Style

Trying Out Fall Lipsticks

Five Fall Lipsticks

It has been one of the sweatiest summers on record, so let’s just say I’ve been embracing my “natural glow.” But as the temps begin to drop, I’m looking forward to having fun with makeup again. I love the way a dark lip looks with your hair tucked into a turtleneck on a crisp day. Fall hues are moody and romantic, but not always easy to pull-off — especially this season’s matte trend. Ahead, are five shades that I’m hoping to conquer, plus some tips from makeup artist Georgina Graham

DEEP RED

Five Fall Lipsticks

Estée Lauder Pure Color Envy Matte Sculpting Lipstick in Irrepressible

After swiping this on my lips, my mood went up a notch — my eyes got a little brighter (and bluer!), my step got a little kickier. That’s the power of a good red lip; and for fall, I want that red to feel as rich as this creamy matte. Georgina says a deep red looks good on everyone — for those with pale skin, try more blue tones, like Irrepressible; for those with darker skin tones, go for warmer shades, like Desirous.

BROWN
Five Fall Lipsticks

Charlotte Tilbury Matte Revolution Luminous Modern-Matte Lipstick in Birkin Brown

As someone who grew up watching My So-Called Life, brown lipstick (a trend that recently resurfaced) felt like somewhere I couldn’t go, again. But this shade feels a little less angsty teen, a little more elegant adult (it’s called “Birkin Brown,” after all). It goes on so sheer, it’s almost slippery, but the texture allows you to build the color so you don’t have to go full Angela Chase.

Helpful tip: When testing out a new shade in a store where you don’t want to put it the product on your lips, Graham says to use your finger pads. They’re much closer to your lip color than the back of your hand.

BLACKBERRY
Five Fall Lipsticks

NARS Velvet Matte Lipstick Pencil in Train Bleu

I call this “my Rihanna moment.” I’m not sure how many more of these moments I’ll have, but it felt good to push my limits and try something out of my usual shades-of-red zone. Also, I loved the smooth application of the crayon-like lipstick — which made it easy to get a clean line. Now I want it in every shade.

Helpful tip: When wearing a dark lip, Georgina suggests going very minimal with the rest of your makeup to avoid looking overdone. Use a little BB or CC cream if you have to, but no heavy foundation. Use mascara only on your upper lashes, skip the blush, and wear illuminator instead of bronzer. I tried that with all these lipsticks, and I think it worked!

SPICE
Five Fall Lipsticks

Mac Lipstick in Spice It Up

Spice It Up would be Goldilocks’ lipstick of choice: it’s not too dark, it’s not too sheer, it’s just right. The color doesn’t have the ability to instantly elevate an outfit like some of the others, but I could wear it every day. And if you’re just testing the dark lipstick waters, this is the perfect way to get your feet wet.

PLUM
Five Fall Lipsticks

Hourglass Opaque Rouge Liquid Lipstick in Empress

Liquid matte lipstick — which is very popular these days — is kind of mind-boggling. A minute after you spread the liquid on your lips (be sure to only use a small amount), it will dry to a vacuum-sealed-to-your-lips matte. It takes a second to get used to, but you’ll soon forget it’s even there — until you catch a glimpse of yourself in the mirror hours later and it hasn’t budged. Thankfully, I loved the color; my lips were a deep yet cheery plum all day long.

Helpful tip: Dry or flaky lips will show even more when wearing dark lipstick, especially if it’s matte — so it’s key to have your lips in tip-top condition. A lip exfoliating product will do the trick, but Georgina says a cheaper option is to run a damp toothbrush over your lips, add lip balm, then blot with a tissue to ensure smoothness.

What lipsticks do you wear? Would you wear one of these?

P.S. An amazing eyebrow makeover and a nail polish favorite.

(Top photos by Ana Schechter for Cup of Jo. This post is in partnership with Nordstrom, a retailer we love for its amazing customer service. Plus, they always offer free shipping and returns. Thank you so much for supporting the sponsors that support Cup of Jo.)

