I really need some help with new wardrobe - really struggling

[Dan1980]

Hi all,

I am 37 year old male. I have never been very self confident, never really had a 'style' and never liked to stand out in any way.

I was divorced about 7 years ago, and just now come out of another 3 year relationship. I'm trying to revitalise my social life, and I'd like to look smart but appropriate for the situation.

To say I am struggling is a huge understatement. I have been shopping two Saturday's in a row, tried on lots of stuff and come back with nothing. I have spent hours looking online for tips and pictures of other men wearing nice things and failed to recreate the look when I'm in the shops.

I don't know what level of formality is right for me, what colours I like, whether to go a bit brighter or keep everything dark blue. Alot of internet searches for smart casual throw up this jeans and blazer look which looks great in the images but when I try it on it just feels too much. In fact whenever I try on anything that isn't a blue jumper I feel like I'm standing out too much.

I currently wear jeans, a dark blue jumper and a t-shirt underneath almost 100% of the time. At work I just wear a basic shirt, charcoal trousers and a plain grey tie, sometimes with a jumper over the top.

I also have problems with fit. I'm 5'11 but skinny short torso and long legs. Many jeans are just way too baggy, or don't fit right around the waist, or the skinny fit types I can't even get them over my thighs for some inexplicable reason (I'm quite skinny really, how can these skinny fit jeans fit anyone??). I tend to prefer a tailored fit or slim fit shirt too because a regular shirt is way too baggy around my torso.

I've got to a point now I just don't know what to do and need some help. I don't want to buy hundreds of things all at once, just one or two nice coordinated outfits suitable for a) a smart casual after work pub situation and b) a work beer bus outing which will probably be followed by a night out.

Please help!

Dan

 

[dapperguy80]

Dan,

I would suggest starting with a few nice shirts, button down shirts that is, and please tuck them in, always. Throw in some nice shoes, a tassel loafer or perhaps brogues or even a double monk strap. Lastly, get a blazer or a sports jacket. That's all that I could think of right now. You could get some chinos and other accessories like pocket squares and knitted ties later on.

Welcome to Styleforum by the way. You're about to get a sartorial makeover.

 

[Dan1980]

Hi Dapperguy.

I think the problem I have is getting the level of formality right. IF I was about to go out in the bars/clubs of Birmingham, I think I'd feel confident enough to go for the shirt and blazer look. But I'm not, Im trying to find something appropriate for a beer bus followed by bars in a busy, but still a bit scummy, town centre. So I'd feel too exposed in it I think. But at the same time I'd like to look smarter than just a shirt under a jumper.

I did buy some new jeans a few weeks ago - dark blue levi 511 stretch. The 32" leg didn't fit right - not enough rise for my hip bone - so I went for the 34" which fit better on the hip but are maybe a tad too long at the ankle. They aren't baggy though so hoping that is a step forward. I would be wearing with dark brown loafers, and brown belt. So I'm hoping I'm ok there, its the top half thats the biggest problem.

Going in and out of pubs and bars I don't really like taking a coat, because I then have to try and do something with it. But as it's winter a shirt on its own is not enough.

What type of shirts do you think - plain or something with a strong pattern? Ive read alot about the Oxford shirts in either pale blue or white, but I found myself gravitating to a navy check shirt in the shops today - this one:

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[dapperguy80]

I think the waist size of the pants doesn't matter. What matters is the fit, is it a slim fit Levi's? Or if it is too long that it gives you a full break, I suggest that you take it to a tailor and have it shortened. Jumper over shirt is nice, it gives you that preppy look, but since I am a warm person, I would still put a blazer over the jumper and shirt, this is just me.

Oxford shirts are fine, but I have a thing for the twill, and if I have a navy jumper like yours, I'd stick with light blue, white or light pink.

Don't be conscious with what the people would say, make it worth their stare. Besides, it's your chance to do a peacock thing and make yourself standout from the crowd, and ladies would notice you for sure. This worked for me especially when there's a hen night next table

 

[Dan1980]

They are slim fit stretch levi's - brand 511 dark blue. I have tried on at least 15 pairs of jeans today as well and none fit right.

This them with the shoes I would wear them with:

These are 32" waist, 34" leg. I did try on the 32" leg in the shop, and they didn't have enough rise on my waist so I felt like they were sitting way too low on my bum almost.

Here are some other jeans I own. Now those Levi's above are 32" waist, 34" leg, these Wranglers below are also 32" waist, but 32" leg. These Wranglers sit higher on my waist, but as you can see are way too short and so I don't wear them. When I tried them on with trainers they seemed ok, but with those shoes are too short. The 34" leg would be way too long.

