Styling Tip – Footwear and Skinny Jeans

Skinny jeans have long been a polarising piece within menswear, yet over the years they have become firmly entrenched within many style-conscious gent's wardrobes. We explore the different types of men's skinny jeans on the current market while showing you how to wear them in a variety of new and contemporary ways for /

A big no-no is crew socks of any colour. Hi Tushar, You can definitely wear sneakers with light blue denim. Warm and cool colours generally do not mix.

Shoes to Wear With Skinny Jeans Now the rule with skinny jeans is simple – if your jeans are super tight then your shoes can’t be too chunky. If your footwear is too big then your outfit will be out of proportion and it will look like you’ve got clown feet – not ideal.
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Skinny jeans have long been a polarising piece within menswear, yet over the years they have become firmly entrenched within many style-conscious gent's wardrobes. We explore the different types of men's skinny jeans on the current market while showing you how to wear them in a variety of new and contemporary ways for /
Try to find a pair of jeans that are slimming but not too tight, skinny jeans will look disproportionate with a bigger style of shoe. Any wash can work well with boots—they can be dressed up with a dark wash, or dressed down with a faded or distressed style.
In general, shoes that look best with skinny jeans mimic or compliment the style of the jeans; lean and lacking bulk. Shoes/sneakers should have a slim profile; not have a bulky sole structure or be bulked up with excessive ankle padding or heavy construction.
The Best Toe Shapes

Chelsea boots have a solid pedigree and date back to the Victorian era [the mids]. These boots come in both plain and suede leather. Both are business-appropriate men’s shoes to wear with jeans. Chelsea boots are higher than Chukkas and Desert boots – which we’ll get to in a bit.

To cap it all off most styles are also fairly slim lined, so you avoid the possibility of your feet looking oversized or clown like. Perhaps more suited to summer usage than in the colder months, they still provide a great casual alternative to plimsolls or lo tops.

Obviously, smarter footwear is not the only style you can use with skinny jeans. Hi tops have come back in a big way in the last couple of seasons and they are a great way to inject a bit of colour and individuality into an outfit. Because of their size and tendency to be made in very vibrant colours they immediately become the focal point of any look, made all the more evident because of the clash between slim legs and chunky feet. What you have to decide is how chunky and loud you want them to be — would you like to create a contrast of styles or retain a pretty slim lined look all the way through?

Generally the offerings from Adidas and Nike are fairly substantial and use bright colours, a clear influence of the basketball background. While Puma and the smaller brands tend to use slimmer lines and more subtle colours I also own the green and white pair from Puma shown below.

Whatever style you go for, try not to do them all the way up and push your jeans down inside the shoe, this helps with the stacking problem and helps retain the skinny profile of the jeans. Use them in your casual outfits or use with more tailored items such as blazers and cardigans for a more sophisticated and fun look. Here we have a good footwear choice for those new to the world of skinny jeans.

Low profile trainers offer the casual, everyday element of informal shoes as well as the ability to be dressed up for a night out. I would suggest sticking to very simple, clean styles in basic colours, because they will be the most transitional, offering you complete versatility and a way of easily incorporating them into almost any outfit. You can of course use them to add some colour to an outfit, in which case Adidas superstars offer a classic style with a lot of colour variation.

I wish to make it clear now that this is certainly not a comprehensive and exhaustive list. As I mentioned earlier, you can wear almost any style of shoe you like with skinny jeans , you just have to tailor your choice to the overall style you are trying to achieve. Just remember, the correct selection of jeans will make a big difference to how good or bad a shoe looks. Spend a little bit more money and time on getting the right pair of jeans and the shoes should follow.

Get all the latest must-read FashionBeans content direct to your inbox weekly:. See all the latest vouchers, discount codes and offers from all your favourite stores for October By Will Colman 29 November The Pointy Shoe Apologies for any lack of clarity in the sub heading, but you get what I mean. Since dark blue jeans are in a neutral colour, they can be worn with almost any shoe colour. This means that the real question is:.

You can learn more about colour matching in my style course. What do you think of dark blue jeans with yellow Onitsuka Tiger M66? Usually I wear my dark brown blundstone with dark blue jeans, but would like a lighter shoe. They are everything a classic sneaker should be and would look great with dark blue jeans and a top or jacket from the autumn or spring seasonal palette.

