Help me find new clothes for going out!
October 30, 2013 2:23 PM   Subscribe

I've outgrown cheap, sparkly, skin-baring clothes from Express. A floor length ball gown would probably be overkill. What does a classy 27-year-old female wear on the weekends?

I've recently gone through a major closet purge, which has left me with a closet full of clothes that I absolutely love! One major causality: all of my "going-out" clothes, which tended to be low-quality, overly revealing, and not exactly my style (think discount bin at Express). Thankfully, my lifestyle has also shifted away from all-night dancing. Nowadays, I tend to spend my weekends at nicer restaurants (I'm a foodie who lives in Chicago, so there's no shortage of those), wine bars/lounges, and get-togethers at friends' apartments. I want to look polished and dressed up on the weekends, but I'm having a hard time pulling it off. Most of the time, I end up looking like I just came straight from work, which is not what I'm going for!

I'm looking for ideas for some items to add to my wardrobe to make dressing for going out easier. This would include clothing as well as accessories/jewelry. Links to specific items are totally cool, but I'm also likely to hunt for these types of things in thrift and consignment stores so I'm happy to hear general recommendations. Ideas for complete outfits and styling would also be very much appreciated.

I know I can just copy my friends/ stylish strangers, but I'm looking for more classic styling (think Parisian chic). Plus, I tend to dress more on the formal side than most people my age, and I'm happy about that. I'm trying to avoid the whole hipster look, although I'm not opposed to vintage elements. A typical nighttime outfit for me would be a white silk button-down blouse, black skinny pants, a tailored red blazer and stiletto heels. This works okay, but it reads more "day-to-night" than "night on the town."

I'm actually quite into fashion, and generally try to wear high-quality, timeless clothing with a little bit of an edge to it. In an ideal world, I'd dress just like Rachel Bilson. I like clothing that's structured, tailored/fitted, and not terribly girly. I mostly wear black, white, red, and blue. Quality is important to me, and I particularly love silk.

A couple of things that have worked for me recently: black dress with a ton of pearls, a la Coco Chanel. Black blazer buttoned over a sequined top and skinny jeans. I'm really into tucking my tops into high-waisted pants/skirts/shorts, to show off my waist.

Some things that don't work for me: I'm 5'1" and in good shape, so the whole over-sized trend overwhelms my frame and doesn't really show off my best assets. I like leopard print but otherwise steer clear of bold patterns and super-bright colors, because that's just not me.

Thanks in advance, fashionistas of metafilter!
posted by therumsgone to Clothing, Beauty, & Fashion (16 answers total) 26 users marked this as a favorite
Madewell's silk dresses and tops are staples in my wardrobe for going out. I find their clothes to be versatile, classic and not overly girly. I've found some perfect going-out dresses at Aritzia too.
posted by blackcatcuriouser at 2:40 PM on October 30, 2013 [1 favorite]

In Chicago, you have the option of All Saints (on Michigan Ave), which definitely fits that aesthetic, but is not inexpensive (my experience with All Saints is that the quality aligns with price for most pieces). Anastasia Chatzka is another option. Store B Vintage on Milwaukee near the Bongo Room skews fashion-y rather than hipster-y.

As for how to style yourself or which pieces to buy, I'm not sure I have specific suggestions. It sounds like you'd be pretty okay in simple monochrome outfits with statement pieces, like jewelry, shoes, or said sequined top.
posted by crush-onastick at 2:40 PM on October 30, 2013 [1 favorite]

I think you might find some good inspiration at CapHillStyle. While she does focus a lot on being office appropriate, there is also a lot of going out clothing that seems like it would match the look you are heading towards. Her Instagram (like this amazing dress) is great too.
posted by zara at 2:52 PM on October 30, 2013 [1 favorite]

HI! Your fashion sense sounds a lot like mine. I have been working a lot more on "going out" clothes. Have you tried high waisted shorts with a cute shirt and a blazer over tights? That's a thing I really like lately. If you are on Pinterest, here's my fashion board which has a lot of ideas for a variety of occasions. I tend to focus on fancier blazers and fun shapes when I go out, focusing on the idea of a cohesive aesthetic from day to night and weekend. For me, a lot of the key to looking like I was going out was to add less formality to my going out clothes. I bought a pair of sequin pants for $20 on Amazon and got a perfectly fitting tshirt to go with them and some heels to look dressed up but not ready to go to a ball.
posted by Nimmie Amee at 3:05 PM on October 30, 2013 [2 favorites]

Try Maggy London. I find them to be good looking and good for day-to-night, and well priced. Get on their email list and there will be a good sale about 4 times a year.
posted by janey47 at 3:12 PM on October 30, 2013 [1 favorite]

2nding Madewell. If you live near one, their sale racks in stores always have more and better stuff than is available online. But, I think their stuff runs kind of big. I also still wear a lot of American Apparel stuff for my going out clothes. Their chiffon tops (over a cami, or something else, rarely just over a bra) have gotten me a lot of compliments. I know that it's not silk, or whatever, but just a thought. I am very petite, and the small drapes nicely and isn't overwhelming.

