How to wear flared pants – tips and tricks and 3 variations

by Sylvia

How to wear flared pants |

If you are thinking of getting some flared pants I have some great tips on how to wear them as well as 3 variations to show you. I did quite a bit of thrift shopping during my stay in New York (article on that still to come) and for a while now I had been looking for flared pants to replace my old white sailor pants.


I normally don’t look for pants in thrift or consignment shops as I prefer to look for more fancier items there, but this shop was quite small and these pants jumped into my eye. They seemed to meet my requirements for white pants as they are stretchy, not too thin, had pockets, were flared and were my size. I noted that they were by Theory, a brand that is very prominent in the US and that I snatched up for other items too.


You may also like my tips on how to wear wide leg pants.


I guess the pants were meant for me as they fit like a glove. I was with 40+ style readers at the time and they all agreed I had to buy these. An easy decision as they were very affordable.


Of course I wore them as soon as I could. When fashion week started the weather had cooled down a bit, therefore perfect weather for pants. I did not have any fashion shows to attend but was going to meet Jamie today and would later attend a special gathering with Garance Doré I wanted to have an outfit that would not draw too much attention, was comfortable for the whole day yet still fashionable.

I decided to combine it with a summer top from Stella Carakasi and a (very old) denim stretch jacket. The icing on the cake was provided by a new necklace and earring earlier bought on a street fair from independent designer AC Agates, who makes the most exquisite handmade jewelry.



How to wear flared pants?

A few tips on how to ware flared pants, especially those (like these) that are not super tight at the top.


  • Make sure they fit well around your waist and bottom. You don’t want them too be too baggy here.
  • You can choose to have your pants tightly fitted around the upper legs (like my Paige flared jeans do) or have the fit a bit more relaxed and skimming the skin as in the white pants.
  • Make sure your top is not too long. You want to show that your pants fit tightly at the top which makes the look more streamlined, lengthening and flattering.
  • Flared pants look best with pointy heels. Both my white and blue jeans flares can only be worn with heels as they are too long to wear with flats. Make sure that your pants almost hit the ground when worn with heels. Don’t think that you can’t wear flared pants when you are short! They can be very lengthening if you follow the tips above.
  • Want even more of a lengthening illusion? Wear pointy shoes in a similar color as your pants.

Here is how I wore the white flared pants back in Singapore



Paige flared jeans


I acquired these Paige flared jeans in Vancouver. They fit like a dream and make my legs seem very long. They were exactly the correct height for me too when worn with with heels. I like these jeans a lot with short tailored blazers. You can either tuck in your tops or have a short top underneath


Who do I think I am?

For a bit of a laugh, have a look at this funny series of images. 40+Style photographer Denton thought it would be fun to photograph me amid the mayhem that was the first day of fashion week. Clearly the woman approaching on the left was not pleased.

This is what I think was going through her mind.

  1. I’m coming through…Wait who is that woman blocking my way?……
  2. Does she not have eyes in her back and see that I’m coming!….
  3. Seriously, you are photographing that? I had to change my path for this woman? She looks ancient! Who does she think she is?!!


I guess next time I should check my direct surroundings that I’m not blocking “important” people before posing….

Outfit details

Top outfit: pants, thrifted, brand is Theory, denim jacket, old, Sportsgirl, asymmetrical top, old, Stella Carakasi, shoes Lisa Tucci, necklace and earrings AC Agates, ring Sistaphyre

Middle outfit: Equipment silk top (on sale), leather and jersey jacket, bought in sale, brand Arma collection,  Lotus pumps (one of the most comfortable pumps ever!, here is a closed heel version), ring and bracelets Sistaphyre, red ring Saskia de Vries Designs

Bottom outfit: Paige flared jeans, very old tank top, H&M blazer, Lotus pumps

Do you like to wear flared jeans?


Photography of first outfit by Denton Taylor

{ 20 comments… read them below or add one }

1 Greetje

You did soooo well with your purchases. The white flared jeans are indeed the perfect replacement for your older pair. And the fact they are not as tight as the Paige jeans is better with white.
You gave me an idea. Perhaps I can use the Eileen Fisher long top with my flared jeans and a short jacket. What do you think? You look bloody perfect in the Paige jeans with the silver shoes (new?) and the blue jacket. AWESOME. Love the necklace and earrings too. Are they copper? If so, can your ears handle that?


2 Greetje

Oh and how did you dare stand in that woman’s way haha


3 Sylvia

You can certainly try even though I also think you would look good with a short top (like your new blue one) and a a blazer.
I got those shoes in The Netherlands. You have seen them as I wore them there and also in Vancouver.
Yes they are copper and they did not give me any issues…


4 Lisa

Welcome to New York. It never has had the reputation for the friendliest public.


5 Sylvia

You know what? I had the best time in New York and the whole of the US really. People have been super friendly throughout. If Denton had not pointed out these images to me, I would not even have noticed this ‘incident’. I had not even seen her, haha!


6 Denton

I didn’t even notice that until I processed the images!


7 Elaine

Great article about your Theory pants purchase, Sylvia. Wish I was as lucky in that shop! They look fabulous styled with your older pieces. Perhaps the lady with the umbrella was admiring your look? Anyway, I will revisit how I wear my flared jeans focusing on how to make my legs look longer.


8 Sylvia

haha, not when you look at her face…. Good luck styling your pants!


9 Sheela Goh

Those flared jeans. That Stella Carakasi asymmetrical top. One of the things I most admire about your style, Sylvia, is your ability to get proportions just right. Picture perfect.


10 Sylvia

Thanks for the compliment Sheela. Proportion in an outfit is indeed very important to me. Something I emphasise quite a bit in my style course.


11 Suzanne

Ha ha! I’m so glad you stood your ground! You look fab in jeans. I really love the ones you got in Vancouver.



12 Sylvia

haha it’s probably good I did not notice her at all. I would have stared right back at her!


13 Miriam

Flared jeans are wonderful for me because I have an inverted triangle body shape. With a simple t-shirt and platforms, flared jeans can look casually stylish, while balancing out my look. I love your white pants. I am going to look for a white slim-fitting tunic to mimic that look with my white flared jeans. Thank you for the post! Loved it.


14 Margaret

I love your style Sylvia and your ability to pull together a stunning look from a mix of pieces. You see lots of possibilities for an outfit which inspires people like me who want a little edge and flair but can get stuck in traditional dressing. You are so not boring! I absolutely love the Paige flared jeans and blazer look. You look amazing!


15 Cynthia

Hi Syliva,

In the picture with the flare pants that you bought in Vancouever. Where did you get the blazer. I love it.



16 Sylvia

Blazer is from H&M but I got it more than a year ago.


17 Petra

Haha – the lady was probably looking at you wondering if you were somebody famous 🙂


18 Jennifer Nastu

Hi, Sylvia. Awesome info. I’m short and always thought, as you mentioned, that I can’t wear flared pants. I will try them with pointy heels in the same or a similar color, which means – yay! – that I better go buy a pair of pointy heels. I don’t own any of those… or flared pants, for that matter!


19 Glenda Bibbero

Sylvia, I used to love flared pants but have not been able to wear them yet this time. They look so good on you I am tempted to try to style them again and give it a go. I love all of the looks on you. You look fabulous! I guess my fave is the jeans but it’s a close race. I’m going to New York City early December and am looking forward to meeting some New Yorker’s myself. LOL I don’t know if I’ll handle myself as well as you did but you are an inspiration to me there too!


20 Sylvia

Thanks and how fun you’re going to New York. I had such a good time. You are going to love it!


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