style your oversized shirt dress with a denim jacket, sneakers, and a crossbody bag for a casual and effortless look.

In the summer heat, toss it on with some espadrilles or sandals and a straw tote bag for a breezy and relaxed vibe.

For the fall season, pair your oversized shirt dress with a cozy cardigan, ankle boots for a chic and layered look.

Lastly, in the winter, layer your shirt dress with a chunky knit sweater and knee-high boots for a cozy and stylish outfit.

If you like oversized clothing, this is a wardrobe must for you! I hope this post gave you tons of new ideas on how to wear this classic shirt.

BTW, what to wear with green pants, and 17 white pants outfits to copy this summer.