Four Winter-to-Spring Transition Items Can Get Now

By: Peter Nguyen
Last Updated: February 24, 2022

February is always a tricky period when it comes to wardrobes.

Spring items are slowly trickling in, but it’s still freezing out. So the question is: Do you hold out on shopping til Spring?

I mean, the last thing you want is to pick up a beautiful coat or jacket to help you brave the winter weather that you can only wear for a few weeks.

Luckily there’s another solution: here are some winter pieces you can pick up now that you can wear deep into Spring.

01. The Classic Sweatshirt

The sweatshirt is a closet essential, and the end of winter is the perfect one to pick one up to add to your wardrobe. It’s a great casual layering piece you can throw under a coat when it’s chilly out. As the weather warms up, it’s a piece that works well on its own.

How to buy the right transitional sweatshirt: If this is your first one, I recommend a classic grey. If you already own one in grey, look for colors like a dark navy or denim blue for a pop of color as you get into Spring.

Where to buy:

How to wear a classic sweatshirt in Winter then Spring:

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In Winter: The classic sweatshirt is on the lighter side in terms of long sleeves, so it’s best used as a layering piece in the winter. I’d recommend adding extra accessories to not just add more warmth but color – like a multi-colored scarf.

In Spring: Nix the coat and swap in shorts and sneakers in place of your wool pants and you got a Spring ready look. When things warm up more, you can even omit the tee and wear the sweatshirt as a solo top. If you want to avoid blisters and smelly feet, don’t forget the invisible no-show socks.

02. The Denim Jacket

Denim jackets are often associating with Spring Summer, but they actually make a great layering piece in colder months as seen below on Daniel Craig. On cold days they look great over knit sweaters. When it’s freezing, button your denim jacket up underneath an overcoat to add a additional layer to block out the wind.

How to buy the right transitional denim jacket: Avoid Fall/winter denim jackets that are lined and look for something unlined.

Denim blue is the traditional color. Medium to light blues are more casual, while darker indigo (raw) are less casual and versatile.

Where to buy:

How to wear a denim jacket in Winter then Spring:

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In Winter: Take a cue from Bond and make your denim jacket a surprising layering piece under your winter coat. Here I bumped up the dressiness of the look by swapping in an oxford in place of the tee. Cords give this look a cozy winter texture, while hiking boots play up the rugged vibe of denim jackets.

In Spring: Here’s a Spring variation of the Winter look. Notice how the color palette is near identical, but our choices in the pieces changes the mood. The henley is more Spring appropriate and casual, while the choice of chinos and desert boots dresses up the look. A great “grown-man” alternative to a denim jacket and tee outfit.

03. The Harrington Jacket

I don’t think the Harrington jacket get’s enough love. It’s the iconic jacket James Dean wore in Rebel Without a Cause. And while I don’t recommend getting it in red (you’ll look like you’re trying too hard), a navy one is hard to beat when it comes to versatility and ease to wear. If you love the bomber style jacket but find it’s a little too casual for your taste (or age), I suggest trying out the Harrington.

How to buy the right transitional Harrington jacket: Harrington’s are often lined, which makes it a solid choice for winter over a wool or cashmere sweater. The linings usually aren’t heavy, which makes them perfect to wear over a tee in Spring.

When it comes color, as I mentioned above, go with a navy, black, or dark neutral color.

Where to buy:

How to wear a Harrington jacket in Winter then Spring:

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In Winter: A thick knit sweater under a lined Harrington will offer you solid protection against the Winter chill. The Harrington’s clean aesthetic can sometimes come off as visually flat, so adding texture in areas like your top, pants (here done with corduroy), and accessories like scarves and shoes are recommended.

In Spring: The key to pulling off a dark aesthetic in Spring is paying attention to your fabric weight and colors. A light airy polo unbuttoned lets your neck and chest breath. Mixing in shades of black and dark greys give your look some depth and prevent you from looking like a black hole.

04. The Leather Jacket

The best time to get a leather jacket is October when the weather starts cooling down. The second best time is right now! We often think of leather jackets thrown over tee shirts and jeans, but leather jackets are one of my favorite pieces to layer in the winter. I love wearing them over a long-sleeve button-up and under a coat. It adds a perfect insulating layer and gives your look some nice visual texture.

How to buy the right transitional leather jacket: Avoid buying winter level leather jackets, like padded bombers. Go for something more all season, like a cafe racer or double rider with light or removable lining.

When it comes to what color to buy, black and brown are the most versatile. If you’re having a hard time picking between black or brown, take a look at your shoes. If you own mostly black leather shoes, go with black. If most of your leather shoes like boots and loafers are brown, go with brown.

For more tips on buying a leather jacket, check out my post “How to buy your first leather jacket.”

Where to buy:

How to wear a leather jacket in Winter then Spring:

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In Winter: If you’ve ever thrown a puffer under your coat and wished for something a little bit cooler, the leather jacket is here to answer your prayers. The key to avoiding the depressing winter greys is to vary the shades and add a pop of color. Since the backdrop is already dark, your pop doesn’t need to be bright. I threw in a beautiful camel colored cashmere long sleeve which adds a shot of color and ridiculously warmth without a ton of bulk.

In Spring: How can you go wrong with this classic leather, denim, and tee look? I’ve made a few subtle upgrades, and I recommend you consider them if you’re planning to add this look to your repertoire. I’ve always found a crisp white tee in these looks too blinding. Opt for an off-white top to lower the contrast a bit and give it more of a vintage feel. Guys will often instinctively reach for sneakers like Converse Hi-tops with this casual look. I say go for an easy boot like a slip-on Chelsea boot to stand out from the pack and make this look a bit more mature.

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