My Favorite Outfits from 2019

Good morning and happy Friday!

Although I have to say, it hardly feels like a Friday. It seems like it’s been one continuous weekend for as long as I can remember, anyone else???

Today I’m rounding up my favorite outfits from 2019. These are all looks from the past year that I’m really proud of or enjoyed wearing a lot.

I set out to choose my 10 favorite outfits, and I ended up with 20. Believe it or not, I could probably have come up with 30!

In years past, I don’t think I could have come up with 30 outfits that I truly loved, which shows how much I’ve honed in on my personal style and what works best for my body type over the past year.

At 47, it’s about time, wouldn’t you say? I wish I’d had this information in my 20s and 30s!

That’s one of the benefits of being a fashion blogger and having all of these pictures — I see things I never notice just looking at myself in the mirror. (You can take daily outfit pictures too, of course. In fact, I highly recommend it.)

So, with that lengthy preamble, let’s get this party started!

My Favorite Outfits from 2019

I’ll provide a ShopStyle link below each picture to what I’m wearing. Of course, some of the statement pieces are sold out now and hard to replicate, but I’ll do my best!

#1. This first outfit harkens back to last February. I did a post on 9 ways to wear white fashion sneakers, and this was one of them. I was tempted to include three of those outfits in this post, but I forced myself to pick just one. I think this is the main thing I’ve gotten better at this year — learning how to put closet basics together in a bunch of different ways.

I love the multiple juxtapositions in this look — the edgy leather jacket with the sporty sneakers, and the luxe cashmere scarf with the distressed jeans — but I’m bummed that this scarf sold out in the grey. I found a similar one, it’s just wider.

Jo-Lynne Shane wearing VEJA Esplar with AG Raw Hem The Legging Ankle Jeans, black Bernardo leather moto jacket, and Everlane cashmere scarf


#2. This next outfit is a quintessential Jo-Lynne Date Night Outfit Formula — fun top with jeans, heels, and leather jacket. I wore this in Arizona at the Rakuten conference I attended last February.

As an aside, I just found these jeans, which sold out after the #NSale, back in stock in all sizes, AND ON SALE! I looove them. So comfortable, great fit, great wash, and a really cool tattered hems.  🙌🏼


#3. The next picture is from said trip to Arizona. I love the combination of colors for spring, and those shoes were amazing. Mine were suede, but they have them now in a really cool snake print.

Unfortunately, I didn’t wear them much here at home. They always seemed a little much for where I was going. Maybe next spring…


#4. I wore this next outfit in so many variations last spring and summer, it was hard to pick just one for this post. These pants were on constant repeat from April thru October, and I can’t wait to break them out again next spring. And happy day, they just went 50% off!!! (I recommend sizing down; I went with the 28.)

I also love this graphic tee from Boden. It’s a little more of an elevated graphic tee, and it looks great with so many pants and shorts. This design sold out, but they have a bunch of others, and it’s on a really good sale right now. Prices vary.


#5. I had to include this next look, as basic as it is, because it’s pretty much my summertime uniform. This tank is super soft and great worn alone or layered under cardigans and denim jackets. I also have the solid grey.

And I know the tattered shorts aren’t everyone’s cuppa tea, but I mostly just wear them hanging out at home. I just like how the texture keeps them laidback and unfussy, plus these are so comfy.


#6. I wore this to a family wedding in May. I love the fit of this dress and the loose floral pattern, and of course the shoes… 😍 (By the way, my nail polish was white, not blue, as it may appear in the photo.)


#7. I only wore this outfit once, but I love the color combo, and the way it all came together. Even though the midi skirt isn’t my typical silhouette, the structured denim jacket keeps it in my lane.


#8. I wore this outfit out to lunch with Paul for my birthday in July. This LOFT blouse was super popular last summer, and I got a lot of wear out of it.

This look goes to show how one budget-friendly statement piece can make an outfit. If you have your season’s wardrobe essentials, you can easily finish off the look with some of your favorite closet basics.


#9. I love this dress — definitely my favorite dress purchase of last summer. I wore it a ton, usually to church. The design and fit is so flattering.


