Oversized Tailoring: The Must-Have High Street Trend You Can't Ignore

Rejoice! Pumpkin spice season is upon us again: and with it, ushered in a captivating fashion trend: oversized tailoring.

This style takes traditional silhouettes and amplifies them, creating a relaxed yet polished look that is both comfortable and chic.

From runways to street style, oversized tailoring is quickly becoming a wardrobe essential, allowing wearers to express their individuality while staying effortlessly stylish.

Let's dive in.

Core Principles of roomy 'fits

At its core, oversized tailoring is about reimagining classic pieces with a modern twist. Oversized blazers, wide-legged trousers, and baggy shirts are the cornerstone of this trend, offering versatility for various occasions. The appeal lies in their ability to be styled up or down; a tailored blazer can effortlessly transition from office chic to weekend casual when paired with a simple turtleneck and sneakers. The key is to maintain balance—mixing structured pieces with softer elements to create a harmonious silhouette that flatters any body type.

Moreover, the trend emphasizes the importance of fit and proportion. While oversized pieces can appear baggy, the right proportions can elevate the look significantly. Layering a slightly oversized blazer over a fitted dress or pairing wide-leg trousers with a cropped top creates an eye-catching contrast that adds depth to the outfit. This intentional styling approach makes oversized tailoring accessible to everyone, allowing individuals to embrace their unique styles while enjoying the comfort that these pieces provide.

"I feel like Vetements really paved the way for the oversize look. It was a real moment that has been picked up as a solid trend, and I hope it never goes away."

Aimée Croysdill, Celebrity Stylist

your cheat sheet to effortless styling

Balance Proportions : Pair oversized items with fitted pieces to create a balanced silhouette.
Layer Wisely : Use layers to add depth to your outfit, mixing textures and lengths for visual interest.
Focus on Fabric : Choose high-quality materials that drape well, enhancing the overall look and feel of the outfit.
Cinch Where Needed : Use belts or ties to cinch oversized pieces at the waist for added shape and definition.
Choose a Focal Point : Highlight one oversized item as the statement piece in your outfit to avoid overwhelming the look.

Accessorise Thoughtfully : Select accessories that complement the oversized vibe, avoiding items that are too small or dainty.
Mind the Length : Pay attention to the length of oversized garments to ensure they flatter your body shape; cropped styles can help elongate the legs.
Mix Styles : Combine casual and formal elements, such as pairing an oversized blazer with distressed jeans for a chic contrast.
Keep It Monochrome : A monochromatic colour palette can help streamline oversized outfits and create a sophisticated look.
Experiment with Footwear : Try different styles of shoes, from chunky boots to sleek heels, to see how they affect the overall vibe of your oversized outfit.

TRY THE LOOK: LAYERED OXFORD SHIRT

The tailored oversized white Oxford shirt is a sartorial classic that transcends seasonal fads.

Its breathable fabric and oversized fit make it perfect for layering or wearing solo, effortlessly transitioning from casual outings to more polished looks.

This timeless piece's understated texture adds a touch of sophistication, ensuring it remains a staple in your wardrobe for years to come.

keys to the look: versatility

The "effortless XXL" trend lends itself well to a myriad of styling options, allowing wearers to play with textures, patterns, and colours. For instance, a monochromatic outfit featuring an oversized blazer and trousers in the same shade creates an elongated silhouette, perfect for a sleek, modern look.

Alternatively, mixing patterns—such as pairing a plaid oversized blazer with striped wide-leg trousers—adds an element of fun and creativity, making the outfit truly one-of-a-kind. Accessories play a crucial role in completing the oversized look. Statement belts can be used to cinch in the waist of an oversized blazer, adding definition to the silhouette while creating an on-trend hourglass shape.

Footwear choices also significantly impact the overall vibe; chunky boots can introduce an edgy twist, while sleek heels can maintain a sophisticated edge. Additionally, oversized bags have become the perfect companion for this trend, enhancing the relaxed yet stylish aesthetic that oversized tailoring embodies.

Do's and Don'ts of relaxed power dressing

DO: Play with Contrast : Combine oversized pieces with fitted garments, such as pairing a loose shirt with tailored trousers, to create visual tension and interest. This contrast can highlight the unique shapes of each piece.
DO: Opt for Statement Pieces : Select bold oversized garments, like a dramatic coat or an eye-catching blazer, that can become focal points of your outfit. Let these pieces speak for themselves by keeping other elements minimal.
DO: Hit the Thrift Store: Look for XXL retro blouses or jackets at thrift stores - or even in Grandma's closet. These unique pieces can add character and history to your look, making your style more distinctive.
DO: Explore Colour Blocking : Pair oversized tops in bold hues with contrasting bottoms to create a striking visual impact. Choose two or three contrasting colours for a cohesive yet dynamic outfit.
DO: Experiment with Textures : Mix fabrics such as leather, knit, or denim to create depth. For example, wear a chunky knit sweater over silky wide-leg trousers to balance textures and elevate your outfit.
DO: Embrace Your Personality : Add personally meaningful touches, like statement jewelry or custom accessories, that reflect your style. Incorporate unique patterns or bespoke pieces to make oversized tailoring feel authentically yours.