You can learn more about the seasonal palettes in Style Genesis. Could they work with dark denim or is it still a no-go? Black Chelsea boots sound great. I found this guide really helpful and those sliders showing 2 different images are really helpful on the visualisation part! I have this pair of DC sneakers; metallic grey all round and maroon at the back of the heel area.

I was contemplating on getting a faded sky blue sort of jeans, any thoughts? At the moment, my grey Vans are my lifeline yes I made a wrong move in getting the DC. Basically, all pants colours from the Summer colour palette would match your shoes. To learn more about which colours you can choose between, check out my style course. Normally I would say get the black Derbies, however in this instance, I think that they Chukkas would probably be a better choice. The reason for saying so is because of the half zip polo, which is considered fairly casual like the Chukkas.

It would therefore look better together with your Chukkas than if you wore it with a pair of black Derbies. Who makes the casual boots in the picture above? Red Wing makes them. I just purchased a nice pair of dark blue Lucky Brand Slim fit jeans. Any recommendations for style? I know how exactly how you feel.

The trick with denim that is tapered, is to wear them with shoes that are small and light. Otherwise, they can look out of proportion with the tapering on your jeans. It is the same with your upper body. Try wearing something light and not too bulky. A simple t-shirt or dress shirt works really good, and you can always top it off with a blazer or leather jacket.

Good shoes to wear with jeans that are tapered more than usual are moccasins, loafers, sneakers, and boat shoes. Hi Vegard, Nice article you have here,very informative. Can you please let me know what brand, color, and model are the pair of shoes in this link:. Will a pair of white sneakers go with dark blue denim, navy blue chinos, beige color chinos, or black denims …. White sneakers will go with dark blue, navy blue, and black pants. However, white is not ideal for beige ivory and oyster white are better options for beige pants.

Regarding your sneaker colour, it depends on your seasonal colour palette and the rest of your outfit. Winters look good with black sneakers Summers look good with grey sneakers Springs look good with light brown sneakers Autumns look good with brown sneakers. To learn more about which colour you look best in, check out my style course here. Hi, I have Blue, Indigo and Black solid jeans. Could you suggest what color of sneakers would match best with each of the color irrespective of the color of the top?

Since blue, indigo, and black are all fairly neutral colours I would simply have chosen a pair of black sneakers to go with all of them. Hi, I really liked your article.

I have a casual dress code at work, and I sometimes wear black jeans to work. I recently bought Nike red sneakers , pretty standard but not too bright.

I like the comfortability of the shoe, but I just feel awkward wearing a red shoe even with black, as I always have worn black dress and darker casual shoes. Since you have a casual dress code at work, you are free to wear pretty much whatever you want, which raises the question:. Since you are pondering over whether or not your red sneakers is right, may it be that you would have felt more confident if you had opted for a darker sneaker colour?

I have Red Tape tan leather shoes. Can I wear it with blue PE tapered jeans? However, since your blazer is light blue, another pants colour that would look great with that outfit would be dark greys.

Red shirt and black tennis shoes are no problem. With a pair of black, dark blue, or charcoal grey pants this will look really good. Here, I got to know about classic sneakers and canvas loafers, shoes I wear every day. I am still confused in slim jeans and skinny jeans. I like your article and I am going to subscribe as well.

You are by far not the first. When I started reading up on footwear back in the early s, I was so confused, because stores I visited and books I read, all had own names for the different types of shoes and boots. I am so glad I found this website!!! My husband is having some kind of identity crisis and decided to go o line and buy two pairs of super fancy shoes… one was a pair of Brogues, and the other pair was grey-ish lace up dress shoes.

They are so long and remind me of clown shoes! He walked out of the bedroom with a baseball cap, baggy jeans, a casual sweater with t-shirt underneath and the fanciest shoes I have ever seen! He was on his way to volunteer at the school, and I simply could NOT let him think he looked good. I then sent him lots of photos of how his outfit should have looked. Needless to say, I will now be investing in a full-length mirror!!!

I like him just the way he is, knows how to dress up when the occasion calls for it, but still my Mountain boy at heart!! He can wear his hiking boots every day, and be better off than he was yesterday!!

If the answers is a yes, which colour of shoes would go with the above denims? Yellow, blue or black? Yes, you can definitely wear a pair of Pharrell Adidas X Human Race sneakers with your denim on casual occasions. For dark blue and dirty wash blue coloured denim I would have chosen yellow or black. The blue sneakers would probably look better on lighter types of denim, not the dark blue ones that you have. The only thing to keep in mind is that light dress shoe colours are best reserved for daytime wear.

