Slip Skirts, Leather Jackets, Barn Coats & Loafers



Joining a few friends to talk fall fashion today! Here’s what I’m buying new – a slip skirt, a leather bomber jacket, and a new barn jacket – and what I’m bringing back from last season (wide leg wool trousers, my favorite pair of Alex Mill jeans, loafers, and oxfords).
Slip skirts are the perfect fall fashion piece to add to your wardrobe, or perhaps bring back from last year! I found the perfect one from Vince! It’s a plaid slip skirt that goes with everything in your closet! There are so many ways to style slip skirts for fall.
Pair it with a chunky sweater or a cashmere turtleneck. Wear it with a cropped barn jacket, trench, or a leather bomber jacket.
You could wear a slip skirt with a J.Crew blazer, or a felted wool chore coat from Buck Mason.
Barn Jackets & Leather Jackets
Oversized Leather Bomber Jacket


This oversized leather bomber jacket is a great jacket to wear with layers. Some leather jackets fit so tightly, it’s hard to wear much under them. This jacket from Quince is finally back in stock, and you can really wear anything under it.
Canvas Barn Jackets
Barn jackets, like trench coats, never really go out of style, but this year they are back and reimagined. The fit or style is a little more feminine. A little boxy and cropped, making it the perfect jacket to wear with skirts, jeans, or wool trousers.
I found this Canvas Barn Jacket at Old Navy, and it’s available in regular, tall, and petite. All three colors are so versatile. It comes in Heritage Green, Antique Rose, and Chocolate Kiss.


Leather jacket layered over a cardigan.


I’m showing it with a cardigan from Uniqlo, similar to the Betty sweaters from Sézane. Under it, I’m wearing my favorite black T-shirt. I have the Rag & Bone Slub Tee as well as this one from Quince for a fraction of the price. It’s also available in long sleeves.
What shoes to wear with slip skirts or any midi skirt


I’ve always liked the menswear look and have never worn heels or pointy-toed shoes. One of my favorite fashion content creators, Hollie Mercedes, wore chunky loafers with skirts during Copenhagen Fashion Week.
I am beyond thrilled that my favorite footwear style is “in style” – I have been wearing oxfords and loafers for years. They occasionally seem to try to make a comeback, but I think this season, they are very much in fashion.
When I invest in a pair of shoes, I have them repaired as needed, and then I keep them forever!



Dressing for the weather…
I always find fall, like spring, a transition season, but so much easier than spring. In the spring, I am always cold. I dress for the weather I want, not necessarily the actual weather. However, in the fall, it seems we are more than ready for sweater weather. But you can layer a t-shirt or a tank and wear the sweater over your shoulders if it gets too warm.
We are currently in the South of France, where this year it is pretty warm, and in years past, it has been terribly cold. A slip skirt (so easy to pack) with a sweater, a barn jacket has been my go-to outfit on this trip. Since it’s been pretty warm, I wore it with a white shirt and Birkenstocks, or a t-shirt and a sweater over my shoulders.
I’ve also been wearing this boxy, cropped Oxford from Uniglo as a lightweight jacket over a tee with everything. I may even get one more! I’ve been using my spray bottle of Vodka to help with wrinkles and to freshen up everything I’ve been wearing on repeat.
Now let’s see what Mary Ann, Cindy, Noelani & Susan have to say!
- Mary Ann – Classic Casual Home
- Cindy Hattersley Design
- Noelani – La Vie on Grand
- Susan – Une Femme

Great choices, Annie! I’m with you on the barn jackets and loafers…so timeless and wearable!
I packed two slip skirts and they really do not take up any space in a suitcase! You look awesome in the skirt and loafers. So chic!
Thanks for organizing us!!
I love barn jackets on others but they do not suit my physique at all. Great choice adding that leather bomber to your wardrobe. It looks great on you!!
Hi Annie,
Love your style so wonderful !! I bought a gorgeous wine ‘merlot’ color cabled sweater from Quince recently and they are really amazing with their prices. The leather bomber looks so good on you and the shoes…perfect!
Don’t you just love this time of year. I am off to London in November for long walks on Hampstead Heath and dear family and friends to see. Cannot wait. Have a wonderful day x
Hi Francesca!
I do love this time of year! I have been home for about 12 hours (just long enough to unpack, do several loads of laundry and put away the suitcases) and I’m jealous of your trip to London in the fall. Long walks on Hampstead Heath sounsds lovely! I have never explored that part…enjoy! It will be here before you know it!
xo
Annie
Oh wow, Annie, that barn jacket from Old Navy is amazing! What a great find. I also love that leather bomber as well! Thanks for letting me be apart of this amazing group!
Hi Annie,
I admire your classic looks and I am in agreement with you about good shoes. At this point in my life , I only invest in high quality shoes that fit well. I wear them for years and have them repaired when needed too.
Hi Rosemary! I agree, I too am at the point where there is no need for shoes that are even the slightlest bit uncomfortable. Not when there are so many styles that are both comfortable and supportive to choose from!
Thank you for reading and taking the time to leave a comment!
Annie
Annie, I love your outfit inspiration for Fall. A slip skirt is perfect to dress up or down.
And barn jackets are another favorite of mine, especially Barbours.
Have a wonderful week.
Elizabeth,
It really is such a versatile piece! You can wear a lsip skirt with boots, flats or even Birkenstocks!
xo
annie