How to Style Old Skool Vans

Old Skool Vans are a classic style of shoe that looks great with almost anything. Whether you want something simple to match with the classic black and white Old Skool shoe, or you’ve got some Vans in a brighter color that you need to style, there’s a way to look amazing and show them off. Find a few different styles that you can build around your Old Skool Vans for any occasion.

Method 1

Method 1 of 4:

Choosing Pants or Skirts

1
Wear a pair of jeans for a casual yet classic look. Jeans are a great and comfortable starter for almost any casual outfit. Throw on a pair of dark jeans with some black and white Vans to start off a skater look, or try some classic blue jeans for a more retro look. Find some jeans that fit you well and that you find comfortable.^{[1]XResearch source}
- Your pants do not need to be a focal point of the outfit. Keep them simple, so you can draw attention to the Old Skools and your shirt.
- Try cuffing your jeans to show off your shoes a little more and keep them as the main part of your style.
- If you’re wearing shoes in a brighter color, you may need to match them with a different color of jeans. Paler shoes can be matched well with beige or gray pants. Shoes in a vibrant color will look good with jeans that are slightly darker in color.
- If you want a more feminine look, try wearing a light blue denim skirt instead.
2
Try some chinos for a slightly more formal look. Chinos are similar to jeans in the way that you can dress them up or down by changing the rest of your outfit. For something a little more formal, wear some darker, dressier chinos with some dark Vans. If you want a more casual look, pick some chinos in a brighter color that go well with your Old Skools.^{[2]XResearch source}
- Avoid cuffing your pants when aiming for a formal look. Your shoes should be a part of the outfit, rather than something you’re showing off.
3
Pair some dark dress pants with monochrome Vans for a formal look. Your pants should be simple so as not to draw too much attention or be too flashy. Choose a pair of well-fitted pants in a dark color, such as black, dark gray, or even dark blue. Match your pants with your shoes to keep your lower body formal.^{[3]XResearch source}
- Avoid cuffing your pants when aiming for a formal look. Your shoes should be a part of the outfit, rather than something you’re showing off.
- If you want a more feminine look, swap the pants or chinos for a pencil skirt in a dark color.
- Make sure to match your belt to your shoes. Stick with black belts for black and blue shoes, and pair brown shoes with a brown belt.
4
Throw on a skirt for a casual, cooler look. Almost any knee-length skirt will match excellently with a pair of classic Old Skool Vans. Choose something bright, vibrant, or patterned to match the color of your shoes. Alternately, keep your skirt more muted if you want your shirt or accessories to take center stage.^{[4]XResearch source}
- As everything goes with black and white Vans, choose a skirt that fits well, is comfortable to wear, and that you like the look of. It’s very difficult to go wrong!
- If you want a more masculine look, try a pair of shorts instead of a skirt.
- Making socks look good with a skirt or pair of shorts can be very difficult to do. Try wear low-cut socks that won’t draw too much attention, or even try wearing your Vans without socks at all.
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Method 2

Method 2 of 4:

