Fall/Winter Fashion

What to Wear: Ball Field to Date Night

Happy October, friends! Today I’m sharing an outfit I wore on a warm Saturday a couple weeks ago to my daughter’s marching band performance outside on the football field, and then to meet friends for dinner afterwards.

I wanted to be comfortable and casual for the cavalcade, but also stylish and a little more dressed up for dinner out, so I decided on a graphic tee with jeans and slip-on sneakers for the band show. Then I brought along a change of shoes and a jacket to throw on over top for our date night afterwards.

I’ve worn this graphic tee sooo much lately, I’m sure y’all (and everyone in my household) is sick of it, but it’s the perfect thing for… well almost everything, it seems! And yay, it finally went on sale! It’s currently 30% off with code TUESDAY, and it runs small. I sized up to a medium.

SALE ALERT >>Save 40% off tees, tops, and shirts (including sweaters!) and 30% most other full price items at J.Crew with code TUESDAY. Also, be sure to sign up for J.Crew Rewards to get free shipping. There are some exclusions, but I rounded up all of my J.Crew Favorites for your shopping convenience in The Shop!

It’s a little nicer than your typical graphic tee, so I was able to dress it up for dinner, and the lightweight slub cotton was cool and comfortable outside at the football stadium in the mid-September heat.

There was quite of bit of walking at the band event, so practicality was key when it came to choosing my footwear. These snake print sneakers are lined with the smoothest leather, and they’ve been a great transition shoe while we wait for cold weather to arrive. I wear them several times a week.

A solid color would look great with this outfit too, but I really like the texture the snake print brings to this casual look. They also come in a grey/black color combo if you prefer, and best of all, they  just went 25% off at Saks! (Be sure to use code FREESHIP for free shipping, if ordering.)

I recommend sizing down half; I ended up with the 7.5. They were a little tight over the toes initially, but they’ve broken in quickly.

For a more budget-friendly alternative, this Steve Madden pair recently went on sale as well, so you can snag them for under $50. I found that pair to run small, so you may want to size up half if you order those.

My exact jeans have sold out, but Nordstrom has another Rag & Bone Cate with a traditional sewn hem that are on sale, and Wit & Wisdom makes a similar pair for less that also comes in petite. And really, with this outfit, any dark denim would do.

For accessories, I wore simple mixed metal hoop earrings and my favorite sunnies, and that was it!

Typically I carry a smaller crossbody to ball games and marching band shows, but I was running late and just grabbed my LV tote because it was already stocked and ready to go.

For dinner that night, I brought along my grey leather jacket and a change of shoes.

FYI, this jacket is still stocked and on sale. It runs TTS or size down if in between; I have the small.

I hesitated to get a grey leather jacket since I have a black one, but I wear the black soooo often that I thought having an alternative might be nice.

As it turns out, I reach for the grey more than I do the black!

The grey isn’t quite as harsh as black, and it looks great with my snake print booties. I know, I know, more snake print . . .  🙈

I just love the texture and added interest it brings to an outfit. And of course these booties sold out in the grey. I keep waiting for Jeffrey Campbell to bring out something similar, but he hasn’t done it yet.

For a similar style, I like these and these. Also, Target has a nice budget-friendly alternative, and if you like snake print but not heels, these slingback flats are really cute and would dress up a casual look too.

I kept the same earrings, but I did swap out my bag.

I threw this black satchel into the car along with my booties and jacket so I’d have something smaller to take into the restaurant. It also coordinates better with the cool tones in this look — although really, I consider the Neverfull a go-with-everything bag.

I love the idea of dressing up a graphic tee for dinner out — it’s not the type of top I typically reach for when I’m getting dressed to go out to dinner, but it was fun for a change.

Outfit Details:

NYC tee // Rag & Bone skinnies (budget option) // snake print sneakers (25% off / budget option) // grey leather jacket // snake print bootie options here and here // black satchel // earrings // sunnies c/o Maui Jim

For the Pinners:

What I wore on a warm Saturday to my child's marching band performance on the football field, and then to meet friends for dinner afterwards. #fallfashion #fashionover40 #outfitinspo

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photos: Alison Cornell

Join the Conversation

22 thoughts on “What to Wear: Ball Field to Date Night

  1. I’ve been eyeing that jacket since you first posted it. The grey seems like it would be less harsh than black at my age. Some of the reviews note that the flaps flap around, however (LOL). Do you find that to be true? I think I would find that annoying.

