Dressing Up Leggings and Sneakers

Happy Tuesday ladies. Our recent rain has knocked most of our colored leaves off the branches which is probably a good thing since it’s almost December. Our seasons shift later than most of the country so I rely on window displays to get my dose of snow. I miss the magic of snow…easy to say from northern California where it never happens;) but I did grow up in Toronto and New York and remember it well.

jennifer connolly of a well styled life wearing lavender cashmere sweater from Ann Taylor
cashmere V-neck on saleearringsfaux leather leggingsshoulder bag budget-friendly option herenecklace similar

For a day of running around, nothing quite beats cozy leggings and comfy sneakers. That needn’t mean overly causal. My version is faux leather leggings and leather sneakers topped with a cozy cashmere sweater.jennifer connolly from a well styled life wearing lavender v neck and black leggings from Ann Taylor

jennifer connolly of a well styled life wearing faux leather leggings and purple cashmere sweater from Ann Taylor
sweater on salepants on sale – sneakers – sunglasses similar – earrings necklace similarshoulder bag

Leggings vary in tightness and width. Jennifer Connolly of A Well Styled Life wearing lavender v-neck cashmere sweater from Ann TaylorI topped them with an easy fitting cashmere v-neck. I love the ease of a tossing a luxe sweater over any bottom during the cool weather. The loose bottom ribbing on this sweater keeps it from clinging at the hip so it hangs like a short tunic. jennifer connolly of a well styled life wearing lavender cashmere v-neck over faux leather leggings with sneakersAnn Taylor makes a great quality cashmere which is usually excluded from their sales. It’s marked down for the next 2 days so I just ordered this one in green alpine.

Shop the Look

 jennifer connolly of a well styled life wearing leather leggings and cashmere sweater from Ann Taylor

I wore these leather sneakers all over Japan this fall. They’re super comfy with a removable innersole so you can add your orthotic or to adjust the width.

This outfit could take you to a casual lunch out or be dressed up easily with a quick change of shoes and tossing a warm coat over it for colder weather.

Ann Taylor is still giving 50% off everything and free shipping with the code CYBER2018

Luxe Picks from the sale at Ann Taylor


Are you a fan of cashmere too?

Thanks for reading ladies and have a great day


  1. Perfect outfit! I love cashmere and wore it today. I don’t have much since good quality is expensive. Like Elaine from Alberta, it’s too cold for bare ankles so boots or booties from now to April! The first snowfall is beautiful and then you shovel…???? i will gladly trade you!

    1. I remember it well. Then the snow piles in parking lots become gray with gravel picked up from the plows, and stand like dirty little pyramids until May! Stay warm

  2. Great outfit! Cute and comfy. Do you like the Gucci. Bag? I am considering purchasing it in the tan. I would love a review.

    1. I love the bag! I had my eye on it for over a year before I finally bought it and couldn’t be happier. It’s compact yet holds everything I need, including my sunglass case. It dresses up and is also great as a crossbody for travel or running around. I debated about the red but opted for black for versitility in my wardrobe.

  3. This is a perfect combination – the soft sweater and the leather leggings. I love how you take a trend and incorporate that into your wardrobe. How you take a tougher/sexy look and soften it for everyday.
    I tried the Ecco runners but they are not available in black. I might get my daughter to check the Ottawa Nordstrom store and see if they are there.

    1. Thank you Joanna! That’s so sweet. I love these shoes. I have them in white too. Also check amazon. You might find them there.

  4. Elizabeth Meinholdt says:

    Love the pants. I have already ordered and received the discount. Whooohoo Thank you.

  5. I just tried to purchase the cashmere sweater from Ann Taylor. Despite applying CYBER2018, it was full price. Mistake?

    1. Cyber2018 is still valid because I decided I needed something else this AM. Open a new browser and try again. It’s an awesome sweater. You could also call customer service. I wouldn’t get an affiliate commission ordering that way but more important, you’ll get the sale price! Let me know what happens.

      1. anne shannon says:

        2 browsers later, still no luck. Apparently delivery and credit card addresses must be identical. I had suggested delivery to usa address. Oh well, Simons in Canada will have to do.

      2. I’m sorry you struggled. I hate when that happens.

  6. I was born and raised in Vancouver and missed the snow when I lived in SAN Francisco and Los Angeles. I now live in Whitehorse, Yukon where I enjoy winter. You often show ankle pants which don’t really work here. I like the leather ones you are wearing because they are not too tight. I used to wear leather pants here; they work!

    1. That’s very far north! My daughter flew there for business last year and was pretty surprised but the cold. You would need boots there all winter long!

  7. Love this whole look! Beautiful on you and right up my alley!

    1. Thank you Sondra. It’s comfy and casual without being so dressed down.

  8. I love my faux leather leggings and my leather sneakers but have not worn them together! Thanks for the inspiration, Jennifer!

  9. Oh this looks comfortable! The color looks beautiful on you and I will check it out. Thank you for styling this!

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