25 Funny Ways to Roast Someone’s Outfit

Funny Ways to Roast Someones Outfit

They say how you dress is how you’re addressed. Some don’t get it though. Perhaps it is for them that we have roasts. 

Do you know anyone who unrepentantly dresses badly? If you’ve been thinking of how to roast someone’s outfit that you don’t particularly like, this article is for you. 

The funny roasts in this article are curated from your favorite movies, beautifully delivered by your favorite actors and actresses. 

While giving these stars their flowers, savor the humor in their words and cast your mind back to the scenes in those movies. 

Dig in. 

Table of Contents

25 Funny Ways to Roast Someone’s Outfit

1. Did you pick that outfit in the dark, or do you just hate mirrors?

Funny Ways to Roast Someones Outfit

This outfit roast comes from the movie The Devil Wears Prada. The words come from one of Hollywood’s stars Meryl Streep.

And she couldn’t have said it better. What better way to roast a person’s outfit than to call into question their relationship with mirrors or darkness.

The outfit has got to be utter nonsense to warrant such a reaction. 

The Devil Wears Prada, Meryl Streep

2. Your fashion sense is like a GPS without signal—lost.

Funny Ways to Roast Someones Outfit

When Isla Fisher delivered this roast little did she know it would be the gem that it is today.

This roast is so funny you can’t use it at a meal. You’ll send the whole family to the ICU. Apparently, a lack of fashion sense is the same as a GPS without a signal.

Use this roast on someone you don’t mind losing their friendship, please. 

Confessions of a Shopaholic, Isla Fisher

3. Are you auditioning for a fashion disaster movie?

Funny Ways to Roast Someones Outfit

Have you seen someone’s outfit and you went, ‘is this person clueless?’ Well, in the movie titled Clueless, this is what we learn from Alicia Silverstone.

Use this roast when the person’s outfit is an utter disaster. It doesn’t matter if they are man or woman, this funny roast hits a home run. 

Clueless, Alicia Silverstone

4. I’ve seen mannequins with more style than you

Funny Ways to Roast Someones Outfit

In a lighthearted banter you can use this roast for someone’s outfit if you think they could have done better.

Mannequins get assistance from human stylists. But there’s a big problem if a mannequin excels in fashion than a human.

This also means this person is so bad with fashion that he or she couldn’t even dress a mannequin. 

Anchorman: The Legend of Ron Burgundy, Will Ferrell

5. Is that a new trend or did you lose a bet?

Funny Ways to Roast Someones Outfit

The outfit in this case is so tacky it has to be a terrible trend no one should hop on. Or the outfit is so depressing it has to be a reaction to a huge loss at the bookie’s.

Hopefully it is the latter. Perhaps to get the hilarity of this roast, you might want to watch the movie White Chicks again. 

White Chicks, Marlon Wayans

6. Your wardrobe has more issues than a magazine subscription.

Funny Ways to Roast Someones Outfit

This is a good roast. And it’s also a great way to be brutally honest, but politely.

The best thing about this roast is the choice of words.

Rather than outrightly say the outfit is terrible, you say it has issues. What else has issues? Magazines. 

Sex and the City, Sarah Jessica Parker

7. Even fashion crimes have standards, and you just broke all of them. 

Funny Ways to Roast Someones Outfit

This one funny roast will have your listener take a moment to think things through, and when the person gets it, they can’t help but laugh too.

There truly are fashion crimes, and they do truly have standards. Breaking a few is forgivable. We don’t know about breaking all of it. Do you? 

The Devil Wears Prada, Meryl Streep

8. Did your closet throw up on you, or is this your actual choice?

Funny Ways to Roast Someones Outfit

A huge LOL here. Picture Anne Hathaway saying those words in the movie. Picture her facial expression as she says it too.

It’s not hard to pass this humor on, like an infection. This person’s fashion choice has to be the most atrocious. Make sure of this when using this funny roast. 

