Oscar De La O Tailor Shop

This shop is amazing he is a excellent tailor no one beats him he is excellent and very professional I would not trust one but him, I take all my clothing him, he is a very busy man but it’s worthy to wait,

I brought Oscar a pair of new selvedge jeans that fit great in the waist but had a bit too much room in the knee and calves. («Slim straight» means something different to every designer, I guess.) I had previously taken the jeans to another tailor to have the legs taken in, but, well, suffice to say, they didn’t know what they were doing. I ended up with carrot-​shaped jeans.
Enter Oscar. He saw the problem immediately, listened when I told him exactly how I wanted the jeans to fit, and had the jeans back to me in less than a week. Result? They fit exactly the way I had hoped. And the price was reasonable, too — not the least I’ve ever paid for this kind of work, but not the most, either. I’d rather pay a few extra bucks to have it done right.
I’ll be back next time I need alterations done. Thanks!

Went there for the first time few days ago. Oscar was very nice, and he did a great job on my skirt. I tried few other stores before, and this is so far the best — would definitely go back.

WARNING: Please be cautious. I didn’t dig deep into the reviews and only looked at the first few reviews when I decided to give him a try. However, after 2 bad experiences, I realized I was not alone. He is a fine tailor but completely undependable. On both occasions, my due date was missed by 2 weeks! Just like the poor review I had found later on him, which said… «He didn’t seem to care, nor even apologized». I know you maybe thinking why did this guy go back a second time after a bad experience the first??”…FYI — I went back a second time because the reviews were so good and I figured he just had an off week. Additionally, the second bad experience was with a new spring wardrobe that I had purchased for an extended trip. Knowing I could not afford to have him miss a second due date, I asked for everything to be ready one week before the trip. Not only was it not ready a week before the trip, but he then promised to have it ready the day before I was to leave. Low and behold, when I showed up nothing was completed!!! Not one piece out of the 20. No apologies, nothing. For what it is worth, he had these items for 2 months!!! If you need your cloths done well and ON TIME, try A Tailors Touch on oak street. They saved my life on the second occasion that Oscar did not deliver! Thank god it wasn’t my wedding day. So disappointing…

Oscar is a lifesaver! I was in chicago for a wedding and discovered upon arriving to our hotel that my dress had a hole in it:(
Even though he was really busy he happily was able to squeeze me in and even had it ready earlier than I expected. He even steamed it for me! I’m so glad I picked Oscar from his rave reviews and he really went above and beyond for me!
Thanks again Oscar!

Oscar is a class act. Very professional and precise in his alterations. I’ve brought him many dresses and he’s been honest about what’s worth altering and what’s not, given the complexity. Reasonably priced as well — a pleasure to work with! Thanks Ocsar!

Oscar does a great job on jackets. I’ve had 3 done by him so far. Not too constricting and still quite form fitting. I’d recommend his work without hesitation.

I brought an ill-​fitting suit (from before I knew how to size myself) to Oscar’s in the hopes that it could be salvaged, and Oscar worked miracles with it. He was incredibly helpful and went into great detail about how he was going to adjust the fit. And in an act of complete class, he noticed a hole in my suit and stitched it up at no charge.
I would recommend this place to anyone who needs a job well done.

It’s not like I can comparative price tailors, so I’ll just say I’m willing to pay. Every suit I’ve taken to Oscar has come back top-​notch. And here’s why I trust him. A tailor can always milk a job by «suggesting» this, that, or the other tweak. Oscar will tell you straight up, no, this suit (or whatever) is fine, it doesn’t need any altering. I’m a customer as long as I’m in the Loop.

I have been going to Oscar’s shop ever since I got back to Chicago. He is simply the best tailor I have ever been to. His pricing is on point and the quality is unsurpassed. I will continue to be a loyal customer from here on forward.

BREAK my heart. After all of the incredible reviews, I was really expecting a lot more from Oscar. I went in to have him alter my Halloween costume (just move the velcro on the neckline over and sew up a bit of an opening in front). He said he would have it ready 10 days later — on a Monday. But when my boyfriend went in Tuesday (the day AFTER Oscar said it would be ready), he said «Sorry, I didn’t get to it. Come back maybe later today or tomorrow.» He then promised that he would call when it was ready to be picked up.
So I call Oscar, obviously frustrated by the situation, he didn’t seem to think it was a big deal and said he wasn’t really sure when it would be ready. He said that normally he says that any garment would normally take him 3 weeks — fine if that’s your timeline, but why did you tell me that it would only take 10 days?!
My boyfriend then called later that afternoon to see if it was ready, which it had been for a while. And they NEVER CALLED US.
The work was fine, but really nothing to write home about. If you aren’t going to have something done on time — CALL THE CUSTOMER. Don’t wait until they get all the way out to your store, brush them off, and then say come back later. Ridiculous.

Oscar made the gown I purchased for my brother’s wedding look stunning. I had an idea of the alterations I wanted, but his suggestions proved to be completely on-​point. I have never received so many compliments for something I’ve worn. I’m already making a mental list of the garments I’ll be bringing to Oscar to tailor.

