How To Wear Sneakers Stylishly In Winter – 3 Easy Tips

Ever wonder how to wear sneakers stylishly in Winter? Me too!

We all have people we look to for style inspiration – whether that’s in a movie, tv show or someone’s street style. My biggest style icon of all time, hands down, is Katie Holmes. She makes everything look effortlessly cool and chic. She doesn’t follow every trend but dabbles in certain ones, and without even trying starts them.

When trying to figure how how to wear sneakers stylishly in Winter – particularly the chunkier ones that are more and more in fashion – she was naturally the first place I looked. And I was shocked to find she was sporting an under $100 pair that are still fully stocked.

The Saucony Jazz Original Sneakers

Wearing the Saucony original jazz sneakers in grey and silver with gray socks. Saucony Originals in Grey/Silver (1/2 size up)

Naturally after seeing pictures of Katie Holmes wearing these I was intrigued enough to order them. Especially considering they are under $100! Well, let me tell you – I am fully obsessed with this sneaker.

These things are like walking on clouds they’re so comfortable. And the grey/silver color way is pure perfection. They look good with black, denim, camel – everything. The lighter color makes them feel fresh and Spring-forward but because they are monochrome and subtle they don’t compete with your outfit. But don’t get me wrong, they aren’t boring. The metallic silver detail elevates them and makes them super special.

They do run short! I suggest going up 1/2 size. I ordered them from Zappos, free expedited shipping and super easy returns if you get the size wrong. But I think you’ll be happy as long as you size up.

So now that we have a seriously cool and affordable pair of sneakers, let’s talk about how to wear sneakers stylishly in Winter…


How To Wear Sneakers Stylishly In Winter –
3 Easy Tips!

Coat (TTS) | Tee (similar) | Jeans (same cut, new wash) | Socks | Sneakers (1/2 size up)

 

(1) How To Wear Sneakers Stylishly In Winter:
Don’t Overthink It

Seriously – don’t overthink it. These days, sneakers are acceptable to wear with just about anything. And the juxtaposition of a fancy piece with sneakers is uber stylish. One of the amazing things about fashion these days is that most of the “rules” have been thrown out the window. So, you do you, and if you’re feeling sneakers with a fancy skirt, dress or trousers. Go for it!

(2) How To Wear Sneakers Stylishly In Winter:
Add Contrast

Coat (TTS) | Tee (similar) | Jeans (same cut, new wash) | Socks | Sneakers (1/2 size up)

 

Probably my #1 fashion trick that I use every.single.day is contrast. It’s what makes an outfit fun, unexpected and edgy. In this particular outfit I’m showing contrast in two ways.

First, I threw a camel coat over a very basic jeans, tee and sneakers outfit. The refined coat and sneakers are in contrast and make this outfit surprisingly chic. Had I paired this with a more casual coat, it would have been fine but the whole vibe would have been different. Two, the grey/silver sneakers contrast in color with the camel coat also adding interest.

(3) How To Wear Sneakers Stylishly In Winter:
The Tricky Part

I think what makes sneakers particularly tricky in the Winter months is socks. If your jeans or pants are long enough to cover your socks, this is a non-issue. But if they peek out at all…what color should they be?? It can be confusing! There are three ways to go here…

The Two Safest Bets

Saucony Originals in Grey/Silver (1/2 size up)

The two safest bets when it comes to socks with sneakers are to (1) match your socks to your sneakers or (2) match your socks to your pants. And don’t fret, this doesn’t need to be exact – just in the same wheel house.

Above, you can see I paired grey socks with these sneakers when I was wearing a lighter wash denim. The socks blend seamlessly with the sneakers and because they’re lighter also don’t compete with my jeans. This is a win and super easy.

The second easy option is to match your socks to your pants. In the above picture, you see that Katie Holmes is wearing a mid-wash denim with either a dark navy or black sock. Because her jeans are darker this totally works. And in this case, makes the sneaks shine even more.

If you’re wearing a black pant you can really go either way here!

Or Go Bold

Katie Holmes showing how to wear sneakers stylishly with pink socks and a floral blouse.

Saucony Originals in Grey/Silver (1/2 size up)

Here, Katie is wearing pink socks with the same Saucony sneakers – a bold choice! If you look closely you can see there is pink running thru her blouse which ties it all together and makes it work. If you’re looking for a way to make a statement with your socks, this is a great example and easy to replicate.


In Conclusion

So, how to stylishly wear sneakers in Winter…Don’t overthink it, and just have fun! Really anything goes these days so experiment. And add some contrast – always! The hardest part of styling sneakers in Winter is those pesky socks, and I hope this article helps clear that up. If you’re looking for a new pair of sneaks, I seriously love these Sauconys. Or check out this article detailing the 2022 sneaker trends, if you’re curious!

And if you are a black Converse fan (or think you’d might like to try them) check out this article on how to style black Converse!

x Rachel


How To Wear Sneakers Stylishly In Winter
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How to wear sneakers stylishly in winter - a simple and chic style board.

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