Regular fit or slim fit? What should an overweight guy wear?

With all of my posts recently about weight loss / being overweight and clothing I thought I would finish off with how I felt when having to decide what type of fitting I should wear as an overweight guy. Should I go for the loose fitting? Or the normal regular fit. Would I be bold and go all slim fit and try and boost my confidence unlike when I was overweight before? What to do what to do. I eventually narrowed it down to two… Kinda. Shall we?

Only regular fit or baggy for you big lad

I spoke before about how when I first started to lose weight, how I would not be comfortable at all in regular fitted clothing because I hated how it looked almost baggy on me. I wanted to show off my new slimness. Well, it turns out that the haunting feeling of slightly baggy clothing hasn’t left me in the slightest and I still hate it. I had thought when I regained the weight that I would be happy to resort back to regular to hide my weight, but this time the shame that I had before didn’t hit me. That was really unexpected on my side as I had no idea that the feeling had left me. I had bought a regular fitted pair of chinos and they felt like sails from the upper thigh down. I felt really uncomfortable in them and felt if anything more noticeable to others for wearing some that I considered ill-fitting. A total surprise and one that I think is a bit of a welcome one in honesty.


This feeling kept with the shirts as well. I knew I had more of a stomach and although I wanted to make sure that the clothing wasn’t bulging or look like it was about to burst at any section, I also really wasn’t happy if it was too loose. A little loose would have been okay, as then as I lost more weight I could drop down to slim fit soon and it proved that my weight loss was working. Whereas regular, just looked wrong. I really couldn’t put my finger fully on it.

Slim fit for the win then?

Not exactly, while I was very uncomfortable with regular fitted clothing due to the looseness, I was also slightly uncomfortable with slim fitted clothing or I currently am at the minute at least. I feel I am slightly too large in the stomach and chest to be comfortable in it as it brings my confidence down a little due to the clinginess of the material. I feel when I get to large and then medium I will be happy with a slim fit but not just yet. It’s the feeling of pressing against something too much and all you can do is think about it and know it’s there… Maddening.

Another reason for my thoughts on this is a little more complicated (possibly) although the size will say (for example) XL, that XL is as close as possible (without being skinny) to a large. That will be great for me when I get close to the larges as then I can transition to a slim fit XL and then get rid of the XL’s completely when I move down to large, but for that annoying little period I don’t want to say fit into a large shirt and have to buy an XL shirt to have it fit the way I want. It is all from a mental standpoint of knowing that I am a certain clothing size, but because of the fit, I have to go back up to the size that I just tried very hard to leave and never return to. I think it gets to you mentally, even though you know and there is physical evidence that you have reduced your weight and size… To go back up just for a slightly better fit is troublesome.

So the question is do you stick with a slightly loose top or trousers for a little while or do you give in and try to make yourself look good and have a mental boost but sacrifice the other part of your brain that remembers that you are still wearing the size you wanted to get away from?

There is another option!

I know, and I apologise, I have misled you regarding this. Regular or slim-fit Scott, I have an out and I always knew I had an out. Again, my apologies.

Tapered trousers are for me a Godsend. I like the slight tightness of a slim fit on the calves and to the legs a bit too. But if I am not in the slim fit stage for those trousers or chinos then I call upon the tapered cut as they are slim fit at the bottom and regular at the top. It is almost as if someone knew this! I kind of have the feeling they were made for people with larger thighs as there is nothing worse than struggling to pull those trousers up and feel comfortable for a lot of walking if the slim fit is just a little tight. It is the perfect middle man and I am pleased to have them in my life. It gives me the chance to have a confidence boost of wearing the size I want, without sacrificing the look.

With the shirts I go (usually) for tailored, especially for work reasons as I feel too baggy looks a bit unprofessional and too tight looks like I am just lying to myself. So I try to look as decent as possible… To varying degrees of success! Ha! If possible I try to do the same with my other shirts but that just isn’t possible. So I have my fail-safe plan, waistcoat. If the shirt is a little too loose or tight, I whip on a waistcoat and I cover myself up! The public will never know my trick!

In the end…

It doesn’t really matter. Why? well, it is all perspective, to be honest. For me tapered or tailored worked best for my confidence. I was able to believe in myself a little. I felt horrible in baggy clothes and although slim fit was grand it was a little too tight-fitting and as I said, it was almost a next level in progress to my weight loss. Tapered or tailored first, then slim fit of that same size and then when I got to the next size down, back to tapered and tailored, so on and so forth.

But as I said, that all worked for me, that might not work for you, wear what you think is most comfortable for you. If something baggy of skinny fit makes you confident, then rock the hell out of it. Own it. If people look then they look, they may look for different reasons and sometimes that is for good reasons.

Build your confidence and make your wardrobe you. I love my waistcoats and shirts as normal everyday wear, that is my style. Look at what interests you and make it work for you. This is probably not the answer you want as I know you want to know if you can wear a slim fit. The answer is simple. You can if you feel confident and comfortable. Why can’t or shouldn’t you? That’s the main question, why shouldn’t you wear the fit you want? Go get it. Until next time!

Weight loss posts

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3 thoughts on “Regular fit or slim fit? What should an overweight guy wear?

Add yours

  1. It’s a tough call to know whether to wear a slim cut or not; especially for men. My husband and I have decided that you really must try on the item in a variety of sizes and cuts to find what flatters your shape best. He hated doing this, because he’s a grab and go kinda shopper. He has learned however that if it doesn’t fit well, don’t buy it —or if has already bought it—keep the receipt and take it back. Thanks for sharing.

    Liked by 1 person

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