Styling a Pinstripe Suit in Winter

I spotted this lovely pinstripe suit from the Canadian workwear brand Judith and Charles and decided to use it as inspiration for creating a winter capsule wardrobe. Black can feel too heavy in summer, so this is the perfect suit for feeling polished and put together during the long cold winter months. Judith and Chales creates beautifully tailored garments in Canada making the brand a more sustainable and ethical option than brands manufacturing overseas.

With a single button and high waist, the fit is relaxed yet sophisticated. Details that matter when adding pinstripes to your wardrobe. A relaxed fit ensures that the stripes hang vertical. Save the fitted tailoring for solid colors. The single button jacket and high waist are feminine details that keep the suit from feeling too masculine.

What to wear with it?

Create an Inspo Board

A quick outfit search on Pinterest shows how versatile and chic a pinstripe suit can be. From bold and dramatic to classic and understated. Each has balanced the masculine pinstripes with a feminine touch—low neckline, belt at the waist, ankle crop.

While I love the more dramatic outfits, a classic take is more practical day-to-day as it can be dressed up or down. This versatility means you can mix and match the suit with other items in your wardrobe. To make a classic pinstripe more dramatic, go for bold tailoring elsewhere in the look or add statement accessories. To dress a classic pinstripe suit down, pair the suit jacket with dark jeans.

Decide what direction you want to take the suit and choose pieces that lean into that style. For this capsule collection I wanted to create a classic look. Analyzing the outfits helped, I could see that too much contrast in the outfits veered into preppy territory. Minimizing the contrast created a more timeless style.

Consider the overall look when choosing pieces for your capsule

I chose white shirts with large cuffs that will show under the suit jacket. A small cuff poking out will not create the same effect. These sleeves can be difficult to find, pay special attention when shopping. Keywords like french cuffs can help narrow the online search. A white turtleneck is a good alternative to a blouse in winter. Fitted styles are more dramatic, whereas relaxed fits are more classic.

A skirt will add variety to your silhouette. A pencil skirt skims the curves of the body adding to the dramatic effect. A-line skirts require a different jacket or none at all. Black pants will work as well. Chances are you have a few pairs in your wardrobe already.

How about shoes? Knee length skirts work best with knee length boots. Avoid ankle boots, though in a pinch tights can help bridge the distance between the top of the ankle boots and the bottom of the skirt. Heels work with skirts as well, I chose a feminine pair with a pearl detail to balance the masculine feel of the pinstripes. These shoes will work with trousers too. Match shoes to the color of your pants to minimize contrast.

Accessories are the simplest way to change the look and feel of an outfit. I chose to add visual interest with a contrasting tote bag. An all black clutch for evening keeps the looks simple and classic. There is room to play here. A colorful bag can make a statement and create visual interest as well.

Jewelry is best kept simple for a classic look. Like your bags and shoes, jewelry is a way to personalize a look. Wear what you already have and love. A necklace will add interest to an open neckline. A watch band can add a pop of color. There is room to play here.

Creating a digital lookbook will help you visualize how all of the pieces will fit together. The biggest mistake my clients make is shopping piecemeal. Start with a vision of how you want to look and choose pieces that will give you the feeling you desire. The exact number of pieces and outfits you need may vary. Be flexible. Start small. You can expand your wardrobe over time by building off your current capsule collection.

Who looks best in this style?

Black and white outfits are high contrast and best suit those with high contrast between their hair, skin, and eyes. Black hair and light skin is one example. This is why Audrey Hepburn always looked so good in black and white. That doesn’t mean if your natural coloring is different you can’t wear this look, but it may mean that you don’t feel quite like yourself in it. What can you do? Try lowering the contrast by selecting black or gray tops to go with your dark pinstripe suit. If you wish to make a statement, choose a bag in lighter (contrasting) shade. Another option is to choose a pinstripe suit in a light color, such as navy or gray.

Get this look

Find shopping links here. Or create your own signature look using my free workbook. It's easier than you think.

Prefer a done for you solution? I create lookbooks for my clients through my wardrobe makeover package. Learn more.

What would you like to see next?

What kind of capsule would you like to see next? Subscribers can send inspo images for a chance to be selected for the next seasonal capsule. Whether you love denim on denim, coastal grandmother, or quiet luxury, I will select one subscriber and turn their inspo images into a shoppable capsule wardrobe that goes out to my subscribers. Sign up now, you could be next!