What I Wore: Sweater Dress + Denim Jacket

Holla! How did it get to be Wednesday? This week is flying. Heck, this month is flying. The weather has been so mild, it still doesn’t even feel like the Christmas season to me yet, but I have two trees up, my cards are all addressed and ready to go in the mail, and I’m about 90% done with my Christmas shopping. I guess I better start playing those Christmas tunes and get in the spirit of the season.


This is the Cozystitch Sweater Dress at LOFT. I love the ballet neckline and shirttail hem, and the texture is pretty too. Originally it came in 4 colors, but they’re selling fast. Grab one while you can! (40% off + FREE SHIPPING with code SNAILMAIL)

In my 3 Ways to Wear a Sweater Dress post, I wore this dress with tights and wedge-heeled knee-high boots. I showed it by itself, with a poncho, and with a shearling vest. All three of those looks were fairly dressy, and I mentioned that I thought it would also be cute with leggings and a jean jacket for a more casual look. Well, here you go! I wore this to church a few weeks ago.


Tights would work just fine, but I chose leggings for warmth and comfort. I debated black vs brown boots and finally decided on the brown to keep the outfit casual and to add interest. These are the Frye Phillip Harness Tall boots in Whiskey. They were a huge splurge for me last fall, but they’re definitely an investment piece that I’ll have for many years. They only get better with age.

SALE ALERT!!! If you’ve had these boots on your wish list, right now Amazon has a similar color, Whiskey Soft Antique, on sale for around $300 (the price changes depending on the size you choose) PLUS 25% off with the code HOLLYJOLLY!!!

Frye Boots

The outfit was still fairly plain with just the dress and jean jacket, so I went to my closet to see what I could find. I swear, this scarf called my name. I didn’t want a blanket scarf because I was afraid it would feel too voluminous. This one is lightweight and easy to style. Plus I love how it pulls the grey from the dress and the black from the leggings, and then the orange adds a much needed pop of color to the neutral outfit. I also added the orange leather wrap bracelet for good measure.

Fashion Over 40: Sweaterdress, Denim Jacket, Leggings & Riding Boots

I wore this to church and out to lunch, and I felt good in it, but I found myself questioning those brown boots. When I got home, I decided to try it with my black riding boots. I also took off the jacket and tied the scarf in the “celebrity knot.”

I guess I’m just a plain jane at heart because I really like this outfit best, although WITH the jean jacket. I don’t feel like the dress gives me enough structure in the waist area, but the jacket fixes that. I definitely prefer the scarf tied this way, and I think I like the dress better with black boots. Mixing grey and black and brown is totally okay, but it just wasn’t working for me in this outfit.


Outfit Details:

Cozystitch Sweater Dress $89.50 (40% off + FREE SHIPPING with code SNAILMAIL)

Similar Denim Jacket $44.99 (40% off + FREE SHIPPING with code SNAILMAIL)

Frye Phillip Harness Tall boots in Whiskey $357.95

Alex and Ani Bangles

Tory Burch Leather Wrap Bracelet $95

similar hoop earrings $39

Kate Spade sunnies $150

* * *

Don’t forget to visit Cyndi and see what she’s wearing today!

Join The Conversation

19 Responses

  1. I agree, the black boots are the way to go. Keeping most of the outfit in the gray/black makes the colors of the scarf really pop.

    1. I love the dress! How tall are you? I am only 5′ and a little thick through the middle. I didn’t know if it would look good on me or not. I usually wear my dresses and skirts just above my knee. Any comment would be appreciated. Thank you!!

  2. Cute outfit! I like myself better with an open neckline, as well. I’ve always read that an open neckline makes you look younger and is elongating, ha! It’s very mild in GA this week, so I’m not having to cover up. But, next week it may be freezing!

  3. I really like the scarf with the dress Jo-Lynne! I agree with some of the other ladies about the black boots looking the best.

    Have a great day!

  4. I love your layering! That’s a gorgeous sweater dress and so many styling options. Jo-Lynne, have you tried a “J. Crew roll cuff” on your denim jacket? It stays put all day and doesn’t get caught on things.

  5. Hi Jo-Lynne, I’m a new subscriber and I love your style! I actually own all the pieces of this Loft sweater dress outfit, although I have different brands for some. I am wondering, do you think this outfit would also look good with booties? Would the suede Toms booties that you featured on another outfit work with this outfit with black tights/leggings? Also, I have neglected my wardrobe and need to build it back up. What pieces should I start with? Thank you. Jackie

Leave a Reply

Your email address will not be published. Required fields are marked *

Close this search box.