5 Ways to Wear Short Pants in Cooler Weather

Not too long ago, short pants were a seasonal wardrobe choice worn mostly in warm weather. Today, they are literally “cropping” up in all seasons giving the trend a much wider range of style interpretations for all.

The look can be preppy and very casual when worn with sneakers and other flat footwear or quite fashion-forward and sophisticated when dressed up with heels, boots and a variety of hosiery. We particularly like shorter pants any time of year because of the heel height options they provide.

Let’s dive into the short pant, cool weather trend to help you wear them well.

#1 The Devil is in the Details
Let’s face it, choosing the right footwear with shorter style pants can be daunting and keeps a lot of women away from an otherwise sensible (& fun!) trend. The best rule of thumb is to balance the fabric, patterns and finishing details (i.e. cuffs, pockets, seams and pleats) with the footwear you choose. Sneakers, flats, pumps as well as tall boots and booties all have a role to play in your “short-pant-cool weather” story. Open your mind to the details that will lead you to good choices.


#2 The Wide & Short of It
First introduced in the 19th century for cycling, wide leg pants (also called culottes and gauchos) continue to stand the test of time. This season, pair them with tall, fitted boots that easily fit under their wide hem for a clean line. For even more elongation, match your pant and boot color. Short boots with a variety of heel heights and hosiery options (think tights, socks and nylons worn alone or even together) is another easy way to bring this trend to new heights in cool weather.


#3 Get Your Prep On

Connect to your “inner prep” by sporting “highwaters” (many achieve this look by rolling a pair of jeans or khakis at the hem) and slipping on simple sneakers or loafers. If you choose to wear socks (some do, some don’t, even in winter), stick with white athletic ones to keep your prep high. Same for sneakers – white works best here too. Can’t believe this look is popular again? Visit any college campus to see how fast this re-trend has taken off!


#4 Show Off Your Socks
Socks are certainly having a fashion moment and shorter pants show them well. Women, bring your style to new heights by showcasing ankle socks with your shorter winter pants. They can be worn on their own or layered over tights for more warmth and creative expression. Men, in most professional settings, pants that are hemmed properly will allow you to show off your socks appropriately – I.e. when seated! If you walk into a meeting and everyone is trying to “read” your socks, your pants are probably too short for the business of the day!


#5 The Skinny on Wearing Jeans, Leggings & Boots
Finally, to tuck or not to tuck is the real question on many minds! Show off mid-calf (including cowboy styles), knee, or over the knee boots by tucking short, fitted pants inside them. This is always a stylish choice. Obviously, skinny jeans and leggings work best here. If you’re wearing booties with your skinny jeans, avoid them bunching up around your calves or ankles at all costs. Sometimes rolling them a bit to eliminate the bulk does wonders. If your internal thermostat is okay with it, baring some skin between the end of the pant and the boot is fine too. Another idea is to wear heavier socks that skinny jeans can be tucked into to eliminate the bulk (while not compromising your warmth!). If your jeans are short with a boot cut at the bottom, pairing boots and socks with them becomes a lot less complicated – promise!


A Word on Traditional Pants
If the pants in your closet are feeling dumpy, chances are they are too baggy and/or too long. In general, traditional pant silhouettes for both men and women are slimmer these days. With their trimmer fit, you want to be sure they are hemmed properly. Generally, that means right at the ankle for women (with no noticeable break or “pooling”) and at the ankle with a slight to no break for men. Our female clients love having a few pair of perfect-fitting slim ankle pants that can be worn with both flats and heels. We source them for all sizes and shapes from designer to discount brands. For the men we work with, we often take good-quality, flat-front pants that they have owned for a while and have them slimmed down on each side and shortened by a skilled tailor. Violà–new pant, new, more modern man!

Scroll to Top