  1. Great article Megan! These colors suit you really well !

  2. Tas says...

    This article inspired me to try a plum lipstick. I have always been scared of darker lipsticks but my colouring is similar to yours so I thought it was worth a go! I’m wearing it to work now with no eye makeup but a fairly strong eyebrow and I feel like the effort:put-togetherness ratio has finally been tipped in my favour! Another COJ winner.

  3. You are so pretty! I love Deep red & Spice

  4. Totally love a good red lip. Instant pick me up!

  5. Gigi says...

    i think it would be great to do this feature with a more diverse selection of women. this trial only helps your readers that have fair skin and brown hair – it’s impossible to know how other women would look with the colors as they would show up so differently. love these posts but please be inclusive of everyone.

    • Megan Cahn says...

      Totally agree, thanks for the feedback! We’d love to do a feature with a wide range of models.

  6. I like the L’Oreal long lasting lipstick. I’ve been wearing “Continual Crimson” (pulled from my blazer pocket to check, haha) and I like that I can layer it on super sheer or a little heavier. The coordinating balm makes it feel nicer after it dries, but I go through that a little fast.

  7. Yippy! I love a good lipstick post. Love the red and spice shades best.

  8. I love mac’s sandy b, I have really large eyes that I like with kohl and sandy b is the only one that sets them off :)

    Shruthi
    http://nyambura.co

  9. Jenny says...

    You absolutely need to post a Beauty Uniform and I loved the reference to My So Called Life! I had the hair color 😄

    Smiles for miles!

  10. Love this post and made me even more excited to start cracking out all my brown and purple lipsticks. I think you really suit the plum shade. Lovely photos x

  11. Kelly says...

    You are so beautiful!

  12. Frankie Rose says...

    I second (or third!) the request for a beauty uniform! I would especially love to know how you care for your gorgeous long hair!

    • Raina says...

      SAME!!!

  13. What colour are you wearing the very first picture, think it’s Decisive Poppy but wasn’t sure :)

  14. Cynthia says...

    All these colors look great on you, Megan. I would try any of these colors myself.

    • Megan Cahn says...

      Awww, thanks!

    • Clare says...

      Oh gosh, I love Audrey! I try it on over and over and I just need to buy it already. :) I’ve been wearing Charlotte to death this year–definitely more in the ultra-deep plum/Train Bleu category. I love it so much. Just enough drama.

  15. Katie says...

    Woooo, girl! That brown looks so good on you! With your easy hairstyle and black top, you look like a classy extra on Friends!

    • Megan Cahn says...

      OMG, I wish! Thanks, Katie!

  16. margaux says...

    they look great on you, but ugh. i abhor matte lipsticks. give me a sheer gloss any day!

  17. I just got the Beauty Bakerie lip whip in Cranberry Stiletto and Hawaiian Cheesecake. These are no joke! They DO. NOT. BUDGE. The colors are gorgeous. I want more!

  18. Laura C. says...

    Megan you look great! Thank you for the suggestion- I am looking for a new lipstick and the Spice one from MAC seems nice. I’ll give it a try!
    Thanks!

    • Megan Cahn says...

      Thank you, Laura! I think that’s a good choice!

  19. Heather says...

    I loved the “Ahead…” lead in. It felt like I was about to go on a lipstick adventure. These all look great on you, a nice statement lip with your minimal makeup. Dark lips are so intimidating, maybe I’ll give the stepping stone dark lipstick, Spice It Up, a try.

  20. kate says...

    This photo layout is terrible! All the photos are too far away to really see the color. Why post four small photos of the same lipstick instead of one larger one?

    • I actually think the smaller photos show what it would look like from the view of someone else. At least for me, I may be able to look at my makeup really close in a mirror, but in reality this is how the makeup would show up in a photo(unless it’s a selfie), or how it would show up to anyone that talks to you or walks by you all day. And I can still tell from the layout what the lipstick color is. Just a thought.

  21. Cindy says...

    You absolutely look fab in all of the shades, Megan! My fave on you would be the Nars or the Hourglass. They really make your skin look incandescent. I am ordering the Hourglass and the Estee Lauder and jumping WAAAAY out of my comfort zone! Thanks for the nudge into fall color!

