How to wear an oversized shirt. White boyfriend shirt

How To Wear an Oversized Shirt: Monthly Makeover

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Thanks to Beatrice for the suggestion of how to wear an oversized shirt. We all know that styles evolve and change, and many of the silhouettes are now bigger and baggier.
If you think this is a recipe for failure, don’t. There are ways to make it work.

Besides if you only stick to the fashion styles from years ago, that will give off a frumpy vibe.

Quote of the day: “Life shrinks or expands in proportion to one’s courage.” Anais Nin

I wanted to use the idea of how to wear an oversized shirt for my monthly makeover to show over 7 ways you can take the basic look and make it have personality.
All of our outfits need some personality otherwise we look bland. Just like with our food, we need spices added and that’s what I’m trying to show.

How to wear an oversized shirt
1-The basics of the outfit
2-Different ways to tuck it
3-Adding color with scarf and shoes
4-Sling bag (or any crossbody)
7-How not to wear it

Admittedly, there was one look that I didn’t think photographed well meaning you can hardly tell that I changed it at all. I saved that for the last and called it how NOT to wear an oversized shirt. But remember, we are all unique, so it may be something you like.

The subject of a white button down has been styled many times on this site. Take a gander at some of the ways we wore them

  1. Layering a blouse under a dress
  2. Styling a blouse as a jacket
  3. 2 blouses paired together

The Basic Look of How to Wear an Oversized Shirt

Basic outfit before adding extras
Pants: Banana Republic~~Shirt: Old Navy~~Shoes: Walking Cradles “Wyatt” Code Jodie15

I wanted to show a basic look that I think you would consider looks nice on its own. Granted it doesn’t have a ton of personality, but it’s basic.

I left the oversized shirt untucked over my olive green chinos. But notice that I didn’t button it all the way down. Leaving it unbuttoned slightly created more asymmetry which helps the proportions.
BTW, the proportions are half and half which is not ideal. But it’s a realistic look that I see often.

Even though the pants are over 8 years old, they are considered the newer silhouette since they are less fitted and have a straight leg.

While you might think that an oversized shirt needs skinny jeans, I wanted to see how it would look with something different.

For my footwear, I added print loafers (these are Walking Cradles loafers that are not only stylish but comfortable with the tiny pillows and extended sizing) and even though they are an animal print, they are neutral and keep the look very muted.
I am wearing earrings albeit olive-colored and not very long. This means they camouflage into my hair and don’t create a focal point.

Old Navy’s Boyfriend Shirt

This oversized shirt is called the Boyfriend shirt from Old Navy. What I love about it is that it is available in regular and tall and petite sizing.
For reference, I purchased the XS Petite size. The sleeves could be a tad short for me, but I don’t mind them.

The shirt I am wearing is 100% cotton, but Old Navy also has a linen-blend one that is similar. I’ve seen mine in the store, but not in petite or tall, which is one of the reasons that online shopping is helpful.

This style of boyfriend shirts is popular right now and Old Navy has them in many different options including striped, satin, and cropped versions.

Insider tip: I had been searching at the thrift stores for a men’s button-down that I could wear, however, they were too overwhelming for what I wanted. But it’s a great option if you have larger shoulders and don’t mind the longer sleeves.

What makes these shirts different is the relaxed fit. You won’t see darts in the front and back that would make them form-fitted.
This means they could be altered to have darts put into them when the style changes or if you need more shaping. Remember, you are the boss of your clothes.

You should definitely sign up for the emails below. Besides the free eBook, my email family gets personal tidbits of what’s going on in my life along with other happenings, sales, information, giveaways, extra photos, and inspirational articles.

Different Ways to Tuck

Of course, you could tuck the shirt into your jeans as we normally do, but there are ways to make it more interesting too.

The version on the left is a faux wrap which shortens it without all of the bulk in your pants. I’ve shown this idea in a video with a plaid, flannel shirt.

Insider tip: I like to tuck the button side over the buttonhole side.

The other option that I see on many influencers is the half-tuck. Obviously, a different half-tuck than what I’ve posted about in the past. You might think it looks strange to have part of the blouse inside the pants and part outside, but it’s a trend. And embracing some of the trends is an excellent way to look modern.

Notice the bright-colored belt in both versions? I think this adds more sass than a plain brown or black belt. BTW, I find inexpensive belts at thrift stores.

Insider tip: Don’t be afraid to add a belt even if you don’t have a waist. That’s exactly the magic they do, they make it look like your waist is there. Don’t believe me? Take a selfie of the outfit with and without the belt and compare. Better yet, send the photos to me, and I’ll give you my two cents.

