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The 2020 Guide to the Classic High-Top Converse

This article is written by a student writer from the Her Campus at McMaster chapter.

When was the last time you owned a pair of high-top Converse? Was it in middle school? High school? With the rising popularity of sneakers like ‘Vans Old Skool’ and ‘Nike Air Force 1’, Converse are rare to be seen on the street. And, it seems like Converse have dropped to the bottom of the shopping list when it comes to sneakers. With a little bit of time still left before boots season, consider digging out this timeless piece from your closet, or get a pair for yourself to spice up your look! Continue reading for some autumn-appropriate styling ideas
 and please make the Converse/skinny jean combo your last resort.

The chic cropped trousers

You can never go wrong with the perfect pair of cropped trousers, where the hem just brushes the top of your high-top Converse. The shoes can instantly elevate your entire outfit with its clean and simple design, and the slim engineering of the shoe elongates the legs and creates a taller illusion. Black trousers, white crew socks and black high-top Converse is classic. But if you are someone who likes to play around with different colours, definitely go for that colour contrasting look to make the whole outfit more interesting. When you are styling your socks, I recommend trousers that go slightly above them, so that you are showing them off!

The vintage 90s jeans

Everyone knows the Converse and jeans combination, but by hopping on the 90s baggy jeans trend, a classic look is elevated. The whole outfit gives off a vintage vibe, as the jeans sit on top of the shoes. If you want to see more of the shoe’s high-top detail, or you think they are hard to pull off, don’t be afraid to cuff them to your liking!

The playful midi-skirt

Since it is getting chilly outside (autumn has entered the chat), you can’t really style high top Converse with your summery mini-skirt and short dress. Instead, opt for a midi skirt which keeps you warm, but still shows the detail of your shoes. The high-top Converse perfectly balances out the feminine feel of the skirt and makes the entire outfit a little more dressed down, suitable for everyday wear. You can even play around with the texture of the skirt; corduroy and leather are both great options as they give off a heavier feel that is very appropriate for the cooler weather. You can also pair them with some colourful crew socks like we did with the trousers to add a bit of character to your overall fit, and most importantly, to keep your feet warm!

The oversized sweatpants 

What else is better other than throwing on a pair of comfy sweatpants during this cold weather? The relaxed feel of sweatpants matches perfectly with the simple and casual high-top Converse. The baggy fit of the sweats balances perfectly with the narrow shoes, which allow the bottom half of the outfit to appear less heavy. As for socks, you can either cover them up or you can pull them over the pants to give it a sportier look.  

The funky overalls 

Overalls are a great option when you are in a hurry and don’t know what to wear. They are easy to throw on without having to put too much effort and thought into a full, cohesive look. Remember that you aren’t limited to simply denim overalls! Many of us are very familiar with denim, so why not pick something different? Again, corduroy and chino cloth are excellent alternatives with lots of colours that can add a fresh twist to your outfit. Depending on the material you pick, it can make the overall look less casual and more sophisticated.

Remember, if you are uncomfortable with styling too many colours, always go for the neutrals; they give you the most freedom during other parts of styling. You’re definitely not limited to the Converse examples I have shown above. There are endless options to choose from in the Converse world and I’m sure there’s that one ultimate pair that screams your name!

Catherine Yu

McMaster '23

Catherine is a fourth-year McMaster student majoring in Kinesiology. Outside of school, she loves to sing, dance, and go on hikes with friends and family! You will often catch her at the candy aisle in the grocery store.