How to Style Shorts in the Winter

This is my last week of work for the year and I am so excited! It’s about time I share how to style shorts in the winter (perfect for those of us in the South especially)!

I suddenly LOVE shorts in the winter. Crazy, I know. I got really excited about them when I realized I need something to wear with my Gucci tights. Immediately I went on a mad hunt to figure out what to wear with them and discovered winter appropriate shorts. I love the idea of shorts because they change up what we typically see this time of year.

I typically wear more casual styles, so I opted for combat boots with both outfits. Both outfits could be dressed up though with a heel or heeled boot as well! When you’re thinking about how to style shorts in the winter and what shoes to wear, wear the same thing you would with a mini skirt.

Winter shorts look great with a plain tight or printed tight. I also like heavier fabrics for cold weather shorts like tweed, or faux leather. I would opt to stay away from denim shorts this time of year, but I have seen other ladies rock them with tights!

A great way to balance out the bottom is to add a big sweater on top. In both outfits I opted for a more cropped sweater, to show off the high rise shorts. You also don’t want the sweater to be too long where it covered the shorts in the back (making it look like you’re not wearing any bottoms!).

For more fall/winter outfits, check out my latest Wearing Lately post here.

Sizing reference: I am 5’4″ and typically XS in tops and 25 in bottoms.

Outfit #1 Red Sweater + Shorts

This first outfit would be perfect for a holiday get-together, or out for drinks like where I wore it (I wore out to Bartaco!)! My shorts fit true to size, but are a little snug. If you are between sizes, size up. I am wearing a small in the Gucci tights (they don’t come in XS). My sweater is super fuzzy and soft and is true to size also.

Outfit Details:

Sweater (c/o), Shorts (c/o), Tights, Combat Boots, Louis Vuitton Bag

Outfit #2 Cream Sweater + Shorts

Outfit Details:

Sweater (c/o), Shorts (c/o), Gucci Tights, Combat Boots, Louis Vuitton Bag