Lenny and Me

This place is cute, chic, and friendly. The staff/​owner are warm, funny and helpful.
i am running out of positive adjectives, but if i had more, i would throw them in this review.

Lenny & Me has pretty much driven me to a Unilocal account, it’s that good and, I felt, important to share. This is my favorite store to seek clothes out in the city, and one of my top spots for Wicker Park-​alongside Wormhole and Myopic. I’m often out of luck with vintage wear being a skinny dude, but I have found fitting items I instantly adore and nearly as instantly purchase every time I have been (so far that includes a vest, a button-​down, a Western and a fantastic blue-​gray wool coat).
And not enough great things can be said about Leigh (Lee? Lea? I’ll ask next time). The first time I visited with some friends, she was very engaging and knowledgeable about the selection, and I think afterward we talked more about how much we liked her than we did about what we purchased. She has treated me with the same enthusiasm every time I’ve been back. Having a good rapport there makes it much easier to make return trips (often).

I love Lenny & Me — Leigh (the manager) is extremely knowledgeable about vintage clothing and designers (as am I) and edits the the store’s inventory/​display/​window so beautifully, it’s a pleasure simply to walk into the store.
I frequently sell to Lenny & Me (as I have a bad vintage shopping habit) and I have always been fairly compensated for what I bring into the store for them. Not only that, but I LOVE trading with them… as they have an amazing selection of dresses/​bags/​accessories/​shoes ranging from the 20s through to the late-​70s…
Having moved here from SF, I have to say the prices are extremely affordable in comparison.
It is a fantastic store. I’d give it ten stars if I could.

This is a neat store and a fun place to stop at if you’re in Wicker Park. They have lots of interesting antiques and trendy items for sale. But I found their prices to be a bit expensive for the quality and condition some of the items are in. I guess some of the items are fairly priced because of their uniqueness but overall a lot of items are too expensive. I find this to be somewhat of a common trend about antique stores… Just because it’s old does not necessarily make valuable or comparable in price to items that are brand new. However, this was a fun stop as I was really just window-​shopping when stumbled into here.

Maybe I’m a little overzealous about this place because it’s a fantastic vintage shop we don’t have back home… but I loved it! The thing I loved the most was the organization of the place, specifically by the decades.
I hate when you walk into a vintage store and it’s just a mess… like your grandma’s attic. I understand some stores go for that feel (with the mothball smell included) but I can’t handle it. I know what era’s I like (hello 50’s housewife!) and I don’t want to sift through bad 80’s heavy shoulder padded finds.
Lenny and Me had the perfect set up right down the line of decades. I found that their general selection was also pretty stellar as well. There were probably 25 – 50 dresses in each section and most of the finds were pretty well maintained and cute. I made out with a fantastic 50’s nautical dress that fit me perfectly and I left sadly without thee FIND of the century… a beautiful black billowing dress with purple flowers and built in crinoline that seemed as if it was taken right out of Betty Draper’s closet. It was A-​MAZ-​ING! Sadly… I couldn’t fit in it… about two inches too small. So if you’re reading this now PAH-​LEAZ go down there and buy it! It deserves a loving home!
I also thought the chick working was incredibly friendly and helpful. Really just an all around fantastic place! A must for the Betty Draper in all of us!

Super cute place with prices that made me die inside. I love antiquing and am willing to pay a hefty price for an awesome find. However, this place has comparable prices to places like the Lincoln and Broadway Antique Malls but the condition of their stuff is NOT as good. I saw delusional prices on furniture with plenty of wear and tear. Fun for browsing, ballz for buying.

The staff is incredibly friendly.
The selection is fantastic.
Bought a (admittedly very hipstery) pink and black houndstooth dress for $ 35. The cost is justified because, through all of my thrift store digging, I could never find anything that fantastic.
Love. :D

This is a very cute store with nice displays and a nice selection of vintage items. I found a couple very cute pairs of vintage boots– one pair was an older Coach brand and another was Etienne Aigner. Lots of contemporary and vintage clothing items. Not a lot of jewelry.
The furniture was overpriced. A simple wooden drafting table was $ 450? I didn’t find anything outrageously wonderful but all of it was pretty nice. They have a little section in the back with items made by Chicago artists like jewelry, t-​shirts etc. All in all it’s worth a stop but a lot of it is overpriced as other reviewers have said.

If I ever move to Chicago, I’d furnish my entire apartment with all the awesome vintage furniture from this lovely store! Everything is a little pricey, but so lovely and nicely refurbished/​cleaned. totally worth it.
Fun to take a walk in anyway. even if you don’t actually need anything.

A little pricey, but they do have som gret stuff for sure.
They have a lot of cool vintage housing stuff and furniture. I always drool when I pass their windows.

4.5 stars.
After sofa shopping along Milwaukee Ave., I passed Lenny & Me and figured I’d look for the elusive robe for which I’ve been searching. I generally have to hunt for robes in vintage stores, but not here; they were organized well and easily found. They even had TWO robes I liked but I opted for the pretty lace number over the paisley-​ish muu-​muu.
Searched through the summer tops, and found several I liked that were reasonably priced. Went with the cute black one with asymmetrical buttons — adorable!
Lindsey was a sweetheart and marked down both items (wihout my asking, but they did have a SALE sign in the window, which — I’d forgotten — is probably the reason I went in). This’ll be a great place to bring all the purses and dresses I no longer wear for store credit or cash.
NOTE to chicks in bands: Tons of great dresses that would look wunderbar onstage!

