The combination of wearing full-length flared trousers and jeans with heeled boots might take you back a decade or four. By flared jeans and trousers, I mean silhouettes that are bootcut, bell-bottom, or wide leg. The all important details of the combination are:

  • Hems that skim or almost skim the surface of the ground
  • Heeled footwear, even if the heels are a low one and a quarter inch
  • The refinement and dressiness of the boots

Although it’s not a must, pointy-toe and snip-toe boots work particularly well because their long toe boxes effectively peek out from under the hems, thereby elongating the leg line. Heels further elongate the leg line and allow the breakline of the hems to fall in a tidier drape instead of a crumpled mess. Footwear can create a low or high contrast with the trousers and jeans.

Here are some visuals:

Over the last ten years, we’ve seen every iteration of skinny and tapered bottoms at ankle (and shorter) cropped lengths make a trendy statement with flat and heeled footwear, while this combination of full-length flares with heels took a backseat. More recently full-length flared pants and jeans made a comeback but at a new and shorter full length. The new shorter length is a lot more practical, weather-friendly, looks equally good with flats, and is maybe a dash more playful. But it’s not as elongating, elegant, conventionally flattering, and dressy.

The sleek, streamlined and vertical integrity of full-length flares worn with refined heeled boots continues to be a hit with many people so it never went away. It was especially popular from 2000 to 2012. Some of my clients swear that the combination makes them walk taller, and with better posture. Unfortunately, the need for dry weather can put a damper on the vibe because soggy hems are awful, and heeled footwear is not for everyone. But a sunny climate and commuting by car helps, and low-heeled footwear works well.

Today, I think of full-length flares worn with heeled boots as a Trendy Classic combination that is always sensational, especially when the wearer feels like a million bucks sporting it. When a person’s ease and confidence comes through in an outfit combination, nothing can beat it. So if this was, or is, your look, milk it.