How To Wear Lipstick Like a Boss

You can do it. I believe in you!

I always get compliments on my lipstick and the fact that I can pull it off, and my friends know me as the girl who’s 99% likely to have a fun color on. But I wasn’t always brave and cray cray when it came to bold makeup, especially lipstick. Now, however, I’ll rock blue eyeshadow (blended tastefully, of course) or a bright purple lip like a boss.
Sound like fun? Well you, my friend, can do it too. Here’s how:

1. Own it. People always say, “I could never pull that color off.” Heck yes you can, girlfran! If you like it, rock it and it will look like it was made for you. I promise, you’re the only one who thinks it’s a thing. You’ll have heads turning and people asking what shade you’re wearing in no time.

2. Coordinate your pout and your outfit. Your lipstick and clothes don’t have to match completely (in fact, they shouldn’t), but complimentary colors can tie the look together and make less of a statement, but still be bold and fun. This way your lips won’t scream, “HEY, LOOK AT ME!” Instead, they’ll softly holler, “Hey, I’m chic and trendy just like my outfit.”
3. Invest in good products. Trust me, I know how painful it can be to spend your hard-earned money on a tube of lipstick. But when you give in and fall victim to the higher-end products, you won’t regret it. Quality really does make all the difference. (And then it becomes addicting. You’ve been warned!)
4. Wear it on the daily
. Not saying you have to wear crazy lipstick colors every day of your life, but I highly recommend wearing some sort of color every day (to work, school, run errands) to help build up your comfort level. Once you’re used to seeing yourself in lipstick, it won’t feel so weird when you make your grand debut at the next social gathering.

5. Grow bolder. Start off with lighter shades and gradually progress to darker, bolder and brighter shades. Baby steps, ladies. Baby steps.

6. Stick to seasonal colors. This will help with the shock effect, too. In the spring, feel out the pinks and pastels. In the summer, go for bright pinks, corals and orangey tones. In the fall and winter, experiment with more deep berry, mauve, purple and brown shades. But red? Red is ALWAYS in season.

7. Pick one or the other. Bold eyes or bold lips – not both. Unless you are going for a dramatic look, pick one or the other. This will help make it easier to accept without freaking you out when you walk by a mirror.

8. Play with formulas. There are TONS of different types of lipsticks – satin, gloss, shine, matte, semi-matte, standard lipsticks, liquid lipsticks, lip creams, etc. You might like one or two better than the rest, so I would definitely suggest playing around until you find a few that are in your comfort zone.
photo 5
9. Find the right shade.
Just because you tried one red and didn’t love it doesn’t mean there’s not another shade out there for you. There are a million shades of the same color, so experiment with different formulas and brands until you find the perfect one for you.

10. Make it last. If you’re worried about being that girl whose lipstick is all over her straw or coffee cup, or you don’t want your man’s face turning red from smooches, try using a long-lasting or smudge-proof product. Matte and liquid lipsticks lipsticks are another great option that won’t budge easily. (Speaking from experience for both of these, BTW.)

*Bonus: Seek advice from a professional! Take some time to walk into a cosmetics store (like Ulta, Sephora, Blue Mercury, MAC …) or visit the beauty department inside a department store. The pros can definitely help you find the right colors for your skin tone, specific event, an even recommend colors to get you on your way to being a lipstick queen.

And there you have it! Ten simple steps you can take to bring the lipstick diva you’ve always dreamed of being but never had the balls to be. Just remember – makeup us FUN! There are no rights and wrongs, no reason to be ashamed to wear it, and no one should tell you otherwise. It’s a way to express youself and switch up your look any time you want to, and you should never apologize for it. Do what makes you happy and OWN IT!

I hope this helps! Share your lipstick pics on Instagram with #SweetTeaAndSkyscrapers so I can check them out and give you some love <3

>> Check out my post 12 Lipstick Shads Every Girl Should Own
>> Check out my post Currently Obsessing Over: LA Girl Lip Paint




  1. March 16, 2021 / 10:01 am

    All details you describe in your blog post about lipstick boxes is very informative for me. Customboxesu provides lipstick packaging wholesale with suitable price.

  2. July 2, 2015 / 11:25 pm

    BRB going to buy a whole collection of fun-colored lipsticks! Great post from a great blog! x

    • Blakeley
      July 7, 2015 / 3:21 pm

      YASSSS! Thanks, pretty lady. Happy lipstick shopping!

  3. July 2, 2015 / 7:57 pm

    I think you’ve picked every single lipstick I love and own. Great post! xx

    • Blakeley
      July 7, 2015 / 3:20 pm

      Haha great minds think alike, I suppose šŸ™‚ Thank you!

  4. July 2, 2015 / 4:36 pm

    I love this! I totally agree that anyone can rock a bold lip if they’re willing. Lipstick is the fastest and easiest way to get a little extra boost of confidence and feel super pulled together. šŸ™‚

    • Blakeley
      July 7, 2015 / 3:20 pm

      Amen, sista!! It’s my favorite makeup product … well, and mascara. Thanks for reading šŸ™‚

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