6^th & final stop on Mini-​me & I’s «vintage tour.»
FINALLY! The first store outta what feels like a million that Mini-​me actually liked! She even bought the cutest windbreaker-​well I mean she picked it and obv paid.
I really luvd this store! The store has the coolest vibe– like you’re walking through someones walkin closet… I only wished it was mine! :)
The store had some really awesome truly vintage pieces mixed in with a dash of the cutest secondhand stuff. A few pieces above some of your expected price points but more of them than not would have been worth the splurge.
I was eyeing a few pieces but needed to maintain my excitement & stay focused. I also found an awesome pair of shoes… if only they had been a half size bigger. :(
We left with Mini-me’s windbreaker & a Dia de Los Muertos print I picked up from the back of the store. But I soooo will be back!!!
***the store further down the block is also awesome in it’s own right. This one has the coolest housewares and I’m just so in luv with acrylic right now.

LOVE LOVE LOVE! Just moved to Chicago and on the hunt for the charming vintage shops. Walked in and fell in love. They have tons of great stuff for the home (which is my main interest) and they also have some cute dresses. Super friendly staff ^.^
Only negative is that they are a bit pricey. Coming from San Francisco where you pay no more than $ 30 for a canister set. In the store they had canister sets for $ 45. Other than that you can find the cutest things: D

They haven’t been around for very long, but it’s quite obvious what they’re trying to do. They just aren’t quite there yet.
The lady and I have stopped in here several times and out of all of the consignment and vintage shops in the area, this is the one the lady walks away from empty handed the most. I like how they’ve split the dresses into separate decades, however it seems as if some of them have been misplaced (you’re telling me they had Swinging London styled mod dresses in the 50’s!?)
What really bums me out about this place is the lack of men’s vintage. Maybe that isn’t one of their target audiences, but in Wicker Park, it damn well should be. I’m looking forward to seeing them grow and mature into a better destination for vintage — they’re certainly going in the right direction!
This review is for the shop near Ashland, not the one which took over what once was the Brown Elephant (though shame on them for closing off that perfectly useable downstairs area!)

I think I saw Lenny, he was in the back and looked like someone from an art film and just about as interested in the world around him as Warhol. I guess he didn’t surmise my demographic– someone who buys more than skinny jeans. They do a lot watching there, from the monitor in the front, stop and vogue, to yeah… Lenny. I am assuming «Me» was the one cleaning the windows and looking out on the street.
(Me did invite us to return, so I give her a star!)
That said, I prefer not to be bugged to buy, at least say hello, especially when I am the only freaking customer. But as a Mid-​Century-​Moderniphile I wanted to look around, because yeah the interior design is so, so captivating. They do a great job, and anyone looking for a Mid Century style would be smart to contact whomever designs their interior– it’s that good.
Their stuff is knockoffs as far as I could see, a lot Danish Modern lookalikes — but good looking all the same and of the era. Worth a regular visit, if you call Ray, Charles and Hans your inspiration.

Stopped in one day thinking it was still the Brown Elephant, and realized this is very, very much not the Brown Elephant.
Yes, the prices can be on the steep side (especially on some of that wonderfully gorgeous furniture), but the way everything is DISPLAYED is really terrific. I love a good color story, and the gals at Lenny & Me are tops when it comes to displaying their wares.
I picked up some adorable tea towels embroidered «Mr.» and «Mrs.» as a wedding present for my friend, but had I had more time (and cash) I’d do some real damage.
It’s not a «thrift store» but it’s a wonderful vintage boutique that will dazzle you with carefully displayed treasures.

Somehow I haven’t been to their original location yet, but I did stop by the new one and found it to be a feast for the eyes. Lovely décor and plenty of fun things to browse through. The woman working there (who I believe was the owner) was extremely sweet, too!
As this was my last stop on an extensive shopping extravaganza, I was flat broke, but lately I’ve been in the mood to go vintage/​thrift shopping so I’m definitely going to pay them another visit!

This is definitely one of my favorite thrift places in the city. A fabulous collection of retro wares, including clothes (which the owner is starting to phase out) and, best of, furniture. Seriously, I could gladly furnish my entire apartment in one shopping trip (if I weren’t a broke college student).
This place is consistently fanfreakingtastic!

They’ve certainly got an eye for some really retrotastic finds… I’ll give them that. If I had a bazillion dollars, this is just the kind of store I’d open. All fantasy-like…but, I’d go to a neighborhood where the rent wasn’t sky high so I could keep my prices in the range of «middle class» affordable.
Ie; remember the cherry red cowboy boots I bought for $ 20 last week at Brown Elephant on Halsted? Well, their twin pair was sitting in Lenny & Me for…$ 80. Dresses (that are NOT drycleaned prior to sale) for $ 40-​$ 75. Shoes starting at $ 35. Furniture is off the charts. $ 400 for an arm chair? Um, no.
So, here’s the thing… if you’ve got some patience, and a good eye for something fabulous and vintage, just scour the thrift stores and save yourself the 100+ percent markup you’ll find here. Or, if you don’t have the time… then you get what you pay for: someone else doing it for you!
Stars for interior design, I love the hanging umbrellas from the ceiling, and there really are some fabulous pieces… I just think they are cruelly overpriced, and that the sales associates are too busy fixing their hair and playing on the computer to say hello.
So, hello Lenny & Me, something’s gotta give. The prices or get nicer people who want to help me find something. Pick. :)
Love the stuff though. Love, love, love.

Eh. I’m guessing this store is hit or miss, but Lenny and Me just didn’t do it for me. I almost settled on a cuteish purple dress just to buy something, but ended up putting it back on the rack and continuing my shopping journey elsewhere on Milwaukee.
I would possibly come back to get rid of some stuff in my closet… the sales woman said it’s consignment so they sell it first and then it’s a ⁴⁰⁄₆₀ split.