How to Dress Like Kelly Kapowski: Wardrobe, Makeup, & Hair

Kelly Kapowski hair
Kelly Kapowski hair

As I previously blogged about, my niece CJ and I went to Saved By the Maxthe Saved by the Bell-inspired diner in Chicago’s Wicker Park–to celebrate the end of seven (long) months of physical therapy and recovery from surgery.  I went as Kelly Kapowski.  I tried to save money wherever possible in building my costume.  Check out my leaning tower of hairspray.  Even though it was eventually toppled by the 80° heat, I’m glad I learned how to create big hair from the late 80s and early 90s.  Kelly’s makeup is very simple–no loud lipsticks or purple mascaras here.

Kelly Kapowski Fashion
Kelly Kapowski Fashion


What you need: light washed denim, white KEDS shoes (or knock-offs), off-the-shoulder grey Bayside Tigers t-shirt

Go Bayside!
Go Bayside!

Light-Washed Denim Pants

I couldn’t wear any of the jeans in my closet because my surgery was on my right leg.  So I had to go out and buy much looser jeans.  I usually wear dark denim.  My Kelly Kapowski jeans are much lighter than the jeans I typically recommend wearing and I know it contradicts my previous suggestions (see my previous post, 6 Tips: How to Wear Jeans When You’re Gaining Weight), but the style of the early 90s was super light jeans.

I have gained weight from an increase in Prednisone and more weight because I could not exercise post-surgery so I bought some forgiving jeans from NYDJ, Not Your Daughter’s Jeans.  The name says it all.  NYDJ jeans are slimming in the tummy and thighs without looking like “mom jeans.”  NYDJ denim also comes in plus sizes, tall, and petite.  (I can’t find the exact pair online.)  The jeans I bought were on sale at Nordstrom Rack; I try avoid buying anything full price if I can help it.  I highly recommend NYDJ!  To create the SBTB look, avoid jeans with the words “skinny” or “flare” in them.

off the shoulder
off the shoulder

Bayside Tigers Shirt

Who can forget Kelly Kapowski’s trademark off-the-shoulder grey Bayside tigers shirt?  I was able to find one made by Superluxe Clothing on Amazon–you can get it here.  In the pictures, I’m wearing a size medium, which fit me just fine.

White Keds canvas shoes (or shoes that look like them)

Keds knock-offs (white Vans)
Keds knock-offs (white Vans)

So in researching SBTB fashion, I saw that everyone in the Bayside gang wore White Keds.  I bought Vans knock-offs that I found on sale at Nordstrom Rack because I personally did not feel like spending $40 on these.  Even at DSW, they were $35! Of course, if you want the classic white canvas Keds shoes, you can get them on KEDS website here for $45.00.  Online, you can get a pair of $16.99 Mossimo knock-offs here at



What you need: pink lipstick, pink blush, black mascara, bronzer

The Perfect Pink: Arbonne's Camellia!
The Perfect Pink: Arbonne’s Camellia!

Pink Lipstick

As you know I’m an Arbonne consultant; Arbonne is vegan makeup.  We don’t use the toxins that are used by 90% of U.S. cosmetics and skincare companies.  In the pictures, I am wearing Arbonne’s Smoothed Over Lipstick in Camellia.  Avoid bright red, orange, or hot pink lipsticks–a soft pink will do.

Kelly Kapowski makeup
Kelly Kapowski makeup

Pink Blush

A light to medium shade of pink blush is good.  The pink lipstick coordinated with pink blush is very 80s.  I recommend Arbonne’s Blush in Taffeta, a soft shade.  When I give makeovers to women who are sick like myself, I use this color because it’s universally flattering and not over the top.

Black Mascara

The mascara I’m wearing is Benefit’s Roller Lash Curling and Lifting Mascara.  To save money, I always buy the travel size of mascara.  At $12.00 at Ulta, it’s half the price of the full size.  As I previously discussed, to avoid putting bacteria into your eye, you should always throw away a mascara tube after three months.  After three months, mascara becomes a breeding ground for bacteria.  This is true regardless of the brand; keeping mascara for longer than that is dangerous.