    1. I was afraid it would bug me, but it doesn’t. When I got it, I noticed they don’t snap down, so I hung it in my closet, tight up against the other coat next to it, and made sure the lapels were open how I like them. I always make sure t hang it up that way. When I wear it, they stay put pretty well.

  2. I love a tee with a leather jacket and boy the grey is gorgeous! Also thanks for sharing the alternative Wit and Wisdom jeans because they come in petite. Speaking of which, yesterday I was on FB on my lunch hour and noticed a post where you asked about petite bloggers and a few posted their link. Now I can’t find the post? Do you remember the two to shared their link and can you pls send them to me when you get a chance?  Thank you ☺️ 

  3. Love how the outfit transitions so nicely with a few tweaks. I can’t wait to start wearing my black leather jacket. It’s just getting cold enough this week… love the tee 

  4. You look great in both outfits!  The grey leather jacket is a great addition to your closet, and I really like how it amps up the outfit.  I am having a hard time finding an elevated graphic tee, but I’m still looking.  I know they exist within my price range.  It sounds like you are feeling better today!  Yay!  We have upper 90’s to deal with thru Friday, then we may turn the corner with the weather.  Have a beautiful day!

  5. You look so good in that date night edgy look! I agree the gray looks less harsh and more interesting since so many people have it in the black.

  6. I love the idea of taking a casual outfit and sprucing it up for dinner. I do that quite frequently where I go out with the family wearing a flat shoe and then swap to heels for dinner later. I have the snakeskin booties, but it’s still so hot here in Virginia that I just don’t feel like wearing them yet. By Friday it’s supposed to get much cooler. I also have that black Rebecca Minkoff purse, which I actually bought (ahem, selected for my husband to buy for Christmas) just before you featured it on the blog! I felt so cutting edge, lol! Anyway, love that purse and wish it was still made by RM. I really like the flaps on either side that can easily hold your keys or sunglasses without having to fish around in the purse. I also bought the grey jacket during the anniversary sale, but didn’t like the flaps. My review is posted on Nordstrom. It looks great on you though!

  7. I love your outfit. That New York tee is a winner. I’m liking a lot of things at J Crew and J Crew Factory lately.

    My new favorite is the Crewneck Pullover, a lightweight sweatshirt. I like that it’s cotton, and comes in lots of colors. I got Guava Berry, a rosy pink. The neckline is comfortable not tight, and the length is nice, especially for me at 5’4″. I might buy the green one next.


      1. Jo-Lynne, I forgot to add that I ordered a Small in that pullover, and it fit perfectly.

        My experience with J Crew has been that I need a Medium in their tees for them to be comfortable (they seem to be designed for flat-chested women lol). But I always order a Small in their sweaters and sweatshirts – and so far that has worked for me.

  8. I told you, I wear things a lot when I like them. LOL!!! I’m enjoying styling more outfits from my closet this year, but if I’m keeping it real, my daily looks are very repetitive.

    I am wearing it right now, and I’m literally trying to remember if I’ve washed it! I’ve worn it so much, it’s crazy to think I haven’t yet. I’m surprised there are negative reviews – now I’m curious and have to go read them.

    Okay, I’m back. Most reviews are very happy with it, and one even says it washed up well. I agree with the one who says it runs small; all J.Crew tees do, so I sized up. 🙂 The only one with the issue had a seam break open, and she should return it — that is a defect and I’m sure J.Crew will replace.

    I don’t have any hesitation recommending this tee, but I’ll update after I wash it.

  9. Was holding off on the T. I LOVE graphic tees that are age appropriate. (Admit it, we’ve all see age-inappropriate tees. ) And I have a couple of dark ones (Banana Republic always has nice ones) but I could use a light one. In my cart it goes. I was also waiting for the Vince sneakers to go on sale but when I put them in my cart, they show up full price. I can’t find a code for friends and family. Anyone else have this problem? I am a points member. Hmmmm. 

  10. I just ordered my NYC t-shirt from JCrew and thought I would share that I think it runs true to size. My girlfriend got a small a few days ago and I tried hers on.
     I ordered an XS which is usually my size in  JCrew. I’m only 5’ 2” tall if that helps.

  11. I have admired your NYC t shirt ever since you wore it first! So excited it went on sale. I also got an additional 15% off the sale price and free shipping so I ordered it. I’m ready for cooler temps but need it to not get too cold so I can get a few wears out of it before winter. 

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