Rainy Day Outfits Built Around a Waterproof Anorak

The simplest way to handle rainy day outfits is to start with the jacket. A waterproof anorak (a lightweight, pullover-style rain jacket with a hood and a front pocket or half zip) covers the hardest job, and almost anything underneath can follow your usual style.

Below are five outfit formulas, what to wear under the jacket, how to pick the right pair of bottoms and shoes, and what to check before you buy.

Section 01

What to wear on a rainy day: the basic formula

Think in three layers. A comfortable base, a mid layer that suits the temperature, and the anorak on top. Keep the bottom half simple: fabrics that dry quickly and hems that will not drag in puddles.

If you will be walking a lot, the layer against your skin matters. The Texas A&M Howdy Health guide to cold weather exercise advises that the layer closest to your skin should be moisture wicking, and it also says to avoid cotton because it absorbs moisture and can keep it next to your skin. That is written for exercise, but it applies to a long wet commute too.

Section 02

Five casual rainy day outfits with an anorak

The everyday errand look

High-waisted jeans, a plain tee, white or dark sneakers and a crossbody bag. The bag keeps your hands free for an umbrella or a coffee. Choose a darker sole if the sidewalks are wet, since white rubber shows splashes quickly.

The walk or light hike

Anorak over a moisture-wicking top and leggings, with waterproof boots and a beanie. For longer trails, see waterproof hiking pants.

The office commute

Tailored trousers, a button-down and ankle boots, with a neutral anorak in black, navy or olive. Clean lines read as more polished, and a matte finish looks calmer than a shiny one. If trousers are your plan, slim waterproof pants keep the hems dry.

The streetwear mix

Joggers, a cropped hoodie and chunky sneakers. This is where a bold anorak works well, because the rest of the outfit is quiet.

The cozy weekend layer

A thick knit under a roomy anorak, wide-leg or straight trousers and lined boots. Size the jacket so it closes comfortably over the sweater without pulling at the shoulders. That is a sizing issue, not a you issue.

Section 03

Leggings or jeans in the rain?

Leggings in a synthetic blend usually dry faster than denim, so they are the easier pick for long walks. Jeans soak up water, get heavy and stay cold, so save them for short trips, and roll the hems up an inch or two. If it will pour, a water-repellent trouser beats both.

Section 04

Which shoes work with rainy weather outfits?

Waterproof boots are the obvious answer, and these boots for rainy day errands cover several styles. A rain boots and trench coat outfit is a classic, and a longer coat pairs well with a boot that stops just below the knee. If you prefer a coat to an anorak, there are waterproof trench coats that follow the same logic.

Comfort counts when you walk in wet shoes. Harvard Health notes that for women the most comfortable shoes are low-heeled, no higher than three-quarters of an inch. Wet pavement and a tall heel do not mix well anyway. Look for a firm sole and a snug heel, and leave some room for your toes.

Section 05

Colors that work on a gray day

Through the lens of evidence-based design, I'd think about contrast first. Under flat gray light, mustard, cobalt or terracotta read brighter against wet pavement, while navy, black and olive look quieter and pair with nearly everything. If your outfit is mostly neutral, let the anorak carry the color.

Texture changes color too. A matte finish tends to look deeper and more grown-up than a glossy one in the same shade.

Section 06

How to choose a waterproof anorak

• Check the label says waterproof, not only water-resistant. Taped or sealed seams help in heavy rain.
• Try it on over the thickest layer you plan to wear. You should be able to raise your arms without the hem riding up.
• Look for an adjustable hood, drawcord waist and cuffs, which keep water from running in.
• If you will be active, choose vents or a breathable fabric so you do not overheat.
• For travel, pick one that folds into its own pocket or a tote.

Section 07

Caring for your anorak

Wipe it down after wearing and follow the care label for washing. Hang it to dry in a ventilated spot, and skip the dryer unless the label allows it. When water stops beading on the surface, a spray-on water-repellent treatment can help. Store it unfolded or loosely folded to avoid hard creases.

For more outfit combinations, see rainy day fashion for wet weather, or waterproof outerwear sets if the forecast is truly heavy.

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