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Fashion Outlets of Chicago near ohare has a lot of outlet stores and discounts. Recently bought 3 new pairs of jeans from Levi’s for $100, bought more at Gap also cheap. This is a solid option if you need a lot of basics for your wardrobe. They do have higher end places on the second floor. I bought a really cool shirt from a designer called Sandro. Answer from alexinquotes on reddit.com
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Kohl's
kohls.com › catalog › clearance-mens-clothing.jsp
Men's Clothing on Clearance: Shop Discounted Men's Apparel | Kohl's
You can find everything from basic tops and pants to more formal dress clothes. Jackets and outerwear are also common in clearance sales, allowing you to pick up essential pieces for cooler weather without breaking the bank. The key to making the most of men's clearance clothing is to explore a wide range of styles and sizes to find what suits you best.
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Yelp
yelp.com › shopping › fashion › men's clothing
THE BEST 10 MEN'S CLOTHING in CHICAGO, IL - Updated 2025 - Hours - Yelp
Welcome to Soul — Skokie’s newest destination for authentic sneakers and latest apparel. Located in the heart of the Chicago suburbs! more ... New price drops on dresses, tops, boots, handbags and more in stores now—so hurry! ... Kayra Imports is an African Clothing and Fabric store with various locations on the Southside of Chicago.
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Target
target.com › c › men › - › N-18y1l
Men’s Clothing : Target
Shop men's clothing, shoes, and accessories at Target. Find shirts, jeans, activewear, suits, & more from top brands. Free shipping on orders $35+.
Discussions

Favorite stores to go shopping for men’s clothing?
Fashion Outlets of Chicago near ohare has a lot of outlet stores and discounts. Recently bought 3 new pairs of jeans from Levi’s for $100, bought more at Gap also cheap. This is a solid option if you need a lot of basics for your wardrobe. They do have higher end places on the second floor. I bought a really cool shirt from a designer called Sandro. More on reddit.com
🌐 r/AskChicago
36
14
February 20, 2025
Millennial men of Chicago, where are you shopping for clothes?
Uniqlo. Stuff is pretty plain but relatively modern looking and generally of decent quality (edit: idk about Uniqlo stuff lasting a long time but in terms of being in your 30s I think it’s a solid match re: looking fashionable-ish but not super young) More on reddit.com
🌐 r/AskChicago
373
266
August 29, 2024
I’m looking for stylish, local, menswear boutiques.
https://independence-chicago.com/ https://mildblend.com/ https://cowboysandastronauts.com/ More on reddit.com
🌐 r/chicago
37
44
September 26, 2023
Where do y’all shop for affordable clothes?
Cheap but solid: H&M, Uniqlo, Target, Old Navy, Gap, Nordstrom Rack Pricier but good quality for the money: Banana Republic, Express, Patagonia, Buck Mason, Taylor Stitch, Proper Cloth More on reddit.com
🌐 r/mensfashion
17
2
November 5, 2024
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Yelp
yelp.com › shopping › cheap men's clothes
TOP 10 BEST Cheap Men's Clothes in Chicago, IL - Updated 2025 - Yelp
It's a pain to go searching through their mess of clothes, but check out Ragstock (near Clark & Belmont). They have a ton of tux apparel in the men's…
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Reddit
reddit.com › r/askchicago › millennial men of chicago, where are you shopping for clothes?
r/AskChicago on Reddit: Millennial men of Chicago, where are you shopping for clothes?
August 29, 2024 -

I'm in my late 30s and have struggled the last couple years with dressing my age, especially in casual settings. I don't want to dress like a college student and I don't want to dress like a boomer. I want to get some versatile pieces that will last me a long time but I just don't know what shops to go to. Any suggestions?

