31 smart and easy ways to style your denim shorts so they don’t look frumpy

The much more comfortable sister to denim jeans, denim shorts, unfortunately, has a bad rep for being frumpy. Banned at even the most casual of work places, and most definitely at high-end restaurants, denim shorts lovers have it pretty rough.

Sick of people telling you that denim shorts are the very embodiment (right behind FBT shorts!) of sloppiness?

These are 31 different ways to style your denim shorts that won’t have people calling you out for being frumpy – you could probably wear this to a party and even get away with it!

1. Pair it with a button down shirt

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Apart from jeans, do you know what else button down shirts go great with? Shorts!

What we absolutely love about this look is how the shorts are great at making the button down look more casual – sort of like an effortlessly chic, casual look that won’t have you chased out of bars, we reckon!

2. Pair it with a fun, graphic tee

A classic combination that people often snub their noses up for, but hey, classics are classics for a reason. Sure, it’s easy for this look to look sloppy – but you can’t just pair any pair of tee with any rando shorts!

When going for such a classic combination, be sure that your denim shorts fit right (and aren’t worn out!), and trendy-looking so it doesn’t risk looking sloppy.

We especially love the ulzzang-style that the girl is pulling off here – a pair of loosely fitted tee and some high waisted shorts – such a simple, casual, everyday combination, yet with the right fitting, accessories, and makeup, you won’t catch anyone calling you frumpy!

3. Pair it with a fitted, plain tee

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Not a fan of loud patterns (perhaps you find them a bit childish)? You can still look chic and casual by pairing plain(er) tees with your shorts.

All you need to do is to find a well-fitted one, tuck it in so it looks less sloppy – easy to wear, easy to match, super stylish (without seeming like you’re trying too hard), and lastly, comfortable as heck.

Note: High-rise denim shorts are the way to go for this look.

4. Pair it with a long sleeved sweater for that extra casual (but not frumpy) look

Make sure to tuck it in to look more put together!

5 Consider long sleeved crop tops

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Alternatively, consider long sleeved crop tops with denim shorts, which pair so wonderfully for a perfect casual, chic summery look. Plus, the crop top will help the outfit breathe if you can’t stand potentially trapping all the heat in!

6. Pair it with a dressy blouse

Dressy blouses make anything casual look nice, that’s all we can say. Heck, people might not even notice that you’re wearing shorts – now that’s what you’d want to achieve!

7. Cinch it with a belt

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Say you’ve lost a couple of inches… but you’re too lazy to go out, and potentially waste money on a new pair of denim shorts that you may also potentially grow out of.

Simply put on a belt, and voila, not only do your old denim shorts fit you, you also look at least ten times less frumpy.

8. Pair it with a thick belt for that paper bag shorts look

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So maybe you want to embrace frumpiness – not the kind of frumpiness that’s traditionally frowned upon – we’re talking street wear chic sort of frumpy.

Consider using a thicker belt, pair it with a pair of shorts that’re extra loose, and voila, you’ve got yourself a more stylish look.

9. Use it as a pair of safety shorts

Love Harajuku style clothes? Use your denim shorts as a safety shorts for a long, boyfriend shirt outfit.

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Plus, it’ll look even more chic if you pair it with shorts that have pockets peeking out from the bottom for even more rebellious pizzazz to your outfit!

10. Pair it with a simple, drapey cardigan!

Scared of coming across as sloppy with just the plain ol’ combination of a plain tee and shorts? Put on a cardigan and you’ll look instantly more polished – we don’t know the whys or the science behind it, but it works!

11. Put on a snazzy blazer to look classy

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An alternative to the cardigan look, a snazzy blazer is a good way to make any outfit instantly more classy.

12. Throw on a leather jacket for that bit of edginess

Prefer an edgy look? Consider other outerwear like leather jackets. Hell yeah.

13. Add on some thin stockings for even more edge

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They’re breathable, and best of all, they help complete the entire look.