I really struggle with jeans fit. I have a high waist - high hip bone, so 'skinny' or 'slim' fit jeans feel like they are sitting too low on my waist. Even though I am skinny myself, I often cannot get skinny fit jeans over my thighs - yet I have slender knees and slender calves.

 

[Jan Capek]

Dear Dan,

Nothing I will write is intended to give offense. You do not strike me as particularly skinny. You have slightly wider hips, appear to be a bit on the softer side, and look somewhat "fatherly". (If "fatherly" is the word I am looking for - my English is somewhat limited.) For this reason, I would:

(1) not force light colors (esp. since they scare you);
(2) forget mesh polo shirts (they do not look good on fatherly figures, esp. when tucked);
(3) not ever reveal the belt buckle you are wearing in the images;
(4) not tuck in shirts or t-shirts in general, unless the custom says you tuck (again, formal events, dress shirts) - remember, you have a short torso;
(5) get used to light cotton coats, or informal jackets that cover your bottom - remember, you have wider hips;
(6) when tucking in a shirt in a semi-formal settings, throw a light cashmere sweater over it (looks fabulous, smart, clean, does not shorten your upper body).

When I was reading your post, two kissing scenes from the movie Hitch came to my mind (you can youtube them). Both of them present a style you might benefit from.

Jan

 

[Dan1980]

Hi Jan, thank you for your post.

I am small framed (those jeans are only 32" waist) - but being 37 years old now, there is a little bit of 'fluff' around my middle. I don't have much of a chest to speak of and thin arms.

Here is a photo of me full length with a tucked shirt and a brown belt. Would appreciate your thoughts.

 

[Jan Capek]

Dan,

Provided the shoes are clean, there really isn't anything wrong with this picture. Yes, the belt does not match the shoes, but so what! Put on a dark brown suede coat (preferably covering your hip area) and I can't see why you shouldn't be very comfortable in your second skin (which is, ultimately, what matters the most).

With respect to other combos, I stand by what I wrote before.

J.

 

[Dan1980]

I would be getting a darker brown belt for sure.

I would just like to look smarter / more fashionable on my top half.

And I am considering a brown leather jacket - but the problem I have with coats when going out to pubs and bars is that they need to be stored somewhere which is awkward. So I would rather have an alternative which I don't need to take off, i.e more layers on top half whilst still looking casual enough and not out of place. This is why I tend to just go out in shirt with jumper - no coat - but I'm always wearing dark blue.

Would really appreciate some examples of looks that you think could work for me? Colour combos etc.

I quite like this one and it would be ok for a pub but not really for a club.

 

[cellphoneguy81]

Hi all,

I am 37 year old male. I have never been very self confident, never really had a 'style' and never liked to stand out in any way.

I was divorced about 7 years ago, and just now come out of another 3 year relationship. I'm trying to revitalise my social life, and I'd like to look smart but appropriate for the situation.

To say I am struggling is a huge understatement. I have been shopping two Saturday's in a row, tried on lots of stuff and come back with nothing. I have spent hours looking online for tips and pictures of other men wearing nice things and failed to recreate the look when I'm in the shops.

I don't know what level of formality is right for me, what colours I like, whether to go a bit brighter or keep everything dark blue. Alot of internet searches for smart casual throw up this jeans and blazer look which looks great in the images but when I try it on it just feels too much. In fact whenever I try on anything that isn't a blue jumper I feel like I'm standing out too much.

I currently wear jeans, a dark blue jumper and a t-shirt underneath almost 100% of the time. At work I just wear a basic shirt, charcoal trousers and a plain grey tie, sometimes with a jumper over the top.

I also have problems with fit. I'm 5'11 but skinny short torso and long legs. Many jeans are just way too baggy, or don't fit right around the waist, or the skinny fit types I can't even get them over my thighs for some inexplicable reason (I'm quite skinny really, how can these skinny fit jeans fit anyone??). I tend to prefer a tailored fit or slim fit shirt too because a regular shirt is way too baggy around my torso.

I've got to a point now I just don't know what to do and need some help. I don't want to buy hundreds of things all at once, just one or two nice coordinated outfits suitable for a) a smart casual after work pub situation and b) a work beer bus outing which will probably be followed by a night out.

Please help!

Dan

Dan, Good luck in your quest. Starting over - in many areas of life can be viewed as fun, or as a challenge. I think you should view the new you as a fun challenge. Enough vague advice.

First, I always like to start a "makeover" from the ground up.

I would start with some new shoes. If you get a decent Black Chelsea Boot, A medium brown Penny or Bit loafer and a white casual sneaker, you can cover the most situations in my opinion. Later you can add things like a some nice oxfords, chukka boots, and fill in from there. Stay away from square toe.

