Oversized Tees – When and How to Wear Them!

If you’re anything like me, the one question I have every day is “what should I wear” for pretty much every situation. Going to work, catching up with friends, or drinks with the girls, I just never know what to wear for the occasion. Thankfully, oversized tees are here to save the day. An oversized tee is a staple in my wardrobe; and really should be a staple in ANY girl’s wardrobe! Why?

Oversized tee’s are just the best. No matter what shape you are, if you’re tall or short, or what colour you are – an oversized tee will ALWAYS look good! They’re also the comfiest things to wear, and so easy to dress up or down for almost any occasion! I’ve been a huge fan of oversized tees for a long time, and my favourite thing to do is to steal my boyfriend’s tees because they were always oversized, and his are more comfy than mine!

In the spirit of supporting local businesses, I’ve bought a few oversized tees from His Shirt is Mine – this is a New Zealand business that specialise in oversized tees! I reached out to Juliet, who started His Shirt is Mine around 18 months ago. She started the business because she, like myself, had a habit of stealing her partner’s tees, hoodies, singlets and even his boxers!


She wanted to play on the habit of women wearing their man’s tees, and there came His Shirt. They currently have a range of tees that are all in mens sizes, for both guys and girls to enjoy – and they have some very exciting things coming for Winter very soon! All of her tees are made out of super soft, high quality material, and I have never worn a single tee more than I have worn my tees from His Shirt!

You can check out their range at: www.https://hisshirtclothing.com/ and check out their instagram at http://www.instagram.com/his_shirt

Now onto styling; Juliet’s favourite way to style her oversized tee’s are either on their own to wear around the house, or styled with some heels for a night out! Here are some of my favourite ways to style an oversized tee for every occasion:

Wear it On Its Own!

The best thing about an oversized tee is the glory of wearing it on its own – no other clothes needed! Oversized tees are designed to cover all of the important bits, while giving you the freedom to go Bra-less all day and lounge around your house in nothing but a tee! Why put together an entire outfit, when the hardest outfit decision you have to make could be “what oversized tee do I wear today?” Throw your hair up in a bun, chuck on an oversized tee and a face mask, and just get cozy girl!

The coolest thing with oversized tees, is there is so many different ways to style them without ANY other clothing pieces! I’d recommend getting your tee super oversized for these different tips.

For a day out and about, a simple knot at the bottom instantly gives the tee some shape, and helps give your body a bit more shape as well. Plus, you have plenty of chance to show off those sexy legs your momma gave ya! Throw on a cute bag and chunky sneakers, and you’ve got a stunningly effortless day to day fit!

A trend going around lately, that we all know, is the super classy Bum Bag. To add a bit of ‘hip’ to your fit, throw a bum bag over one shoulder or around your waist for a bit of shape and texture to your look!

Of course, wearing it on its own with a cheeky handbag and heels is also a great way to stay comfy, while looking flawless for a night out with your girls.

Comfy with Cycle Shorts!

We all know of the infamous cycle shorts trend that took over the internet last year – and these paired with an oversized tee is super chíc as well as being super comfy. It’s the perfect outfit to look like you’ve put in heaps of effort, but really you just threw it on, and still look super cute. This is perfect for hanging at home, a day of errands, or chilling with your girls!

I absolutely love wearing a tee with cycle shorts for a chill day. I paired this look with some sunnies from Cotton On and some white chunky sneakers from Boohoo. This is the best way to feel confident and comfy, as well as rocking a super cute outfit. Can’t get much better than that!

But why stop there? Statement chunky boots and high socks are a totally grunge look that throws off some badass vibes, and are still super effortless and comfy. This would be perfect for those oversized tee’s with statement prints, or darker statement colours that you really want to accentuate!

If you’ve got a statement pair of cycle shorts you want to show off, simply tie a knot in the front of the tee to really sinch in that waist, and show off your cute shorts!
Side note: I realised I’ve been tying my tees all wrong and Tik Tok gave me the solution!
Check out an even better way to tie your tee here: https://www.youtube.com/watch?v=lDWx7LF6gto

Cycle Shorts – the Dressier Version

You could dress this up even further for cooler weather with a jacket over top! My favourite is throwing a denim jacket over my shoulders for a bit ore cover, or actually putting it on if its getting cold. You could also try a leather biker style jacket, or even a coat for those chilly mornings heading out to the office! Pop on your favourite chunky sneakers for a casual day out, or you could throw on some heels for a dressier look. If you’re feeling even more daring, why not try this with a pair of thigh high boots for an even edgier look!