How to make a $ 50 dress look like a million bucks? Take it to Oscar.
I got a Cheongsam in Chinatown that I needed tailored, so I’d look like a supermodel for my birthday party. I took it in, Oscar pinned it.
I came back. No! Not snug enough! I’m 50, not 80! This has to be CURVY, not dowdy. I grabbed handfuls of material, and he assured me he’d make it right. I needed it quickly, and he reassured me. An honest man who does what he says he’ll do. Rare. Very rare.
Next day, I come back and I’m freakin’ Cindy Crawford in my curvy Cheongsam. Slim Shiny, baby. Just add heels and red lipstick. Oscar rocked it.
Take your cheap dress to Oscar, and he’ll make it look like haute couture. Not cheap couture, REAL couture. ‘Cos it’s the woman inside the dress that makes it couture, but the tailor is essential.
And the price? Wow. I’ll bring other clothes back here to get them taken in so everything I wear will fit to perfection.

Great guy, very professional. In my previous experiences with a tailor, I’ve had nightmare results. He listened to my concerns and delivered on his work.

Oscar can do anything. We keep going back every two weeks to alter more. There is nothing he can’t do. We’ve given him a dress that need major altering, a jacket to be re-​lined (not sure if that is a word), suit jacket, and many pants. Every has look great. The dressing room and location aren’t fancy or anything but the service and work is awesome.

Last week I took two dresses here… one to be shortened and one to be taken in. I just picked them up and they fit fabulously! The service was quick and friendly and my clothes look great! I will definitely bring my clothes here for alterations in the future.
The only con I have is that the mirrors used for the fittings are right next to the windows of the shop… so I felt a little on display. That said, the shop is on the second floor of a lobby, so there isn’t too much foot traffic. It won’t stop me from going back.

Oscar is the best! I’ve been to other tailors that have left my pants flooding or do just the bare minimum. Oscar takes his time, really looks at how the clothes fit your body and has a sharp eye. With my jeans, he puts the original hem back on as opposed to other places that just cut the them off and stitch from there. Major difference!
I trust Oscar so much that I just brought my wedding dress to him for alterations. My dress was made a little «off» in the bust area and I couldn’t figure out what was wrong with it until he measured and saw that one side had a half inch more room than the other. He was able to fix it and it’s perfect! If I thought about it sooner, I would have had Oscar make my dress. I’ve seen his custom work and it’s pretty amazing.
Personal service, quick turnaround and fairly priced for the quality of the work.

A good tailor is hard to find. Oscar gets high marks for his knowledge, friendliness, keen eye and low prices.
For a long time I took my pants and jackets to a local dry cleaner who did a passable job. I was never thrilled with the work, but for the price it was acceptable. I was always looking, however, for a tailor with more experience and skill in men’s clothing and at an affordable price point. Oscar fits the bill and then some.
I recently brought Oscar a heavy peacoat that looked about a size too big on me. The sleeves were huge, too long, and the shoulders looked big. He was quick to inform me that the shoulders and sleeve length were actually correct, however the body needed to be taken in and the sleeve width tapered. This is the sign of a good tailor. He marked it up with tailor chalk and informed me it would cost $ 60. Not bad at all considering the thickness of the wool and the work involved. The finished coat looks and fits fantastic and you would never tell it was altered.
I brought in a dress for my wife, instructed to hem it by three inches. An average dry cleaner would just measure and chop. Oscar, on the other hand, insisted she try it on in person and instantly decided three inches was too much for her body – two would be better for a classic look. Twenty dollars later, the dress looks incredible.
Oscar works with your body type to find the best possible fit and truly cares about making it look good. His prices are competitive and his work is professional. Highly recommended.

Mr. De La O gets TEN STARS for every reason all of the previous Unilocalers have stated. I learned the secret of «looking good» is to wear clothes that fit. Well. That’s a novel concept considering we all shop «off the rack,» but no one told us (not for free any way) that one should NEVER wear ANYTHING «off the rack.» Your tailor is your secret weapon no matter what end of the cost spectrum your clothing. Looking good is in the FIT, and Mr. De La O is your secret weapon.
I practically have a whole new wardrobe because there’s such a HUGE difference in how something looks when it doesn’t fit and when it DOES FIT. And it fits your body.
If you went on a diet and/​or started working out last month, you want to take your Spring clothes to him so everyone will be able to SEE your «fitness.»
He is an artist! Trust him.

Since moving to Chicago, I’ve been looking for a good tailor who knows traditional men’s clothing and does good work for a reasonable price. So far Oscar seems to fit the bill nicely. I tested the waters with a pair of trousers that needed to be taken in in the seat (I’m cursed with the Northern European Butt, which is to say, no butt at all). Oscar pointed out that the fabric really needed to be raised up into the waist area, not removed from the back of the crotch area. He has an excellent eye.
Satisfied with the trousers, I decided to really test him with a suit jacket from the early ‘90s that has much broader shoulders than it should. I did bring in a made-​to-​measure jacket that fits me perfectly as a sample, but even with that as a guide, re-​doing the shoulders on a men’s suit jacket is one of the most difficult operations that can be performed. I’m happy to say he did a great job.
There are many little things that no tailor will discover until the wearer actually puts on the garment, and some tailors might just assume that you won’t notice if, say, the fabric bulges out a little around the back of the shoulders or if the front of the jacket wrinkles a little when buttoned. Not Oscar. He’s patient and cares enough about his work to suggest small adjustments after the first fitting to ensure that the final piece fits perfectly.
If you need something done right away for a friend’s wedding tomorrow, he may not be your best bet (but hey, give him a call, he’s a nice guy and might be able to help). But if you really need something done right, Oscar is one of the better tailors in Chicago.