How to Create a Street Style Look with Oversized Dungarees

by

How to Master Street Style: The Definitive Guide to Oversized Dungarees

Oversized dungarees are no longer just for toddlers or tradespeople; they’ve become a cornerstone of modern street style. This guide will walk you through the precise steps to transform this seemingly simple garment into a high-fashion statement. We’ll move beyond the basics and dive into the specific, actionable techniques that separate a sloppy outfit from a curated, confident look.

The Foundation: Choosing Your Canvas

Before you even think about styling, the selection of the right oversized dungarees is paramount. This isn’t a one-size-fits-all situation. The wrong fit can derail your entire aesthetic.

1. The Perfect Drape and Fit:

  • Avoid the “Sack” Effect: The goal is a relaxed fit, not a garment that swallows you. Look for a pair that offers ample room through the torso and legs but still has a defined silhouette. A key indicator is the shoulder straps—they should sit comfortably without pulling or sliding off.

  • The Leg Profile: Straight-leg, wide-leg, and slightly tapered styles are all viable. A straight-leg cut offers a classic, balanced look. Wide-leg styles create a more dramatic, avant-garde silhouette. Tapered legs can be tricky but work well when you want to showcase your footwear. Avoid overly flared or skinny-fit dungarees; they contradict the oversized aesthetic.

  • Length is Crucial: The hem should ideally break at the top of your shoes, with a slight bunching. This creates a relaxed, effortless puddle effect. If the length is too long, you risk looking unkempt. A simple cuff can fix this and add a deliberate stylistic element.

  • Quality Fabric: Denim is the classic choice, but look for a medium-to-heavy weight. Cheaper, thin denim will wrinkle easily and lack the structured drape necessary for a good street style look. Canvas or twill are also excellent, durable options.

Example: Instead of grabbing the first pair you see, go for a brand known for its quality denim, like Carhartt or Dickies. Look for a ‘boyfriend’ or ‘relaxed fit’ style. For a wide-leg silhouette, search for keywords like ‘barrel leg’ or ‘skater fit.’

Layering Essentials: Building the Look from the Inside Out

The beauty of oversized dungarees lies in their ability to act as a blank slate. What you wear underneath is the core of your outfit’s personality.

1. The Subtle Base Layer:

  • T-shirts and Tanks: A high-quality, heavyweight cotton t-shirt is the ultimate no-fail option. Think of it as your foundation. Crewnecks are universally flattering. A ribbed tank top adds a touch of texture and can be a great choice for warmer weather. Stick to neutral colors like white, black, gray, or earthy tones. This keeps the focus on the dungarees and the overall silhouette.

  • Long-Sleeve Shirts: For a more polished or layered look, a long-sleeve shirt or a fitted thermal top works perfectly. A striped Breton shirt can add a touch of classic French style to the urban aesthetic. A solid black or navy long-sleeve tee is a sleek, minimalist choice.

  • Cropped Tops: This is a bold move that works exceptionally well. A cropped top peeking out from under the bib of the dungarees creates a balanced, modern silhouette. It defines the waist and adds a flash of skin, contrasting the oversized nature of the garment. This technique works best with high-waisted dungarees.

Example: Pair your dark denim dungarees with a crisp, white crewneck t-shirt from a brand like Uniqlo or Everlane. This creates a clean, classic contrast. For a more subtle look, opt for a black long-sleeve ribbed top. When feeling adventurous, a black or white cropped tank from a brand like Alo or Nike will give you a dynamic silhouette.

2. The Elevated Mid-Layer:

  • Hoodies and Sweatshirts: The ultimate in casual comfort. Layering an oversized hoodie or sweatshirt underneath your dungarees adds a cozy, streetwear vibe. The key here is to find the right balance. The hoodie should be a slightly less oversized fit than the dungarees themselves to avoid looking bulky. Pull the hood out and let it drape over the bib for an intentional, relaxed look.

  • Knitwear: A fine-gauge knit sweater or a chunky turtleneck sweater can instantly elevate the dungarees from casual to smart-casual. A ribbed turtleneck in a neutral color like cream or camel adds a sophisticated texture and warmth. A slouchy V-neck sweater works well for a more relaxed, bohemian feel.

  • Button-Down Shirts: This is a classic styling trick that immediately dresses up the look. A crisp, white oxford shirt or a light-wash denim shirt creates a preppy, polished feel. You can wear the shirt buttoned up or open with a t-shirt underneath. For a bolder statement, try a flannel shirt layered underneath, playing with different patterns and colors.

Example: Layer a heather gray crewneck sweatshirt under your navy dungarees. Let the sweatshirt cuffs peek out from the dungaree legs. For a smarter look, try a camel-colored merino wool turtleneck sweater underneath. The smooth texture of the wool will contrast beautifully with the rugged denim.

Footwear: The Grounding Element

Your choice of shoes can drastically alter the direction of your outfit. They are the anchor of your look.

1. Sneakers and Streetwear:

  • Classic White Sneakers: This is the most versatile and foolproof choice. A pair of chunky white sneakers (think Air Force 1s or a similar style) creates a clean, balanced base. A more streamlined, minimalist white sneaker (like a Common Projects style) offers a sleeker, more refined aesthetic.

  • High-Tops: High-top sneakers like Converse or Jordans add a vintage, retro feel. They work particularly well with dungarees that are cuffed to showcase the shoe. The height of the shoe adds a sense of proportion and intentionality.