Selecting a Shirt

1
Bring a pop of color to your outfit with a graphic shirt. While you won’t find anything more classic to the skater look than a Thrasher top, any colorful T-shirt with a graphic on it will allow you to customize your look to make it your own. Choose a bright shirt that contrasts with the rest of the outfit and that has a large graphic to break the outfit up a little.^{[5]XResearch source}
- A T-shirt in a single block color will normally be a little too minimalist for the skater style. Choose something with the logo of a brand or band that you like to make the look a little more interesting.
2
Match a T-shirt with the color of your shoes to keep your outfit classic. Pairing the color of your shoes with the color of your shirt will start to tie the look together and keep a classic aesthetic. Pick a T-shirt in a block color that matches or complements the color of your Old Skools.^{[6]XResearch source}
- To make the shirt a little more interesting, pick something with a simple graphic on the front. Keep the graphic low-key so as not to overcrowd your outfit with patterns.
3
Choose a button-up shirt in a light or pale color for a formal look. A clean and well-pressed button-up shirt can make any outfit look a little more formal. Go with a plain white shirt to keep your outfit mostly monochromatic and very formal. Stick to pastels and light shades if you want to add some color. Light blues, purples, and pinks can all add a little personality without dominating the outfit.^{[7]XResearch source}
- Make sure your shirt is ironed or pressed. A wrinkled shirt will make your outfit look far less formal.
- A lightly patterned shirt can also work but it will be more difficult to accessorize with.
4
Contrast your shirt with your shorts or a skirt for a more summery outfit. If you went for a brightly-colored pair of shorts or a skirt, stick with a light-colored, pastel, or even white shirt to balance out your style. Alternately, if your shorts or skirt is a little more muted, add a bright pop of color with a vibrant t-shirt or blouse.^{[8]XResearch source}
- Avoid matching the color of your shirt with the color of your shorts or skirt, as this will normally make your outfit blend together a little too much. If you opt for an outfit that’s all 1 color, pick a shirt, skirt, or pair of shorts that are patterned in some way to break it up a little.
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Method 3

Method 3 of 4:

Layering Your Outfit

1
Throw on a baggy hoodie or jacket for a classic skater look. A loose yet warm hoodie or jacket will add some layers to your outfit, as well as keeping you warmer. Pick something that matches with your shoes and throw it on to complete your look.^{[9]XResearch source}
- Try to match a jacket, hoodie, or even a flannel with the main color of your shoes. It might take a little trial and error to get this looking exactly right with your shirt, but it’ll tie your whole outfit together if you can make it work.
- Anything will go with black and white Old Skool Vans. Pick something comfortable that you think looks good.
2
Wear a cardigan or leather jacket to for a retro-casual style. If you want to keep your style a little more casual, add a leather jacket or a coat in a neutral color to complement your t-shirt. For something a little more formal, try a cardigan that’s light gray or beige to add some layers to your look.^{[10]XResearch source}
- Rather than matching your shirt to your shoes and adding a more neutral layer over the top, you could keep your shirt neutral and add a brighter cardigan or jacket that matches your shoes for a more vibrant yet classic style.
3
Add a blazer or coat to keep your outfit classy. Wear a full suit by matching a blazer to your pants if you want to look as formal as possible. For something a little less formal, try contrasting a light gray or blue blazer with your darker pants. Alternately, wear a dark trenchcoat or winter jacket to stay warm yet formal.^{[11]XResearch source}
- Make sure that your blazer is fitted properly. A poorly fitted blazer will normally look less formal than not wearing a blazer at all.
- To take your look to another level, wear a waistcoat to make a full 3-piece suit.
- Stick to fleece or woolen trench coats rather than thinner rain jacket type coats.
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Method 4

Method 4 of 4:

Accessorizing Your Outfit

1
Try a snapback cap or a beanie. If you want to add a little more personality to your outfit, accessorize with a snapback or loose beanie that you like the look of. Either match your hat to your shoes, contrast it with your shirt or hoodie, or pick something that’ll stand out and catch the eye.^{[12]XResearch source}
- A neutral color beanie will work well with almost any outfit.
- Make sure the snapback you choose doesn’t clash too much with your shirt. Too many colors and patterns might go beyond eye-catching and become grating or difficult to look at.
A nice watch, a leather satchel, or a sophisticated handbag can help make any outfit a little bit more formal. Try pairing 1 or 2 classy accessories with your outfit to dress it up slightly.^{[13]XResearch source}
Pairing a good pair of sunglasses with a formal or classic outfit can make you look a little more laidback and cool. Choose a simple pair of sunglasses, so as not to outshine the rest of your outfit, and throw them on whenever you want to dress your look down slightly.^{[14]XResearch source}
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Tips

Old Skool Vans will look good with almost anything! Try mixing and matching different items of clothing and see if you can find your own style that you like.
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Old Skool Vans have a thick sole and low tops, giving them their classic plimsoll style.
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Old Skools were the first to pioneer the Sidestripe or “Jazz Stripe” that’s now an iconic part of the Vans aesthetic.
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