Dark dress shoe colours, on the other hand, can be worn both at day and night. I usually wear plain black tapered jeans. Do you think it is a good combination? Also, what outfit do you reckon would suit a pair of light grey low cut VANS sneakers? On another note, I would like to thank you for this extremely informative, clear and useful article.

It is a wonderful guide for people including myself: Dark grey sneakers is a good combination with black tapered jeans, as long as the occasion is right for it.

My go-to classic sneakers outfit that I wear all the time consists of: With grey sneakers, I would have worn a light grey pair of jeans, an off-white, pink, or red top, and a dark grey leather jacket. I have a pair of black shoes not Oxfords and a pair of dark blue jeans. What color of shirt or T-shirt should I wear with these two? Black dress shoes and jeans are one of the most versatile and good looking jeans combos out there.

I say wear a t-shirt in your seasons white because white is super easy to layer, which means you can wear whatever jacket you want over it. How about closed lacing brogues? I have seen quite a few of them in the stores. Are they considered too dressy for jeans?

You are absolutely right. Checkered shirt and dark blue straight denim with dark brown boots, looks good with sued watch and retro wayfarer. Your outfit sounds good looking. I would definitively go for the grey Brogues, especially since your blazer is mid-grey. As for pants and shirt colours, I would have picked the light blue dress shirt and paired it with your mid blue jeans. Pair them with any of your jeans and the black dress shoes for a great look.

This is perfect for occasions where you want to seem less serious, such as when barhopping with friends or watching a movie at the cinema. You might consider two very appealing combos: Both boot types are masculine, both are interesting, though neither work particularly well with a tie.

Open neck button down shirt works best. Instead of tan, I would try finding shoes that are grey or taupe grey-beige. Will a pair of white sneakers go with dark blue denim , navy blue chinos , beige color chinos or black denims… And which color sneaker should i go for, to pair with dark or light shaded denims? For beige pants, I would wear brown, navy, or cordovan brown-red sneakers. Which type of sneakers you should wear with light and dark shaded denim, depends on which season you are.

Can sandals like these be worn with jeans? My 2 reasons for never wearing sandals with jeans are: For a classic combo like that you can wear almost any type of the footwear mentioned in this article. However, since it sounds like a daytime outfit because of the light pants I would have opted for a slip-on shoe in black like your blazer.

Would it be nice if i match a pair of blue jeans with a pair of brown derby. And also what is your suggestion for top that match with blue jeans Thanks. I always wanted to wear them together with my brown quarter brogue leather shoes. I teach at K level so running behind kids is all in a days work. I like the Brogue and the Derbie shoes, with the open lacing option, my only worry is how comfortable they would be and where best to buy them from in India?

I did find some option online, but for shoes I must try them out before buying. If you can get hold of any of these brands or a brand similar you should be just fine! What brand is that? With black footwear and black jeans, I would have opted for a navy, black, or charcoal coloured blazer with black buttons. With red loafers, I would have chosen a winter colour for my clothes. I would say that depends. If the dress code is rather casual I say go for them. I was going to wear black jeans with a brown slip on leather shoe… but thankfully your advice helped me out.

I really appreciate it! Sir my height was 5. If the shoes are in a rich blue colour, they could definitely be paired with brown pants. I have a dark grey wool blazer and a dark blue jeans. Will brown coloured chukka boots go well with them this outfit? From where I stand, it seems that navy or grey chukka boots would be a better option. I say that because they will probably match your grey blazer better than a pair of brown boots.

Can I wear these with jeans and if I can, what colour of jeans? The dark brown colour of those shoes would look great with dark washed jeans in a deep rich blue colour. I have always loved the look of converse ever since I was in high school, and I am hooked. I always wear the high tops, and lace them as tight as I can. The high-tops do look awesome. I usually wear slim not skinny fit denims, but I am confused about the colour. Would grey look good? Grey sneakers also look great with dark washed and light denim.

I bought a pair of shoes similar to the derbies in this article and the tip is a bit high. How high should the tip of the shoes bee? I understand what you mean. If you feel that your shoes look weird or have a very high tip, I suggest getting a pair with a lower tip especially for business and formal occasion.

I have a pair of loafers dark navy blue , can I pair them with jeans or khakis? What color shoild I use? Thanks in advance and very informative site. Navy blue loafers can be worn with any jeans colour of your choice black, dark, grey, and white.

