I’m all for experimenting with style, especially in the summer when dresses and easy shoes are practically a uniform. But after one too many mornings spent staring in the mirror wondering why my outfit looked off, I finally figured it out: the dress wasn’t the problem—the shoes were. Or more specifically, the combination of the two. Some dress-and-shoe pairings just don’t work, no matter how cute they seem on paper.
Whether it’s mismatched proportions, outdated silhouettes, or just bad visual balance, certain combos can instantly take your look from effortless to awkward—and worse, frumpy. So I did the trial and error (and some public outfit regret) so you don’t have to. Here are the seven dress-and-shoe combos I tried that completely missed the mark—and what to wear instead if you want to keep your style feeling fresh, flattering, and totally summer-ready.
1. Maxi Dress + Chunky Athletic Sneakers
Envision yourself in a flowing maxi dress, ready to take on the day. However, pairing it with chunky athletic sneakers introduces a weighty contrast. The sneakers’ bulkiness clashes with the dress’s elegance, creating a clunky appearance.
Opt for minimalist leather sneakers or low-profile slip-ons for a more cohesive look. The lighter footwear complements the dress’s flow, enhancing a casual-chic vibe without overpowering it. A sleek pair of shoes transforms the ensemble, keeping it light and stylish while allowing the dress to shine.
2. Shift Dress + Round-Toe Ballet Flats
Shift dresses exude simplicity, but pairing them with round-toe ballet flats can unintentionally evoke a childlike aura. This combination lacks the sophistication many desire, especially when the flats feature bows. Consider loafers or almond-toe flats with a slight heel for a polished appearance. These alternatives provide structure, elevating the outfit and ensuring a modern flair. The added height and shape bring new life to the dress, steering clear of a dated look.
3. Midi Dress + Wedge Sandals (with Thick Straps)
Midi dresses paired with thick-strapped wedge sandals often result in a visually heavy ensemble. The boldness of the wedges can overwhelm the dress, especially if it’s printed or A-line. Change gears with sleek heeled mules or espadrille wedges with thinner straps to achieve balance. These choices provide a more graceful silhouette, ensuring the dress maintains its charm without competing for attention. The refined footwear offers a modern touch, alleviating any dated feel.
4. Fit-and-Flare Dress + Flip-Flops
The fit-and-flare dress flaunts femininity, yet flip-flops introduce a laid-back vibe that falls flat. The casualness of the footwear diminishes the dress’s sophisticated appeal, leading to an incomplete look. Swap these for block-heel sandals or strappy flats to uphold the dress’s elegance. The right shoes add a touch of refinement, completing the ensemble with poise. Maintaining a feminine shape ensures a harmonious outfit that feels intentional and stylish.
5. T-Shirt Dress + Bulky Combat Boots
T-shirt dresses are casual staples, but bulky combat boots can distort the intended vibe, making it feel overly contrived. This mismatched pairing often reads as trying too hard, lacking cohesive style. Instead, choose sleek ankle boots or platform sandals to retain a laid-back aesthetic while enhancing the dress’s simplicity. The alternative footwear complements the ensemble, offering a balanced and contemporary touch. It’s about achieving effortless style without overcomplicating the look.
6. Floral Sundress + Orthopedic-Style Sandals
Floral sundresses bring a hint of whimsy, but orthopedic-style sandals can undermine that with their practicality-heavy design. This combination lacks visual appeal, often coming across as overly safe and matronly. Opt for feminine slingbacks, flat espadrilles, or refined gladiators to inject charm without adding bulk. These alternatives offer structure, accentuating the dress’s playful essence while keeping the overall look fresh and youthful.
7. Bodycon Dress + Stiletto Heels (from a past era)
Bodycon dresses hug curves, but pairing them with outdated stiletto heels often leads to a throwback vibe. The shoes’ dated aesthetic can overshadow the dress, particularly if they’re patent leather or overly shiny. Modernize the ensemble with kitten heels or square-toe sandals for a fresh silhouette. These alternatives align with current trends, offering a sleek and updated look that enhances the dress’s allure without feeling stuck in the past.