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.
Contents
- Matching Dolce & Gabbana Crop Tops
- Baggy Sweaters
- Sleek Sweaters
- Try Sneakers with a Maxi-Skirt
- Sandals for Comfort and Style
- Booties for a 1990 Retro Style
- When You Love Heels
- Wear a Belt
- 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.

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.

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

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.

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.

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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