I also always look and feel more "dressed up" wearing trouser or bootcut jeans with heels. I am also pretty short, and a pair of high-waisted flare jeans plus heels makes my legs look crazy long.

Do something nice with your hair! Wear killer lipstick! Wear awesome shoes that you can't wear to work!
posted by ablazingsaddle at 3:45 PM on October 30, 2013

Also, a silk button-down and blazer reads kind of "I just came from work" to me. How about a blazer over a cami? Or ditch the blazer and wear a cool sweater?
posted by ablazingsaddle at 3:50 PM on October 30, 2013 [1 favorite]

You must own and wear a pair of quality leather boots. The height of the heel doesn't matter. Smooth leather or suede, brown or black, up to the knee. These can be worn with anything, and will look smashing. You'll get what you pay for.
posted by BostonTerrier at 5:04 PM on October 30, 2013 [1 favorite]

I like White House Black Market for both work and going-out clothes.
posted by fingersandtoes at 5:15 PM on October 30, 2013

You might like Ann Taylor Loft, and they have a lot of petite styles.
posted by BlahLaLa at 8:20 PM on October 30, 2013

I would recommend this checklist as a good way to build up a classic wardrobe. Once you know what you "should" have in your closet, you can decide which items you can splurge on and which items you can get at a thrift store or secondhand.

For some items on the list, I have several of the same item, each suited for different occasions, i.e. an everyday, matches with almost everything navy cardigan (would wear to run errands or see a close friend) compared to a high quality, very specific pattern/printed red cardigan (would wear on a date or a dressy event with people I didn't know very well). Same thing goes for listed items like black pumps, classic oxford shirts and jeans.

I mostly shop at J. Crew and Anthropologie (on sale and using eBay strategically) and they both have Petite options. In order to not overspend or regret purchases, I buy things that transcend style trends (classics with interesting details). I also only purchase a piece that if I were to see someone else wearing I would have to complement them. It must WOW me in order for me to buy it.

One last thing that will really help you is to identify the color combinations that look the best on you. This will help you to mix and match your wardrobe most efficiently. I've sent you a MeMail with my Pinterest board on Color Combos and also my wardrobe aesthetic. Good luck!
posted by alice ayres at 8:31 PM on October 30, 2013 [1 favorite]

If you replaced the blazers in those two examples with a shrunken moto-style leather jacket you'd have it nailed. It's the blazers that are making it seem day-time-y. Even Lucky agrees!
posted by marylynn at 9:49 PM on October 30, 2013 [1 favorite]

I've bought a few Everlane silk blouses lately and am really happy with them. I just wear them with skinny jeans or cuffed jeans and boots (tall or ankle, depending on the jeans). They could pair easily with a pencil skirt (like a jersey type fabric, not a suiting fabric) or cigarette trousers and heels if you want to dress up a little more.
posted by citron at 9:55 PM on October 30, 2013

Though the "statement necklace" is very on-trend right now I think it's got staying power. Basically the same concept as your piling on lots of pearls. For me I like to pick up cheapie costume jewelry at Target or Cost Plus World Market, nicer things at thrift/estate sales/consignment or make your own if you are crafty.

Big chunky cocktail rings are also fun and have a similar effect on an outfit as the statement necklace.

It sounds like you're more into separates, but I've been really into dresses lately. You may have to shop a little harder to find what you like and what works for your body, but once you've got a dress you love in your closet there is NOTHING easier than throwing one item of clothing on plus shoes and jewelry (as opposed to coordinating several pieces.) Basically, the classic "cocktail dress" concept, in between dressy/formal and casual sundress, something that hits above the knee. I have a high tolerance for cheap fashion which it sounds like you're moving away from, but again all my favorite "party dresses" are from Target and have held up for years.
posted by dahliachewswell at 10:24 AM on October 31, 2013

I am going to make a weird suggestion but one that has worked for me.

I suggest going to the Unique thrift store, where things are so cheap that it doesn't matter if you end up wearing them often (warning - they don't have dressing rooms - wear leggings). Go through everything and find the hidden gems - quality items in nice fabrics. Get a big pile. Don't be picky - if something looks like it's good quality you should try it, even if it doesn't seem like your usual style.

Try on everything. For each piece, think about what you might wear it with. Think about whether it could be the starting point for a good outfit.

I have found some nice silk blouses there, two cute dresses, some skirts, and a good cardigan. Some of it is vintage-y, some of it is recent. I have also purchased some stuff I never wore but it only costs about $5 per item so who cares.

Once you have done this experiment a few times, you might have a better sense of a personal style that works for the new you. Then you can spend money on pieces that go along with that style.

As far as avoiding the business-casual vibe that it's so easy to fall into, I recommend showing close-fitting items either on top or bottom or both, and either bare arms or a short skirt. I am of the opinion that women of any age can wear short skirts if they want to.
posted by mai at 12:32 PM on October 31, 2013

Oh! And ankle boots with a heel or wedge.
posted by mai at 12:33 PM on October 31, 2013

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