Knitwear is where I check the neckline first. A crew, a funnel and a polo collar each frame your face differently, so hold the sweater up before you commit. The Wool-Blend Roll Neck Crew Sweater in navy has a cream and light blue Fair Isle yoke, and it is cropped, so it sits well over a high-rise jean.

The Cable Half-Zip Sweater in cream is the cozy one, and I would wear it with the dark wash wide-leg jean on a gray morning. The Wool-Blend Easy Funnel Neck Sweater has tan, cream and yellow stripes, which makes a plain pair of trousers look planned. The Easy Jacquard Funnel Neck Sweater in light blue is quieter, with texture doing the work.

For something sharper, the Airspun Cotton-Blend Collared Sweater in red is relaxed and ribbed, and I would put it under a camel coat. The Cotton-Cashmere Sweater Polo in cream and black stripe has a contrast collar and a slim fit, so it looks neat with a pencil skirt. The Merino Wool-Blend Cable Short Sleeve Polo in black is body-skimming, with a four-button placket.

In the fitting room, pull the cuff down over your wrist and see if the rib springs back. What I would skip: a chunky cable like the light blue Textural Stitch Cable Crew Sweater if you plan to wear a fitted jacket over it, because the sleeves will bunch.

Outerwear wants a quick test with your arms: reach forward as if you are hailing a cab and see if the shoulders pull. If they stay put, the coat is right. The Carrie Wool-Blend Trench Coat in oatmeal is double-breasted with a tie belt, and I would wear it over the navy cable mini dress or a plain knit and jeans.

The 100% Wool Mid-Length Coat in camel has a classic lapel and a full lining with an interior chest pocket, which is a small detail I always appreciate. The West Village Wool-Blend Bomber Jacket in black is modeled on vintage styles, and it sits on the hips with a zip front and elastic hem. The Wool-Blend Barn Jacket in brown plaid has a corduroy-style collar, so I would pair it with straight jeans and boots. The Slim Zip Vegan Leather Jacket in brown has burnished panels and a fold-down collar for a short, sharp line.

Then the dresses. The Madeline Cable Mini Sweater Dress in navy is comfortable and easy with tights. The Dylan midi in chocolate brown has a scoop back, three-quarter sleeves and a pleated skirt, and the rose cotton Dylan midi has a corset-style bodice with wide straps. I would wear it with a cardigan over my shoulders. What I would skip: the cap-sleeve midi under a bulky coat, since it will crowd the straps.

I would begin with the jeans, because they set the shape of everything else. Pick one pair, try it with a sweater from the second group, and see if the outfit works before you add a coat.

Then I would choose one knit I will wear weekly, and one layer for the cold. If a piece does not go with at least three things I already own, I leave it.

The company that once outfitted trips into the wilderness is now asking what you will wear to get through a Tuesday. I think the answer starts with a good pair of jeans. If you want to keep browsing, I also put together Cotton On and Denim Beyond Jeans.