What to Wear: A Dash of Yellow

Reader Request

My favorite color is yellow but unfortunately, I look really pale and sickly when I wear it. Do you know of any way to wear a color when it's not flattering?

Yup - just keep it away from your face! If you wear yellow bottoms, shoes, or accessories, you can keep your favorite hue in your wardrobe without looking pale.

Top $50 // Jeans $30 // Shoes $60 // Bag $28 // Scarf $36 // Bracelets $17

What to Wear: 3.1 Phillip Lim for Target Sweatshirt

Reader Request

I bought the BOOM! sweatshirt from 3.1 Phillip Lim for Target because I thought it was cute, but I have no idea how to style it. So far I've just worn it to yoga with leggings but I wondered if you could help me put a stylish outfit together with it.

I just posted about fancy sweatshirts yesterday - they're everywhere and you can easily make them more sophisticated by pairing them with some sleeker pieces. I actually own this same sweatshirt too, and it's been too warm to wear it so far, but here's how I plan on styling it once the temps drop a bit more.

Sweatshirt $30 // Shirt $18 // Jeans $65 // Shoes $50 // Bag $50 // Earrings $9

What to Wear: Going Away Party

Reader Request

I'm moving across the country next month and my friends are throwing me a big going-away party. It's going to be an outdoor thing in my friend's backyard with a bonfire, a barbecue, and beer, so it's nothing fancy, but I want to look cute. What should I wear?

That sounds like a lot of fun! I'd stick with something casual and comfortable, with lots of layers for a nice early fall evening.

Jacket $25 // Top $20 // Pants $60 // Boots $50 // Bag $39 // Hat $25

What to Wear: Colored Tights

Reader Request

I just turned 30. Am I too old to wear colored tights? How do I pull them off without looking like I'm 6 years old?

I think that anyone can wear colored tights. The trick is to keep the rest of your outfit sleek and sophisticated. What do you think of this?

Top $50 // Skirt $69 // Tights $15 // Boots $70 // Bag $40 // Earrings $8 // Bracelets $8

What to Wear: Winery Bachelorette Party

Reader Request

My friend's bachelorette party is in a few weeks. A bunch of us are renting a limo and going on a winery tour in the afternoon, and then out to dinner at a gastropub. I've never been to a winery so I'm not sure what to wear or how fancy they are. I want to look nice but I don't want to be overdressed or underdressed. What should I wear? Help me please!

I've been to a bunch of wineries and you definitely don't have to be dressed up, especially during the day. You can expect to see plenty of people in jeans. But since it's a festive activity that ends in a dinner, I can see why you'd want to gussy up a bit. So here's an outfit that's both daytime and nighttime appropriate, and will be comfy for getting in and out of a limo all day. Have fun!

Dress $18 // Jacket $47 // Sandals $35 // Bag $65 // Bracelets $7 // Necklace $11

What to Wear: Comfort at the Office

Reader Request

I just got a new job after several years of working from home. My new office has a very casual dress code (most people wear jeans, t-shirts, and sneakers) but I'm coming off of years and years of wearing yoga pants and sweats all day, and I got used to wearing stretchy, comfy clothes 24/7. Now, I'm trying to be as comfortable as possible without looking like I'm in my pajamas or gym clothes. Do you have any suggestions about something that's stylish but as comfortable as my sweats?

You're a woman after my own heart! If it was socially acceptable to go to the office in my pajamas, I'd totally do it. I spend almost the entire summer in lightweight, stretchy knit dresses and flat sandals. But now that fall is approaching, here is a comfy office-appropriate look for cooler weather.

Sweater $54 // Cami $2 // Jeggings $21 // Boots $99 // Bag $59 // Scarf $10

What to Wear: Frye Boots in Saddle

Today's featured item from the What the Frock? Shop are these fabulous Frye boots! Here's how I'd style them.

Top $58 // Jeans $16 // Boots $80 // Bag $65 // Hat $32 // Scarf $10

What to Wear: Banana Republic Sequin Shift Dress

Today's featured item from the What the Frock? Shop is this Banana Republic Sequin Shift Dress. This dress is perfect for a fancy party or a night of dancing and cocktails. I've styled it with some stylish items from popular stores.

Dress $20 // Tights $17 // Shoes $49 // Clutch $50 // Bracelet $11 // Earrings $9

What to Wear: Bright Floral Skirt

I'm taking a short pseudo-break from Celebrity Looks for Less for a while, and will return after Labor Day. But you're not entirely rid of me for now! I'm going to be posting some stylish looks featuring items from my new online thrift store, the What the Frock? Shop.

Today's featured item is this gorgeous Elevenses Floral Skirt, originally from Anthropologie, which I'd have snapped up in a heartbeat if it was my size!

Top $30 // Skirt $35 // Shoes $70 // Clutch $30 // Necklace $28 // Earrings $7

What to Wear: Bartending

Reader Request

I got laid off from my job a few weeks ago, and picked up a bartending job to make ends meet until I can find something new. I haven't tended bar since my early 20's (I'm 30 now) and have realized that I don't know what to wear. Last time I worked behind a bar, I had to wear a uniform, but my new job is at a casual gastropub and I can wear whatever I want. 

The problem is, my wardrobe pretty much consists of business casual clothes that I wore to work, and jeans and t-shirts that I wear on weekends. I want to look cute while I work, but since I'm running around for 8-hour shifts, I need to be comfortable. And since everything I wear will end up covered in beer, I don't want to spend a lot of money. Do you have any suggestions?

I was really excited to get your email because I used to tend bar at a casual gastropub! When I tended bar, I'd keep it simple - jeans or shorts, comfy closed-toe flats, a cute but basic top, and maybe one piece of statement jewelry that's short enough to stay out of the way. And I stuck to dark colors or prints, so that spills weren't as noticeable. Here's an example of a staple outfit from my bartending days that I think will work very well today.

