How to Dress Cute Classic

How to Dress Cute Classic

You can dress cute and classic at any age

dress cute without looking childish

“You’re so cute! But cute isn’t the right word. I mean you are cute, but you’re…something else, too.” I smiled as I listened to this stranger try to compliment my friend. She does dress cute! As a button! But she’s also…something else. She’s classic with a cute flair. She is serious with a side of fun, flirty and light.

If you’ve been following along with the classic closet series, first we covered how to dress classic without looking dated. You can also read about Edgy Classic Style, Minimal Classic Style, Soft Classic Style and Sporty Classic Style.

I hope you read all of the versions because sometimes wearing the wrong details is as big as wearing the right details. If you’re not sure what your Classic Style Twist is, take the quiz below to find out!

What cute and classic says about you

My mom dresses cute and classic, and she always jokes that there are two different women living in the same body because she can be so different from moment to moment. 

She gets down to business, she’s an introvert, she’s practical, but she can be silly, fun, and the life of the (very, very small) party when the mood strikes her. Social gatherings really stress her out, but she will talk up a storm and laugh with someone one on one.

Always friendly, but not outgoing, and she loves sparkles. Ever since childhood my mom has always had a classic minimalist capsule wardrobe, but sometimes that feels too serious and heavy to her. She wants to lighten it up without seeming silly, because that’s not her either. She’s a fun combination of both.

Pink floral skirt

cute details in your clothes

If you want to dress cute classic, it’s the subtle details that will tell the story. Look for lightweight fabrics, floral prints, polka dots, hearts, sequins, glitter, sparkles, circles, bows, and ruffles. That sounds like too much, doesn’t it? Keep reading. I’ll show you how to make it perfect for you.

Your key words are light, round, sweet, shiny, and fun.

Lightweight fabrics

Lightweight fabrics can include chiffon, lighter/softer wash cottons, knits, linen, etc. Instead of a really structured, stiff broadcloth cotton button up, you might prefer a thin crepe that is lighter. Not flowy or baggy, just lighter in weight and visual.

Mix bulk and heavy-weight fabrics with lighter options. If you are wearing jeans you might want a lighter weight top. Going with too much lightness in fabric could leave you feeling ungrounded, and too much structure could feel like a straight jacket. Ask yourself, “Could I frolic in this?”

Kate Middleton’s dress and trousers are lightweight, and the scarf in the middle picture is light and airy. The color palettes, structure, and style and clothing items are all very classic.

Floral and Fruit prints

Floral prints speak of summer fun and vacations. They make us think of a tropical getaway or a garden party. Flowers are happy and bright, and make everyone smile.

Larger scale florals with distinct, crisp lines (rather than fuzzy or hazy) will feel best. Floral prints and stripes mixed together are the perfect classic and cute combo. If you love florals, but they can feel over the top, try it in a smaller dose, like peaking out from under another layer, on a shoe, or even a bag.

Fruits are flowers that have become edible, and they count in this category as well.

In the photos below Reese Witherspoon is wearing a gorgeous floral skirt in a classic pencil style with a a sleeveless button up shirt, a structured bag, and wedges. This outfit stands the test of time.

Next is a beautiful floral sweater with a classic crew neck style, dark wash jeans, and a structured bag all in a neutral color palette, and a bold pop of red on her lips.

Her fun fruit-themed top gets a lady-like look with a blazer and classic jeans in neutral navy, and bold red heels in a timeless style and structured bag. Do you see the floral bag charm as well? Notice that all of these prints are bold, nothing tiny here.

Polka dots and circles

Polka dots are basically bubbles, and bubbles are lighter than air. They are an easy print to find in a variety of items and colors, and easy to mix and match in a classic wardrobe. A crisp polka dot button up or pencil skirt adds a little fun to an office wardrobe. Polka dot shorts or a knit tee is perfect for a casual look. You’ll probably be happier if the polka dots are a little larger and lined up symmetrically instead of random.

 

Circles are like empty polka dots and can be a pattern in your clothes, but they can come into your outfit in other ways as well. Consider the shape your jewelry, classic hoops or links in a necklace, the round toe of a shoe, and grommets on a shirt.

 

The circle pattern in the cardigan is subtle but adds a lot to her otherwise simple outfit.

 

Michelle Williams’ blouse is crisp and structured, and her polka dots are large and symmetrically placed.

 

Reese Witherspoons’ circles come in the form of the scallop edging on her tote and jeans, and the perforated circles on her tote.

Hearts

Hearts are sweet and light, and are another great pattern that can be a subtle nod or a shout, depending on how you wear it. Something as small and subtle as heart-shaped earrings or a pendant necklace are great, or you can wear a heart-patterned blouse peaking out from beneath a sweater, a heart-print sweater, a  dressed covered in hearts made out of candy-canes, like Reese did below.