Find elsewhere
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Marshalls
marshalls.com › us › store › shop › mens-clothing › _ › N-2085788411
Men's Clothes For Less | Stylish Apparel for Men | Marshalls
Tawny Port CHRISTIAN LACROIX Men's Extrafine Merino Wool Long Sleeve Quarter Zip Pull Over Sweater $29.99 Compare At $60
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Chicago Loop Alliance
loopchicago.com › explore › shop › mens-app
Men's Clothing Stores in the Loop
Shop and buy men's clothing in downtown Chicago to ensure you always look your best with the latest trends and top brands.
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Discoverchicago
discoverchicago.city › en › best › men-s-clothing-shops-chicago
Men's Clothing Shops Chicago [Cheap discounts 2025]
Chlothing store for men Enjoy up to 80% off on cheap and discounted designer menswear from the UK's largest men's clothing sale. Take advantage of sales with up to 50% disco... 97 users are already VIP · Trapstr-Chicago Exclusive Deal: Hoods From $50. Up to 40% off on AllSaints.
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Independence
independence-chicago.com
Independence | Chicago | Curated Menswear
A well-edited collection of mens clothing and accessories from Engineered Garments, Gitman Bros. Vintage, Kapital, OrSlow, Lady White Co., Oak Street Bootmakers, and more.
Address   1909 W Division StreetChicago, IL 60622
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Yelp
yelp.com › shopping › fashion › men's clothing
THE BEST 10 MEN'S CLOTHING near THE LOOP, CHICAGO, IL - Updated 2025 - Hours - Yelp
Best Men's Clothing in The Loop, Chicago, IL - Last Updated October 2025 - Jugrnaut, Charles Tyrwhitt, Syd Jerome, Macy's, ESQ, American Giant, Hammer Made, Arthur and Lucca, Goodlife - Chicago, Jos. A. Bank
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Reddit
reddit.com › r/chicago › i’m looking for stylish, local, menswear boutiques.
r/chicago on Reddit: I’m looking for stylish, local, menswear boutiques.
September 26, 2023 -

As a woman, I have lots of options for shopping at neighborhood boutiques. When traveling, my husband and I will explore trendy areas, seek out vintage boutiques, and get a souvenir outfit to remember our trip, and support small businesses. Oftentimes though, the menswear sections are very small, have poor selection, or are entirely nonexistent. Do you have a neighborhood clothing boutique to recommend that has a great selection of stylish menswear? We would love to shop vintage, or contemporary, see accessories, and use fitting rooms. Not particular about the neighborhoods, though I’d prefer to avoid downtown. Less so, clean-cut “business/professional” and more so “Subtle Goth” or “Dapper Dan Man” if that helps. Haha. Thanks in advance!

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Clark Street Sports
clarkstreetsports.com › collections › chicago-mens-apparel
Chicago Men's Hats and Apparel - Clark Street Sports
Then be sure to shop in-store or online from Clark Street Sports for best, most affordable, and exclusive Chicago merchandise. When men look for apparel, one of the first things they often think about are shirts and tees. A good shirt needs t.
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Menswearhouse
menswearhouse.com
Men's Wearhouse: Shop Men's Clothing, Suits & Tux Rentals
Shop the latest men's clothing — suits, shirts and more featuring top designers, modern fits, and trending styles. Enjoy great prices and free shipping!
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Menswearhouse
kgstores.com
Men's and Women's Clothing, Childrens', Shoes ...
We cannot provide a description for this page right now
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Culture Kings
culturekings.com › culture kings › shop streetwear clothing, sneakers, jerseys and hats | culture kings
Shop Streetwear Clothing, Sneakers, Jerseys and Hats | Culture Kings | Culture Kings US
2 weeks ago - Culture Kings World Famous for Streetwear, Sneakers, Hats, Adidas Originals, Nike, NBA Apparel, New Era, Loiter and so much more.
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Yelp
yelp.com › shopping › cheap men's dress clothes
TOP 10 BEST Cheap Men's Dress Clothes in Chicago, IL - Updated ...
Top 10 Best Cheap Men's Dress Clothes in Chicago, IL - Last Updated August 2025 - Yelp - Arthur and Lucca, Richard's Fabulous Finds, Buffalo Exchange, Men's Wearhouse, ESQ, Una Mae's, Formally Modern Tuxedo, BALANI Custom Suits Chicago, Nicholas Joseph Custom Suits
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Target
target.com › c › shirts-men-s-clothing › - › N-5xu28
Men’s Shirts & Tops : Target
2 weeks ago - Men's Shirts for Every Occasion at Target. Find dress shirts, casual tees, polos & more. Free shipping on orders $35+.
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Ford General
fordgeneral.com
Ford General - Premier Chicago Boutique
Discover our exclusive Chicago boutique, offering a curated selection of menswear, womenswear, and gifts from Europe and beyond.