  22. I wear dark or bright lipstick almost every day. I love Autumn shades best, I wear burgundy, bright red, brown and dark pinks on a regular basis. I sometimes wear nude, orange or purple (but purple more because bold lips forever). I would wear pretty much all of these shades on a regular basis

  23. Tilly says...

    Deep red looks the total bomb.

  24. And a My So Called Life reference to boot! Love you!

  25. Theresa says...

    I have a darker skin tone, so have always loved reds. I don’t wear any other make up, but lipstick, and not even everyday, so don’t like to spend a lot on lipstick. I recently discovered Burts Bees lipstick…love, love!!! Fits my budget and the lipstick is creamy and moisturizing.

  26. Kate says...

    Love all these! Can’t wait to experiment. Does anyone have any suggestions for blonde hair/fair skinned colors? Thanks for posting!

    • Cynthia says...

      Have you tried Clinique’s Almost Lipstick in Black Honey? It’s plum color that is flattering on everyone, but not too dark if you are fair skinned. It has some shine, as I don’t like matte lipsticks. I also recommend Clinique’s Chubby Sticks for lips in Chunky Cherry, Pudgy Peony, and Whole Lotta Honey.

    • sabe says...

      I’m also pale with blonde hair, and Nars Cruella is perfect for us. It has a blue undertone that goes well with blonde hair, and it’s not so dark that it makes us look goth or sick.

    • Kate says...

      Thank you!! 😊 I will get myself to Sephora pronto!

  27. Daynna says...

    Megan, you’re absolutely gorgeous. So, naturally, all of the lipsticks look outstanding on you. But my favorite was the last one, plum, I think it was. That is so your color. Red is second.

    Thanks for this! Not only has this post (which is fun and flirty and light and inviting) inspired me to try out a few new colors (and I almost never use lipstick…), but I’m also far more committed to letting my brows grow in after the other post you guys had up maybe a week ago. I want full eyebrows like you guys! They’re beautiful.

  28. Erin says...

    Megan – would love to know your Beauty Uniform!! Pretty please

  29. Leslie says...

    Megan, I love your hair color! Your highlights look so natural I have to ask, are they natural?? Either way I will be showing these photos to my colorist next visit!

    • Megan Cahn says...

      Thanks, Leslie! It’s actually not natural, I got these highlights about six months ago. I’m always hesitant to get highlights because I’m afraid they’ll look streaky and fake (been there), but I’ve been really happy with how these turned out. They are the work of this color genius in NYC:
      https://www.instagram.com/auracolorist/?hl=en

      xoxo

  30. I’ve never been much of a lipstick wearer, but this year I’ve been bitten by the bug. This post has definitely given me a few products to put on my ever growing shopping list. Loved all the little tips too!

    Brilliant post!

    Jamie-Leigh
    MissJamieLeigh | http://missjamie-leigh.blogspot.co.uk

  31. Random Q, but where is your t-shirt from? I’ve been looking for one exactly like it.

    • Megan Cahn says...

      It’s from American Apparel!

  32. molly says...

    Not to be creepy, but you have GORGEOUS eyes!! Great post!

    • Megan Cahn says...

      You’re so sweet! Thank you!

  33. Nars Terre de feu and volga are my favorite Fall lipsticks. I’m sorry but I hate the matte liquid lipstick trend, it’s a little too Kardashian/plastics to me. Oooh but has anyone tried the new Pat McGrath lip kits? I ordered the venom and can’t wait to try it.

  34. I wear red tones year around. My favorites are NYX Matte Lipsticks (Perfect Red, Dark Era, Alabama, etc.) the color is great and the price is right. Revlon Dark Cherry is a great tried & true for Fall. Its easy to use as a stain or build the color.

    xo Lendy
    http://www.twoplusluna.com

  35. Rebecca says...

    Anyone have recommendations for a line of organic/natural lipstick?

    • Samantha says...

      I’m really into Kosas these days. I believe it’s natural and very moisturizing.

    • Mandy says...

      A friend of mine started a company making vegan liquid lipsticks and they are amazing – Aromi http://www.aromibeauty.com I wore Sweet Marsala almost every day last fall.

    • Sara says...

      Try Axiology! It’s made by hand in Bend, OR with natural pigments and is 100% vegan. The packaging is very chic as well and has a click mechanism to open. I only have one shade so far, but it’s really creamy and long lasting.

