The Simmons sisters were spotted out this weekend in NYC in some very comfortable looking outfits…


Warm fuzzy Ugg boots were in full effect, as were stretchy tights and down jackets.
I’m personally a subscriber to Fabulosity Law # 10, “Dress like you might run into your worst enemy,” meaning the most comfy I’ll go are Tory Burch ballet slippers or Miss Sixty flat leather boots with jeans and a sweater.
But what about you guys? If you’re relaxing on the weekend, do you make an effort or just sayeff it’?

21 thoughts on “Style Verdict: Comfort or Fashion?”

  1. NEVER. I am a male, and I always try to leave the house like I am going to meet my worse enemy. Many times, I may be uncomfortable….but F it, cause the feeling of looking good over rides it!

  2. One day I was feeling kind of whatever, but still wore this v neck wrap dress. Not great, but not bad. So I’m walking, walking, and who should I see but my ex boyfriend. I was never happier to be wearing something flattering. He got to see what he missed out on!

  3. i’m usually “on” but SOMEtimes i really don’t care and will run out with pink uggs jeans and an unflattering winter coat. . and on those days i AM on the lookout for people i know – i’m not beneath hiding behind something to avoid being seen :)

  4. I try to have off days that dont look like off days. My comfy flat winter boots are quilted leather so they look good . Add it w/ the uniform of skinny jeans and a V-neck sweater, and I look semi-decent on most days.

    But there are days like today, when I had a dentist appointment and had on Nikes, fleece pants, and a pea coat. I didn’t look that hot.

  5. It depends. I grew up in Florida, so when I’d go out on the wknds to run a quick errand, and wear some nonsense bc noone could see me (like if I were going thru a drive thru). But now that I like in New York, I can’t just hide out in my car. So in a city where pple walk around etc, it’s much better to put your best fashion foot forward. As for the Simmons sisters, if I were getting followed and photographed all the time…there’s no excuse.

  6. looks fine to me, plus it was hella cold in ny so it works, sometimes you gotta walk out in your whatever outfit

  7. I try my best to be on all the time and my coats are pretty nice but my cute shoes are not nearly as warm as my uggs!

  8. Here is the rule: Cute goes out the window when the temperature goes below 28 degrees…here in Chicago, this has been the coldest winter I can remember…I have only been able to wear my cute coat less than 10x’s this season…I can’t wait till SPRING!

  9. I will rock some Ugg boots and make them look darn cute. Don’t get me wrong I wear my 5 inch Christian Louboutins, Gucci, Prada…, but I do love my Uggs. Please don’t know them until you have tried them. I Used to the they were Ugg-ly until I found a pair on sale and tried them on — I have been hooked. The Air Nike Cole Hann or nothing else can compare. You MUST try a pair!

  10. I think it’s all about confidence. And they look like I’m still the hish, so whatever. So more power to them. Especially my girl Angela who has her own quirky style and is unapologetic about it. You go girl!

  11. personally i think V looks a little more put together than her younger sister. Ang looks like she had baby Miley pick her ensemble. im from DC.. i know what cold is. but i happen to think that some of the most cutest clothes are made for the winter months. these two being "clothing/shoe designers" should know this.

    but because i love me some V & A.. theyll get a pass this time

  12. hmmmm I’m torn on this one… cause believe me as a college student downtown Chicago, it’s so cold you don’t give a DAMN what you have on as long as that wind doesn’t hit you- and you’ll always have another opportunity to show up your enemy…
    you can be fab and comfy though- its just a little tricky

  13. Vanessa has the right idea, Angela on the other hand…no excuse. Nothing’s wrong with their outfits, but honestly if I was a celeb, I’d be like Mariah, J.Lo, Beyonce, Mary J… ALWAYS fitted out.

  14. I don’t think you have to sacrifice comfort to be fashionable, or sacrifice being fashionable in order to remain comfortable. Besides, it doesn’t matter what you wear, if you rock it with confidence, that will show. I have no issue with stepping out of the house in a pair of skinny jeans, some Uggs, and my down puffer. I think Vanessa looks great… Angela on the other hand… I’m not a fan of tights as pants, and her scarf is entirely too bright and much too long.

  15. well since its freezing in NY, and its always gray and snowy, ive lost my motivation, i wear whats gona keep my ass warm! lol which means layering and lots of it. I’ll be back to full fashionista mode when the weather breaks. I think “fly girls” are allowed to take a “break” because they always bounce back when its time.

  16. Does it even matter who u might run into? u should always wanna look ur best…i think they look comfortable and cute (minus angela’s shoes lol) at the same time. why give up one for the other?

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