SEquins, glitter and sparkles

Sequins, glitter, and sparkles are all light, reflective, shiny and the ultimate cute detail. My mom loves them on shoes and accessories. The key is to keep it on a smaller scale so you don’t give off more cute than classic, and so you don’t feel childish. Shoes and jewelry are great places to add some sparkle and shine.

Patent leather is another way to add shine to an outfit if sequins, glitter or sparkles aren’t appropriate, like at the office. Blingy jewelry can also be very dressy and chic, yet professional. Add round shapes and you’ll be able to dress cute in the courtroom or any other professional setting.

bows, pleats, ruffles, and gathers

Dressing cute with bows, pleats, ruffles, and gathers add a sweetness to an item and are perfect on a small scale, like on a purse, a sleeve, or a neckline, as long as they aren’t so big they overwhelm you or the classic cut of the clothes. Gathered sleeves can create lift or a flutter to the sleeve like on Kate Middleton’s yellow dress. A gathered waist adds flare to a skirt.

A ruffled detail along the placket of a top or jacket is a hint at your fun side. Crisp pleats are neat and structured, but come with a flared shape that is cute classic, and Kate’s outfit below has both, with the ruffled placket of her blouse and the crisp pleats in the back of her blazer.

To keep the bow on the classic side, make sure it is neat and structured, like on this black bag.

Animal print

If you are looking for a fun animal print, think zebra which is a little zany and wild, but not dangerous. Zebras don’t eat people. Or choose the elusive white leopard/cheetah, which looks like polka dots.

Every Style Twist can wear traditional leopard. Including the right details, like the ones I’ve mentioned here, will make it perfect for you. Look for a neat bow on a round-toed flat, for example.

Reese’s leopard print is actually hearts! Not everyone can wear such a large amount of print and feel comfortable, especially if you are primarily a Minimal Classic, so if you are drawn to leopard print, try a small dose like a pair of shoes, or the heart leopard on this sweater.

Color combinations

Some colors are also more fun and light, like pink, yellow, blue, and white. Certain color combinations are also more fun. If bold pink and black is an edgier way to wear pink, then try pairing it with navy instead. Combining with other colors like pink and yellow, pink and white, and pink and blue are lighter and airier.

CUTE accessories

Jewelry

Look for shiny, blingy, round, lightweight, maybe slightly jingly if you are really in a party mood. Keep your jewelry light and bright. A circle pendant necklace, hoop earrings, diamond studs, circle link necklaces, beads, pearls, and maybe even a charm bracelet are all good options. This is also a great place to bring color into your outfit.

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Shoes

Your shoes will probably make you happiest if they have more round toes a.k.a. half circles, and are comfortable. As an edgy classic I’m more likely to sacrifice comfort for style, but as a cute classic, you don’t want to wear anything that will ruin your fun, like pinched toes or super high heels that are hard to walk in. Shoes are a great place for the shine, sparkle and bling because it’s a small dose of fun.

Patent leather, jewel details, glitter, bows, and sequins all make shoes cute and fun, but it’s not so much that you feel like an 8-year-old. Cat flats, like the ones below are subtle, but bring the adorable in classic black. The glitter pumps in the middle (worn by Duchess Catherine) remind me of Cinderella’s shoes, and who doesn’t want to be Cinderella at the ball? Red patent flats with a large structured bow bring a fun pop of color on her feet without sacrificing comfort.

Makeup

Makeup is another way to keep it light. You may prefer a more neutral, natural eye makeup look, and bring the fun with a bold lip, or keep it all light with a clear, light pink MLBB (my lip but better). Add a little highlighter on your cheeks for a shimmer, but stay away from glitter on the face. 

Hair

Hair won’t be too severe. You would probably enjoy curls, and styles that are a little more youthful. That could be a pixie with some curl or wave, long curls, or anything in between, but probably nothing that covers your face like a heavy bang. A straight, smooth hairstyle might be too severe for you, unless you want it to balance other cute details in your look that day.

Dress cute with these classic brands

There are some brands that were made for you. J. Crew, Kate Spade, who epitomized cute and classic, Betsey Johnson, Boden, Draper James, Brighton, Chaps, Ralph Lauren, Tommy Hilfiger, Polo, Jessica Simpson, Jones New York, Jack Rogers, Talbots, and Lilly Pulitzer (though about half of it is more cute than classic, so evaluate carefully if it’s too busy and fussy for you). Sometimes Ann Taylor, Loft, and Banana Republic. They are all classic, but their undertone can vary from season to season with the trends.

Floral pants

wait a second, where is the classic?

