You are currently viewing Celebrities in Retro Skirts: What To Pair Them With

You’ve probably seen a lot of celebrities going with retro skirts recently. When shopping Dolce & Gabbana items, for instance, you will likely see a healthy mix of 1950s flares, 1970s florals, and 1990s miniskirts. You can also find slits and maxi skirts. Now the question is, what to pair with retro skirts? Here’s how celebrities are styling and accessorizing these options.



  1. Matching Dolce & Gabbana Crop Tops
  2. Baggy Sweaters
  3. Sleek Sweaters
  4. Try Sneakers with a Maxi-Skirt
  5. Sandals for Comfort and Style
  6. Booties for a 1990 Retro Style
  7. When You Love Heels
  8. Wear a Belt
  9. What to Pair with Retro Skirts in a Nutshell


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Matching Dolce & Gabbana Crop Tops

Trending right now are crop tops. Celebrities match them with the retro skirt or with different patterns; you can go with cropped tanks or tees as well. Leave a thin line of skin or your entire midsection. There are many ways you can play with cropped tops. Cropped tops look adorable with a knee-length flared-out skirt in floral print, although, they work with pretty much any option. Plus, D&G offer matching crop tops for their retro-inspired skirts.


Baggy Sweaters

Most women over 40 are shy to  expose their midsection? No problem. Just complete the retro look with a baggy sweater. A flare skirt and baggy sweater will surely bring out the 1950s and 1960s vibes. Obviously, this look might even work for the office in a casual work environment. The combination is suitable to create thermal comfort in über-airconditioned places. Plus, you can still wear the style on chilly  evenings and as a summer-to-fall transitional outfit.


stylist pairing a retro maxi skirt with sneakers and a baggy sweater
Retro maxi skirt outfit idea: Baggy sweater c/o Femme Luxe, maxi skirt c/o Coolibar, Puma sneakers


Sleek Sweaters

Okay, you worked hard for the nice abs and flat tummy, but crop tops and baggy sweaters are not your cup of tea. Instead, try a form-fitting sweater to show off your figure, while your midsection stays covered. A sleek or body-conscious knit sweater looks adorable with mini and flared skirts to keep the retro vibes up.


stylist showing what to pair with a retro skirt
Retro skirt outfit idea with sleek knit sweater, belt and strappy sandals: Details: DIY skirt, DIY belt, Very Fine Dance Shoes sandals, Hermes collier de chien bangle, Winkwood sunglasses, Covered Perfectly top


Try Sneakers with a Maxi-Skirt

Now, what footwear should you wear with a retro skirt? A super-cute option many celebrities choose is sneakers with a maxi skirt. That’s going to leave you with a sporty and comfortable look perfect for summer.


Sandals for Comfort and Style

If you’re not a sneakers kind of gal – I’m not – go for a less risky sandals and skirt combo. Sandals are great because you can choose from various options. Best they’ll work with almost any style of retro skirt. Here some suggestions to try:

  • Flip flops for running errands and the weekend
  • Toeless sandals
  • Flats
  • Wedges for a bit of height while still walking comfortably
  • Glitter for date night or a night with the girls


blue 1970s style wrap skirt paired with wedge sandals, matching print top crop jacket
Outfit idea what to pair with retro skirts: 1970s inspired midi wrap-skirt and print top both c/o Coolibar, Paloma Picasso sunglasses, Fossil denim jacket, and Tony Hilfinger wedge sandals



Booties for a 1990 Retro Style

When you’re going for the 1990s look, go with a miniskirt and booties. Sure, you could wear knee-high tall boots with a miniskirt, but then you’d get weird tan lines you have to cover up. Plus, you wouldn’t show off those calves you’ve worked so hard to sculpt. So nowadays, celebrities are pairing retro skirts with booties.


stylist showing what to pair with a1990s inspired pencil skirt paired with booties
1990s inspired Banana Republic pencil skirt paired with teardrop key hole top c/o Covered Perfectly, and Michael Kors baseball jacket, DIY statement belt, and Musse & Cloud booties


When You Love Heels

When you’ve to dress up that retro vibe, wear a pair of heels. Heels work with mini, midi, pencil, flared, and maxi skirts. Yes, that’s pretty much all of them. The higher the hemline, the lower the heel. It’s all about balancing the look. Therefore, go full retro with classic heels, or add fun patterns for a modern touch.


Wear a Belt

Finally, how do you accessorize your retro skirt outfit? Some celebs have paired thin belts with their skirts. If a midi skirt is your go-to retro option, try it with a belt. Just remember, it’s for fashion, not function. Don’t pull it too tight. More on accessorizing with belts.


Alaskan blogger Nicole in summer look with skirt and T-shirt
Retro skirt outfit idea with graphic T-shirt, belt, plateau sandals. Details: Outfit details: Talbots floral print skirt, Michael Kors orange patent leather cork wedges, statement garnet necklace and bracelet, Hermes collier de chien leather band, Paloma Picasso sunglasses, enamel and jade buckle belt



What to Pair with Retro Skirts in a Nutshell

You can do a lot with retro skirts like with modern skirts. The celebs have been showing us that this summer. Try it out, if you like what you see, wear it.

Photos of me: G. Kramm

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