You can also wear them with chinos in any cool colour. Regarding socks, I always like to go barefoot in loafers, but sneaker socks are a great alternative. A big no-no is crew socks of any colour. As you said about adjusting the length of jeans, do you usually cut it off or do some other adjustments? I am bit uncomfortable on the cutting off part , it could hamper the overall look and feel of the jean.

I was also looking to buy a pair of grey sneakers. I used to own a pair of dark brown ones. Wanted to know what are the possible jean color combinations for gray sneakers. Posting the link for your reference:. Yes, my shoemaker or tailor usually cut off the excess fabric when I hem the jeans.

Regarding the grey pants, as long as you stay clear of black and pure white jeans, you should be good! I want something that is casual but looks nice with button-up shirts or t-shirts. Great site by the way! I like desert boots a lot, and it happens I have a dark blue one. Any idea on what kind of jeans to wear with it? Ah, desert boots are great! I am glad that I found you, your guideline really helps. My suggestion is that you post more fashion samples so that people can follow the guide more easily eg: For suede navy shoes here are three combos I think looks nice: Navy shoes, grey pants, pink shirt.

Navy shoes, black pants, light blue shirt. Navy shoes, navy pants, red shirt. That depends on the green. Is it a warm green green with yellow undertone or is it a cool green green with blue undertone? Last time I just forgot to ask you that what color jeans or shorts I should wear below my white polo shirt? It has orange and dark blue stripes on it.

Also what shoes do I wear with it. Since the orange in you polos stripes is a warm colour, I would have worn the polo with denim in a colour from the autumn palette rich dark blue.

As for your shoes. You can learn more about colour in my style course. Check it out here. I have a pair of dark washed jeans and a pair of tan double monkstrap leather shoes. The tan color is light, not wood brown. Light tan shoes almost beige can suit dark washed jeans really nicely. All you have to remember is to wear a jacket, shirt, or top that is equally light.

That way you will balance out the contrast between your shoes and jeans. Hi, I bought a trendy red v-neck, the red is not too bright. What kind of shoes and color will go safe with it if I wear dark jeans?

But i cant figure out what type are these shoes which i just bought recently http: I bought them bec theyre comfortable to wear but i dont exactly know what pants should i wear. I tried it with denim and and as per my subjective feeling, they look great. But can i wear them casually? What other pants should i wear to match these boots? How about shirt or tshirt colour? Can i wear them in formal ocassions i. Weddings or corporate meetings? If yes, what suit and shirt colours should they match?

I would call them ankle-high Chelsea boots. I would wear them with denims, chinos, trousers, and suits. When pairing them with denims and chinos the look is rather casual, however, they can be dressed up as well. Just pair them with trousers and suits and wear them to dressy occasion and corporate events.

Olive green, rust red, and camel are great choices. I just bought these pair of boots: I like the style and the colour so I purchased them. But can these be paired with denim? How about in more formal occasions like weddings or corporate meetings? This rich brown colour is best paired with denims in a deep rich blue colour not light or black denim. The same goes for weddings and corporate meetings. Which colour should I go for? Will brown be all right? Since brown is a warm colour and black is a cool colour, those two colours clash not good.

I would, therefore, wear light blue and black jeans with red, dark red, and navy shoes, in addition to the black of course. What do you think about wearing Twisted X Cow Dog boots? Also I like wearing Doc Martin dress combat boots. Martens boots are both great casual shoes.

So if I were to wear them, I would only do so on casual occasions. If the occasion is dressy or business-like, derbies and Chelsea boots are better alternatives. Also, I want to ask you the best match pants, shirt for a suede navy shoes.

I have 2 pairs of these:. Since the grey loafers and the navy suede captoe derbies your posted links to are both in the summer palette, I would stick to grey or dark blue pants. For the shirt, off-white, lavender, or a pink or light blue shirt with grey undertones are all great choices.

Will these look good with black jeans and a white shirt? These are kind of hard to match as they incorporate both brown a warm colour and black a cool colour. Warm and cool colours generally do not mix.

I need help on what to wear together basically i have herbal converse trainers but i do not know what jeans to wear with them. The herbal converse shoes would look great with dark washed or warm grey jeans. Khaki or brown coloured chinos would also look awesome with these sneakers. I just came across your website and have a question. I have jeans in different colors and like to pair them with good t shirts for casual wear. With that outfit, I would wear neutral coloured shoes, preferably in black or navy for two reasons.