The classic is in the style and fit of the clothes. classic includes button ups, dark wash, tailored jeans (even if they have a ruffle hem), shirt dresses, stripes, chino shorts, pencil skirts, flats, loafers, trench coats, and a very tailored fit. The overall look of the clothing is classic, and you sprinkle in some cute details to add a whisper of fun.

Your favorite striped Breton tee might have a peplum waist or bell sleeves. Skip the pencil skirt and go for a fit and flare. Button ups might be a thin cotton with a polka dot pattern and roll tab sleeves. You might enjoy a finer stripe in your clothes than a wider, bolder stripe.

Add some cuteness to classic black pumps with a round toe and a bow, or a jewel detail. Pair a classic shirt dress with bold colored beads and matching shoes. Sticking to more solid colors, and keeping the patterns in a smaller dose also keeps the cute from consuming you. All the details with a lot of pattern might be too much for you.

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it's all about balance

I just listed a whole lot of options for adding cute and fun details to your outfits, but don’t wear all of them at the same time. The trick is to pick and choose. If you have fun details in your top, then go for classic pants, meaning no extra polka dots, ruffles, or bling.

Wear a floral skirt with a classic shirt to keep it balanced. There is big fun jewelry, and small fun jewelry. Choose the size based on the level of cuteness in the rest of your outfit. If you already have enough going on in your outfit, choose little round or heart studs instead of big blingy earrings.

Only you will know the perfect balance. Do you feel overwhelmed with too much color or pattern or detail? Take off some accessories or switch the top or pants. Some people feel better in more, and some can only take so much. Also, don’t forget the bold hues. Those say you mean business.

so are you ever too old to dress cute?

Just like with edgy style, some women feel like they have outgrow their need to dress cute. Do you have to grow up and stop being silly, or stop wearing glitter because it is too juvenile? No. You don’t.

If cute and fun is who you are, then it’s more like a public service announcement to represent it in your style. I think of it as truth in advertising. You might be a hummer, you might have a purse full of glitter, and you might also be an accountant who bedazzles her calculator.

Reaching a certain birthday won’t change that. You won’t suddenly one day become the type of person who is always serious and in charge, so why should you be expected to change your style to reflect something you’re not just because of the number of candles on your cake?

let's see it all in action

Since I’m definitely not a cute and classic, let’s look at someone else, Kelly Larkin from Kelly in the City. I’ve followed Kelly for years, and her posts always bring a smile to my face. Even though I don’t dress Cute Classic, I often get inspiration from her outfits. Plus, she is adorable. One thing I admire about her is that her style is very consistent, and very KELLY. She doesn’t change her style to match the trends. And neither do I.

Outfit 1

Kelly in the City polka dots and scallops

Kelly brings the Cute to her Classic with the polka dot blouse and the scalloped edges on her cardigan. Her classic pendant necklace also has small circle medallions. The style of the blouse, cardigan, jeans, pearl studs, and wedges are all extremely classic, as is the color palette.

Even though she is (likely) wearing a heel, they look quite comfortable with the rounded toe box and low heel. The stuctured jeans and substantial cardigan are balanced by a lightweight blouse. The whicker bag suggests she might have sandwiches in there, and could be heading for a picnic.

Outfit 2

Kelly in the City polka ric rac dress

Ric rac is SO CUTE, but the large scale paired with the neutral navy and white color palette and the classic A-line dress make it classic and grown up. The round shape on her statement earrings and red pointed toe kitten heels (?) dress up this sophisticated look, and the rattan clutch keeps it from being too serious.

The heel height is enough to dress up her outfit, yet walk unassisted, which always makes you look more attractive (walking unassisted, that is). 

Outfit 3

Kelly in the City colorful top

A large floral pattern in multiple bold and bright colors is a major Cute Classic statement, so Kelly kept everything else low key and neutral, like the white skinny jeans, the large circle stud earrings, and the simple slides. Even though her sandals are neutral, the shapes and details make them interesting without distracting from the top, which is the focal point.

Outfit 4

Kelly in the City navy swing dress with circles

Simple circle embroidery and structured bow details on the hem make a basic navy shift dress a Cute Classic staple. Her sneakers keep it casual and comfortable, and her simple pearl earrings add some polish. The secret to dressing Cute without looking immature is balancing with the Classic, which Kelly always does perfectly.

Outfit 5

Kelly in the City Noodle sweater

Wearing any animal on your clothes is adorable. What makes this even more adorable is the animal is a dachsund (which, cuteness), but Kelly has one of her own, so this is a nod to her beloved Noodle. Everything else in her outfits is very classic, from the color palette, to the blazer, classic jeans, bag and booties.

This is the post that made me reconsider brown leather and decide to bring it back to my wardrobe. I have always loved that particular shade of brown leather, and I missed it.

