I had a Holiday dress that needed an alteration and I called to make an appointment knowing its a busy time of year. Oscar was so kind and said to "come on over" so I did. The shop is located on the mezzanine level near the CTA station on Clark & Lake (the Loop). As I opened the door, Oscar came up to the front and greeted me, asked me to try the dress and was completely honest with me that the dress was not an easy alteration and it would be very costly to do. I appreciate that. There's many places that would just do it and charge bigtime! Not here... Oscar said he won't risk his reputation and will be honest with everyone. He also said he isn't sure he could get it to me in time either and suggested I save myself the headache and expense, to perhaps find a different dress for my Holiday Party. One thing is for sure: Oscar wants to do honest work! I'll be back when I need a good tailor. read more

Oscar De La O Tailor Shop - Sewing & Alterations Near Me - Chicago, Illinois

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This is a master tailor with years of expertise and genuine artistry in his craft. I brought in an important suit for an upcoming work trip, and he delivered exceptional results--quickly and efficiently. I highly recommend this shop and will definitely be returning. 10/10 experience! read more

I've been going to Oscar for a few years now and he's always been extremely reliable. I've had jeans, pants, and dresses hemmed, and I'm always happy with the results. The only thing to note is that he doesn't usually take rush jobs - turnaround is typically three weeks to a month depending on workload. If you plan ahead, he's a great choice. read more

If I give this ZERO or negative stars, I would. Do NOT waste your money here, this guy is a hack! I brought in a bridesmaid dress to get it hemmed, and he chastised me for not bringing it in sooner when I requested it be turned around in 2.5 weeks. 2.5 weeks for a simple hem. Turns out all he needed was half hour to completely ruin the dress. I called in at 2 pm today to see if it would be ready by tomorrow, my scheduled pick up date. Not only had he not worked on it in the 2.5 weeks he had it, he was like "I can have it ready anytime you want to pick up today" implying it could be done within 4 hours. that's great buddy, I'm glad you yelled at me for only giving you 2.5 weeks when the day before I pick up, you haven't even touched it! I tried it on, it's shorter than I wanted, which can't do anything now seeing as it's cut up. I looked at the hem line, crooked and uneven and obviously rushed. I asked him if he can steam it and he said he doesn't have a big steamer so can't. When I called him out on it being more wrinkled now than when I brought it in, he has the nerve to say "I don't think so". He also said he's not a dry cleaner so should not be expected to steam something to make it more presentable. No apology or accountability that he messed up, no discount offered and no customer service skills. Just so rude. Never coming back here and would recommend you spend your money elsewhere. Oscar is a hack. read more

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. read more

Had a pretty tight timeline to get a suit jacket and pants adjusted before leaving on a trip. The jacket needed to be brought in and the sleeves shortened and the pants needed to be hemmed a bit. Oscar did a great job with both! Very happy with how they turned out (: read more

Oscar De La O Tailor Shop - Suit - Sewing & Alterations Near Me - Chicago, Illinois

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Oscar does all my suits, jeans, shirts, basically anything. He takes something that looks like a tablecloth on me, and turns it into a custom-looking ensemble. He tailored my entire wedding suit. And it was perfection. Trust Oscar with your your smallest items and your most important ones too. You won't be disappointed. read more

Wow wow wow! Love this tailor shop. He was so friendly the second I walked in the door. When he went to measure my pants, you could tell he was knowledgeable. He talked about keeping my wide trouser pants longer, my tight fitting pants shorter, but he always asked my preference regardless of style norms. This meant a lot to me, having experience with hemmed pants making me look like a dork because they are hemmed too short. One of my dress pants were severely frayed and tattered because I wore them even though they were too long, and a belt loop was ripped. Not only was he able to clean up the ripped ends of my pants and successfully hem them, he fixed the belt loop too; both FLAWLESSLY. He sewed it back in the exact style the other loops are, and the pants had a unique hem to it which he also emulated. I was impressed just dropping off my pants, and picking them up, I was even more impressed. They are the perfect length. Phenomenal work. I'm so please for his work I just want to tell everyone to go to him; I want to find things for him to tailor, even though I don't need it, that's how impressed I am. Oh, and I thought the price was phenomenal. I saw some tailors who possibly charge $50 - $75 for a simple hem. He only charged $15, which is exactly what I feel a hem job should be. read more

Had a suit fitted to slim proportions here. Ace job, this guy is so nice as well. The fit is perfect. read more

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Oscar is a great guy. Got a few suits done by him a while back. Will definitely go back.