It was much too hot to put the jacket on fully, but you get the idea. I love contrasting the colour of my jacket with the colour of my tee – in this case I wore a light denim jacket on a darker grey tee. The contrast helps to make the outfit look a bit more put together; plus the denim jacket gives you pockets!

This outfit would also look super cute with a full length coat in colder months – when you’re going from nicely heated rooms out into the cold outside. Similar to how you would with a dressy look – you’re just a lot more comfy!

Worn as a Tee

Oversized tees can also be worn as a normal top, especially in cooler months! My favourite thing to do with an oversized tee is pair it with my favourite high-waisted jeans (usually my super distressed ones from Glassons) and wear the tee tucked in. I’ll pull it out a little bit so it looks a little baggier, but still classy. This outfit could be paired with a pair of cute boots, chunky sneakers, vans, or some heels for an evening look. Don’t forget to throw on a jacket if it’s cold!

Image from (Ida Marshall) Pinterest

If you’re feeling super comfy (like I currently am) you could throw your tee on over a comfy pair of joggers. While writing this I’m wearing some super soft RPM joggers with my His Shirt tee, and it is 10 out of 10 cozy! Its definitely perfect for a comfy day at home when it’s a bit colder, or out and about for a comfy casual look.

For a day out and about – styling an oversized tee like this over jeans or leggings with some cute accessories is an effortless look that will have people staring. I love any kind of oversized tee with black jeans to really make the top stand out, but lately I have also been obsessed with this black on black look.

Another thing I love to do is wear the tee tucked into jeans, or just tucking the front by the jeans button, and letting the rest sit loose. I think this style looks so classy and effortless, and helps to give your bod just that little bit more shape. Basically, why aren’t you wearing an oversized tee right now?

The Oversized Tee: Event Ready!

If you’re feeling super confident, possibly a bit daring, and your oversized tee is long enough, you could 100% wear it on its own as though it’s a dress, and completely dress it up for a night out. Pop on your favourite strappy heels, some statement jewellery, and a waist belt around the middle! The belt will help to give your body a bit more shape around the middle, and make the tee look super flattering!

Image (Tiger Mist) Pinterest

I love this idea of a super oversized tee, sinched in with a belt, and just killing it babe. It gives you the best of both worlds; comfort and class!

We’ve all seen the corset trend that’s been going around (especially since Perrie from Little Mix started rocking it!) and I am really starting to love its vibe! A corset belt with an oversized tee just does wonders; sit it up just underneath your chest and really pull it in to give your body that shape and style – and it looks just so classy and stunning! Perfect for a night out with the girls, or even a date night if you’re other half is into it!

I’ll definitely be having some fun with this trend, trying new tees and belts (maybe even a corset or two) and really finding out what works best for me!

Comfy Active Wear

Being comfy when you work out is so important; for me it helps me focus more on what I’m doing than worrying about being uncomfortable! When I’m out in public I always have an oversized tee or singlet on (mostly because it’s cold, but still working on that body confidence too…) simply because of the ultimate comfort I get from wearing one!

I’ll mostly wear an oversized tee when I’m out for a walk or a run. With it being oversized, it’s not clinging to your body if you get hot and sweaty, and there’s room for the breeze to blow up and cool you down a bit. Plus, if you have somewhere to be after your workout, you don’t really have to change out of different layers!

Oversized tees with activewear are perfect because they generally suit anything you wear. I either wear Nike Pro Cycle shorts, Nike 3″ running shorts, or a pair of leggings – an oversized tee thrown on works with all of these options.

You really can’t beat having an oversized tee in your wardrobe – it’s the staple for absolutely every occasion! Whether you just want something to throw on around the house, or a comfy outfit to wear in town, all you need is an oversized tee and some accessories! I highly recommend picking up a few in various sizes and colours to see what works best for you, and feel the comfort! The true question; why AREN’T you wearing an oversized tee right now?

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