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  • Writer's pictureSheryl

9 ways to wear your t-shirt out every summer... or for any occasion really.

I need to learn how to style t-shirts. Desperately.

Casual summer t-shirt outfit ideas, RollingBear Travels blog.

Ahh, t-shirts. What an amazing invention, don't you think?

You can wear them to school, sports, at home, to sleep in.

But for someone whose wardrobe consists mainly of t-shirts,

I am NO t-shirt-dressing-expert / stylist. No sir.

And because they have become such a BIG part of my wardrobe, everytime I think of 'dressing up', t-shirts just don't come to mind! My brain will be like "yo, you wear t-shirts every day, and you're still going to wear it out? Really? Push the boundaries girl."

Until I was in need of a deep frills/girly stuff detox after styling too many lace, florals and generally very girly tops in June.

As a new 'Instagrammer', or style blogger really, I constantly feel the need to churn up perfect outfits all the time. And I forgot that the reason I started this journey in the first place was to:

  1. Build self-confidence in my dressing and styling.

  2. To learn from others.

I really needed t-shirt outfit inspirations, so I thought that this would be a whole lot more fun to talk about the outfits that have inspired me from my fellow Instagrammers! Plus, doing this with friends is so much more fun than constantly talking to myself anyway.

Also, THANK YOU SO MUCH, @petitestylereport, @build_a_brina,, @eunoiainspired and @kiranxkajal for allowing me to use your pictures for this! Honestly, I dived into Instagram feeling very intimidated by the Instagram community. But along the way, I met some really friendly, amazing girls with the same interests and I don't know guys, it just feels so nice to be able to meet new friends so unexpectedly! Sorry, rambled a little there. Anyway.

Let's get to it! :)


- The classic T-shirt + Jeans Combination -

// The Boss Babe / Business Casual //

photo & outfit by @petitestylereport

White tee + Grey jeans + Black military boots + Blazer

White tee, grey jeans, blazer, black military boots outfit by petitestylereport, RollingBear Travels blog.
White tee, grey jeans, blazer, edgy outfit by petitestylereport, RollingBear Travels blog.

Natalie has a really cool, edgy vibe when it comes to her outfits. I am a sucker for military boots and edgy fashion, so I really love this! I think the blazer elevates the whole outfit. And the t-shirt just became a whole lot cooler.

I think that this is such a comfortable and versatile Boss Babe kind of outfit that I'd love to wear to any interview. Or anytime I need the extra punch anyway.


// The Clean White //

photo and outfit by @build_a_brina

White graphic tee + High-waisted white skinny jeans + White sneakers

White graphic tee, white jeans, white sneakers, white purse outfit by build_a_brina, RollingBear Travels blog.
White summer outfit : Graphic tee, jeans, sneakers, purse, by build_a_brina, RollingBear Travels blog.

You know the cool vibe that you get from white sneakers? I feel the same way with this outfit, but with TRIPLED coolness given that the whole outfit is white!

I like how versatile Sabrina's style is - she's constantly experimenting with girly outfits. And then switching them up for street-style cool, like this outfit. I'd love to wear this outfit to any outing! Plus, it's like street style, but not so edgy? The purse adds a feminine touch to it.


// The Effortless Chic //

photo and outfit by

Oversized white tee + Mum jeans + Heeled black boots

White graphic tee, mum jeans, black heeled boots outfit by, RollingBear Travels blog.

Joyce's feed is filled with minimalist outfits. Sometimes I tend to go overboard when I think of 'dressing up'. Because I'd think: my dressing is too simple, it is not good enough for a style feed. But Joyce's wardrobe always reminds me that sometimes, less is more. That simplicity makes the best outfits.

OK first, I think that that is such a CUTE TSHIRT. Dang I love the graphics. And I love how she styled it with faded mum jeans and heeled ankle boots. The whole outfit looks so effortlessly put together and elegant! The hoop earrings are a nice touch.

// Boyfriend jeans + Sneakers variation //

Uniqlo Pokemon white tee, ripped boyfriend jeans, Converse sneakers outfit, RollingBear Travels blog.

UMM... looks like 'effortlessly chic' just turned into 'awkward laughing mess'.

ANYWAY, this is how I usually style my oversized white t-shirt - with my one pair of very shredded boyfriend jeans and Converse sneakers. This is my standard go-to outfit every time I travel (short distances only!!) or when I get tired of skirts. It's so comfortable and easy to put together!

I love Joyce's elegant variation of this scruffy/edgy outfit of mine. I've worn this outfit so many times, it was really nice to see a different way to dress it up.


- Too hot for jeans? Here's a cool biker shorts outfit! -

photo & outfit by @eunoiainspired

Graphic tee + Denim Jacket + Sneakers

White graphic tee, biker shorts, blue denim jacket summer outfit by eunoiainspired, RollingBear Travels blog.

Comfortable, cool, simple.

Does it get any better than that? Tina's feed is on fire: every picture has a unique concept behind it and she's just owning every outfit she wears. If I take anything away from her page, it is that you can literally wear ANYTHING you like, however simple it may be. But wear it with confidence, and kindness because that's really the best accessory, no?

I'm personally not a huge fan of biker shorts. But I'll definitely add this look to my repertoire, with denim shorts instead!


- Turn your oversized t-shirt into a dress! -

photo & outfit by @kiranxkajal

Oversized graphic tee + Strappy Heels

Yellow graphic t-shirt dress, strappy heels, white purse outfit by kiranxkajal, RollingBear Travels blog.
Yellow graphic t-shirt dress, strappy heels, white purse outfit by kiranxkajal, RollingBear Travels blog.

Kiran's style is at once edgy, elegant, fiery and so cool.

I really like the graphic of that t-shirt. Plus, the lemon yellow theme just emanates summery vibes!

I was always under the impression that oversized t-shirt dresses were very edgy. And knowing me, I'd probably pair it with sneakers. I love how Kiran paired it with strappy heels and an elegant purse. She's made the dress look so effortlessly classy and just the right amount of casual! I really love the elegant twist to the outfit and I'm definitely trying this!


- T-shirt + Skirt -

I actually wear a lot of skirts... more than I realised.

Loose white tee + High-waisted black skirt + Oversized shirt + Beret + Combat boots

Denim and Supply white tee, high-waisted black skirt, AllSaints military boots, black beret outfit, RollingBear Travels blog.
Zadig & Voltaire olive military oversized shirt, loose white tee, high-waisted black skirt, AllSaints military boots, black beret outfit, RollingBear Travels blog.

This outfit was actually inspired by an autumn outfit I saw, but I switched the oversized sweater for an oversized tee.

Fun fact: I used to hate caps AND military boots when I was younger. The obsession really began after walking past too many AllSaints stores with so many stylish mannequins. Yup, I get lots of outfit ideas from mannequins.

What do you guys think?


My t-shirt dilemma has been going on for a while now. I mean, I even had to have a CONFIDENCE CHAT with my graphic tee (yup, you heard that right).

Well, hopefully, there's something for everybody here, and that it'll inspire you to wear anything you want. I think ultimately, the key to any outfit is confidence. It is in embracing what we like first and then experimenting with that, that truly expresses us.

This is something that I definitely need to learn because I am such an awkward bean. And even though this little online journey of mine has been helping my self-esteem, it does at times put me down too. I started to feel like if I wanted to stay relevant or even valid, I needed to dress a certain way. And that how I like to dress isn't good or creative enough.

When actually, no.

Everybody has their own flair. So, wear whatever you want because that'll make you shine! :) OWN IT!

Thank you for reading!! If you enjoyed this, or have any suggestions, please leave it in the comments below!

- Sheryl

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