Cast your minds back to the ‘90s when bootcuts and wide legs were the look in bottoms for both dressy and casual. Flared silhouettes were full-length and worn with flat sandals, slides, mules, combat boots, square toe pumps, cowboy boots and chunky platform sneakers. It’s flares with sneakers that I’m highlighting today, because flares look fresh, and sneakers are the shoe of our fashion era. 

I like full-length dressy and casual bootcuts, bell-bottoms and wide legs with extra long hems that skim or almost skim the surface of the ground. I prefer the look with a front break line, especially when the footwear is flat. All pant lengths here look perfect to my eye. Luxurious, intentional, elongating, comfortable, and practical as long as it doesn’t rain.

Here are four ways to combine flared bottoms with sneakers. The sneakers are white because that’s the trendy benchmark, but feel free to sport refined or chunkier athletic sneakers in a colour that’s more to your taste. Use any colour palette.

1. Relaxed and Pretty

Combine FULL-LENGTH denim bootcuts or wide legs with a pretty top like an eyelet, ruffled or boho blouse, or girly cardigan or pullover. Finish off the look with sneakers and a dressy bag. Here, the white zips of the top pick up the white of the sneakers, which pulls together the look.


2. Belted and Complemented

Combine a pair of dressy bootcut or wide leg trousers with a fluid tee or pullover. Tuck or semi-tuck the top, and add a belt that works with the palette of the outfit. Add white sneakers. Here the pattern on the sneakers matches the pattern of the belt, which creates a fun complement. Add a denim jacket, moto or blazer as a topper.

Boden Exeter Wide Leg Pants

3. Casual and Comfy

Combine a pair of casual bootcut or wide leg chinos with a pullover and sneakers and Bob’s your uncle. Wear the pullover untucked or semi-tucked. It’s that easy!

Anthropologie Sanctuary

4. Sporty Luxe

Combine a bootcut or wide leg trouser suit with a tee or top, and finish off the look with sneakers. The white top picks up the white in the sneakers, but you can wear any colour top. A patterned top with white in the patten would work well too. Or colourful sneakers with white soles. Add jewellery, watch, eyewear and handbag as desired.

ASOS DESIGN Tailored Check Slim Flare Pants

I started sporting bootcuts with white sneakers last year and like the combination because it looks different amidst a world of skinnies and leggings. I bought the toffee Sanctuary chinos and they’ve become excellent travel pants for long flights. I also pulled out my nine-year-old charcoal pinstriped Theory suit which is in immaculate condition, and had the trousers shortened to wear with sneakers. So I’m doing #3 and #4 already, and hope to do #2 , since I have my eye on those pants. Here are the exact items from my wardrobe. It’s wonderful to repurpose an old suit!