Emily Flores
Jeans never lose their charm, but past 40, the shoes you pair with them start to matter more than ever. Some styles suddenly feel clunky, others lose their comfort, and a few just don’t sit right. The best part is, the right picks still keep denim looking sharp. Here are five to skip and five worth slipping on.
Chunky Dad Sneakers
Those “dad” sneakers definitely bring nostalgia, though pairing them with jeans can feel tricky. Their oversized shape adds bulk that drowns slim or straight cuts, easily throwing proportions off. Rooted in the ’90s athletic wave, many pairs feel heavy during extended wear.
Square-Toe Boots
Square-toe boots have a history rooted in horseback riding, but wear them with denim, and things turn clunky. The stiff shape clashes with denim’s easy flow, making ankles look wider. Retro streetwear fans love them, yet casual outfits often drown in their overly rigid vibe.
Loafers With Thick Soles
Prep-school vibes aside, chunky loafers rarely vibe with denim. Its heavy soles overshadow the laid-back energy of jeans, sometimes weighing more than hiking boots. What was once a uniform staple now feels mismatched—too stiff, too dressy. When casual is the goal, bulky loafers miss the point.
Ballet Flats
Chic at first glance, ballet flats rarely live up to their reputation. They weren’t designed for long strolls or standing. With no support, feet ache fast, and the absence of cushioning worsens things. Worn with jeans, the effect leans youthful and cutesy, never truly polished.
Flip-Flops
These offer zero structure, making jeans look sloppy. First worn in ancient Egypt, modern flip-flops provide almost no support and can tire feet quickly. Their beachy vibe rarely suits cooler weather or polished outfits. Luckily, not every shoe fights your denim—some step in to make styling effortless.
Ankle-Strap Sandals
Now that tricky pairs are behind us, ankle-strap sandals show how jeans can really shine. Perfect for warm months, they balance cropped cuts while adjusting easily for comfort. Offering support without sacrificing style, they’ve been chic for decades—making waves in fashion magazines as early as the 1920s.
Chelsea Boots
Chelsea boots nail that sweet spot between polished and easygoing. Victorian England gave them their start, and The Beatles boosted their fame. With elastic sides and ankle-hugging lines, the boots sharpen denim looks without shouting, “I’m trying hard.”
Low-Profile Sneakers
Few shoes play nicer with jeans than slim, low-profile sneakers. Lightweight and breathable in canvas or leather, these sneakers keep outfits versatile. Born from 1970s tennis courts, they now swing easily from office casual to weekend errands without overpowering denim.
Sleek Slip-On Mules
With origins tracing back to Ottoman royalty, today they lend effortless polish without effort. Cushioned insoles keep them wearable, while minimalist designs flatter straight or wide-leg jeans. Easy for spring or fall—mules are fashion’s shortcut to looking pulled-together.
Classic White Sneakers
Nothing balances jeans like crisp white sneakers. Initially mass-produced in the 1910s, they’ve since become the universal antidote to styling stress. Their clean lines make legs look longer, and maintenance is effortless; just a quick wipe does the job. On top of that, these sneakers pair with every wash.