How to Achieve 'Classy' Cool Girl Style with These 5 Fall 2023 Outfits

[@bahia2342]

Très beaux outfits. Je suis fan de ton Birkin. Tu as raison pour le tee shirt Anine Bing, il est top avec les manches coupées. XOXO 🥰💕

[@Ladybug-lz5un]

Lisa I just discovered your channel! You are such a beautiful classy woman. I myself like classy clothes. You are an inspiration.

[@deborahwalburger1272]

Love your style! Thank you for the videos!

[@michshops9436]

Lisa this was truly an incredible video. I watched it three times. I put my express pants away because I’m working from home. Well I ran to the attic and pulled them back out. What an incredible stylist you are. I am so thankful for all of your hard work. You really do make my life easier.

[@LisaLisaD1]

YAY! Thank you so much!! 🩷 Lisa

[@LisaLisaD1]

5’6” 😘😘

[@shawnasommers6297]

I'm so glad wide-leg pants have come back in style and all of these are great ways to style them. Thank you, Lisa!

[@DonnaJeanHD]

Love all of these outfits! I think the small blazer has enough of an oversized look to it; it's just right!

[@marieschmidt9416]

Loved classy, cool girl look. Keep these videos coming.

[@Federstedt]

Wow Lisa. Your style has evolved so much during the years and you are the ultimate cool girl! Love the way you styled every outfit. Amazing!

[@angelamiller7164]

You looked so good in the low rise jeans , belt and pin stripe shirt! That was my fave! Loved the pink Johnny Cash shirt!

[@HollyL56]

My favorite outfit was the one with the Johnny cash tee, love the colors and vibe of that outfit.❤️💗💚

[@JessicaPerez-jr3ow]

Lisa , I loved all the outfits my favorite is what you were wearing.

[@terihillgartner5702]

I love the fit of the pin striped blazer on you. Although, if you are planning to wear it casual size up. If you are planning to wear cool girl style tailored, then I like the one you have.

[@AndreaJeanne88]

A couple months ago I remember thinking "I hope cargo pants come back in style." Fast forward to now and they are everywhere! I just bought some yesterday.

[@Mileyandmandytv3]

My favorite outfits #1 and #2….love love love the jeans with black jacket and the stripped shirt💜💜💜

[@jshearer9827]

Love your makeup and hair in this video. You look gorgeous!

[@reneegini1214]

I like 1,3,4. Love the look with the Samba’s too. I’m having a hard time doing the extra large blazers. I definitely like you in the size you purchased not one size bigger.

[@lolareid9656]

I can't pick just one!!! I love the graphic tees with trouser with the Adidas. Lisa, you have helped me so much with style and the joy of bing a woman!!!!

[@christinatruchon1924]

I enjoyed all the outfits. My style.

[@LisaLisaD1]

Thank you, Christina! 💗 Lisa

[@367Play]

Oh yes,,,all great inspo. love #2 and #4 with khaki flares. Outfit #5 made me nervous LOL because of the leggings length. Relieved you said they were too short😊 PS the “upcoming ring” is beautiful.

[@Ladyiayia]

Hi Lisa! Try curving the brim of your Polo cap....for me it makes all the difference.

[@SoulPowered]

Girl, all of the looks you created were perfect! Thank you for the inspiration!!

[@tinathornton2089]

Please style the Free People barrel jeans for over 50 in different ways. I bought two pairs in two different sizes one TTS one oversized in the Lucky Me from your videos and now I have no idea how to wear them . Loved your first #1 Cargo jeans with Chanel style Jacket . but all the looks are amazing as always. Size up on the blazer to a Medium.

[@LibbyGreenberg-f1i]

Know you're in NC coastal area, so hope you did OK without any damage. Great video!

[@phacker24]

Love all your videos!

[@Bg-cr2vx]

Enjoyed the your video Lisa and my favorite outfit are the jeans and button down; jeans appear to be very relaxed and laid back 🌹🌹🌹

[@juliebeck3796]

Love the Marissa Webb jeans, the Johnny Cash tee, and the Anine Bing Elton John tee! 😍

[@SondraMarshall]

I love the Johnny Cash Tee shirt on you as it fits perfectly just had to mention that I saw him perform in the Highwaymen with my late husband. Good memories for me.

[@joyeld5095]

Lisa, can you do a video on fall/winter fashion that’s practical? Like what to wear on raw/rainy days but you still need to run errands, walk the dog, etc? I find that’s where a lot of us lack fashion - is when it needs to be practical. Don’t want our jeans dragging through puddles! LOL

[@sunnynights68]

You literally look amazing in everything! Love these looks.I would love to see a video on how to make slim cut jeans more modern.

