How to Successfully Wear Bold or Dark Lipstick

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Tips for wearing dark or bold lipstick - how to care for lips, kieep lips even, and choose the right product by Wardrobe Oxygen

Do you have a specific process or any tips for applying a bold lip? Any dead skin on my lips takes the stain and creates ugly dark spots, and I can't seem to apply liner that looks natural, symmetrical, and that follows the line of my lips. I'm wondering if you use a lip conditioner or have a process for the dead skin, and if you use a liner that you would recommend?

Lipstick scared the crap out of me for years. In college I did rock the Revlon Toast of New York or Coffee Bean on the regular, but I was also a high-maintenance sorority girl who had no issue reapplying hourly, didn’t eat in public very often, and drank even her beer with a straw. As a fully-functioning adult who is too busy to spend 20 of her 24 hours focused on her appearance, lipstick seemed too difficult.

I went to a midnight showing of Rocky Horror Picture Show with my sister. I borrowed a wig, a feather boa, and a tube of Revlon Matte lipstick in In the Red. Long time readers who follow my beauty details may know where this is going… I never gave back that lipstick. I finally found a red lipstick that not only looked good on me, but didn’t get on my teeth, my chin, and leave me looking like I was wearing only liner by lunchtime.

I still have that lipstick; it’s now discontinued so I bought what I could find – one in Wine Not (dark wine color) and one in Really Red (a bit brighter than In the Red). I feared Revlon Matte was a unicorn and I’d never find another product that didn’t dry out my lips, didn’t feel gross, but also didn’t feather and smear and disappear.

I was getting older and felt the glossy black cat eye and shiny nude lip look was a bit dated (I will admit I was inspired by a late ‘90s Playmate of the Year) and emphasizing the negative (hello fledgling crow’s feet). Everyone compliments me on my smile, why not play it up? I decided to branch out from Really Red and Wine Not and see if I could carry them off. This was 2012, I even wrote a post about the lipsticks I tried that year.

Even though I found some great colors and gained confidence wearing a bold lip, I found lipstick required maintenance. Not college-level hourly maintenance, but lip care, proper application, re-application, and being choosy with formula. My tips below:

Exfoliation is Key, Especially in the Winter

We’re all familiar with body scrubs and know that exfoliation is good for the face. But exfoliation is also a necessary step for achieving a bold pout. The cheapest and easiest way to do this? Keep your old worn out toothbrush and gently rub your lips with it once a day. I recommend doing this at a time that makes sense for you; I exfoliate at night after brushing my teeth, before putting on lip balm.

I felt lip scrubs were a waste of money. Gosh you can make your own with some coconut oil and sugar, and why can’t you just keep using the old toothbrush? Thing is, I never made my own and the toothbrush didn’t seem to be getting the job done in the winter when the air is so dry. A couple years ago after seeing it hyped on so many blogs and added to still lives with peonies in empty Diptyque candle jars I bought the lip scrub by sara happ.  Yeah, it’s better than the old toothbrush. It gently scrubs, smells amazing, and leaves my lips hydrated. It’s so yummy I don’t dread that part of my bedtime routine. The next morning, my pout is soft and ready to wear all sorts of crazy colors.

Hydrate Inside and Out

It’s imperative you keep your lips hydrated. While lipstick may seem to stick and last longer on dry lips, hydrated happy lips will actually perform better and look better (less cracks/wrinkles and darker patches). I have a lip balm in my office desk, my purse, my car, in my medicine cabinet. Next to my bed I have this Vitamin E ointment I put on my cuticles, elbows, and lips before going to bed. This may seem obsessive, but it has become a habit and one that keeps my lips happy even in the dead of winter.

Lip balm will only do so much if your body is dehydrated. Drink that water, it will make your skin look better, you’ll be less achy, and your lips will look and feel better. Before I go to bed I drink half a Kleen Kanteen of water. When I wake I drink a full one. At work I have a 48 oz. “bubba” water bottle. I drink and refill every day.

I also take fish oil pills purely for the skin benefits. I take 2-1,000mg pills each morning and come fall and winter take another 1,000mg in the evening and it keeps my lips from cracking and prevents the raw red skin under my nose.

Apply, Blot, and Reapply

Instead of lipliner, I find the most success with applying, blotting by pressing my lips to a tissue, then applying a second coat. This gets in all the nooks and crannies without being so thick it will smear or bleed.

Some believe in having a base coat of lip liner. This way it's easier to draw the line because you're just filling in your lips and you can do short strokes and blend. Try to find one as close to your lip color as possible or consider a clear lipliner. I have this clear lip liner and it’s my go-to when I need to be sure my lipstick won’t disappear mid-presentation or champagne swilling at a networking event. The lipliner base is what I did for my wedding day and it made my overpriced Chanel lipstick survive the receiving line.

Find a Balance Between Hydrating and Long Wearing Formulas

Many hydrating formulas will smear, fade, and bleed. However, long-wearing formulas can dry out your lips. The Revlon Matte formula was great because it was that happy medium. I’ve found NARS lipsticks to also be that happy medium and do pretty well with Revlon’s Super Lustrous, Lancome L'Absolu Rouge, and Bite Beauty's Amuse Bouche.

Try a Lipstick Alternative

Long-time readers know I'm a huge fan of the Revlon Colorburst Balm crayons.  They come in hydrating, matte, and lacquer versions and aren't as thick or opaque as a traditional lipstick.  They were like a gateway drug for me into red lipsticks; I first bought Romantic and then Smitten and now I own a half dozen different colors (check out Shameless it's amazing for fall!).  They are so easy they can be put on without a mirror, don't need a pencil sharpener, and make the most chapped of lips not only look but feel better.  Several different brands now have tinted balms and balm stains out there that merge deep color with hydration but aren't so thick and juicy they slip and slide off your face.

