Best Dark Lipstick For Fall Winter Look 17
Best Dark Lipstick For Fall Winter Look 17

36 Best Dark Lipstick For Fall Winter Look

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Every woman should own at least one amazing lipstick. Lipstick is a total style accessory, like a stunning pair of heels or a beautiful handbag. And like heels or a handbag, there is no such thing as ‘the’ perfect lipstick. This is a good thing… actually a great thing! It means there are¬†multiple¬†perfect lipsticks for every woman.

For that reason, it bothers me when makeup artists quote blanket rules: Pick a lipstick two shades darker than your natural lip color or, if you have this skin tone, wear this color. You wouldn’t limit yourself in such a way when picking a clutch or pump, right? Lipstick is no different–it is an accessory like any other. Treat it like one.

This is not to say there aren’t some guidelines. Let the following be your framework the next time you find yourself faced with a sea of lipsticks, each one screaming “pick me, pick me!”

Question 1: Do you want a bold or neutral lip?

This is the fundamental question. When picking a lipstick, deciding on the color family feels like the natural starting point. Don’t start there. Instead, start by deciding on either a neutral or bold lip. Lipsticks fall into two general categories: neutral or bold. Neutral lipsticks blend with the rest of your makeup. Bold lipsticks contrast the rest of your face. Boldness results from a lipstick’s “value”, which is ‘the lightness or darkness of a color.’

Keep in mind that not every shade within a color family is bold or neutral. A particular red lipstick can be bold, while another red lipstick can be neutral. Similarly, a color that is neutral on fair skin women may actually be bold on a woman with darker complexion. For this reason, bold or neutral should be your first question.

To determine if you want a bold or neutral lip, ask whether you want your makeup to standout? If no, then go with a neutral lipstick. If yes, then go with a bold lipstick. [Note, you should typically refrain from pairing a bold lipstick with smokey eyes. This is because you don’t want both your lipstick and your eyeshadow to be bold–otherwise your face may look too cluttered.]

Question 2: Are you gravitating towards a particular color?

If so, go with it. Let your intuition be your guide. Many makeup artists rely too heavily on rules based on skin tone. If you have skin tone X, they say stick with colors A and B and avoid colors C and D. I find this approach far too rigid. Certainly skin tone can be an important factor when considering a lipstick. But don’t get too wrapped up in it. Rather, view it from the perspective that some colors “compliment” certain skin tones. Of course if you eventually decide a lipstick is too light or too dark for you, you can always darken or lighten. [Just see any one of my featured lipsticks posts for an example of how to alter a lipstick.]

Reds: Typically classified as the boldest choice. Realize, though, that reds vary tremendously. They range from bright to dark to very sheer (meaning they just add a transparent wash of color). Reds can “compliment” all skin tones. Deep pigmented reds flatter medium and darker skin tones.

Pinks: Exceptionally versatile and always very feminine. Pink lipsticks can be good for any occasion.

Corals/Oranges: These colors look great on all skin tones. They especially compliment women with warmer undertones, such as those with a golden complexion and yellow to their skin. This color family is more favorable in warm weather, but can be incorporated year round.

Purples/Plums/Berries: A great choice if you want to add more color to the face. These colors are best for the fall and winter months.

Browns: Great everyday colors that easily pair with the rest of your makeup. Lighter shades tend to blend nicely with more fair complexions and deeper browns suit darker complexions.

Question 3: What is more important to you: lipstick longevity or lipstick comfort?

If you are looking for a lipstick with staying power, go with a matte lipstick.

Matte: Matte lipsticks are the longest lasting lipsticks. They grip the lips and even leave a slight staining effect that won’t easily come off.

If you are looking for a comfortable lipstick, go with a sheer or creamy lipstick.

Sheer: Smooth and shiny. They are very lightweight and usually feel like you are wearing a lip conditioner… it’s possible you may not even realize you’re wearing anything at all. [Note, sheer lipsticks are low pigment and therefore have very little color payoff. Sheers are washes. See Important Consideration below.]

Creamy: Exceptionally smooth on the lips because it contains the most moisture. Great for those with drier lips.

Important Consideration — “Color Payoff”

Color Payoff is the measure of how much a product colors your lips. A seemingly vibrant lipstick may actually be barely visible when on the lips. Such a lipstick is said to have a poor color payoff. Sheer lipsticks have the lowest color payoff. With sheers, expect the lipstick to be more like a ‘wash’ that allows your natural lip color to shine through. On the other hand, matte lipsticks have the greatest color payoff. With mattes, what you see in the canister will basically be what you’re going to get on your lips. Creamy lipsticks typically have moderate color payoff.


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