However a short sleeved shift dress can be teamed with a roll neck jumper, over the knee flat boots and opaque tights as I've done here for an easy A/W day look. Be sure the neckline on your dress is round and the sleeves of your jumper are slim fitting. I would also steer towards heavier fabrics for the dress, that's why faux leather or real, wool or wool mix work well for the colder months.
I'm wearing black layers underneath but a light grey works well with burgundy too. I'd then wear a black over coat, grey tights and black or grey boots.
Notice how I've put different textures together to soften the hardness of the faux leather with Carvela 'Supper' suede over the knee boots and Autograph wool over coat. If you do wear leather footwear with a leather look dress make sure that they are ankle length, to break it up; see my inspiration board below which also shows it with a Wrap 'Erin' knitted sleeveless jacket if a coat is too heavy.
No shopping links today as the change in season in stores make it harder to find similar products available now. Hopefully you'll have similar elements already in your wardrobe to try this look and make your shift dresses work harder.
Have a good weekend and thanks for stopping by.