“I love the relaxed tailoring and trouser trend but can’t for the life of me figure out how to choose the right trouser for this. I have several pairs but they all feel more formal that other people’s do in photos!”.
I can absolutely relate to feeling this way so I wanted to try and decipher a few simple techniques that can help make any classic trouser feel less corporate and more casual. I’ve really enojyed experimenting with The Way-High Drape Pant (bought by me) and think they’re the perfect example of how a trouser can work in a more easy-going context.
Read on to see 6 simple ways to transition those trousers from work to weekend!
Casual Trouser Styling Tip #1
SKIP THE BELT
One easy way to make any trouser feel less formal is to skip the belt. This helps them feel less structured and more relaxed.
Casual Trouser Styling Tip #2
ADD A T-SHIRT & SNEAKERS
I love styling my trousers with a white tee and sneakers. The look still feels fresh and crisp but easy-going. A trench coat adds a bit of dimension and warmth and a minimal bag is the perfect accessory to keep things classic and simple.
SHOP LOOK 1
Way High Drape Pant – tts for relaxed fit – I’m wearing my usual size 4 in the 32” inseam
Long Mac Coat – tts – I’m wearing my usual size Small in outerwear.
Low 1 White Sneaker – tts
Pinnacle Tee – tts
Sarah Crossbody Bag
Casual Trouser Styling Tip #3
MIX IN UTILITARIAN ELEMENTS
Adding utilitarian elements like an olive green tee, rolled shirt sleeves and a chunky boot all help to offset the tailored vibes of a trouser. By tucking the tee into the pants you still get a touch of shape, while an oversized oxford and lug sole boots give the look a hefty dose of 90’s vibes.
Casual Trouser Styling Tip #4
ADD AN UNTUCKED, UNBUTTONED SHIRT
Nothing says off-duty quite like a button-up that’s been freed from the clutches of a waistband and left open to billow in the breeze. Because a button-up is from a similar category within the closet, there is a clear connection between the pieces except they’re found in a much more casual context.
SHOP LOOK 2
Way High Drape Pant – tts for relaxed fit – I’m wearing my usual size 4 in the 32” inseam
Cotton Basic Tee – runs a size big – olive is old but other colours available
Way Long Oxford
Cortina Black Leather Boot – tts
Taupe Tote Bag – old
Casual Trouser Styling Tip #5
CUE THE CONVERSE & CANVAS
There are very few looks that a pair of Converse can’t make more cool and casual. Even in this case, I’m technically wearing a suit with these trousers and blazer, but thanks to my sneakers, the look feels very chill. This is supported by choosing a canvas tote bag, which helps to bring out the creamy tones in my sneakers. Keeping the base all black, also helps the cream tones stand out in contrast.
SHOP LOOK 3
Way High Drape Pant – tts for relaxed fit – I’m wearing my usual size 4 in the 32” inseam – More colours available.
Sipima Cotton Micro Rib Tee – tts – Lots of colour options for this personal favourite staple.
Brown Plaid Blazer – old Reformation – similar option here and here
Chuck Taylor 70’s High Top – tts
Canvas Tote Bag – Baggu
Casual Trouser Styling Tip #6
SOFT TONES & TEXTURES
Here you can see how texture works to soften the feel of a tailored trouser. Ribbed cotton and flax linen help the look feel instantly more laid-back. I also intentionally chose a long sleeve tee, linen duster and suede boot all in a similar soft tone and by keeping the palette to just two colours the look still has impact.
SHOP LOOK 4
Way High Drape Pant – tts for relaxed fit – I’m wearing my usual size 4 in the 32” inseam
Ribbed Long Sleeve – old KOTN
Linen Duster Coat – old ONLY CHILD
Corticella Taupe Suede Boot – tts
Half Moon Bag – old The Stowe – I love this option for a similar vibe.
LOOKING FOR PETITE FRIENDLY TROUSER OPTOINS?
I would take a look at the following:
The Effortless Pant from Aritzia
(I’ve heard these are great for petites and come in a range of fit options.)
The Harlow Pant by Madewell
(a reader recommended these and they come in a range of sizing options too.)
The Mason Pant by Reformation
(These also come in petite sizing and appear to have a slimmer fit.)
THANKS FOR TUNING IN!
I hope this post helps anyone who’s been wondering how to make their trousers work in a more casual context! Feel free to let me know which outfit you plan to try!