With both green and purple in your outfit already, one extra colour could easily get overwhelming. Keeping to a neutral sneaker colour such as black or navy is the safest, and in my mind, best-looking option. So the smartest thing is probably to stay away from beige, rust red, orange, and brown as these are all warm colour.

Does dark jeans and light-grey chinos work? With black shoes, you can definitely wear dark and black pants. Regarding your boots soles. Rubber is always a good option. If you have any questions, let me know. Where are the pictures of the hiking boots from. And I really want some like that. I took the photo of he hiking boots in my studio. Hi, I am planning to wear peach polo shirt with black pants.

My shoes is a high-cut green converse. I have a question for You. And by casual I mean using a plain t-shirt of casual shirt, with blue jeans or dark navy blue jeans… Hope I was clear enough because Its difficult to express in an other language, thanks Vegard, very nice advices you give in your articles!

I say it depends. I would have chosen navy or brown. Hi I have a pair of Levis which are a fairly bright blue but light. With light blue denim, brown shoes can sometimes be hard to pull off. I see a lot of guides that say to wear no show socks with Vans, but I would really prefer to wear socks that cover my ankles. For socks to go with jeans, would navy socks and grey socks go well with the outfit, or another type of sock work better? If you wear regular socks, try getting the color as close to your pants as possible.

Coat pants and dress pants can be worn with pretty much any type of shoes. If the occasions are dressy, Chelsea boots and derbies are sure winners. If the occasion is casual, I would wear brogues or leather loafers. I need your suggestion… What should I wear with black jeans? It would be great if you can suggest me a good pair …. For colour, choose a cool one not warm. What about Polo Tedd high-top sneakers? The colour of those high-top leather sneakers looks great. However, I do think the apron toe is a bit too much.

Since sneakers are all about young and cool, I do think they should have a plain toe or a captoe, instead of an apron toe. For that reason, I would have bought the Geffron or Jeromy high-top sneakers from Ralph Lauren instead. I have a pair of oxford wingtips brogue shoes. Oxfords closed-lacing shoes usually look too dressy for jeans. However, they do look really good with chinos. Let me know if you have any questions regarding apparelillustrated.

Sure, Nordstrom has results for shoes size 6. Since we will be doing A lot of walking, something with arch vs flat shoes. Thanks for the info!! However, with question two I would say bring Derby shoes, no doubt about it. Now I think I have better choices and preferences regarding which type of shoes or jeans to wear or not. And now i think i better buy pair of canvas loafers. Good luck with your new canvas loafers.

Very good article on the best shoes that go well with the best jeans. I have a sky blue Gucci loafer with me. What would be the best jeans combination for it.

If at all i am going to buy a chino which color would u prefer for the blue loafer. Please reply, thanks a lot. Light blue jeans and grey chinos look exceptionally good with sky blue shoes. I am 14 years old and I am from Brasil, do you think there is any problem using fashion sneakers instead of loafers because IMO it looks more casual?

And my second question is, Does my black leather watch has to match the colour of my brown shoes if I decide to wear them? Loafers and classic sneakers are for those who want a more smart-casual look. I am happy to have got this site, otherwise I was in a thought that my leather shoes were a waste and were just lying around. I have tried the boots so far and it was awesome, it went really well just as you described. Hi Vegard, First of all, really nice article you wrote there.

I hope you have an answer there! You can check out their sneakers here: I m going to buy a leather boot. I m confused which color it should be to perform versatile role?

Let me tell u i oftenly wear deep blueskinny jeans. I have a question. I wear dark blue jeans with my Woodlands shoes. I only recommend wearing hiking and running shoes while hiking and running. When it comes to shoes, I usually practice style before comfort. Just think of uncomfortable women must have it, walking around in high heels all day.

Hi Vegard, great article. I have a dilemma I will be bicycling around the USA and will only be taking 1 pair of hiking shoes Merrell Goretex, not boots with these I will be wearing jeans and jean shorts for everyday use and at night for pubs and restaurants. My question is grey or black. They both look like a heavy duty runner if that helps.

I understand your dilemma. I would definitively choose black. I had some questions, basically what would you recommend as a first time buy or what would your number one pick be for jeans and dress shoes for a casual going out at night, going out during the dayear look. What would you top choice of shoes be, with dark blue jeans and some black jeans for these occasions? The number one pick is without a doubt dark blue jeans dressy and Derby shoes. This look is perfect for smart-casual daytime and nighttime occasions.