The jeans situation. A lot about this is what your budget is, but there are good jeans at almost any price point. Nordstrom has style consultants on site, not sure the cost. If you want to go cheap J.Crew Factory has nice 100% cotton slim jeans that look great for work. If you can afford to spend more, I actually love Banana Republic Traveler Jeans (so comfortable!). In the sub $100 price point, I think that Michael Kors slim fit are some of the best jeans out there. Levi's 511's are great, but the fit can be inconsistent. As someone else said don't be afraid to go to a tailor. Length is the least important and can be easily fixed. Stick with darker washes as they are the most versatile, especially ones without any holes, fading or whiskering.

As far as other pants, Chinos and dress pants can be more complicated. Take your time and use the tailor.

Having good looking and fitting shoes and jeans will provide a good foundation. From there then yes, as someone said get some good basic shirts. Start with a a couple solids, whites and light blues that fit well. From there go to a couple plaid, striped. Once again, if you want to start cheap, a good place for this is J.Crew factory. They have slimmer fits and you can get all of the shirts above. If you have more $$$ than the standard J.Crew is a great option. There are of course a million places you can get this stuff, but I find sticking to a couple good stores in the beginning makes it easy and harder to make wrong choices.

To layer on that, add some basics like wool sweaters (slim fitting), a nice quilted jacket for the winter. For the summer stick with cotton polo's, but a thinner lighter weave and some basic chino shorts that are slim and above the knee.

Lastly, sport coats/blazers should be a staple these days. Start with a brown or camel, tweed is good. Then maybe a medium gray and navy blazer. These go with about everything.

I will gather some pictures and come back and post some hopefully helpful looks, fits to watch out for. But take your time. This does not happen overnight. Even "experts" struggle if they have to make over a man in one day (those TV shows are mostly fake). Like most changes in life, it's a journey. Enjoy it.

 

[cellphoneguy81]

Dan, Good luck in your quest. Starting over - in many areas of life can be viewed as fun, or as a challenge. I think you should view the new you as a fun challenge. Enough vague advice.

First, I always like to start a "makeover" from the ground up.

I would start with some new shoes. If you get a decent Black Chelsea Boot, A medium brown Penny or Bit loafer and a white casual sneaker, you can cover the most situations in my opinion. Later you can add things like a some nice oxfords, chukka boots, and fill in from there. Stay away from square toe.

The jeans situation. A lot about this is what your budget is, but there are good jeans at almost any price point. Nordstrom has style consultants on site, not sure the cost. If you want to go cheap J.Crew Factory has nice 100% cotton slim jeans that look great for work. If you can afford to spend more, I actually love Banana Republic Traveler Jeans (so comfortable!). In the sub $100 price point, I think that Michael Kors slim fit are some of the best jeans out there. Levi's 511's are great, but the fit can be inconsistent. As someone else said don't be afraid to go to a tailor. Length is the least important and can be easily fixed. Stick with darker washes as they are the most versatile, especially ones without any holes, fading or whiskering.

As far as other pants, Chinos and dress pants can be more complicated. Take your time and use the tailor.

Having good looking and fitting shoes and jeans will provide a good foundation. From there then yes, as someone said get some good basic shirts. Start with a a couple solids, whites and light blues that fit well. From there go to a couple plaid, striped. Once again, if you want to start cheap, a good place for this is J.Crew factory. They have slimmer fits and you can get all of the shirts above. If you have more $$$ than the standard J.Crew is a great option. There are of course a million places you can get this stuff, but I find sticking to a couple good stores in the beginning makes it easy and harder to make wrong choices.

To layer on that, add some basics like wool sweaters (slim fitting), a nice quilted jacket for the winter. For the summer stick with cotton polo's, but a thinner lighter weave and some basic chino shorts that are slim and above the knee.

Lastly, sport coats/blazers should be a staple these days. Start with a brown or camel, tweed is good. Then maybe a medium gray and navy blazer. These go with about everything.

I will gather some pictures and come back and post some hopefully helpful looks, fits to watch out for. But take your time. This does not happen overnight. Even "experts" struggle if they have to make over a man in one day (those TV shows are mostly fake). Like most changes in life, it's a journey. Enjoy it.

 

[dapperguy80]

You should see the movie "Crazy Stupid Love", or at least the wardrobe makeover part.

Don't worry Dan, we got your back.

 

[Dan1980]

Hi guys,

Thank you all for the help and images youve posted so far. I like the jumper with shirt underneath look and maybe I'll be tempted to go for a coloured shirt under to give it a bit of colour rather than the white/grey i always go for.