[@LisaLisaD1]

Thank you, will do, just got some in NM! 🩷 Lisa

[@murielrenee2475]

I love everything you showed in that video. Perfect style!

[@hairologywithkelliecarroll]

how about a tutorial on cutting your shirts, I am obsessed 😁

[@melodyholt1922]

Love everything! Order the medium blazer

[@tammysmith7312]

Oh my boy was this a good one . I love love the Black pants on u .love all the outfits omg I want it all going to order both jeans. Thank u for all u do for us. Love u so much💖

[@michellesapp7867]

My fav was #1 looks very classy but cool girl also. ❤

[@jarvis9283]

A wee tip Lisa (last outfit) best not buy pants that have stitching up the front of the pelvic bone stitching draws attention to that area not a good look 😮 everything else fab !

[@minorityfringe387]

Agree.

[@k.m.2080]

Love your videos! You are by far my favorite!! More cool girl style please! Also love your WalMart videos. You find the best items. Thank you for sharing!😊

[@des1180]

Love outfit 1 !

[@kathleenbenjamin4567]

I love the cargo pant I purchased a pair that you showcased from the Gap. I get so many compliments on them.

[@LisaLisaD1]

YES!!! Those are good ones, too! Not so over the top 😍 Thank you for watching!! 🥰 Lisa

[@danapride]

I agree about too short. Even the jeans now are too short. Sometimes I like something longer, especially when it’s colder.

[@CarrieMay-h2f]

Lisa- I have been watching your videos for months and I enjoy them. Just wanted to know I bought a few things you recommended, but what I want to thank you for the most is recommending that portable ice maker. The one in my refrigerator went kaput, and I did not think I could afford one, but I took your advice and looked it up and I can. Thanks from one NC girl to another.

[@divinemiss4284]

My favourite outfit was the 1st one. Cargos with Black jacket. I would like to see you style different ways a couple of denim button down dresses maybe one mini and one longer. Blessings to you and your audience.

[@Jwatty461]

Got the denim cargos. 👍🏻

[@charlottemilam2733]

It would be so cool if you had a graphic tee with your image on it. I'd buy it.

[@heatherweiler]

My vote on the blazer size: small. it looks killer on you, and it's something different since you already have oversized ones. "Model off-duty"...i love that phrase!

[@donnamcdermott443]

The Jonny cash outfit was my favourite

[@jillwarford3041]

perfection!

[@mireyacurtis4637]

Happy birthday Lisa! I’m new to your channel and I love your personality! Thankful for you ❤️

[@44779sarah]

Happy Birthday Lisa! I have been with you since the beginning and like you have evolved over the years personally. I think of you as my girlfriend in Wilmington and always look forward to your videos. I hope you and John are enjoying yourselves on your special day! Thank you for all of the encouragement, advise, recommendations etc. if there was only one channel I could watch it would forever be LisalisaD1!❤

[@thatwendygirl68]

Would love to see a video about how you declutter/purge clothes and shoes!

[@sandrag6500]

Oh yes!

[@lisah1507]

Your style videos always inspire me! ❤

[@karlamullen7387]

I was wondering what color is your Birkin 35? Beautiful bag! 😊

[@lindaleal997]

Lisa! You nailed this video 🔟🔟 🔟🔟🔟🔟

[@alisonshaw7563]

Lisa that’s so spooky! I watched the Carolyn Bessette Kennedy documentary thing on KZbin! It was amazing. I want to change all my wardrobe now 😍 x

[@styleitwithjess]

You have styled everything to perfection! All beautiful clothes!! 🥰🤍

[@ireonlebeauf7273]

Can we see styles with the slip skirt, slip dress and sweatshirt?

[@nahirhoffman4878]

Love that you show us your looks on you and not just sit and show fashion on others ♥️

[@gailmonte2425]

I enjoy these types of videos, and since you asked, I would like to see you show how to style your black leather biker jacket. I am finally going to pull the trigger and purchase one…. Thank you !

