Boyish Shoes Are Back in Style for 2026: The Menswear-Inspired Footwear Taking Over

Yes, boyish shoes are definitively having their moment for 2026, with Oxford shoes, brogues, and structured loafers leading the charge as the season's most coveted footwear trend. I've been working as a stylist for over twelve years, and I haven't seen this level of excitement around menswear-inspired footwear since the early 2000s. What's different this time? The styles feel infinitely more wearable, sophisticated, and versatile than their predecessors.

The runways have been absolutely saturated with crisp tailoring and collegiate references for AW25 and SS26. From Victoria Beckham's sleek Oxford shoes paired with tailored trousers to Calvin Klein's minimalist brogues styled with midi skirts, the message is clear: structured footwear is back with a vengeance. The beauty lies in how these shoes ground an outfit whilst adding an element of unexpected polish.

Why This Trend Makes Perfect Sense Now

There's something deeply satisfying about slipping into a proper pair of brogues or Oxford shoes. They speak to our current desire for clothing that works as hard as we do - practical enough for busy days yet polished enough for important meetings. After years of uncomfortable heels or flimsy ballet flats, boyish shoes offer the perfect middle ground: structure, comfort, and serious style credentials.

I've noticed my clients gravitating towards these styles because they solve so many wardrobe dilemmas. Need something professional but comfortable for all-day wear? Oxford shoes. Want to elevate weekend denim without looking overdressed? Brogues. Seeking that perfect smart-casual balance? Structured loafers every time.

The Key Styles Dominating 2026

Classic Oxford Shoes

The closed-lacing system creates that distinctive sleek silhouette that elongates the leg beautifully. Look for clean lines and quality leather construction rather than overly chunky interpretations. The key is choosing contemporary proportions that feel modern rather than costume-y.

Statement Brogues

Those decorative perforations aren't just pretty details - they add texture and visual interest whilst maintaining the masculine aesthetic. From subtle quarter-brogues to full wingtip designs, the perforations prevent all-black outfits from looking too severe whilst injecting personality into professional wardrobes.

Structured Loafers

The slip-on ease makes them perfect for our busy lifestyles, but it's the structured shape that keeps them looking sharp. Whether you choose penny loafers, tassel styles, or sleek minimalist designs, they offer unbeatable versatility.

How I Style Boyish Shoes for My Clients

The secret is all about balance and proportion. I always tell my clients to think of these shoes as the anchor of their outfit - they're substantial enough to ground even the most feminine pieces.

For work, I pair black Oxford shoes with cropped tailored trousers and a silk blouse. The contrast between the structured shoe and fluid fabric creates visual interest whilst maintaining professionalism. Add a blazer and you're sorted for any boardroom situation.

Weekend styling is where these shoes really shine. Brown brogues look fantastic with boyfriend jeans and a cashmere jumper - the masculine shoe prevents the relaxed denim from looking too casual, whilst the perforated detailing adds enough visual interest to elevate the entire look.

For evening, try sleek black loafers with a midi skirt and fitted knit. The unexpected pairing feels modern and confident without trying too hard.

My Go-To Styling Rule: If you're wearing structured shoes, balance them with softer silhouettes elsewhere. Think flowing midi skirts, relaxed knitwear, or fluid blouses that create beautiful visual contrast.

Where to Shop: My Brand Recommendations

High Street Heroes

Zara consistently nails sharp, contemporary takes on menswear classics at brilliant prices. Their Oxford shoes often feature modern twists like cleated soles or unexpected colour combinations that feel perfectly 2026.

COS excels at that minimal, architectural aesthetic we're all craving. Their loafers and brogues have Scandinavian precision that makes them genuine investment pieces rather than throwaway fashion.

Mango offers exceptional quality-to-price ratio on their structured footwear. I particularly love their leather brogues which often feature thoughtful details like contrast stitching that elevate the overall design.

M&S has seriously upped their game with boyish footwear - their leather Oxford shoes rival much more expensive options whilst offering that reliable British quality we know and trust.

Whistles brings distinctly British sensibility to menswear-inspired shoes. Their seasonal colour updates keep classic styles feeling current without compromising on timeless appeal.

Jigsaw specialises in refined, grown-up versions of menswear classics. Their attention to leather quality and finishing makes their shoes feel far more expensive than the price tag suggests.

Reiss perfectly captures the modern professional woman's needs. Their designs strike that perfect balance between classic and contemporary that works in absolutely any wardrobe.

Premium Investment Pieces

For superior craftsmanship, Church's remains the gold standard for traditional British footwear. Their heritage expertise translates into shoes that improve with age whilst maintaining impeccable construction standards.

Tod's offers Italian refinement with their structured shoe collections. The brand's luxury leather goods expertise results in footwear that feels both polished and effortlessly chic.

Luxury Designer Options

Prada continues setting the standard for modern interpretations of classic menswear footwear. Their boyish shoes often feature unexpected proportions or details that make them feel distinctly contemporary.

Gucci brings Italian glamour to structured footwear, incorporating heritage elements like horsebit details that make their shoes instantly recognisable and utterly covetable.

Independent Brands Worth Discovering

Grenson represents the perfect marriage of traditional British shoemaking with contemporary design. Their women's collections feature playful takes on classic men's styles that respect tradition whilst feeling utterly modern.

Paraboot offers distinctive French craftsmanship with that chunky aesthetic perfectly aligned with current preferences. Their robust construction means decades of wear whilst developing beautiful character over time.

Investment Advice: Making Smart Choices

Quality boyish shoes represent incredible wardrobe value. Unlike trend-driven pieces that feel dated within seasons, well-made Oxford shoes or brogues improve with age and never lose relevance. The structured construction maintains shape far better than softer styles, making them ideal for daily wear.

From a cost-per-wear perspective, one excellent pair of black Oxford shoes will serve you better than multiple cheaper alternatives. There's something about quality leather soles on pavement that makes you walk with more confidence - it's impossible to quantify but absolutely real.

Find Your Perfect Fit with tellar.co.uk

Getting the sizing right on boyish shoes is crucial since many styles run differently from typical women's footwear. tellar.co.uk is the UK's leading sizing tool that matches your measurements exactly to over 1500 brands instantly - never look at a size guide again!

How Tellar Works:

1. Measure once using bust, waist, hip measurements, or your existing brand size.

2. Use their Store Size Lookup tool to get your precise size in any brand - COS, Reiss, Whistles, and hundreds more brands at: tellar.co.uk

3. Always free - no downloads needed, works perfectly in-browser at tellar.co.uk

The Tellar Fashion Hub

Beyond sizing, Tellar offers an incredible Fashion Hub - a library stacked with free posts from top stylists. Honest. Unbiased. Independent and always free. Style advice, top picks, and brand recommendations covering every fashion query.

Essential Tellar Reads:

Care Tips for Longevity

Proper maintenance is crucial for keeping boyish shoes looking sharp. Invest in quality shoe trees to maintain shape between wears, and establish a regular polishing routine. Rotating between multiple pairs prevents excessive wear whilst allowing leather to rest - I always recommend clients have at least two pairs in core colours.

The Bottom Line

The boyish shoe trend represents more than fashion - it's about empowerment through practical, beautiful design. These structured styles offer the perfect foundation for wardrobes that work as hard as we do whilst maintaining style standards that make getting dressed a pleasure.

Whether investing in your first Oxford shoes or expanding an existing collection, remember quality trumps quantity every time. One perfectly fitted pair of brogues serves you better than a wardrobe of uncomfortable alternatives. The boyish shoe trend has serious staying power because these classic styles simply work - and that's exactly why they'll still be relevant long after 2026.