  • Skate Shoes: Brands like Vans or Etnies are a natural pairing. Their flat, sturdy profile complements the relaxed, utilitarian nature of the dungarees. Choose a neutral color or a classic black and white checkerboard to maintain a cohesive look.

Example: Pair a classic pair of black Vans with a dark denim pair of dungarees and a black graphic tee. Cuff the dungarees to show off the iconic side stripe of the Vans. For a more modern look, a pair of chunky New Balance 550s with a wide-leg dungaree creates a strong, balanced silhouette.

2. Boots and Edgy Aesthetics:

  • Combat Boots: Chunky combat boots (Dr. Martens are the quintessential choice) are perfect for a grungier, tougher street style look. They add a sense of weight and attitude to the outfit. Pair them with a pair of dungarees with a slightly cropped or rolled hem to show off the boots.

  • Work Boots: Classic work boots like Timberlands or Red Wings are a natural, utilitarian pairing. They lean into the workwear origins of the dungarees. This is a durable, practical choice that looks effortlessly cool.

  • Chelsea Boots: For a surprising, elevated twist, try a sleek pair of Chelsea boots. The clean lines and fitted silhouette of the boot contrast beautifully with the relaxed fit of the dungarees, creating a smart-casual look. This works best with a fine-gauge knit underneath and a cuffed hem.

Example: Wear your dungarees with a black t-shirt and a pair of polished Dr. Martens. Roll the hem of the dungarees just above the top of the boot. For a rugged look, pair them with a flannel shirt and classic tan Timberland boots.

Accessories: The Finishing Touches

Accessories are what transform a good outfit into a great one. They are the details that show you’ve put thought into your look.

1. Headwear:

  • Beanies: A simple knit beanie in a neutral color adds a casual, cool-weather vibe. Black, gray, and forest green are safe bets.

  • Baseball Caps: A classic baseball cap can add a sporty, effortless feel. Choose a cap with minimal branding or a simple logo.

  • Bucket Hats: A bucket hat adds a trendy, ’90s-inspired feel. It’s a statement piece, so make sure it complements the colors in your outfit.

Example: Top a t-shirt and dungaree combination with a simple black knit beanie. For a warmer-weather look, a classic black or off-white baseball cap from a brand like New Era can add a sporty, casual finish.

2. Bags:

  • Crossbody Bags: A small to medium-sized crossbody bag is both practical and stylish. It breaks up the large canvas of the dungarees and adds a modern touch.

  • Tote Bags: A sturdy canvas or leather tote bag leans into a more practical, utilitarian aesthetic. It’s perfect for carrying essentials and adds a relaxed, effortless feel.

  • Fanny Packs/Belt Bags: Worn across the chest, a fanny pack is a quintessential streetwear accessory that adds a functional and fashionable element.

Example: Cinch a black leather belt bag across your chest over the dungaree bib. This adds an instant edge and breaks up the large expanse of fabric. For a classic feel, carry a large, natural canvas tote bag.

3. Jewelry and Watches:

  • Chunky Chains: A simple silver or gold chain can peek out from under your top, adding a subtle touch of a tough, urban aesthetic.

  • Layered Necklaces: For a more delicate approach, a few layered necklaces of varying lengths can add visual interest.

  • Watches: A watch with a substantial face and strap (leather or metal) can add a masculine, practical element to the outfit.

Example: Wear a simple, heavy silver chain under a black t-shirt. The glint of the silver adds a focal point and a hint of deliberate styling. A classic Timex or a vintage Casio watch can add a retro, functional touch to your wrist.

Master the Details: Final Touches and Styling Hacks

These are the small but impactful adjustments that make all the difference.

1. The Cuff:

  • A single, neat cuff at the hem of the dungarees is a clean, intentional look. It’s perfect for showcasing your footwear.

  • A double or triple cuff adds a more casual, rolled-up feel. This works well with boots or high-top sneakers.

  • The “puddle” effect: If the dungarees are long, letting them bunch at the shoe creates a very relaxed, fashion-forward silhouette.

2. The Straps:

  • One Strap Down: This is a classic street style move. Unfastening one of the bib straps and letting it hang down casually creates an asymmetrical, deconstructed feel. This is a key gesture that immediately communicates confidence and style.

  • Both Straps Up: The most traditional way to wear them.

  • Let the Bib Hang: For a truly avant-garde look, unfasten both straps and let the bib hang down, wearing the top as if it were simply oversized pants. This works best with a more fitted top underneath.

Example: For a powerful, effortless look, wear a black long-sleeve tee under your dungarees. Put one strap up and leave the other hanging. Cuffed the legs of the dungarees to show off a pair of high-top sneakers. This combination is a definitive street style statement.

3. The Fit of the Top:

  • When wearing a baggy top underneath, a small tuck at the front into the waist of the dungarees can create a more flattering silhouette and prevent the entire outfit from looking too bulky.

  • Layering a baggy top with a belt cinched around your waist (under the bib) is a more advanced styling trick that can define your shape.

The Street Style Manifesto: Beyond the Garments

Street style is more than just clothes; it’s an attitude. Oversized dungarees are a vehicle for self-expression. They are a nod to workwear history, comfort, and an effortless rebellion against overly restrictive fashion.

The key to truly mastering this look is to own it. Wear your dungarees with confidence. The way you carry yourself is the ultimate accessory. The slouch of your shoulders, the purposeful stride—these are the intangible elements that make the difference between someone wearing a trend and someone who is an icon of style. Experiment with different textures, colors, and proportions. Don’t be afraid to mix and match. The oversized dungaree is a symbol of creative freedom. Use it as your canvas to paint your unique sartorial story.