I didn’t start wearing bronzer until after I got myasthenia gravis eight years ago.  My face started changing dramatically.  At the height of my weight gain when I gained ten dress sizes (between 2008 to 2010), I could not even recognize myself.  Prednisone creates fuller cheeks and has a way of hiding our cheekbones.  So I started using bronzer, which makes me look and consequently feel a little more like my old self.  Here, I am wearing Arbonne’s Bronzer.   I use bronzer to contour and sculpt.  I apply it on my cheek bones going diagonally from the apples of my cheeks to my hairline, on my chin, and a little on my forehead.  People often complain that bronzer doesn’t work–that’s usually because they tend to use the same brushes we use for blush or foundation.  Bronzer is different.  For contouring, I use a stippling brush with my bronzer.  A stippling brush has two kinds of fibers to ensure that the pigment is deposited on the cheeks as you sweep upwards from the apples to the hairline.  Because stippling brushes are the most expensive kind of brush, I take extra good care of them.  I’ve had this Professional Stippling Brush from Japonesque, $32.00, for six years.  You can get one here at Ulta’s website.

backcombing and teasing tools
backcombing and teasing tools


What you need: backcomb brush, teaser comb (for the bangs), extra-hold hairspray, bobby pins, patience

The above tutorial from All Things Hair, UK was super helpful in creating the big hair look.  I was a young child in the late 80s and early 90s so I wasn’t teasing my hair.  I am sure I used more hairspray last week than I’ve used over the past two decades.

Marilyn Teaser Brush, $16.00 at Ulta

I was careful to use the exact brush in the video and I’m glad.  This is a brush used for backcombing, which is a very specific technique.  It rats the hair and gives it volume.

Extra Hold Spray

So I should have listened and used the hairspray recommended in the video, which is TRESemmé Firm Hold Hairspray, which you can get at Ulta.  But I was trying to save money so I bought a travel size of another brand, which was a mistake.  The other hairspray helped me create the big late 80s/early 90s hair but the heat toppled down my leaning tower of hairspray before we even started dinner.  Some people said I should have used Aquanet because it is impervious to the weather.  You can purchase Aquanet’s Professional Hairspray Extra Super Hold here at Walgreens.

Bobby Pins

You can purchase Goody Bobby Pins at Target or your local grocery store.  If you have blonde hair, get blonde-colored bobby pins.  If you’re a brunette like me, get darker colored bobby pins.  Bobby pins are supposed to blend in with your hair.  You only need a one to three (depending on how thick your hair is) to pin your hair to one side.



Bonus note: The Bangs

The All Things Hair YouTube tutorial helped me create the big hair (but not the bangs specific to the late 80s/early 90s).   The day before we went to The Max, I texted my friend Christi (of Bipolar Hot Mess) a picture of me in my yellow PJs practicing teasing my hair–a “dress rehearsal” if you will.  Christi told me that even though I had the big hair, I did not have the bangs down yet.  I couldn’t find any online tutorials for this but Christi showed me how to do it over Facetime.  You need extra hold hairspray and a comb with fine teeth to do it. Thankfully, I already happened to have a rat tail comb from my days dressing up like a woman on Mad Men.  You can get the Diane Ionic Anti-Static Rat Tail Comb here at Ulta.  If I ever dress like Kelly again, I’ll make a YouTube tutorial on the hair.

Invite me!

I haven’t celebrated Halloween in years.  But I really hope someone invites me to a Halloween party so I can wear my Kelly Kapowski costume again, especially now that I’ve figured out the hair thing.

–Your Stylist, Jessica Gimeno



Hi there! I am a patient advocate, writer, and public speaker most well known for my TEDx Talk, “How to Get Stuff Done When You Are Depressed.” As someone who is juggling 5 illnesses: bipolar 2, myasthenia gravis, endometriosis, psoriasis, and asthma, I’m passionate about helping people who navigate life with both chronic physical & emotional pain. If you’re interested in hiring me to speak at your event, check out the CONTACT tab.

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