DON'T: Go Completely Baggy : Avoid dressing in all-loose pieces, which can create a shapeless look. Include at least one fitted element to provide balance and structure to your outfit.
DON'T: Neglect Proportions : Pairing oversized pieces without considering proportions can lead to an unflattering appearance. Be mindful of how each garment interacts visually.
DON'T: Mix Too Many Styles : Combining multiple bold patterns or styles can feel chaotic. Choose one statement piece and keep other elements cohesive.
DON'T: Compromise Comfort : Oversized tailoring should feel relaxed, but it’s essential that your outfit remains comfortable. Avoid pieces that are so loose they hinder movement.
DON'T: Under-Accessorise: While it’s best to avoid overly chunky accessories, don’t skip them altogether. Thoughtful touches like a sleek belt, bold earrings, or structured bag can add polish without overpowering your oversized pieces.
DON'T Skip the Details : Oversized pieces can lose impact without thoughtful styling. Pay attention to cuffs, hems, and finishing touches that elevate the look, adding polish and intention to your relaxed fit.

power dressing without the fuss

Oversized tailoring combines the authority of traditional suiting with a modern ease, which makes it feel relaxed and unrestricted.

Oversized blazers, boxy coats, and wide-legged trousers bring a “soft power” vibe to oversized tailoring. This trend offers a blend of structure and ease, ideal for balancing authority with a relaxed, unrestrictive twist.

The loose structure creates dimension and depth without feeling rigid, offering fresh, fashion-forward silhouettes, especially in upcycled retro styles. Oversized pieces add a hint of rebellion to classic suiting, disrupting traditional lines with an "unstructured yet sophisticated" shape.

The aesthetic allows for chic, high-low contrasts—pairing a citrus-hued satin blazer with fleece sweats and trainers, for example—that elevate simple ensembles with understated elegance.

"Keep the shirt underneath tight or something else fitted within your outfit so that you can see your body in some way. Personally, I like to do that with a baggy trouser, a crop top and then a baggy blazer. It’s all about dressing for your body type."

Meve Reilly, Celebrity Stylist (Megan Fox, Ciara, and formerly Hailey Bieber)

The rise of high street

The street style scene has been instrumental in popularising oversized tailoring, with fashion influencers and celebrities showcasing their unique takes on the trend. Instagram and TikTok are awash with outfit inspiration featuring oversized blazers, relaxed trousers, and creative layering. This visibility has sparked a broader interest in tailoring, pushing the boundaries of traditional office wear into everyday casual ensembles that resonate with the modern consumer.

As fashionistas begin to incorporate oversized tailoring into their wardrobes, they’re experimenting with different textures and fabrics.

Luxurious materials like wool, corduroy, and satin add depth to the look, while vibrant colours and playful patterns ensure that oversized tailoring remains visually striking.

This trend is not just about oversized pieces; it’s about embracing the individuality that comes with them, allowing each person to express their unique style while remaining comfortable and chic.

As consumers become increasingly conscious of their environmental impact, many are seeking high-quality, timeless pieces that withstand changing trends.

Oversized tailoring fits perfectly into this narrative, as these pieces can easily transition across seasons and occasions, making them a worthwhile investment.

Additionally, the rise of second-hand shopping has allowed fashion enthusiasts to find unique oversized tailored pieces that carry their own stories. Thrift stores and vintage shops are goldmines for discovering one-of-a-kind blazers and trousers, allowing wearers to embrace sustainable fashion while achieving that coveted oversized look.

This fusion of style and sustainability is not only eco-friendly but also encourages a more thoughtful approach to personal fashion.

Conclusion

With voluminous suiting emerging as a dominant trend this season, the fusion of comfort, versatility, and individuality has never been more appealing.

Its ability to blend classic tailoring with a contemporary twist makes it a wardrobe staple for both men and women, encouraging creative styling and self-expression. As oversized pieces continue to dominate the fashion landscape, they remind us that style should never be sacrificed for comfort.

Instead, oversized tailoring invites us to explore new dimensions of fashion while embracing sustainability and personal flair. With this trend on the rise, it’s time to embrace the oversized revolution and redefine our wardrobes for the season ahead.

Frequently Asked Questions

How do I find the right fit in oversized clothing?

When shopping for oversized clothing, consider your body shape and proportions. Look for items that provide structure without overwhelming your frame, and try on different styles to see what flatters you best.

What should I avoid when styling oversized pieces?

Avoid wearing too many oversized items at once, as this can lead to a shapeless look. Instead, balance oversized pieces with fitted garments to create a more defined silhouette.

Can oversized suiting work for petite individuals?

Absolutely! Petite individuals can wear oversized suiting by opting for shorter lengths or cropped styles, which help maintain proportions. Tailoring specific pieces can also enhance the fit.

Are there specific fabrics that work best for oversized tailoring?

Fabrics like wool, linen, and cotton work well for oversized tailoring, as they provide structure and drape nicely. Look for quality materials that enhance the silhouette without adding bulk.

How can I accessorise oversized pieces, like a blazer?

Keep accessories minimal and chic. Use statement belts to cinch oversized blazers at the waist, and opt for sleek footwear to maintain a sophisticated vibe. Avoid heavy or chunky accessories that compete with the outfit.