Skirts 101: A Guide to Classic Styles and How to Wear Them



Of all the items in a woman’s closet, the skirt is one of the most classic and feminine pieces she can turn to for any and every occasion. The skirt can be simple, sweet, sophisticated, subtle, serious, sexy, or show-stopping. You need to chase around your toddler? There’s a skirt for that. Got a black tie gala? There’s a skirt for that. Dressing for success? You guessed it — there’s a skirt for that, too. This versatile piece offers so many fashionable options. But with so many different cuts and styles, it can get a bit confusing as to what skirt is best for your body type and how to wear it. Have a skirt in your closet that you love but just don’t know what to wear it with or where to wear it? Well you’re in luck because Skirts 101 is in session; get ready to take a few notes!


1. The Pencil Skirt

Skirts 101

Purchase similar top from Nordstrom, $69 / Purchase similar skirt from J.Crew Factory, $49.50 / Purchase similar shoes from Nordstrom, $69.95 / Purchase sunglasses from Ditto, $250

The pencil skirt is a staple of any woman’s closet. Its classic shape, resting at the waist and tapering along the leg to hit just above the knee, means it will stand the test of time. Known for its clean tailored lines, this is a must-have for any businesswoman. I love to wear it in bright colors and pair it with a neutral, shiny top and a pair of nude shoes.


2. The Denim Skirt

Skirts 101

Purchase similar T-shirt from J.Crew Factory, $34.50 / Purchase similar shirt from Old Navy, $24.94 / Purchase similar skirt from Gap, $49.50 / Purchase similar shoes from Sole Society, $41.97

The denim skirt has made a strong comeback in the last two seasons. It’s similar to the pencil shape, but less tailored and a bit more casual. Denim is a neutral and can be paired with just about anything! For a cleaner, more polished look go with a dark denim. If you want a more laid-back vibe, opt for a lighter wash with some distressing. The denim skirt can go casual-hip with a button-down untucked with the sleeves rolled up, layered beneath a knotted graphic tee. I love to add a pop of color, like with these bright red platform sandals.


3.  The A-Line Skirt

Skirts 101

Purchase top from Old Navy, $39.94 / Purchase skirt from Boden, $103.20 / Purchase similar shoes from ModCloth, $44.99 / Purchase sunglasses from Ditto, $250

The A-line skirt is universally flattering, as it hits the smallest part of the waist and then bells out at the bottom and hits just below the knee. It doesn’t hug the hips or thighs and really showcases the waist. (I adore Boden’s A-line cut skirts!) Don’t be afraid to pair a patterned skirt with a pattern top, as seen here. I love a thick, clean stripe on top, tucked into a busier print on the bottom — just remember to keep to a complimentary color palette.


4. The Fit-and-Flare Skirt

Skirts 101

Purchase top from Target, $16.08 / Purchase skirt from Leanne Barlow, $130 / Purchase similar shoes from Nordstrom, $69.95 / Purchase sunglasses from Ditto, $250

The fit-and-flare skirt is every girl’s dream, and it’s ideal for twirling …and twirling … and twirling. It’s feminine, fun, and similar in shape to the A-line — just more voluminous. This shape was perfect to wear after I had a baby because it fit up higher on my waist and hid all the areas that still looked a bit … still pregnant. Also, it’s a vintage cut that has become super modern. This LeAnne Barlow skirt is charming with the bow belt around the waist. I paired it with a tucked-in button-down covered in swans to keep the look fresh and lighthearted. Top the look off with a nude heel, which will always elongate the leg.


5. The Midi Skirt

Skirts 101

Purchase similar top from Francesca, $34 / Purchase similar skirt from Forever 21, $19.80 / Purchase similar shoes from Rebecca Taylor $237

The midi skirt should hit mid-shin/calf if it fits like it’s supposed to. This cut is a little trickier to wear as it cuts the leg. Women with shorter legs should probably steer clear of the midi unless you find it in petite sizes for a more flattering fit. I also opt for a higher-waisted style like the one I’m wearing, which gives definition and shape and elongates the lower body. This particular skirt also flares out at the bottom, a fun retro detail. Keep it chic by tucking in a blouse-y but tailored top in a silky material. A pair of heels (no flats!) is a must to keep if flattering. I love the metallic “shootie” for a modern kick.


6.  The Tulle Skirt

Skirts 101

Purchase Similar Top from F21 $17.80 / Purchase Skirt from Shabby Apple $88 / Purchase Similar Shoes from Bloomingdales, $140 / Purchase Bracelet from Jewel Kade, $44

The tulle skirt is the princess skirt for grown ups; it’s froufrou in all the right ways. This is my first tulle skirt, and it’s as magical as I hoped it would be. It’s airy and whimsical and feels like its floating around your frame. Opt for a higher fitted waist, but be weary of too much tulle as you can get lost in it and lose all form and shape. The tulle skirt can be kept fancy with a fitted blouse or cashmere sweater, or you can mix it up for a juxtaposed look with a rocker tee, like I’m wearing here. It’s all about having fun and looking feminine.

7. The Maxi Skirt

Skirts 101

Purchase body suit from ModCloth, $24.99 / Purchase similar skirt from Forever 21, $27.80 / Purchase necklace from Strands, $18.99 / Purchase similar hat from Zappos, $28

The maxi skirt is every mom’s dream, or really, every woman’s dream. It’s comfortable and easy to move around in, allowing for a full range of motion to bend down or sit without worrying about showing anything. The breezy bohemian style is a great option for a casual day or for going to church. For skirts that tie at the waist, I love to wear a clean simple body suit underneath to really flatter the waist and keep it from looking to voluminous on top. To keep with the vibe, throw on a long necklace and a floppy hat on top to finish off the look.


8. The Jersey Maxi Skirt

Skirts 101

Purchase similar T-shirt from Target, $12.99 / Purchase similar skirt from Target, $17.99 / Purchase Saltwater sandals from Navy Perl, $32.99 / Purchase hat from Forever 21, $10.99

The jersey maxi skirt has also become a girl’s best friend over the past few years; it’s stretchy and offers loads of comfort. I lived in maxis while pregnant to accommodate my growing belly. I still wear them day to day, whether going to the park with London or heading to a band practice. Pair it with a graphic tee knotted at the hip to keep your shape. A fun pair of sandals and a straw fedora keep this look fresh and not frumpy.


9. The Ball Skirt

Skirts 101

Purchase top from Gap, $59.95 / Purchase skirt from Shabby Apple, $95 / Purchase similar shoes from Nordstrom, $29.95 / Purchase sunglasses from Ditto, $250

Lastly, the ball skirt is big and bold and goes for the gold. This is not your everyday skirt, but a special piece for special occasions. It’s voluminous and grand, and like it’s name suggests, ready for the ball. It’s great to wear to an event or gala, but it’s okay to think outside the box with this one and pair it with a Western-style denim top tied in a knot for an unexpected feel. You could wear this to your birthday party or on a stage somewhere because it’s just super fabulous.

All photos taken by Priscilla Chang


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