You Do You

I know many a woman who just won’t do a bold lip because it’s a PITA (pain in the… artichoke). And there’s nothing wrong with that. While the stereotypical French woman with a fresh face and red pout is considered the epitome of style, there is nothing more chic than knowing yourself and dressing the part.

My Favorite Bold and Dark Lip Products:

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  1. Thanks for the great follow up post! I’ve got several products in my Amazon cart, and am hunting for a clear lip liner that will ship to me overseas. I didn’t even know that was a thing! I’m excited to put all this in to action and go forth with my dramatic fall pout!

  2. I’m a little older and wrinklier so I moisturize around my lips, apply clear lip liner just outside my lips and then do a base layer in a long wearing shade. Because the long-wearing lipsticks are drier I apply a glossier shade over the base layer as the day goes by.

    For the most part I go with berry/brown shades, but recently I picked up Revlon Black Cherry. My Fall wardrobe has moved to dark colored cottons with more than a few orange/green/brown/burgundy shades and the dark lipstick goes well with that. At $7-9 it’s a splurge I can swing.

    1. Which clear lip liner do you use? I’m wondering if that might be the solution to my red lipstick bleeding issues!

      1. When Allie posted about the 20% off Luxury Beauty at Amazon sale on October 24th and recommended the Julep Get in Line Invisible Lip Liner. It’s perfect for girls like Ginger and I who have some lines around our lips and need a barrier to create a nice lip line. Even though I’ve only used it a couple of times, so far, I am very pleased with the results.

  3. One of my favourite comfy longwearing formulas is ysl glossy stains and the new rouge vinyls 🙂 They do stain )which is a plus and the finish is fabulous. Alternatively i love revlon super lustruous and the matte balm stains . But another good finish is the Guerlain KISS KISS ones and the lancome rouge in love 🙂
    For a good drugstore option the new balm stains from loreal ( YO LO YO LA) is a nice dupe ( if ever slightly more slippery ) for the clinique chubby balms ( in mightiest maraschino) which are also just lovely. Quite resistant, hydrating , beautiful punchy ( or soft depending on the pick) color . I keep one on them in my purse one at the office. And a revlon matte balm in my bag 🙂

  4. Do you have any tips to prevent lipstick bleeding? I have a Chanel Rouge Coco lipstick and the colour is great as is the hydration (no dry lips!) but I haven’t successfully got through a whole day without it looking messy by the end…

    1. Have you tried a primer ? I find mac’s one quite useful in that regard. Also working it in the lips in thin layers + blotting makes a lipstick more resistant in my experience

      1. I haven’t! I’ve tried layers and blotting but over the day it just seems to creep out onto my face… From this post I’m thinking clear lipliner might be the way to go – happy to take any recommendations!

        1. Personally i like the ozone liner from urban decay. But better the ozone multipurpose stick/crayon think. That can be used as allover primer and liner . Of course you can try with a matching pencil in a stiffer formula ( like mac). or with a longer lasting less creamy lipstick.

  5. I have always enjoyed bright reds on special occasions and tend to favor blue reds. My current faves are Laura Mercier’s Red Amour and Bobbi Brown’s Red 10. Both give me the bold “stay all day” color I require without having to reapply more than twice a day. The one thing I’ve learned over the years is to apply them properly so that I don’t accidentally stain my fingers or clothing with any residual lipstick.

  6. I was always intimidated by bright lipstick and thought I could never pull it off until 2 years ago. I decided at that point I was just going to try it and own it. Now I wear bright lips more often than not. Red, poppy, orange, hot pink…..I’ve got them all. The L’oreal La Matte crayon in whatever the red shade is called is perfect and very reasonably priced. My other favorite bright color is the Revlon HD lipstick in Poppy, which is a lovely mix between a red, orange, and pink.

  7. I have found a red lipstick that stays all day, and I wear it everyday. It is Stila “Stay All Day- Liquid Lipstick” in Fiery. I have recommended this brand and color to many, many women. I can eat, and that stuff still stays on. Give it a whirl.

    1. I have too have used Stila’s Stay All Day lipstick in Fiery, but on my complexion, it makes my lips appear almost neon glow-in-the-dark red. And, as the day wears on, it wears off in patches. I prefer using Stila’s more muted version of Stay All Day Vinyl Lip Gloss in Scarlet Vinyl. Either way, they both require a steady even application for the best look.

  8. Love this topic! I’ve always appreciated your choice in lipstick. While I tend to default to a berry pink for everyday, I just love a darker or bolder lip for evening (especially now that it’s fall.) My go-to red is Maybelline Creamy Matte in the shade Siren in Scarlet. It brightens my skin tone and makes my teeth look whiter, and it fades really evenly. And it’s really comfortable.

    Also, for lip exfoliators, I was always awful at remembering to do it, but now I just use this as part of my regular makeup routine. It’s weird as heck initially but it really works and you can’t argue with the cost: http://www.elfcosmetics.com/p/lip-exfoliator

  9. Toward the end of a hot shower, use a fingernail to gently scrape the dead skin off your lips. After you get out of the shower, apply lip balm, preferably oily as opposed to waxy. Voila, you have smooth lips. Sounds gross, but it works.

  10. Allie,

    How on earth did you find time to fiddle with your lipstick all the time when you were in college? You must be way, way smarter than I am. When I was in school, any time I wasn’t in class I was working on a project in one of the labs, studying, or using the computer for one of my classes.

    I was lucky to swipe a comb through my hair on the way out of the bathroom.


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