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. read more

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. read more

Mr. De La O gets TEN STARS for every reason all of the previous yelpers 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. read more

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. read more

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. 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. read more

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. read more

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! read more

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! read more

Oscar is the best tailor in Chicago. I probably see him once a month and have brought dozens of clothes to him for different alterations over the past five years. Whatever you need he can do and your clothes will fit amazingly. He is also a super nice man. I see some negative reviews questioning his turnaround time...please...he's a busy, hardworking man. read more

Oscar sewed a button back on to my topcoat, and reinforced the remaining two while I waited. The one had come off while I was leaving my home on a bitterly cold December day, and I felt its absence on my walk to the el and then to my office. Oscar was fast, professional, and reasonable with the charge for the work. I highly recommend him, and his business. read more

Oscar and his wife are the best! I've brought a bridesmaid dress, a nice romper I wore for a wedding and all my boyfriend's dress clothes are tailored here. Everything always fits beautifully. I highly recommend this spot. It is definitely my go to! read more

worst tailor ever. left three suits with him. ghosted me for months. after going to inquire on the status, I saw he had not done anything. came back after he claimed to have finished the work. the suits had required major alterations to fit me flyer having lost weight. other than hemming the sleeves and pants, nothing was done and he charged me as if he had taken them apart and reassembled them. liar and thief. read more

I was traveling and two buttons from my overcoat came loose. He was very friendly considering that I asked him to take care of it while I waited. I lost one of the buttons and he was able to scrounge one that was very close. He charged me a very reasonable amount and quickly had me on my way. read more

Oscar was wonderful! He was able to alter a dress size 10 for a size 6 person. The dress made of lace, chiffon, tulle, and heavily beaded with pearls and crystals was completed in the promised time at a reasonable cost. Oscar's attention to detail, knowledge of material and skills, took an off the rack item and 3 weeks later delivered a couture dress. Oscar is my favorite tailor and the only tailor I will use. read more

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. read more

The tailor told me I was too large to have my clothes tailored. My looked at the dress size, and told me it is too large, and he did not want me try it on. For the record, I am 5'5", and the dress is a size 14. If I wore a size 8, I wouldn't need tailoring (sigh). read more

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. read more

Oscar is amazing, he is the best tailor I have been to in Chicago. From Jeans to suites he does a great job!! Professional, fast, and fairly priced. Highly recommended. read more

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. read more

Was looking for a good tailor and after reading several reviews I decided to check out Oscar. I had a custom made suit elsewhere and after being tailored twice it still didn't come out right. That's when I decided it's best to give someone else a shot. I have to say I'm very happy and I'm able to wear the suit now thanks to Oscar. His prices are very reasonable in fact I felt I got a bargain. For his quality of work in comparison to what other tailors charge I will definitely come back. He also makes custom suits and has high quality fabric. I wish I would have came here first. read more

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. read more

Oscar is such a cool guy and does great tailoring. Highly recommend anyone on an alteration project to come here. His rates are very competitive. read more

I just wanted to do another write up praising Oscar's services. He is an excellent tailor. I have personally saved hundreds of dollars by having Oscar take in shirts or switch a boot leg to a straight leg on suit pants. He really knows a woman's shape and is always careful not to make things to clingy in the hips. He also makes custom suits. He has a very convenient location just near the Clark/Lake Brown line stop. Want to save money and have clothing tailored for your body - go see Oscar. read more

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. read more

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. read more

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. read more

I cannot express how pleased I am with the job Oscar did for me. He took an ok, not that great fitting blazer and made it look like it cost ten times what I paid for it. On top of that, I asked him at the last minute to rush the job and he completed it a day early at no extra charge. I wore the jacket back to my office and was stopped three times by coworkers asking where I bought such a great fitting garment. Thank you, Oscar. read more

I had a great experience with Oscar De La O. I brought in several pairs of pants that needed to be hemmed and adjusted in the crotch/seat. I also brought in a suit jacket that I wanted the waist taken in. Neither of these are particularly complicated jobs, but Oscar is very good about advising on exactly how much should be taken in, and where. And everything fit perfectly when he was done. He's very good at imparting his tailoring knowledge without completely dictating how your clothes should fit. As he should, he leaves that decision up to you. read more

Wonderful! I called Oscar on a Saturday morning, hoping to get some pants hemmed with a quick turnaround (needed them for an event that night). He happily obliged and I was able to get in right away. I saw him around 10am and they were ready before 4pm! He did a great job and the price was super reasonable, especially given the tight deadline! I will be back in the future for any tailoring needs I have. read more

I needed a fully beaded floor length gown hemmed and of course I waited until the week before to take it in. It was so complicated and time consuming that I was turned away from two other places before I found Oscar. He got it done for me in time and I didn't have any issues during the event. Oscar definitely got me out of a jam! read more