#10. This is another LOFT floral blouse that was popular last summer, and I wore it well into fall in a lot of different outfits. This one is my favorite because the grey jeans and denim jacket are kind of an unexpected combo, but they both work really well with the blouse. And the shield sandals dress up the look and give it a bit of an edge.


#11. This next look was my attempt to style crop flare jeans (or maybe they’re more of a crop straight.) This look is really edgy and fun, but it’s a little much for my day to day existence.

I still wanted to include it anyway because I really like it, and I think it’s a good example of how to make this crop straight trend work.


#12. And this was my token flare jeans outfit for the season, haha!

This camo sweater is one of my favorite fall purchases, and it was just restocked! It’s on the thinner side, so I haven’t worn it as much lately, although I did wear it to lunch on Christmas Eve under a leather jacket when the weather was mild. I also want to try it under my black puffer vest.


I also wanted to include the above outfit because Alison gave me a really cool Christmas gift that used that picture as the muse… Alison is my photographer, and a friend of hers did this artsy sketch from that photo that she took of me last fall, and she framed it and gave it to me for Christmas.

Isn’t that so fun? I put it on my desk.

#13. I couldn’t do this post without including what I wore to a black tie optional wedding last fall.

As y’all know, I worked hard on this outfit — finding the right dress, and then the accessories I wanted to pull it all together. I absolutely love how it turned out.


#14. If there’s a theme in my favorite outfits, it’s definitely a fitted jacket… I had to work really hard to narrow down my favorites from all the outfits I wore with a denim or leather jacket.

This camel cashmere sweater with the denim jacket and black jeans has an upscale casual vibe that I love, and then the shoes really complete the look.


#15. This sweater actually appears twice in this roundup because it’s so good, especially for the price point. It was the first item I went for when I got to the store on the #NSale preview day. I had seen it in the catalog and fell in love with the relaxed styling and huge ribbed cuffs. It’s also suuuuper soft.

I really like this oatmeal color paired with white jeans and taupe boots for a monochromatic look.


#16. I also had to narrow down the various looks I created with this graphic tee — there were so many! I chose this one because it’s the one I’m most proud of. It’s a little out of my norm, with the long cardigan, and I even added a belt!

Plus the Chelsea boots are new to me as well. I think they look better with a straighter jean, but I didn’t have quite the right thing, so I cuffed these skinnies.


#17. I loved almost every outfit I wore with this stripe cardigan in fall hues, and I’m loving the winter one too.

I chose this look because I like the way the combination of warm and cool neutrals from the sweater is echoed in the jeans and shoe pairing.


#18. Of course I had to pick an outfit with this vest, since I wear it about once a week! Unfortunately it’s gone now, but any burgundy vest would do, although I really love this layered look.

I usually wear it over a grey or black sweater with blue jeans, or grey or black. I try to mix it up each time I wear it. Also, the snake print booties add texture and pattern to the rest of the solids in this look.


#19. I’ve worn this next outfit quite a bit since I got the sweater from Trunk Club last month. For some reason, I always end up wearing it with grey jeans and black boots, although I think I wore it once with light wash blue jeans. It just looks so good with the grey.

And let’s give a shout-out to the grey jeans while we’re at it. I am such a blue denim girl at heart, but grey jeans have really given them a run for their money in my wardrobe this fall! The grey seems to go with just about everything, and it gives my outfits a casual but edgy vibe.


#20. This final look is one I threw it together at the last minute to visit with friends last week, and I love it. It’s super simple, but the color combination is so nice.

This cowl neck sweater and booties were both #NSale purchases that have served me well this fall and winter, and the jeans are my current go-to AG Farrahs. I have them in 2 denim washes as well as a black pair. So good.

I almost didn’t buy these boots. I waited until almost the end of the #NSale to take the plunge, but I’m so glad I did. I have them in tortilla suede, and they go so well with the light neutrals I’m gravitating to these days. I’m tempted to order one of the snakeskin prints, now that they’re on sale again… definitely take a look if you’re in the market for a pair.


And that’s a wrap!

This was a fun walk down memory lane… I hope you liked it. I have some more recaps coming over the next week. ‘Tis the season!

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