[@LisaLisaD1]

YAY!! I love a good Moto, I will FOR SURE be styling that often, it's actually coming up in a video I am working on now! 🖤 Lisa

[@donnamcdermott443]

For great flats Massimo duty Napa leather ruched toe ballet flats with the strap amazing 😍 try pointed toe flats if you prefer pumps and heels it still elongates the outfit in the same way ❤

[@LisaLisaD1]

Thank you, Donna!! I agree, I have some pointed ones on the way, I will look at the others, too!! 💖 Lisa

[@Mileyandmandytv3]

So excited just bought the cargo jeans to go with Skims body suits🥰

[@jackie230473]

Hi Lisa - thank you for the inspiration! What size Samba did you order? xxx

[@cparker7431]

Your style always looks designer put together!! I wish I were a couple inches taller😅😅 5"1' no waist, apple shape. I have a hard time trying to look like I have any shape. But I have great hair!!!😅😅😊

[@slh819]

I want to attempt every one of these outfits!!😍I adore your style and fun personality, Lisa. Thank you for all the great inspo, please keep these videos coming!😘

[@LisaLisaD1]

Thank you very much, I will! 🩷 Lisa

[@shabchique7149]

Love this cool girl video. My favorite is the last one.

[@carolejean63]

Love it all !

[@carolsandford8722]

Every outfit was a hit as always you nailed it Lisa :)

[@LisaLisaD1]

Thank you so much, Carol! 🩷 Lisa

[@anniepapineau]

Love all of them , favorite chanel jeans , 🎉bonne fête Lisa , I said it last week but I was too early . I wish you a good beach day Thank you for being you and do it gracefully A bientôt

[@Kristiehornbuckle]

Thank you Lisa for a post on a Thursday. It was perfect not to have to wait until Friday. YOU have the best ideas ever. I LOVE all the outfits, off to Carmel for my cousins wedding. Have a happy weekend!

[@LisaLisaD1]

Thank you for being here, Kristie! Have fun at the wedding!! ❤ Lisa

[@staceymaignan5407]

This is my favorite style! The last outfit was my favorite. Happy Birthday!

[@GigiG-be4xu]

Gosh you're gorgeous...n your highlights are amazing! Your hair also looks so healthy and silky.😍😍

[@sandrag6500]

I just LOVE these type of cool girl outfits! So livable and fun! Blazers, Graphic tees, and sling backs. Brilliant Lisa

[@LisaLisaD1]

Thank you, Sandra! 🩷 Lisa

[@ssssssow8218]

How about your bag collection? I would love to see them.

[@tammygozel7771]

Always a great video, I think the blazer sized up, I love the baggy look.

[@LisaLisaD1]

I know, I hope the medium gets back in stock--thank you!! 🥰 Lisa

[@traceyrussell5994]

I would love to see the shirt with the stars you bought from your last shopping trip lisa..that shirt was gorgeous and iv been hoping to see you in it. X

[@annetteincairns3528]

🧡💜❤️ I’m not a TShirt gal but I love your high end bags in this video. Mademoiselle Chanel matches your colour scheme. ❤️💜🧡

[@ladonaoneal8137]

At Wal mart I saw a pair of plain Jean bib overalls and a pin stripe. I was drawn to the pin stripe, but I didn't buy them. What is your take on bib overalls. I thought it could be a fun choice.

[@Yogadivasdivinelife]

Lisa, as always, thanks for sharing. Love your videos. I would love it if you would do this type of style on someone with a different body type-shorter and a little heavier frame. The clothes always look lovely on you, but I think this look in particular can be challenging to pull off for some. It would be fun for you to do a style my friends video with some different bodies!

[@marybuck5946]

LOVE every outfit!! You nailed it. And I think the small blazer is absolutely perfect.

[@LisaLisaD1]

Thank you, Mary!! 🖤 Lisa

[@jilll934]

I cannot believe I have never looked at Marissa Webb before. I’m on her website and will get a few pieces. They look amazing, kind of like ALC.

[@designerdiva1103]

I’d love to see the CBK documentary! Where is it airing?

[@jacque3737]

Have you tried Tala for flared leggings? I’m 5ft 6 and they fit me perfectly and the length is great x

[@hart-coded]

Pinstripe jacket darling definitely go up a size. It’s pinstripe so a little more masculine. I think the bigger size will go a further distance ❤

[@Tina-ec5lt]

I love love love the tee shirt that you have on. I love that whole outfit🥰🥰also knowing you like I do, I think the blazer looks great in the small, but you like things a little oversized so I don’t think you will be satisfied with it until you exchange it for the medium. That’s just my opinion. I love these type of videos!!! It makes my mind go in a million different directions from clothes I can style differently in my own closet to actually purchasing some of the pieces that you show❤️❤️🥰

[@SevilayKuhr]

I never thought of cutting my shirts before… Thank you for the idea! 🎉🎊😊

[@maryriggert1167]

I would be interested in seeing a capsule wardrobe, neutrals and maybe one classic color…. 5-6 pieces, max. Is this even possible to get several outfits, using only a limited amount of pieces?