Top $21 // Jeans $38 // Shoes $33 // Necklace $7 // Bag $34

What to Wear: to the Newport Folk Festival

Reader Request

I'm going to the Newport Folk Festival with my sister and her husband this weekend. I've never been to a music festival before and I don't know what to wear. Help!

The most important things to keep in mind while dressing for an outdoor festival are staying comfy, keeping cool, and looking good while doing it!

Top $19 // Skirt $15 // Sandals $30 // Bag $42 // Hat $30 // Necklace $16 // Sunglasses $14 // Bracelets $5

What to Wear: Company Picnic

Reader Request

My company picnic is next week and I'm not sure what to wear. There will be food and games so I'll want to wear something lightweight and comfortable. My office is pretty conservative and I wasn't here last year, so I don't know exactly what I should wear. Normally I'd wear a tank and some shorts, but is that appropriate for a company event?

I think that shorts and a tank can be perfectly appropriate, as long as they're not too tight or revealing. Here's how I'd style it.

Top $50 // Shorts $18 // Shoes $40 // Hat $25 // Bag $22 // Sunglasses $22

What to Wear: Day to Night Wedding

Reader Request

I'm going to a wedding in August. The reception starts three hours after the ceremony ends, but I live two hours away, so I won't be able to go home and change. I'd like to wear a dress that is appropriate for both the church in the afternoon and the banquet hall at night, if possible. Does something like that even exist?

I found a dress that will work for either scenario, and I'd recommend a quick swap of shoes and accessories to take it easily from day to night. 

Day: Dress $85 // Cardigan $44 // Shoes $60 // Clutch $20

Night: Shoes $40 // Clutch $30 // Necklace $55

What to Wear: Fundraiser Gala

Reader Request

I'm attending a fundraiser gala later this summer. It's black tie but I can't afford $500 for a gown. Can you help me by putting together something cheap that doesn't look cheap?

Here's an elegant look that's much, much cheaper than it looks. Enjoy!

Gown $115 // Shoes $44 // Clutch $40 // Earrings $16 // Necklace $46

What to Wear: Sunday Brunch and Shopping

Reader Request

I recently moved to a new city and am trying to make friends so I joined a local Meetup group. I'm going to my first meetup the week after next, for Sunday brunch. After we eat, we're going shopping downtown, so since we'll be walking around, I'll want to wear comfortable footwear. I've never met any of the other attendees in person so I'd like to look nice. What should I wear?

You can't go wrong with a cute dress, am I right?

Dress $60 // Shoes $80 // Bag $41 // Earrings $42 // Sunglasses $36

What to Wear: Hot and Rainy

Reader Request

I live in Philly, where for the past month it's been hot and humid, but also really rainy. And every day, getting dressed is a nightmare. When it's cooler and it rains, I wear layers and rubber boots, but it's way too hot to deal with that right now. Any suggestions?

I'm in Philly too, and I agree, getting dressed has been a challenge with all this rain. I've found that the best bet is to stay with lightweight summer clothes (I'd rather dry off my bare legs than walk around in wet jeans after I've been caught in the rain). As far as shoes go, try a pair of waterproof flats that are comfy and cute.

Dress $75 // Shoes $59 // Bag $45 // Umbrella $19 // Earrings $30

What to Wear: Chambray on Denim

Reader Request

Can I wear a chambray shirt with denim shorts, or will that get me in trouble with the Fashion Police?

I say go for it! I'd go with two different shades of blue, but do whatever you like, Fashion Police be damned!

Top $25 // Shorts $40 // Sandals $38 // Bag $96 // Bracelet $9 // Earrings $20 // Sunglasses $26

What to Wear: To a Barn Wedding

Reader Request

I'm going to a wedding next month and have no idea what to wear. It's an afternoon wedding taking place at a farm, in a barn. So I don't want to be overdressed, and I don't know what shoes I should wear. Help!

If I were you, I'd go with a simple summer dress with a pretty print, and flat sandal.What do you think of this?

Dress $54 // Sandals $28 // Clutch $30 // Necklace $50 // Earrings $15

What to Wear: Mature but Not Stuffy

Reader Request

I just turned 35, and I've recently realized that I dress way too young for my age. My work clothes are age-appropriate, but I still buy my casual and going-out clothes at places like Forever 21, because I refuse to spend a lot of money on trendy clothes that will go out of style in six months. I'm told that I look young and I'm in pretty okay shape, but I don't want to dress like a college student anymore. Can you help me find some age-appropriate weekend clothes that aren't stuffy or expensive?

I'm in my late 30's and guess what? I also shop at stores like Forever 21 sometimes. Most stores that sell to younger women carry at least some items that can be worn by an older woman. It's all about the fit and how you style your clothes.

So, here is a stylish but age-appropriate look that I put together from very inexpensive brands that usually cater to much younger women. It's still possible!

Top $23 // Jeans $8 // Shoes $20 // Bag $28 // Necklace $8

What to Wear: Decades Party

Reader Request

I've been invited to a Decades Party, where we have to dress up in a costume from a decade of our choosing. I can't even decide on a decade, let alone a costume. Do you have any ideas?

The tough part is choosing a decade - after that, the costume will come easily. For some inspiration, here are some decade-inspired looks I've put together in the past:

1920's // 1930's // 1940's // 1950's // 1960's // 1970's // 1980's // 1990's

The 60's is my favorite decade for fashion, so that's the decade I recommend for your party. What do you think of this swinging 60's look?

Dress $92 // Boots $35 // Bag $68 // Sunglasses $4 // Earrings $45 // Lashes $3 // Lipstick $12