I have the same issue with being skinny. I wear the Topman skinny chinos and they come out as a slim fit on the leg for me (just perfect).
As far as desert boots go, stick with the standard tan/beige colour (in suede). They go with anything. I wear them with my skinnys turned up to just above the top of the boot (with invisible socks on underneath) and it works a charm.
I'd agree with Will about buying good quality shoes, it's an investment that will pay off.
Urban Outfitters sell some great quality shoes and you can pick them up very cheaply in their frequent sales. I've bought two H by Hudson shoes at less than half price now. My little tip there. :)
TK Maxx and the Gap and Zara sales are good for some nice 'blend in' items, if you feel uncomfortable changing then don't go for something radically different. I got some nice suede lace-ups from Zara which i'm currently wearing a lot in place of my old Vans slip ons/106's. Depending on what else you normally wear you don't necessarily need to change the kind of things you wear, just get a better fit or wear it differently. Just think how different people can look in jeans and a check shirt depending on the fit and how it's worn (ie jeans rolled up, down, skinny/slim/regular fit, tucked shirts, buttoned up/undone etc)
To be honest mate it sounds like you could just change your Vans for some Brogue boots or Desert boots as mentioned and it would completely update your style. I have some Hudson Angus Brogues Buy H By Hudson Angus Brogue Boots, Tan online at JohnLewis.com - John Lewis which I appreciate may be a little out of your price range, but I'm sure you can pick up something similar from Asos. They look very good with skinny jeans (I am a skinny wearer myself) and are more mature and classy than trainers / daps.
If you are in Bristol then there are a wealth of TK Maxx stores- I swear by these and have found some ridiculous bargains over the years. In particular, get your arse up to the Brislington one; everyone around there wears Umbro and Le Coq Sportif, meaning that the designer bargains are left for us!
In short I really think one decent pair of boots will totally update your look. You will also not suddenly be wearing a totally different style, meaning you can gradually incorporate different pieces without it being an obvious reinvention.
I've always been slightly wary of brogue boots, although i know so many guys that look amazing in them. I think they have a ever so slightly macho image, which is really not me. I do quite like these clarks orginals desert shoes though. "Clarks Original" Beige Desert Boots - Casual Shoes - Shoes - TOPMAN
Opinions? Slightly doubtful they'd work with black jeans though and I don't want to throw all mine out!
I wouldn't pay that for those mate, they look a bit chaply made imo. Check out the All Saints archive site links below. Good quality handmade leather and suede boots at less than the ones you posted. In fact the All Saints Archive is another (probably the best) tip for saving money on premium styles- they have loads of nice knitwear on there for bargain prices at the moment too.
AllSaints Dusk Boot
AllSaints Flex Boot
AllSaints Spark Funnel
AllSaints Haze Crew
They're Clarks desert shoes. They'll last forever. Those things are built to withstand a nuclear attack.
Originally Posted by Pin Money
I have the desert boots by Clarks (the original and still the best) that have been through festivals and gigs and all manner trials and still look as good as ever.
I know they're Clarks but they just look a bit ropey to me. Plus those in the link weren't really boots.
I would advise you to go for desert boots in tan or beige too, they can be dressed up (chinos or trousers, shirt, jacket) or down (jeans and a tee) and look great paired with any colour, black included.
Here are some options from ASOS:
ASOS | ASOS Lace Up Desert Boots at ASOS
ASOS | ASOS Suede Desert Boots at ASOS
I'm a big fan of those ASOS ones, thanks. And a good price as well. I think footwear is my first thing i need to tackle and a pair of those would instantly made my image appear a bit more grown up.
Any advice on sizing when it comes to desert boots. I'm somewhere between a 10 and 11 depending on how slim the fit of the shoe is.