A Fun Way to Wear Fashion Sneakers for Fall

Hello, Monday! It’s hard to believe, but we’re wrapping up 22 Days of Fall Fashion this week and bidding adieu to September. It’s kind of amazing how fast this year has gone, considering everything it’s thrown at us, but I’ll take it.

I’ve had a lot of requests for outfits with fashion sneakers, so I styled my favorite P448s with a drapey moto jacket and jeans for a dressed-up casual look that will take you from the carpool line to a casual dinner out with ease.

I picked up this faux suede drape front moto jacket on sale last spring, but I didn’t get a chance to wear it so I’m excited to bring it out again for fall!

This jacket is on the thinner side, and it’s unlined, but it’s amazing how much warmth it adds. It’s super soft and comfortable — the perfect chic, light layer for a fall day.

My t-shirt is the Banana Republic slub cotton-modal scoop-neck tee that I often wear when I want to layer over a white tee. The neckline is so flattering, and the slub cotton-modal fabric has just enough texture to give you that cool factor without being see-through.

For size reference, I have a medium in both the t-shirt and the jacket.

To keep the look casual and on-trend, I wore a lighter wash denim with some subtle distressing. These are the Kut from the Kloth Donna skinnies with the button-front that I’ve styled a few times. They wear in well and are comfortable all day long.

They have such a flattering fit, and the  27.5″ inseam is the perfect ankle-length on my 5’5″ frame.

Notice how there’s an inch or so of my ankle exposed between the hem of the jeans and the sneakers — that’s more slimming and looks less sloppy than when your jeans touch the top of the shoe.

While it was my first inclination to wear ankle boots with this outfit, I love the style these P448 sneakers add to this look.

They’re spendy, but the quality and comfort and unique details warrant the price tag, and they do go on sale from time to time.

I love the snake print accent and the black tab on the heel. They grey laces are a nice detail as well — not as stark as black, but not as plain as white.

Of course, you could substitute your favorite fashion sneakers and recreate this look on a budget. Steve Madden has lots of good options — like these and these.

And look at all of these fun Vintage Havanias at Macy’s. Also, these Tretorns are under $100, and I really like my J.Crew Saturday sneakers.

I wore one of my Victoria Emerson wrap bracelets to add some texture and shine to the look, and I added a pair of silvertone hammered hoops.

Unfortunately these exact pieces are sold out, but hopefully this gives you some ideas for shopping your closet.

And to show you a different spin on this outfit, here it is with grey suede ankle boots. This time, I’m wearing the Milan boho cuff.

As you can see, this version is a bit more sophisticated, but still casual and comfortable. Either works, it just depends on where you’re going and the look you’re after.

Shop the Post:

drape front jacket // scoop neck tee // button fly jeans // P448 sneakers (also at Nordstrom; similar for less) // similar grey boots // similar silver hoops // Victoria Emerson bracelets c/o // sunnies (similar for less)

Be sure to visit Cyndi Spivey and see the fall look she’s styling today!

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photos: Alison Cornell

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26 Responses

  1. Wow did this month ever fly by! Great casual outfit thanks for styling the sneakers:) I’m always looking for new ideas.

  2. You look fantastic and I love how you pulled this together with the sneakers. I have a similar drape jacket in a light pink/blush color and never thought to wear it with sneakers and the sleeves are too long so I usually would cuff them up but I like how you just pushed them up. Definitely going to try this look. We had our first cool front come through San Antonio early this morning so time to take out the light jackets. 😃

  3. I’m just not a fan of outfits with white sneakers. I think it goes back to high school physical education classes. However, I really like the outfit with the gray booties! Have a wonderful week!

  4. Love this look! The drape front moto jacket is a stylish twist on a regular moto jacket. The sneakers or booties are a nice touch. Thanks for the reminder of the VE bracelots sale – good Christmas gifts! Hard to believe September is nearly over.

