How To Wear Oversized Shirts

How To Wear Oversized Shirts

Oversized shirts are a timeless staple – they let you play around with different proportions and silhouettes while offering fluidity and comfort. Read on to discover how to confidently style and accessorize various types of oversized shirts.

Choosing the Right Oversized Shirt

Body Shape and Proportions

Oversized tops are often airy and freeform – the undefined shape allows you to emphasize other parts of your outfit such as flared legs, pleated hems, knee boots or statement bags.

Tying, tucking or cinching oversized tees and shirts allows you to play with shapes and create a more tailored look that’s unique to you.

Fabrics and Textures

You can find oversized tops in most fabrics and textures – shop for the type of occasion and to your taste. Cotton or poly-cotton blended oversized tops are popular, along with corduroy, denim and linen. It’s also common to see chiffon or silky fabrics.

types of oversized shirts

Styles and Designs

Designs can vary from simple boyfriend tees to textured tunics. Here are the most common styles of oversized shirts:

  • Oversized graphic tee: A t-shirt with a design element such as a slogan, logo or image on the front, back, sides or arms of the tee. These can be either long or short-sleeved.
  • Oversized button-downs: Button-down shirts vary from more tailored dress shirts, to warm plaid flannel, to textured corduroy.
  • Oversized shirt dress: These are either regular shirts worn in purposely larger sizes or are intentionally designed with extra room and length. Oversized shirt dresses come in a variety of lengths and are typically straight cut or with a slight flare.
  • Oversized tunic shirt: Tunics are loose, casual garments with sleeves – an oversized tunic shirt usually has a hemline that comes down to the hips, thighs or knees and can be worn with bottoms or as a dress.


Styling Oversized Shirts

Pairing with Different Bottoms

Skinny Jeans or Leggings

leggings and oversized shirts

Oversized shirts work well with leggings. For an aesthetic oversized t-shirt and jeans outfit, wear skinny jeans. Mix up the look by tucking in or tying up your shirt.

Shorts or Skirts

skirts and oversized shirts

Embrace the oversized shirt and biker shorts trend for a comfortable, sporty vibe, or try semi-tucking a baggy tee into denim cutoffs.

When wearing a skirt, you can loosely tuck in an oversized top for a cool drop waist look – this looks great with flared and A-line skirts.


Wide-Leg or Flare Pants

jeans and oversized shirts

Baggy outfits are a style choice in themselves, so don’t be afraid to wear oversized tops with baggy jeans. Try a shirt tucked into a more structured wide-leg jeans.

Create a drop-waist effect with a longline tee over flared jeans, giving you a relaxed top half and a more contoured bottom half.


Layering with Other Pieces

Sweaters or Hoodies

Layer up for warmth with a roomy hoodie or sweater – try zip-downs for variation or an oversized sweater vest for a more preppy look. Let shirt collars, hems and cuffs peak out of sweaters for added style. Try out layers that are both shorter and longer than your oversized tee or shirt for different looks.


Crop Tops or Tanks

A button-down oversized shirt provides its own layering opportunity – wear a plain or patterned shirt open with a fitted crop top or tank underneath for an easy everyday look.




hats for oversized shirts

More casual oversized tee styles go well with bucket hats and baseball caps. Wear a beanie when the weather gets cooler.

Roomy tailored shirts and oversized tunics welcome panama hats and straw sun hats.


jewelry for oversized shirts

An oversized top can be the perfect opportunity to wear long or layered necklaces. Give a large eye-catching pendant a try.

Large hoops and statement studs work well to balance the simplicity of oversized shirts. Though you can pull off any style, this is an opportunity to go big with earrings.

You can also try out a minimal necklace or choker with your oversized shirt and cami outfit.


bags for oversized shirts

Invite contrast with a mini handbag or micro crossbody bag in a contrasting color. Or carry everything you need in an oversized tote.

Summery baggy tees and oversized tunic looks work well with woven handbags in earth tones.


Oversized T-Shirt Tucking Methods

Tucking or semi-tucking your baggy shirt into bottoms can really change up your oversized tee look and give your outfit a custom feel.

For a relaxed look, you can loosely tuck your t-shirt hem into high-rise bottoms for a blouson-style waistline, or try tucking the front into jeans, joggers, or shorts, and leaving the back free.

For a modern asymmetric look, leave a few buttons undone and tuck one side of the shirt in and keep the other side loose.

How To Tie an Oversized Shirt

Transform a baggy shirt by tying it into a crop. You can use the knot-tie method by gathering and twisting the hem into a knot and pulling the fabric through. Reinforce it with a hairband for added security.

Try the under-bra method by folding up the bottom hem and tucking it under your bra, creating a baggy cropped look.

Oversized button-down shirts can be tied into a traditional knot using the shirt corners, giving a more relaxed vibe.

how to tie oversized shirts

How To Make a Shirt Tighter

The easiest way to add definition to your oversized shirt outfit silhouette is to wear a belt. Try a textural belt, like woven or leather, with an oversized button-down or tunis, or opt for a statement belt with a fun buckle, like metal or tortoiseshell, against an oversized graphic tee or shirt dress.

To define your shape without an accessory, put your shirt on inside out and tie it in the back using a hair band. Flip it right side out, keeping the knot under your shirt, and you have a tailored top.

Creating Different Outfit Looks

Here are some styling and outfit ideas to inspire you.


chic oversized shirts

For an elevated outfit, try pairing oversized shirts with textured leggings and a faux leather jacket. Add chunky boots or your favorite heeled sandals.

A structured shirt dress with some top buttons undone draping off one shoulder serves a stylish look, with or without a belt to cinch.


boho oversized shirts

An oversized patterned or embellished tunic is inherently boho so match with jeans and a wide-brimmed hat, or shorts and a shoulder bag.

Wearing a large t-shirt draped over a maxi skirt is a great go-to. For a more retro appeal, pair with flared pants or jeans.


sporty oversized shirts

A popular go-to is a baggy tee and joggers outfit – mix it up by tucking, tying up or leaving your tee loose. Create different looks with differing or matching bottoms.

You can keep it sporty in warm weather with different styles of shorts – cycling, runner, or basketball. Try pairing with a tennis skirt for a fun twist that adds a bit of structure and movement.

Dos and Don'ts of Wearing Oversized Shirts


  • Do experiment with different proportions.
  • Do consider the occasion and dress accordingly.
  • Do wear layers underneath for style and weather-readiness.
  • Do try a range of footwear and accessories for different looks.


  • Don't be afraid to tailor or alter if necessary.
  • Don't ignore the overall balance of the outfit.
  • Don’t wear anything you’re not totally comfortable in.

You can dress an oversized shirt up or down, and create modern comfortable outfits with versatile styling options. Effortlessly pull off comfy-cool looks for any occasion.