Colorful Scarf and Shoes

Adding color with scarf and shoes for how to style an oversized shirt
Ballet flats: Shoedazzle

Adding color at both the top and bottom of the look really gives it that “je ne sais quoi”, right?

I just tied a small square scarf around my neck to fill in the “v” and then wore my red ballet flats. I think with the colorful aspects of this option, you don’t focus on the half-and-half proportions of the outfit.

And as I talked about in the Spring Trends for 2023, ballet flats are making a comeback, so make sure you have a pair or two.

Insider tip: Yes you can find supportive ballet flats even with online shopping. Look for ones that aren’t perfectly flat to the ground, read the reviews, and make sure the return policy is easy.

Sling Bag

Sling bag for midlife women
Sling bag: from Just Be Youtiful

I chose the sling bag for this example to create something of interest in the middle of the outfit. I know many of you commented about these bags when I showcased them in the Spring Trends of 2023 article that the idea of a purse on your boobs seemed weird.
But as I say about all new styles, don’t knock it until you try it. I didn’t think I would be a fan either, but I actually like this bag and how it hangs.

Remember, most can be adjusted to have it sit where it feels comfy. I’ve always said that crossbody bags weren’t my favorite because the strap created a canyon between the girls. And the sling bag doesn’t do that (at least this one doesn’t).

Insider tip: If you have a belt bag, you can wear it this way also.

How to Wear an Oversized Shirt with a Vest

Styling a sweater vest and how to wear an oversized shirt
Vest: CMD from a local boutique

Popping a vest over your oversized shirt is a fabulous way to add color, interest, and texture to the look. I love how sweater vests are more popular lately, but you could also wear any other type of sleeveless clothing item like:

  1. Zippered vest
  2. Tank top
  3. Even a short sleeve shirt

My vest is shorter so I let the ends of the shirt hang out underneath. I really like how this breaks up the half-and-half proportion. However, if you have a longer vest, that would work as well.

Insider tip: Remember you can “make” a vest out of a large scarf too. Imogen shows 2 ways to do this in her YouTube video.

Layer with an Oversized Blazer

Add a blazer for how to wear an oversized shirt
Blazer: INC-Macy’s from the men’s department

For this option of how to wear an oversized shirt, I added an oversized blazer. What makes it oversized? This blazer is from the men’s department and I wore it with a pink skirt in the past.

Wearing any kind of sleeved topper would work as well. Think of a cardigan, a short blazer (letting the ends hang out as I did with the vest), or even another shirt.

Oversized Shirt as a Topper

Wear your button up as a jacket
Cami: Transformed from a dress

One of my mantras is to remember to layer both over and under your clothing. Since we have put things over this oversized shirt, it’s time to try layering under it.

I decided to wear a satin camisole to give the look color and texture. You may think camisoles are only for hidden layering, but when they are pretty, there is no reason not to show them off.
Adding the white shirt as a “jacket” is a perfect way to not have to worry about bra straps.

Insider tip: Some of your pajama tops would be a perfect “camisole” so don’t forget to check that drawer.

How NOT to Wear an Oversized Shirt

Small accessories with how to wear an oversized shirt
Earrings and Pin: from Just Be Youtiful

My original idea for how to wear an oversized shirt was to add statement earrings and a fun pin. But once I looked at the photos, I realized that they didn’t do the trick.
Sure the earrings are big in person, but in comparison to the large expanse of white and olive green, you just don’t notice them.

Even the pin on the pocket gets lost. In fact, if you saw this look from a normal distance away, you couldn’t tell any difference between it and the basic look without the accessories.

How I’d fix this

I think if you were choosing to add accessories to give the outfit more personality, I would choose a layered necklace option instead. This would create more visual interest on the front of the white shirt and draw your attention up. If you need inspiration for layering your necklaces, I’ve written an article about that.
Then these earrings might be noticed more because you are focusing more on that area of the body.

If layering necklaces seems like too much work, then one bigger necklace in a contrasting color would be nice too.

Insider tip: I’ve read a couple of articles about how statement necklaces are “out of style” but I would venture to think with an outfit like this, it’s more about the focus than the trend.

Facts: Jodie’s Touch of Style is supported by my readers. I partner with affiliate platforms where commission may be earned based on your purchases. If you decide to buy anything I’ve promoted, I appreciate you using my link. These links help bloggers like me to fund the content that we provide, plus it tells companies that blogging marketing works. Thank you for your ongoing support.

Related post: Easy way to add interest to a t-shirt and leggings outfit

How to wear an oversized shirt with olive green pants

Photo credit: Rob Filogomo

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