    1. Not usually, this one hasn’t. I know a lot of ladies have that issue, though. There are various theories – it rubs against the button or the belt buckle, or it rubs against the kitchen counter… I don’t seem to have the issue tho.

      1. Jo-Lynne…..wish I could figure out what causes the holes. Its been a problem for me for years and years and now that the front tuck is in, it helps.  Otherwise I have to wear cami’s under my t shirts and I don’t want to do this in the Summer time.  Can’t understand why you wouldn’t have trouble.  

    2. Cyndi…..I have always had the trouble of getting little holes in my t shirts and so I’ve had to go to wearing cami’s under them to save them.  Now that the front tuck and higher waist jeans are in, its nice I can front tuck the t shirt and eliminate that issue if too hot to wear a cami under the t shirt. It is sooo annoying and I can’t figure out what exactly does it.  

  5. I purchased the same jacket last spring.  Love how your styling it.  

    I have an idea for future post.  How about nail polish colors for fall.  I’m stumped for something creative.

  6. Love this outfit!  I have a feeling I’m going to be wearing more sneakers than boots this Fall/Winter, since all I seem to be doing is hopping out of my car to open/close my hatch for my grocery or Target pickup these days.  And we are still doing church at home.  So life is still very casual.  I like the sneakers with the light jacket and jeans!  Put together, yet casual and comfy.

  7. Thanks so much for a post with this draped jacket! What else would you wear this with, besides white? I’m on the verge of returning it for a deeper buff color because I don’t know how to style it. I appreciate your help. 

    1. I think it would look pretty with lighter shades of pink and blush. It’s hard, though, I admit. I don’t care for it over black, at least, not with any of the pants I’ve tried it with.

      I do like it over a leopard blouse that I have, along with my faded black jeans, but I didn’t figure out the shoes with that look.

      1. I have the jacket and wore it with a leopard print sweater  (your inspiration) , ripped black jeans and black booties. Got TONS of compliments 

  8. I really like this look on you!  Oh how I can’t wait for my sacroiliac to be pain free so that I can wear my jeans.  I hope that you have had a great day!

  9. You look so cute all the time when you style moto jackets. Just you. 🙂  I love this look and your hair looks so nice this length.  Have a great Monday.  

  10. Thanks for this post, Jo-Lynne. I bought a pair of P448 sneakers a couple of weeks ago and have not worn them yet because I haven’t been sure how to style them. After reading your post, I now have lots of ideas to put into play. I’ve also hesitated wearing them because the pair I bought has a little bit of glitter on them. Not a lot, but it’s definitely noticeable. I know my husband is going to tease me the first time I wear them, but I don’t care because they make me smile, and the more I can find to smile about these days, the better.

    I would love to see a blog post on which items from last fall and winter you’re excited to put back into this season’s rotation. Which items were worth your investment and why? Also, how would you style those items differently now than you did last year? This information would help me as I pull my own items out of basement storage bins and figure out what to keep and how to make it feel fresh.

    I would also love to see a blog post on fall and winter nail polish colors and how to choose colors that relate to your wardrobe.

    Thanks for all of your hard work and for always being a such a great resource!

  11. You look great and seems to be comfy. Definetely these are the sneakers which I use on my way to work and back. Stylish and comfortable and my feet keep cool, no sweat at all like when wearing other sneakers. I wear these sockless all the time.
    Don’t know if its me but I like to have a pair of sneakers which is fine to just slip on without socks.

    1. I have found them to be inconsistent. I had to size down in one pair, and I went with my true size in the other. SO… it’s hard to say. You may want to try two sizes and see which feels most comfortable.

      1. Thanks for the tip. Just so you know your sneakers are 50% off on the P448 website! What a great deal!! 

  12. Love the Tretorn sneakers, they’re always right and never go out of style! I cannot embrace the P448 sneakers, Steve Madden sneaks, Rezza styles or the selection of Vintage Havanias. They remind me of the unkempt footwear favored by tween and teen VSCO girls.
    That gorgeous drape front and Victoria Emerson bracelets look so fresh and classy.

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