Made To Measure Answers – Upgrading Your Casual Look
“I’m a recent graduate in the UK, looking to move away from the ill fitting hoodies. I’ve had a massive clearout of all the questionable graphic tees and unflattering jeans, and now I’m figuring out where to start! I’m on a limited budget and I don’t have the need for any suits, so I’d be really interested in what order you would go about building a casual, yet presentable wardrobe? I like wearing blazers, that’s about as far as my tailoring needs go I think.”
Name: James
Profession: Illustrator
Hometown: UK
Website: www.daviesjames.com
I’d like to congratulate you, James, on a job well done shedding the baggy jeans and graphic tees that so many mistake as stylish.Hopefully in this post I’ll be able to help you achieve a good look without pushing you too far from what you may be familiar with. Since you are a creative person I think we need to aim at keeping your style a little more free and youthful but with a cleaner edge.
First off it sounds like everything you were wearing was at least two sizes too big for you. So if your waist size in jeans is a 32 and you are buying a size 36, please stop and buy your ACTUAL size. Make sure purchasing jeans that they have a “Tailored” or “Fitted” style. You do not under any circumstances want Skinny jeans that make your legs look like sausages. You just want to go fitted and clean. Avoid any and all distressed looks (rips, intentional stains, etc) because your jeans will do all of that over time if you are wearing them for years and the more natural they age the better. For your new wardrobe, buy one pair dark and one pair light and you will not have to replace them for years. Plus they will go with virtually everything.
The good news is that you will not have to give up wearing hoodies. I am actually a huge fan of them especially on Sunday errand running or when I am at home relaxing. What you have to do is find one that is fitted, not tight. My personal favorites are from American Apparel. They are on the expensive side but damn are they comfortable and have an excellent fit. I bought my own in a dark green and it goes with everything. When a hoodie is fitted you can layer it well, too.
Although you may have no need for a suit I do suggest you purchase at least one for your wardrobe. If you have a wedding or any other formal occasion but do not need one all the time I suggest finding a mid priced Charcoal Gray or Navy Blue suit with a tailored fit so you can mix and match the blazer and pants as well as have something handy when you need it. Buy a few white dress shirts, a good tie, and a nice pair of dress shoes in brown or black and you are set. Since you live in the UK you have an advantage of Saville Row tailoring and some of the finest work the world has ever seen in terms of suiting. Please take advantage of this. Ben Sherman usually offers some decent fitting suits at a reasonable price. You can probably find those all over the UK. If not, try an affordable custom piece so it’s fitted just right.
Here are a few more upgrades you can try:
- Buy some plain fitted t-shirts.
- Replace your old sneakers with more streamlined ones (think Adidas).
- One pair of high quality dress shoes will look great with your jeans or khakis. Two pairs are even better.
- Replace any kind of backpack with a nice leather messenger bag that you can easily fit your laptop into.
Below are some looks I wear when feeling on the casual side that you may be able to use as a template when shopping or dressing yourself. Again, these looks are my personal preferences. I encourage you to build on this in your own way.
So there you have it, James. I do hope this was helpful to you as well as my other reades who have been anticipating a casual post from me. Just remember that FIT is the most important thing. If you wear any of these outfits baggy you’ll most likely ruin the looks. You want to keep it all streamlined and clean.
As an illustrator, I’m sure you understand this very well.












Dennis -
wow! I really can’t thank you enough, I really wasn’t expecting you to go through this much trouble in response to my question, but this is really just so excellent. You’ve pinpointed everything I was unsure about, and given me so many ideas.
Thankyou so much! Time to get shopping, now the clearout is done.
James
You are very welcome James. I’m sure all my readers can get something from this post.
Have a great time upgrading your look. I have a feeling you will nail it!
My best,
Dennis
James, let me add two things to this excellent advice related to style norms unique to the UK.
Regarding a suit, it is a smart idea to have one, as is suggested. Go with dark charcoal grey (NOT black, unless you are the chauffeur), or navy. Weddings happen, job interviews as well if you’re lucky, and unfortunately, so do funerals and the occasional court appearance. Whereas in the states we could maybe get away with brown shoes, the UK, however, adheres to the notion that only black shoes are acceptable with a suit and that brown shoes, unless you’re in the country, are downright vulgar. So start off with adding black dress shoes to your wardrobe, and when in doubt, use them over brown.
Secondly, you, being from the UK, probably know what a regimental necktie is. In England and the rest of the UK, those stripes on a tie have meaning. Avoid mistaken association and avoid being scoffed at when discovered you’re not a member of what your necktie purports you to belong to. So avoid any necktie with stripes. Solid ties are the most formal and patterns, a step lower on the formal scale, are more versatile and recommended.
Thanks,
James
Birmingham…, Alabama
Solid set of looks. Could you give me some details about the shoes in the second set? They look like canvas Adidas?
You are correct, sir, they are canvas Adidas. I’m not sure of the exact make. I’ll have to check when I get home tonight.
Quick questions for you Dennis. by the way, great suggestions! im a tall and athletic guy but also slinder, 6’8” 200lbs. its very hard to find clothes that fit my body, any suggestions on that? also, gonna have to go check out those AA hoodies, very nice…
Hi Steven,
In your case I would consider custom or made to measure clothing. Many places are offering more and more made to measure services and is probably just the same price as off the rack.
Where are you located?
-Dennis
Dennis-
where are those chinos from in the pic with the green cloth belt?
I’ve yet to find a nice pair of fitted chinos/khakis. Everything I see seems to be either pleated/balooned at the waist or way to skinny.
Thanks.
Hi Khurram,
Those are TAILORED STRAIGHT FIT khakis by THE GAP. I bought them right off the rack with no need for tailoring. Amazing fit and are 100% durable AND comfortable.
Thanks for reading!
Dennis
Thanks Dennis.
I’m headed to GAP right now to get a pair of the new selvage jeans they have. Have you checked those out? I’m a big fan of the authentic fit 1969 pair that you also love.
Dennis,
I am located in Huntington Beach, CA. south of LA about 30miles.
-Steven
Hey,
Can you give me more information about the grey jacket in the first ensemble? (The one with the black hoodie)
thanks,
alex
Hi Alex,
That blazer I purchased at UNIQLO about a year ago. It’s a size small.
Best,
Dennis