    • Amanda says...

      Alima has some great shades. Both their lip tints and lipsticks are nice and completely natural.

    • Cheryl says...

      BITE Beauty! You can find it at Sephora.

    • Kris says...

      Ilia Beauty lipsticks and lip conditioners are my fave! https://iliabeauty.com

  36. The blackberry one is definitely my favourite, it really makes her eye colour pop! So beautiful!
    It’s funny because I feel like most women stay away from dark lipsticks during the summer, but I literally wear them all year round! (including on hot summer days!) xoxo

    • Me too!

  37. Alice says...

    This is so fun!

  38. Spice makes your eyes pop!

  39. AJ says...

    Top one = gorgeous. Your eyes do look so blue!

  40. Catie says...

    The deep red is beautiful! Would love to see how each shade looks on a variety of skin tones :)

  41. Madie says...

    I have a hard time with the bright/bold lipsticks – like a previous poster, I have naturally very pink/rosy cheeks, so pair that with red lips and I feel clownish. Or worse – like a full on hussy (lady of the night??) I have pulled it off once or twice with a nice dark red, but had to do almost no eye makeup to compensate – just mascara. Maybe it’s a desensitization thing…

    • I love Sarah, the photographer Arrow and Apple (blog and Instagram), and she is adorably rosy and pulls off a great bright red lip. I also feel that I look washed out without a teeny bit of pink in my cheeks, so I just try not to overdo it. Don’t be afraid if it is fun for you! I think we ponder it much more than the people around us will.

    • I have insanely pink cheeks that go red in the heat but bold lipstick is my favourite beauty look. I say try it, I bet everyone else will think how amazing you look with red lipstick

    • Madie says...

      Thanks for the encouragement, ladies! XO

  42. Kate says...

    I have been looking for a good plum color–I might need to try that! Thanks for the round-up.

    I recently bought the Maybelline Color Sensational Creamy Matte in Siren in Scarlet, and it’s my dream red. It’s blue-toned so my teeth look whiter, and it stays on incredibly well while also being comfortable to wear. I don’t wear red too much so being able to find a drug-store option always makes me happy.

  43. Tina says...

    I loved Blackberry, Plum and the red ones on you! Those shades are hard to pull off, but you nailed them! Also, you look so luminous! Love the natural make up look on you. I too agree, you do look like Courtney Thorne-Smith! You also look like a friend of mine too!

  44. Annie says...

    I’ve never been able to find a red that doesn’t make me look clownish. My problem is I have quite fair skin but I also have very pink undertones and red rosy cheeks naturally. (Think Prince Harry but not as tan and a bit rosier!) basically it looks like I’m always wearing quite a bit of blush. So I either look clownish with red lips and red cheeks or look way overdone with a ton of foundation to cover my redness and red lips. Is there a color or technique you could suggest? I would love to get that boss lady feel people talk about while wearing a bold red!

    • Julia says...

      I have this same skin tone, and I realized that I was the only person that thought I looked clownish in a red lip. I started wearing it every day, and got used to it/got lots of compliments. Definitely go for a blue red, too.

  45. I am newly OBSESSED with Charlotte Tilbury lipstick in Very Victoria for a really nice neutral/brownish color. It’s the perfect color for when you want to look polished and understated. I also love the NARS lip pencils, they’re fantastic!

    xoxo http://www.touchofcurl.com

  46. Deep Red: Tom Ford’s Diabolique. It’s incredible- I splurged on it for my wedding lipstick. It makes me feel like a million bucks every time I wear it (maybe because it costs just about that much!).

  47. Rebecca says...

    I’m loving the Glossier Generation G in Jam! I also like Mac Relentlessly Red

  48. Megan, I love the spice most of all on you and the deep red too. Thanks for modeling all those cute shades!!

  49. Megan, I love dark lipstick on others but often feel like it’s too much on me. Maybe I should give it another try, these look beautiful! I especially love the spice and deep red! PS Has anyone told you that you look just like Courtney Thorne-Smith??

    • Megan Cahn says...

      You definitely should! I’ve never heard that about CTS, but Lexi agrees :)