14. Play around with different types of stockings

The good thing about denim shorts is that they expose your legs. This gives you room to play around with patterned stockings like fishnets…

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Or even coloured or patterned ones – the works!

15. Transform long sleeve shirts into your own DIY, off-shoulder chic outfit

Alternatively, you could transform long, baggy boyfriend’s shirts into an off-shoulder chic looking shirt – you won’t ever catch anyone else wearing this (apart from Hailey Baldwin, we suppose)!

16. Consider vests, if you can’t take the heat!

Source: sazan.me

Can’t stand anything long-sleeved, especially in Singapore’s humid weather? Consider vests, which not only makes a look pop more, but also adds a certain chic sleekness to it.

17. Ombre shorts, if shorts are too dull for you

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Sure, the time for ombre may have passed just a few years back, but come on, they still look cool as heck (and we’re secretly hoping for a revival of the ombre some time in the near future!).

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Too dull to satiate your need for colours (don’t we all)? Consider galactic ombre shorts. We may be (somewhat) over the trend of ombre shorts, but galactic patterns? Not so!

Lazy to source out for a new pair of shorts? Simply DIY it with just some bleach, dye, and voila – you have your very own pair of ombre shorts!

18. Consider paper bag shorts for a casual, cute look

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Want a pair of shorts to define your waist? Paper bag shorts are excellent for that, plus, the ruffle right at the top makes the outfit look extra cute!

19. Consider torn denim shorts, just because

Let’s be honest – torn anything (as long as it’s done artfully and not an actual tear!) almost always looks good. No exceptions.

20. Wrap your outerwear around the waist for a more pronounced look!

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If you’re pairing your denim jacket with any sort of outerwear, you’ll eventually have to go out into the scorching sun, and hey, nobody wants to straight up boil in the heat just to look fabulous!

Simply wrap your jacket, flannel, or outerwear of choice around the waist – great at covering up food babies too, if you ate too much during your lunch break.

21. Wear sneakers for a casual, athletic look

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We’ve mentioned frequently, in our fashion articles that shoes really do maketh the person. This applies here too, naturally.

Throw on some sneakers for that athletic casual look.

22. Consider a nice pair of sandals for that beach vibe

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And when we say sandals, we don’t mean flip flops. Flip flops are an absolute no-no in our book, especially when paired with denim shorts!

23. Want to look formal? Wear some heels!

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Just like how makeup makes one look way more put together, regardless of how casual their outfit actually is, heels work no differently. A girl’s gotta have at least one pair of heels in her arsenal, after all!

24. Consider some boots

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Like heels, but with more swag, and less girly, if you’re uncomfortable with being tooooo girly.

25. Legs for days? Consider Bermuda shorts!

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If you’ve been blessed with long legs, how ‘bout some bermudas? Plus, you know for sure that as a tall person in Singapore, you’re probably one of the lucky few who can pull this look off!

26. Consider caps, for that extra summery look!

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Shielding your head from the sun while looking totally swag? Count us in!

27. Try on some hats, to class up your outfit

If you consider yourself more of a classy girl who doesn’t quite dig the athletic casual look, consider donning something more classy, like a fedora…

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Or a sun hat!

28. Try denim on denim!

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We’ve all got at least a pair of denim jacket, and a pair of denim shorts in the closet. Never thought of pairing the two together? You’re welcome.

29. Consider donning a pair of sunglasses for that extra oomph

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Speaking of easy looks that we likely already have in our closets, don a pair of shades for that extra swag factor.

30. Accessorise with some chokers!

You just can’t deny how much the chokers and layered necklace transforms a basic off shoulder top and denim shorts outfit, into something completely unique.

31. Don’t throw out your low and mid-rise shorts

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Just because they’re (currently) out of trend over the highly saturated market of high waisted shorts doesn’t mean they won’t ever come back! Plus, if you work out often, show off the fruits of your labour (read: abs!) by pairing a low or mid waisted pair of shorts with a bralette.