Oversized Hoodies: What to Wear Them With & Best Quality Brands (UK & USA)

Oversized hoodies have evolved from lazy-day loungewear into streetwear staples and capsule wardrobe essentials. Comfortable, cool, and easy to layer, the oversized hoodie is now a core piece in both men's and women's wardrobes. But styling them without looking shapeless—and knowing which brands deliver quality—makes all the difference.

This guide covers:

How to style oversized hoodies for different occasions
The most flattering pairings by body shape and height
The best quality oversized hoodies to buy in the UK and USA
And how Tellar.co.uk can help you find your exact fit every time

1. Why Oversized Hoodies Work for Every Wardrobe

Oversized hoodies offer structureless comfort without sacrificing style. They:

Provide warmth without layering complexity
Flatter most body types by skimming rather than clinging
Lend themselves to high-low styling: sneakers and joggers one day, trench coats and boots the next

But proportion is key. Done right, the oversized hoodie can elongate the frame, balance out broader shoulders or wider hips, and create a nonchalant, off-duty model vibe.

2. What to Wear with an Oversized Hoodie

A. With Leggings or Cycling Shorts

This is the classic silhouette—perfect for petite frames or casual weekends. Add high socks and trainers for a sporty vibe, or throw on an oversized blazer and gold hoops for streetwear polish.

Best for: Apple, rectangle, and petite body shapes

Proportions tip: Add height with chunky trainers or platform boots

B. With Straight-Leg Jeans

Balance the volume of the hoodie with structured denim. This pairing works well for tall or hourglass figures. Tuck just the front hem (a "French tuck") to define the waist.

Best for: Hourglass and tall frames

Try with: Raw hem jeans and a fitted crossbody bag

C. With Mini Skirts or Skorts

Ideal for transitional weather and elongating the legs. Layering a hoodie over a short A-line skirt plays with proportions while keeping the look feminine and fresh.

Best for: Pear and petite shapes

Bonus: Layer with knee-high boots in cooler months

D. Under Oversized Coats

Layering a hoodie beneath a tailored wool coat or trench gives an instant street-style look. Keep the rest monochrome or tonal to maintain sleek lines.

Try with: Camel coats, long-line puffers, or leather trenches

Footwear: Chunky boots or trainers

E. With Wide-Leg Trousers

For true fashion-forward balance, pair oversized hoodies with wide-leg cargos or trousers. Works best when the hoodie is slightly cropped or cinched at the waist with a crossbody bag.

Style tip: Keep colours muted or monochrome for sophistication

Pro tip: Go full tonal (e.g., charcoal hoodie with slate trousers)

3. Best Quality Oversized Hoodies: UK & USA

The key is fabric weight, softness, and structure retention. Look for heavyweight cotton (400gsm+), brushed fleece interiors, and reinforced ribbed hems.

Here are the best brands for quality and shape:

UK Brands:

● Pangaia

Fabric: Organic cotton, treated with antibacterial finishes
Fit: Relaxed and oversized, holds shape after washing
Price: £100–£120

● Wax London

Fabric: Loopback French terry, crafted in Portugal
Fit: Premium streetwear style, elevated finishes
Price: £80–£110

● Weekday (by H&M Group)

Fabric: Sustainable cotton blends
Fit: Oversized unisex shapes
Price: £30–£60

● Represent

Fabric: Heavyweight cotton (480gsm), garment-dyed
Fit: Streetwear luxe, structured and voluminous
Price: £110–£160

USA Brands:

● Reigning Champ (Canada/US)

Fabric: 100% midweight or heavyweight cotton fleece
Fit: Premium athletic tailoring, made to last
Price: $130–$160

● Fear of God ESSENTIALS

Fabric: Cotton-polyester blend, signature boxy fit
Fit: Iconic oversized silhouette, dropped shoulders
Price: $80–$120

● Everlane

Fabric: French terry or fleece, certified organic cotton
Fit: Clean, wearable basics in unisex fits
Price: $60–$90

● Los Angeles Apparel

Fabric: 14oz fleece, ultra-heavyweight
Fit: Boxy, vintage style
Price: $70–$100

4. Oversized Hoodie Fit Advice by Body Type

Body Type	Hoodie Tip
Petite	Go for slightly cropped or pair with mini skirts to elongate legs
Tall	Full oversized styles suit best; experiment with wide-leg bottoms
Apple	Choose V-neck or zip-front hoodies to open neckline
Hourglass	Add waist definition with a bag, belt, or French tuck
Pear	Show leg shape with shorts or skirts to balance bulk

5. Why Sizing Matters More with Oversized Fits

Even oversized fits need to be intentional. If it’s too big, the result is sloppy. Too small, and you lose the relaxed aesthetic. That’s where Tellar.co.uk comes in.

Tellar.co.uk: Get Your Exact Hoodie Fit in Seconds

Tellar.co.uk is the UK’s Leading Sizing Tool—designed to match your real body to the perfect fit in over 1,500 brands instantly, including all your favourite hoodie labels from COS, Everlane, Reiss, and more.

You can use:

Your actual body measurements (bust, waist, hips)
Or your known size in a brand you already wear

And Tellar will do the rest—removing all the guesswork.

How to Use Tellar

✅ Create your free profile

✅ Enter 3 measurements or select a brand you already wear

✅ Use the Store Size Lookup to check your hoodie size in any brand

✅ Explore the Fashion Hub for free tips, styling advice & more

Follow Tellar for Fit and Styling Tips:

Instagram: @Tellarsizing
Twitter/X: @Tellar100
Facebook: Tellar Sizing
Pinterest: TellarUK

Find your size in 1,500+ brands real-time. It’s free & easy.

Oversized hoodie or fitted knit—shop knowing it will fit, every time.