Life is short, wear whatever — but when summer rolls around, a few fresh ideas can make getting dressed feel playful instead of like a chore. This year, one of the quietest yet most telling shifts is happening right at our feet: leather flip flops have edged out rubber slides as the shoe of choice for everything from morning coffee runs to rooftop parties.
7 Summer Trends That Make Getting Dressed Fun
1. The Oversized Button-Down as the Ultimate Anchor Piece
Every summer wardrobe needs that one lightweight layer you can throw over anything and instantly feel pulled together. An oversized button-down does exactly that — it works over a swimsuit at the beach, knotted at the waist with high-waisted shorts, or worn open as a breezy topper with a slip skirt. The magic lies in its versatility and the way a single piece can anchor half a dozen different looks.
The go-to version Cup of Jo calls out is a linen oversized button-down that comes in a remarkable 15 colors, making it easy to find a shade that suits the rest of your warm-weather palette. Linen’s breathable texture and lived-in drape mean it looks better the more you wear it, which only adds to its charm. Keep one in a soft neutral like oatmeal or chambray blue, and you’ll reach for it on repeat all season long.
2. White Midi Skirts Are Suddenly Everywhere
If you’ve spent any time in a park, at an outdoor café, or even sitting outside a bookstore playing gin rummy lately, you’ve probably noticed the same thing: women in pretty white midi skirts are popping up in droves. These skirts have a soft, romantic quality that feels both nostalgic and current, hitting just below the calf or at mid-ankle in airy cottons and organic blends.
The trend has a remarkably attainable entry point, too. One 100% organic cotton white midi skirt clocks in at just $50 and has been spotted out and about on real people — not just on styled mannequins. Pair it with a simple tank and leather flip flops for an easy-breezy look, or dress it up with a fitted top and statement earrings for a dinner date. The key is the crisp, clean silhouette that somehow makes every outfit look intentional.
3. Track Shorts: Sporty Cool for Any Summer Adventure
Track shorts refuse to fade away, and the reason is simple: they combine comfort with a retro sportiness that works for bike rides, beach walks, and impromptu ice cream runs alike. The cut is typically relaxed through the hip and thigh, often with a drawstring waist and side stripes that nod to classic athletic gear without feeling like gym clothes.
For a slightly sweeter take, keep an eye out for a scalloped hem — it adds a subtle feminine detail that elevates the shorts beyond the ordinary. When you slip them on with a crisp white tee and those black leather flip flops, the whole outfit feels balanced: part tomboy, part sunny ease. And because they’re made from quick-drying fabrics, they handle humidity and splashes with zero stress.
4. Blockprint Everything Is Popping Up Even More Than Usual
Blockprint fabrics have a handmade charm that seems to multiply every summer, and this year the prints are bolder and more varied than ever. Think soft lilac florals, earthy brown geometrics, and deep indigo repeats that look like heirlooms the moment you unfold them. The technique — where artisans carve a design into a wooden block and stamp it by hand — gives each piece a slightly imperfect, utterly human feel.
During a weekend trip to Fire Island, one writer wore a blockprint cover-up with bare feet all weekend and described it as pure bliss. That easy, sun-soaked vibe is exactly what you should aim for: a single blockprint piece, whether it’s a maxi dress, a pair of wide-leg pants, or a tiered mini skirt, can carry your outfit without any extra effort. Let the print do the talking and keep everything else low-key, maybe just a neutral bag and those leather flip flops.
5. Jumbo Ric-Rac: The Dinner Dress That Does the Work for You
Jumbo ric-rac trim is turning simple dresses into conversation starters. The oversized wavy braid, applied generously along necklines, hems, and sleeves, adds texture and whimsy that feels celebratory without being formal. It’s the kind of detail that makes you want to twirl a little when nobody’s looking — or maybe when they are.
The perfect dinner dress in this category has a short, swingy cut that pairs beautifully with salty hair and barely-there sandals or, naturally, black leather flip flops for a streamlined finish. The beauty of big ric-rac is that it does the decorating for you; you don’t need much more than that dress, a swipe of tinted lip balm, and a relaxed attitude. Toss it on at golden hour and you’re ready for whatever the evening brings, from a patio dinner to a backyard movie night.
6. Leather Flip Flops: The Shoe That Took Over Summer Parties
Not long ago, the phrase “fashion party footwear” would conjure images of strappy heels or sleek mules. But at one recent gathering, the unanimous choice was black leather flip flops — worn by nearly everyone in the room. This observation from Cup of Jo’s editor wasn’t just a quirky anecdote; it signaled a real shift. Leather flip flops have quietly earned their place as the new statement shoe for summer gatherings, offering a blend of polish and ease that few other sandals can match.