[@Kristina-bk8lj]

Anine Bing tees are my favorite for sure~❤️

[@brenharwood7736]

Wow, each outfit was on point! Love your style Lisa. I bought that Jenny Bird necklace 2 weeks ago and get so many compliments ❤

[@laurar4290]

Hi Lisa. Great video, please list the Marissa Webb style of jeans you purchased. Thank you.

[@jeanettehigginbotham]

I would love to see different ways to style high waist wide leg trousers with tucked in luxury blouses and shoes for winter. A classy but casual... maybe business casual.

[@Connie-S]

Hey Lisa, I hope you have been hurricane free so far. The pin striped blazer - go up a size. The yoga pants were blech = that whole pant reminded me of my college days and bell bottom pants. LOL I love the colors in the Cash tee. I finally got my Bardot tee. One question on cutting the tees - I think I screwed up with my Nirvana tee. Should the tees be the same size? My AYR tee is a medium but I got the Nirvana tee in a large so it looked funny. Guess I will need to make some adjustments. Plus I think the drape of the fabric matters too. I like the flowy look of that blue and white blouse. Looked really comfie. Fun video as always.

[@debrarozich2456]

This is just the inspiration I need now. Love classy cool girl style. I am in my equestrian clothes so much and Sometimes I need a reminder re: new outfit ideas. 💞, Cowgirl Deb

[@akachloescarlett]

Wow! Every outfit is amazing Lisa! Such good inspo 🔥

[@LisaLisaD1]

Thank you for watching!! 🤍 Lisa

[@shawnasomers9127]

Here’s my humble opinion on the Smith Blazer. Of course it’s up to you however I think the small is a nice size for this blazer. I love oversized blazers on you, however you wear that amazing Zara black linen on repeat ( I say that in a positive way, I love it) so maybe the smith can be slightly more non oversized if that’s a term. Having said this, you always know what you like and what makes you feel great. Carry on my friend. 😍

[@brgreens]

Loved this! I think my fav was #1, with the cargo denim and Chanel look jacket! A close second is #2 😂, with the jeans and button down shirt. I have a very casual lifestyle and those are right up my alley! I’m older than you, 60, but love to stay up to date with my clothing! I love seeing your creative ideas for styling, and I love mixing styles like this. I do have a request for something I’d love some help with. Last year o bought a pair of lug-sole black booties. I think they are so cute, but I never got up the nerve t wear them. Every time I put them on I felt like I just didn’t hit the mark. It would be super helpful to see how to style these. I mostly wear jeans in fall/winter and have mostly straight leg and slim straight jeans. Thank you! 😘

[@LisaLisaD1]

YAY! I just got a new pair and have styled them in an upcoming video--I will keep trying them with different outfits for us!! 🥰 Lisa

[@melodybrooks7214]

I’d love to see you style chunky soled shoes. Thanks for the video!

[@shaunnyr]

Hello Lisa! I'm new to your channel and love your content. Could you consider classy outfits with skirts or dresses for those of us who aren't into pants? 😊

[@LisaLisaD1]

👌🏻🩷😘

[@lauratice8490]

I would love to see you recreate some Carrie Bradshaw outfits!🙏🏻❤

[@mommad8666]

Challenge: I had a really bad break, left ankle, years ago and can't wear heels more than an inch high. Any ideas for low heel shoes?

[@jesm9240]

Can you wear platforms? I am a huge fan of the Stella McCartney Elyse oxfords. They come in a ton of classic and outrageous colors and are that statement that some outfits need. I don’t wear heels as I have a fairly wide toe box and narrow heel so most heels don’t fit well. I gravitate towards platforms or clogs. Even a great pair of platform sneakers can make an outfit.

[@dawnrandolph1962]

Gorgeous cool girl style! Do you have a tutorial on cutting tshirts?

[@midlifemom5829]

Wish I could find this style proportioned for my petite frame (5'3", 115 lbs).

[@LisaLisaD1]

I would find some celebrities about your size and look them up on Pinterest--I will do it, too!! Brooke, my daughter is 5'3"--I'll ask her! 💖 Lisa

[@midlifemom5829]

@@LisaLisaD1 you are a sweetheart! I end up spending extra $ on alterations so they fit properly

[@sherriesq]

You just the best! Can you suggest some alternatives for the Marissa Webb jeans?

[@deyon6003]

Hey Lisa I love all of these cool girl outfits!! I tried to find the marissa Webb jeans but none on sale so where did you find them? I neeeed those jeans!! Brought me right back to 90’s but in a funky cool girl way😂