The Princess Diaries, Anne Hathaway

9. Your outfit is so last season, it’s practically vintage. 

Funny Ways to Roast Someones Outfit

Oh well. There’s some mildness in this delivery. I can picture Emily Blunt’s sultry eyes as she says it, with a devilish smirk to crown it.

She will probably add a late chuckle to the roast. What kind words to describe an outfit that’s so 2008. Vintage. 

The Devil Wears Prada, Emily Blunt

10. If fashion were a crime, you’d be serving a life sentence.

Funny Ways to Roast Someones Outfit

This roast is for your friend who just murdered her outfit, literally. There’s bad that means good, and there’s killing it that means doing it the best way.

In this case, we at RoastHow think this person did something with their outfit deserving of prison. 

The September Issue, Anna Wintour

11. Wearing that must require a permit for disturbing the peace of style.

Funny Ways to Roast Someones Outfit

It’s Emily Blunt again with her sultry takes on fashion in the Devil Wears Prada. This time, she’s spot on let’s us know there’s something called the peace of style.

Some people’s outfits are guilty of this crime. You can say this roast with a straight face, or with whatever shape of face you want for that matter. 

The Devil Wears Prada, Emily Blunt

12. I didn’t realize fashion emergencies were a thing until I saw you.

Funny Ways to Roast Someones Outfit

Fashion emergency means this person’s outfit must not be allowed into the event in the condition that they’re in.

Perhaps events should have standby medics for outfits. They would have first aid boxes filled with scissors, sewing needles and threads and other styling tools. 

The House Bunny, Emma Stone

13. Is this a new trend, or did you just forget how to dress?

Funny Ways to Roast Someones Outfit

Lindsay Lohan said these words in Mean Girls. We think it’s a mean thing to say to a girl. But we don’t care.

That’s what roasts are for, to make people laugh and objectively weigh how much harm they’ve done to humanity with their outfits. 

Mean Girls, Lindsay Lohan

14. You’re not making a statement; you’re screaming for a wardrobe intervention

Funny Ways to Roast Someones Outfit

We know a few celebrities we’ve seen at award shows who need this roast screamed at them.

Some outfits are just flat out outrageously unclear in their aim. Some are beautiful but there’s few of those.

Stars love to impress their fans in the media.

Everyone wants to grace the pages of tabloids but few actually pull it off. Okay, I’m ranting. But you get the drift of this funny roast. 

Confessions of a Shopaholic, Isla Fisher

15. Fashion is about expression, not an excuse for a visual assault.

Funny Ways to Roast Someones Outfit

Ben Stiller never misses. A confrontational roast here, funny as can be if you deliver it well. In fact, there’s no way you drop this that isn’t funny.

The best thing about this funny roast is that it admits a person’s freedom to express themselves anyhow they want style wise.

Ben Stiller lets us know there’s what’s called visual assault. You can look at a person’s outfit and admit that you’re choking on the dismal fashion. 

Zoolander, Ben Stiller.

16. Your style is like a Picasso paintingconfusing and not everyone gets it.

Funny Ways to Roast Someones Outfit

This quote is from the movie Confessions of a Shopaholic. It was said by the character of Isla Fisher. It was in response to someone’s terrible fashion.

On one hand the person may have been flattered when they heard the name of a famous artist being associated with their dressing.

But the delight is short-lived after hearing that this artist’s work had a curious effect of confusing admirers. 

Isla Fisher, Confessions of a Shopaholic

17. I didn’t know mismatched socks were the new black.

Funny Ways to Roast Someones Outfit

In the movie Easy A Emma Stone plays the bubbly Olive Penderghast. She mouths off the above roast in the movie and it’s a gem.

It is a simple yet biting observation to make about someone’s outfit. This roast seems to feign ignorance, as if asking the other person to prove themselves.

It is a veiled attempt at derogation with the use of the word mismatch.

Also suggesting the socks were the new black was a way to give some credit, even if little, to an unintentional fashion win. 