Why Fashion Insiders Are Embracely Flip Flops Over Sandals
There’s a practical reason for the switch: most leather flip flops eliminate the discomfort of buckles, ankle straps, and stiff footbeds, yet they still read as intentional. The leather material instantly upgrades the silhouette, giving the classic flip flop shape a more expensive, curated look. When the leather is black, the shoe becomes a chameleon that can anchor a white midi skirt just as convincingly as it can ground a cropped linen pant.
You may also enjoy reading: I Thought Summer Was Curly Hair’s Season: 5 Mistakes.
The Shift From Rubber to Leather in Summer Footwear
For years, rubber flip flops dominated boardwalks and pool decks, but they always carried a faintly “off-duty” vibe. The move toward leather represents a desire for footwear that transitions seamlessly between environments. A reader who avoids flip flops because they feel too casual might find that a well-made leather pair — with a cushioned footbed and subtle hardware — changes her mind entirely. The difference is in the details: smooth, burnished straps, a contoured sole, and the way the material molds to your foot over time.
How to Style Leather Flip Flops for a Polished Casual Look
If you’re wondering how to make leather flip flops look dressy enough for a party, start with the outfit formula: high-waisted trousers or a flowing midi skirt, a fitted top, and minimal, intentional accessories. The flip flops provide the grounding contrast, keeping the whole look from feeling stuffy. For someone who lives in a hot climate and needs a shoe that works for both errands and dinner out, black leather flip flops are the ultimate solve — they’re easy to slip on during a busy morning with kids, yet they still appear pulled together enough for a patio lunch with friends.
Comfort-wise, reviewers emphasize that the pair often recommended by the Cup of Jo community is remarkably cushy, with plenty of arch support for all-day wear. That means you can walk a couple of miles, stand through a long cocktail hour, and still feel good. Even a busy mom juggling school pickup and a coffee date will appreciate a shoe that requires zero buckling or tying, while still reading as polished.
7. Matching Sets: The One-and-Done Outfit Equivalent of a Jumpsuit
If summer had an official uniform for looking put-together without a single extra thought, it would be the matching set. A coordinated top and bottom — whether it’s a cropped shirt with wide-leg trousers or a drapey blouse with a flared skirt — functions as a complete outfit in two pieces. You don’t have to wonder if the patterns clash or the proportions feel off; someone already solved that for you.
The appeal is similar to a jumpsuit, but with more flexibility. You can wear the pieces together for a seamless look, or split them up to stretch your wardrobe further. Even though some designer versions carry a steep price tag, affordable alternatives have cropped up in breezy linens and soft cotton blends. Pair a neutral-toned set with those leather flip flops and a woven tote, and you’ve got an ensemble that works for brunch, a gallery visit, or a casual Friday at a creative office.
Frequently Asked Questions
How do I keep leather flip flops looking good after lots of summer wear?
Start by wiping them down with a soft, damp cloth after exposure to sand, salt, or dust — this prevents grit from scratching the leather. Every few weeks, apply a small amount of leather conditioner to keep the straps supple and prevent cracking, especially if you wear them in intense heat. Avoid leaving them in direct sunlight for hours when you’re not wearing them, as that can dry out the material and fade darker shades. With minimal care, a quality pair of leather flip flops can last multiple seasons while maintaining their polished appearance.
Can leather flip flops really work for a summer party, or are they still too casual?
Absolutely. The key is choosing a pair in black or a rich brown with a slim, refined strap rather than a chunky, sporty silhouette. Dress them up with a midi skirt or wide-leg pants, a silky camisole, and a few pieces of elegant jewelry; the flip flop acts as a cool contrast that keeps the outfit modern. At a recent fashion party described by Cup of Jo, nearly everyone was wearing black leather flip flops, which speaks to their acceptance in settings that used to demand heels. The secret lies in the leather material itself, which reads as intentional and luxurious compared to rubber alternatives.
Are leather flip flops comfortable enough for walking long distances in summer heat?
Many of today’s leather flip flops are built with cushioned, contoured footbeds that provide real arch support, not just a flat slab of material. The pair frequently recommended as “super comfy” by readers offers a soft leather strap that doesn’t dig in and a sole that absorbs impact well, making them suitable for neighborhood walks, shopping afternoons, or even a full day at an outdoor festival. Because leather naturally conforms to your foot shape over time, the fit only improves with wear. For anyone who usually avoids flip flops due to discomfort, a well-designed leather version can be a genuine upgrade that feels like a slipper with structure.
If any of these summer fashion ideas spark joy — especially the quiet power of leather flip flops — lean into them. After all, the best style rule is the one that makes you want to get dressed in the morning.