Really nice write up. I want to ask a question. I have a brown leather belt that i wear with my blue jeans. I have been wearing yellow and blue puma sneakers with it. Or should i buy some brown casual shoes? And does the shade of my brown belt match with the shade of the brown shoes i will buy?

Yes, I would wear brown casual shoes with your brown belt …. But the closer you get the better it is. You can also check out my article on belt colours and types.

I would greatly appreciate your advice! It is hard for me to suggest what color and shade you should go for. It usually takes a color analysis and thorough understanding of your styles color palette. If you want to learn more about which colors and tints, shades, and tones that work together, I suggest you check out my style course, Style Genesis. I have a pair of tan brogues, what colour jeans would you recommend looks the best? Tan shoes always look good with dark blue jeans in a rich blue colour.

Light blue jeans are also a good option for tan …. I am wondering if black dress shoes work with black skinny jeans. Is that a good combo? Im moving to somewhere new and I need to remove the swag and start with class. Great article by the way. Thanks, glad I could help. Black dress shoes with skinny jeans is definitively a good combo. Hi Vegard, Couple of little questions. Could you give me your opinion on these combinations? White jeans, suede tan driving shoe.

Or should you only wear shiny tan? Also, can you wear brown belt with white pants, same as shoe colour? I was wearing today the white jeans with a white and blue canvas belt, white dunlop volleys with same colour blue stripes and a blueish tshirt. Blue canvas bracelet and watch with light tan leather strap. Personally i think it looked great but still new to dressing with pride.

Do you think that sounds ok? Fairly slim, northern italian looks. White pants can easily be combined with tan shoes both suede and shiny. You can read more about belts in this belts for men article I wrote.

Your last outfit sounds like an awesome spring and summer outfit, definitively something I would wear myself! Great article it was very helpful an is just the information I was looking for. Worker-inspired looks are fantastic at this time of year. With rugged fabrics, a focus on layering and a pair of tough winter boots, the unchangeable weather we tend to experience during autumn is handled with ease. The long-sleeved tee brings additional depth and texture to the look and a pair of lighter wash jeans helps tap into that traditional, vintage, blue collar aesthetic.

A good pair of boots is a must here, so choose something rubber-soled and hard wearing. Roll up the jeans a couple of times to reveal the details or add a pair of chunky socks as a stylish alternative. Finish off with a knitted beanie or baker boy cap:. But as fashions change so do our clothes, and the ones we keep have to adapt. Thinking of new ways to wear your existing staples is one of the most important skills any well-dressed gent should learn.

With that in mind, how would you rethink your skinny jeans? Get all the latest must-read FashionBeans content direct to your inbox weekly:.

See all the latest vouchers, discount codes and offers from all your favourite stores for October Article By Will Colman on 17th November So how should we be rethinking our approach to the skinny jean? Spray-On Jeans Spray-on jeans should be firmly restricted to a lucky few: Sports Luxe The muted, monotone colour palette utilised below makes this look very wearable.

The quilted bomber adds a layer of textural separation between the tonal elements of this look, while some classic slip-on trainers and simple accessories keep things practical and comfortable: Oversized Outerwear Raglan sleeve overcoats are relatively new , but they are just the thing if you want to make a splash this season. Smart shoes with a solid sole finish off this ensemble: How To Wear A key consideration with standard styles is the severity of the lower leg taper.

Throw a parka over the top for those really cold days and wear with some good, chunky-soled shoes: Suede Chukka Boots Outfit Inspiration:

Shoes to Wear with Men’s Skinny Jeans. Almost any shoe can be worn with skinny jeans. There is no right or wrong pair! Just make sure your chosen jean fits you well. Formal shoes can be worn with skinny jeans. For smarter occasions, loafers and brogues are your best options. RECOMMENDED: Men’s Outfits with Skinny Jeans Ways to wear Skinny Jeans #15 – Brown/Black Casual Boots with Skinny Jeans Brown or black casual shoes will be a nice match with skinny jeans and your shoes will be prominent as a plus point. Shoes to Wear With Skinny Jeans Now the rule with skinny jeans is simple – if your jeans are super tight then your shoes can’t be too chunky. If your footwear is too big then your outfit will be out of proportion and it will look like you’ve got clown feet – not ideal.