How to Style an Oversized Shirt in 4 Simple Ways (2023)

This post is all about how to style an oversized shirt and how to wear oversized shirts in general.

There are few items in a woman’s wardrobe that are as classic, yet as versatile, as a freshly pressed tailored shirt, and whilst these can look incredibly sharp underneath a tailored suit or blazer, it’s fair to say that times have moved on a little.

Gone are the days when shirts had to be well-fitted, starch pressed and formal. With the newfound athleisure and athflow fashion trends having gained traction in recent years, the rules of play have changed and stylish doesn’t necessarily have to mean uncomfortable.

Enter the oversized shirt – the sophistication of a classic shirt, with the comfort of a sweater. That’s not to say the oversized shirt is a replacement for a classic tailored shirt. Of course there is still a place for them, it just means that the spectrum of shirts has broadened, and it’s yet another item of clothing that deserves a place in every wardrobe.

There are so many ways how to style an oversized shirt – and that’s what this article is all about: how to style oversized shirts to still look smart and sophisticated. The truth is, it doesn’t require very much effort at all.

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Just like the classic tailored shirt, oversized shirts can be worn in so many different ways but have the added benefit of being much more comfortable.

The perfect garment for that ‘just out of bed‘ chic that works for so many different occasions, whether that’s working from home, going shopping, out for lunch or heading into the office.

No matter what the occasion, or what the oversized shirt will be paired with, how it is tucked in is the first place to start.

Before diving in to how to style the oversized shirt with different garments from your wardrobe, we’re taking a look at how to tuck in oversized shirts, if at all!

It may sound quite straightforward, but the tuck can be the downfall of an outfit if done carelessly. We’re breaking it down step-by-step to make sure you don’t end up with unnecessary bumps and duck tails.

1. Start by putting on the shirt first, before the shorts, skirt or bottoms.
2. After putting on a skirt, lift it up and pull down the shirt from the bottom. This is obviously not possible if wearing shorts or pants – in this case, try to pull the shirt down as much as possible before doing up any buttons or zips.
3. Once the skirt, shorts or pants are on and done up, raise your arms to the sky and let the shirt loosen a little, so that it’s not as tightly tucked.
4. Lastly, take a look in the mirror and adjust accordingly. Gently tug at any pieces that are still tucked in too tight, to make it even all around.

The ‘French tuck‘ is simply a name for a shirt that has been ‘half’ tucked in. It was coined by Queer Eye co-host and celebrity style guru Tan France, who explains that to master a French tuck, one simply tucks in the front of the shirt by about an inch or two, while leaving the back completely untucked.

Some have argued that this can appear scruffy, but we disagree. It’s true that this could appear a little unkempt if using the French tuck on a fitted shirt, but it works perfectly well with any kind of baggy top – whether that’s an oversized shirt or oversized tee. It elevates the casual outfit without trying too hard, and is great for elongating the legs by revealing just enough waist to give the outfit some shape.

Love it or hate it, the French tuck, or half tuck, doesn’t look like it’s going anywhere. It exudes effortless chic and despite the term ‘French tuck’ being relatively new, shirts have been worn like this for a long time. One only has to look back at the fashion weeks of recent years to see that oversized tops have been styled this way on the runway long before it became a ‘labelled’ trend.

Instead, leave the shirt slightly unbuttoned at the bottom and use the two sides of the shirt to tie a little knot. The back of the shirt can be left untucked or tucked – it’s all down to personal preference. One thing is for sure, cotton shirts would be better here as opposed to anything silk or satin.

Leaving it totally untucked offers even more options – does the oversize shirt need to be buttoned to the top, buttoned half way to reveal beautiful lingerie or corsetry (be sure to check out our article on all the different types of lingerie available!), or can it be left completely undone with a pretty camisole or crop top underneath? The choice is entirely up to you and really depends on whatever feels right on the day.

Trade in your plain or graphic tee for an oversized shirt to instantly dress up the outfit. Add your favorite pair of strappy sandals in warmer months or swap for a blazer or leather jacket and perhaps the currently trending lug-sole boots during the winter.

Don’t forget to accessorize with some chunky gold jewelry to instantly elevate your look, without much effort!

This is a great ensemble to play around with and experiment with different styles. French tuck the oversized shirt into the jeans, leave it completely untucked with the buttons done up halfway to reveal glimpses of a pretty French bra, or perhaps leave it completely undone, with a little silk camisole underneath.

Swap out heels for some white sneakers for that ultimate street style.

Pair it with a large tote bag and some comfy sneakers or biker boots for that ‘dishevelled chic’ look that’s perfect for every day wear in summer.

If you’re determined to wear your oversized shirts with denim shorts in the cooler months, add a pair of black tights, throw on a blanket scarf, and your favorite knee-high or thigh-high boots. Accessorize with chunky gold earrings.

Looking to shake things up a little? Swap out the denim shorts for biker shorts for a completely different vibe!

How to Style an Oversized Shirt with Leggings

Sometimes, we just want that added little bit of comfort. On those days, throw on a pair of your favorite leggings with an oversized shirt, and pair with white sneakers.

For those cooler months, throw on a warm knit sweater either over your shoulders or over the shirt, and pull the ends of the shirt slightly out of the sweater.

Alternatively, pair it with a complementary oversized blazer and swap the sneakers for heels – from day wear to instant night-time glam, whilst remaining equally as stylish.

How to Style an Oversized Shirt with Any High-Waisted Bottoms

There are some occasions when an oversized shirt looks best when fully tucked in and that is when worn with high-waisted bottoms, whether a mini skirt, shorts or palazzo pants.

High-waisted bottoms are great for accentuating the waist and revealing your silhouette, and you may risk hiding it if the oversized shirt is not tucked in! Our favorite is to pair a white oversized shirt with high waisted black trousers/pants, paired with a black blazer with gold oversized buttons for a little pop of color.

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