My sister came with me today to help me choose some stuff. I only have time to post this one now but will post some more tomorrow.

Would be very grateful for your opinions. I would never normally wear as light a blue top as this, but my sister convinced me. The jacket is a very lightweight one ideal for the pub. I do intend to get some white trainers, but ran out of time today so have to stick with the blue ones I already own.

Now about jeans. The ones in this pic are from Next, size 32 R and slim fit. They feel ok, but when I sit down the lack of rise (they sit lower than I'm used to), well it feels like they are pulling down and underneath my bum, and opening up at the base of my spine (think builders bum). My sister says all low rise modern jeans are like this, but would appreciate some advice on it. Is it not possible to get jeans that are slim in the leg yet higher rise on the waist?

 

[cellphoneguy81]

Hi guys,

Thank you all for the help and images youve posted so far. I like the jumper with shirt underneath look and maybe I'll be tempted to go for a coloured shirt under to give it a bit of colour rather than the white/grey i always go for.

My sister came with me today to help me choose some stuff. I only have time to post this one now but will post some more tomorrow.

Would be very grateful for your opinions. I would never normally wear as light a blue top as this, but my sister convinced me. The jacket is a very lightweight one ideal for the pub. I do intend to get some white trainers, but ran out of time today so have to stick with the blue ones I already own.

Now about jeans. The ones in this pic are from Next, size 32 R and slim fit. They feel ok, but when I sit down the lack of rise (they sit lower than I'm used to), well it feels like they are pulling down and underneath my bum, and opening up at the base of my spine (think builders bum). My sister says all low rise modern jeans are like this, but would appreciate some advice on it. Is it not possible to get jeans that are slim in the leg yet higher rise on the waist?

First off. Sorry - I did not realize at first you were in the UK - some of my store choices might be less applicable. However, overall look and fit the same no matter where you shop. I am around the same age as you, and a bit heavier at the moment, though I was roughly your size a couple years ago.

I am not used to calling it a "jumper" so I will stick with sweater . First of all, a sweater with a t-shirt underneath of any color, including white is a dated look. If you are going to wear the v-neck shown above, looks like there is a bit of room, but it's not super loose. That's perfect to wear a button down shirt underneath. You need to find one that is not too long to wear untucked underneath. You can also tuck it in but sometimes that will create a bulge around the waistline, try it both ways. If you are slim enough, tucked in looks good with the right fits. If you want to wear it just like that, get a v-neck t-shirt underneath it that does not show, but in my opinion that look is harder to pull off than the button down underneath. The light blue is fine. I prefer crew neck sweaters if you want to just wear them with a t-shirt underneath (and as before, the t-shirt should not show). Gray, Brown, Navy and a deep red/cranberry are the best colors for sweaters in my opinion.

The jeans look ok for casual, going to the pub. I would not wear them to a work, or a more formal date or evening out. The fit is decent. For nicer events you need a darker wash jean...something like the color I posted before, with little fading and make sure the length does not have a lot of break. But what you are waring above is better that most guys, and of course you want to do the most with what you have, understanding new clothes and shoes can be expensive. You are right about the rise. Most slim fit jeans have a lower rise, thought you can find them in medium rise in some brands. Try a thick belt to help keep them up.

One other piece of advice is to slim down. Most guys are always trying on a size to large for them. If you are used to wearing medium, just try small to see how it looks. Or try a slim fit medium if you can find a brand that has slim fits available. Don't be scared to at least try it on.

I have attached a couple more images for you on what I am talking about that also illustrate proper fit for an adult male that is a full grown man. I am not a fan of the shirt in the jeans pic below, but it's a great example of how jeans should fit and adult male, perfectly slim without too skinny.

Good luck.

 

[breakaway01]

I've got to a point now I just don't know what to do and need some help. I don't want to buy hundreds of things all at once, just one or two nice coordinated outfits suitable for a) a smart casual after work pub situation and b) a work beer bus outing which will probably be followed by a night out.

Some good advice above.
My advice is to start with only a few items that can be used interchangeably. Think about layering for versatility, both in terms of temperatures/seasons and also to change up your outfits. Also think about variety in terms of surface texture/visual interest.

1. Add a couple of base layers (e.g. a henley or a long sleeve polo) in neutral colors (e.g. navy, grey, olive, cream).
2. Add a jumper or two with a textured/variegated wool e.g. a donegal or shetland wool sweater, or a textured knit (e.g. a 'bubble' knit wool sweater)
3. Consider a shirt jacket/'shacket' for layering
4. Definitely upgrade footwear - I'd suggest a dark brown suede chukka boot to start.
5. Something other than jeans. Chinos are fine but also consider a pair with a little texture e.g. moleskin or corduroy