Outfit 6

Kelly in the City gathered sleeve top

An otherwise classic-style blouse gets a cute upgrade with the gathered sleeves at the shoulder and the cuff. Pairing the pink with bright yellow and her sparkly round necklace adds some fun and sparkle. Kelly’s classic jeans and nude heels ground the look. Notice the bounce and curl in her hair as well. 

Outfit 7

Kelly in the City polka dot dress and pink shoes

First let me say, who looks that beautiful right after having a baby? She’s glowing! The random polka dot pattern is balanced by the black and white color palette and simple a-line shape of the dress. A splash of pink in her shoes brings all color she needs, and a simple bracelet of round stones and classic pendant necklace are perfect. 

OUtfit 8

Kelly in the City gathered sleeve top

Perfectly structured pleats at the bottom of a classic black and white Breton tee gives an unexpected and adorable update to an otherwise iconic clothing item. The bows on her slides add some sweetness, without giving us a cavity because the whole color palette is neutral. Kelly’s Burberry jacket and Coach Court bag come from the Classic Style Hall of Fame.

Outfit 9

Kelly in the City polka dots and rain boots

Perfectly placed polka dots, pleats, and glossy red hunter boots paired with a classic dress? Very cute without being too much. The overall neutral color palette with one bold color and the polka dots on a classic fit and flare dress provide the balance between cute and classic.

what's not cute?

As important as it is to add the cute elements you want, it’s equally important to avoid certain elements if you want that fun, flirty vibe. Learning about all of them will help you avoid  the details that will take away from your cute and classic look.

Are you cute and…something else? How do you show that in your classic outfits? If you are not sure what your style is yet, take our Classic Style Twist quiz below, and then read about the different Twists here to learn how to bring your own personality type through while still embracing classic style.

Join the conversation!

Discuss capsule wardrobes and classic style with a fun community of like-minded women in the Capsule Wardrobes for Classic StyleFacebook group

This post may contain affiliate links, which means if you purchase through my links I get a small commission, but it doesn’t cost you anything extra. Thanks for supporting my blog!

18 thoughts on “How to Dress Cute Classic”

  1. Hello April,
    Where can I find the shopping links for classic, cute items? I just bought the style guide and as you mentioned it is strict classic. Now I look for a little more cuteness like in the style in this post.
    Where to look?

    1. Stunning Style

      Hey Barbara, if you click on the links below each item in the catalog you’ll see different styles of the items listed. With the next book I might start labeling the options so they are easy to find.

  2. Tara Carpenter

    I loved this entire post! And thank you so much for the long list of stores there were made just for me. I had no idea where to start! I am so not into fashion so I learned about new things like the Breton tee and Chino shorts. Thank you for all your help! I know my style (and it keeps improving) but I’ve never really had the vocabulary or stores to help me out.

    1. Stunning Style

      Tara I’m so glad this was helpful! Knowing what to ask for and look for can make all the difference!

  3. Loved this! I am not edgy, but I love your classic styles. Looking forward to your feminine classic. I’m assuming that is 4/2. Thanks so much for helping us see how to find our own look. You are wonderful!

    1. Stunning Style

      Thanks Peggy. I was inspired to do this series by some people in my life. A friend asked me about edgy classic, so I wrote that post. Then my mom inspired this post. The series has been so popular that I’m probably going to expand it. I thought about adding casual classic, sporty classic, minimalist classic, and boho classic. These are based on people in my life, but if you have any other suggestions, I’m happy too explore them.

  4. I can’t wait to see the next installment of classic. I do however like the black blazer. Can you please provide a link?

  5. Wow… this was amazing! I feel like I finally understand why I’m drawn to certain items and what my style is: I’m classic cute! Reese Witherspoon and Kate Middleton are my style icons. I love all the brands you listed. I have never enjoyed pointy toed shoes, destroyed jeans, sharp jewelry… I love a good bow or ruffle. I love white leopard animal print! This was so spot on, I feel like I finally know what my style is! Thank you!!

    1. Stunning Style

      Erin I’m so glad this was helpful to you! It feels so good to nail the details, and it makes shopping and getting dressed easier.

  6. Ohhh, if I was in doubt before about my style, you have taken all doubt away. You have explained this style the best that I have ever read!!! Your examples are perfect. I love both of these ladies styles. Thanks April

    Janet

    1. Thank you Janet, I’m so glad this spoke to you and helped you clarify your style. I love both of their styles, too, and wish I could feel comfortable in this style, because it’s so cute! It’s just not me.

  7. My Dear Mom was a true Southern classic lady, who loved her florals, polka dots, frills, pastels, and matching clothes, shoes and accessories. And, she looked lovely, all of the time. I, on the other hand, like a touch of frill, but on a neutral-colored top. And, I adore polka dots!

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