Emma Stone, Easy A

18. Your outfit screams ‘I give up on adulting today.’ 

Funny Ways to Roast Someones Outfit

Do you know how bad your outfit has to be to earn this roast? It is a suggestion that the person’s outfit is totally childish and unfit for the public.

For one thing, an adult should not be seen wearing it. Neither should other adults be associated with you in that dress.

Jennifer Garner said the above words in the movie 13 Going On 30

Jennifer Garner, 13 Going on 30

19. Is that a fashion choice or did you accidentally get dressed in the dark? 

Funny Ways to Roast Someones Outfit

To get how hard this roast hits, imagine yourself getting dressed with your eyes closed. It’s as good as dressing up in the dark.

In Mean Girls, the character of Rachel McAdams said the words above to another character about their dress.

When you use this roast, the offender is forced to rethink their fashion priorities. They are more likely to go with the latter reason for the fashion putsch. 

—Rachel McAdams, Mean Girls

20. I’ve seen scarecrows with more fashion sense.

Funny Ways to Roast Someones Outfit

This roast is hilarious to even contemplate. You have to think about a scarecrow to appreciate the picture being painted here.

Anyone who gets compared to a scarecrow has done something unforgivable.

Fashion wise, that is. There’s an intuition to fashion. Most scarecrows are covered in layers of rags. The fashion in this roast conjures in the mind, something worse. 

—Katherine Heigl, 27 Dresses

21. Are you auditioning for a role as a walking abstract art installation?

Funny Ways to Roast Someones Outfit

Anne Hathaway in The Princess Diaries was looking at an undefined piece of absurdity. It was someone’s idea of fashion.

Seems like 3 out of 5 people have this sort of outfit, and once a while, they come out into the world, dressed in those absurdities.

This is a roast for an outfit that can’t be named. Like abstract art. 

—Anne Hathaway, The Princess Diaries

22. I didn’t realize ‘laundry day chic’ was the new trend.

Funny Ways to Roast Someones Outfit

This roast from the Legally Blonde movie takes a jab at sloppy fashion. Or an outfit that’s considered unkempt.

It suggests that the person ought to be at the laundromat, not out in the street. On the surface this quote suggests that the outfit is good enough for a trend.

But there’s a reprimand somewhere in the undertone. For this roast, tone and facial expression is everything. Just think of Reese Witherspoon’s face. 

—Reese Witherspoon, Legally Blonde

23. Your clothes are so loud; they’re drowning out your personality.

Funny Ways to Roast Someones Outfit

Sometimes the problem is colors. At least that’s what it seems Alicia Silverstone is going on about here in the movie Clueless.

Or it could be the inappropriateness of the fashion which announces itself from Mike’s away.

So if you have someone who dresses in such a way that makes so much noise, this roast is for them. 

—Alicia Silverstone, Clueless

24. That outfit is so last season, even time travelers wouldn’t be caught dead in it.

Funny Ways to Roast Someones Outfit

There’s nothing wrong with retro fashion. There’s always a time and place for it. And maybe that’s the problem here.

Meryl Streep said the above words in The Devil Wears Prada.

There’s a measure of vintage that screams classic while there’s another that no one wants to be caught dead wearing. We think everyone gets this. 

—Meryl Streep, The Devil Wears Prada

25. Is that a fashion statement or did you lose a bet with your wardrobe?

Funny Ways to Roast Someones Outfit

Most likely a fashion statement. Everyone invariably wears what they feel comfortable in.

Yet, there are at least a few times people have worn outfits that call their wardrobe sense into debate.

Ben Stiller in Zoolander seems to think a bet could be involved too. Use this roast if you agree. 

—Ben Stiller, Zoolander


Outfits are a serious matter. They can appeal to the eyes, or they can cause anguish for the brain.

Especially if you’re Meryl Streep in The Devil Wears Prada. Or Ben Stiller in Zoolander. 

This roast for someone’s outfit has come to you from movies we can’t forget. Screen gems with quotable quotes. Use this roast at your own discretion. 


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